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CAS

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Diisopropyl azodicarboxylate, also known as DIAD or DIPA, is an azodicarboxylic acid derivative that is an orange-red transparent oily liquid with a special smell. It is soluble in almost all organic solvents and plasticizers, and has good thermal stability. It is commonly used as a reagent in the production of various organic compounds and as a liquid blowing agent for vinyl resin.

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  • 2446-83-5 Structure
  • Basic information

    1. Product Name: Diisopropyl azodicarboxylate
    2. Synonyms: AZODICARBONIC ACID DIISOPROPYL ESTER;AZODICARBOXYLIC ACID DIISOPROPYL ESTER;DIAD;DIISOPROPYL AZODICARBOXYLATE;LABOTEST-BB LT00454155;diisopropyl azodiformate;Diisopropyl azodicarboxylate [DIAD];Diisopropylazodicarboxylate,95%
    3. CAS NO:2446-83-5
    4. Molecular Formula: C8H14N2O4
    5. Molecular Weight: 202.21
    6. EINECS: 219-502-8
    7. Product Categories: API;Aromatic Esters
    8. Mol File: 2446-83-5.mol
  • Chemical Properties

    1. Melting Point: 3-5 °C
    2. Boiling Point: 75 °C0.25 mm Hg(lit.)
    3. Flash Point: 223 °F
    4. Appearance: Clear to slightly turbid yellow-orange to red/Liquid
    5. Density: 1.027 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.00463mmHg at 25°C
    7. Refractive Index: n20/D 1.420(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
    10. Water Solubility: insoluble
    11. Sensitive: Light Sensitive
    12. BRN: 1912326
    13. CAS DataBase Reference: Diisopropyl azodicarboxylate(CAS DataBase Reference)
    14. NIST Chemistry Reference: Diisopropyl azodicarboxylate(2446-83-5)
    15. EPA Substance Registry System: Diisopropyl azodicarboxylate(2446-83-5)
  • Safety Data

    1. Hazard Codes: Xn,Xi,N,F
    2. Statements: 36/38-51/53-5-43-36/37/38-11-48/20/22-40
    3. Safety Statements: 36-61-47A-36/37/39-29-26-16-60-36/37
    4. RIDADR: UN 3082 9/PG 3
    5. WGK Germany: 1
    6. RTECS:
    7. F: 4.10-8
    8. HazardClass: 9
    9. PackingGroup: III
    10. Hazardous Substances Data: 2446-83-5(Hazardous Substances Data)

2446-83-5 Usage

Uses

Used in Chemical Synthesis:
Diisopropyl azodicarboxylate is used as a reagent in the production of many organic compounds, particularly in the synthesis of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers, and acceptor-donor-acceptor organic dyes.
Used in Pharmaceutical Industry:
Diisopropyl azodicarboxylate is used as a pharmaceutical intermediate, playing a crucial role in the development and production of various pharmaceutical products.
Used in Rubber and Plastics Industry:
As a foaming agent for vinyl resin, Diisopropyl azodicarboxylate is used to create light-colored vinyl foam with a uniform pore structure. Different formulations and processing conditions can result in either closed-pore or open-pore foam.
Used in Mitsunobu Reactions:
Diisopropyl azodicarboxylate is commonly used as an oxidizer in Mitsunobu reactions, which are widely used in organic chemistry for the inversion of stereochemistry and the formation of new carbon-heteroatom bonds. It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.
Used as a Dye Intermediate:
Diisopropyl azodicarboxylate is utilized as a dye intermediate, contributing to the production of various dyes used in different industries.
Storage Stability:
Diisopropyl azodicarboxylate has excellent storage stability, with its decomposition substance being colorless, non-toxic, non-polluting, non-blooming, and odorless. It can achieve high gas evolution in the temperature range of 40-120 °C.
Chemical Properties:
Diisopropyl azodicarboxylate is a clear orange liquid that reacts with dioxaphosphorinanes and iron catalysts to generate rearranged phosphonium ylide products.

Purification Methods

Purify the azo compound by distillation at as high a vacuum as possible. Since it is likely to explode, use an oil bath for heating the still, and all operations should be carried out behind an adequate shield. [Kauer Org Synth Coll Vol IV 412 1963, Beilstein 3 III 233]. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate and DEAD above].

Check Digit Verification of cas no

The CAS Registry Mumber 2446-83-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,4 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2446-83:
(6*2)+(5*4)+(4*4)+(3*6)+(2*8)+(1*3)=85
85 % 10 = 5
So 2446-83-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+

2446-83-5 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (A1246)  Diisopropyl Azodicarboxylate (40% in Toluene, ca. 1.9mol/L)  

  • 2446-83-5

  • 25g

  • 130.00CNY

  • Detail
  • TCI America

  • (A1246)  Diisopropyl Azodicarboxylate (40% in Toluene, ca. 1.9mol/L)  

  • 2446-83-5

  • 100g

  • 390.00CNY

  • Detail
  • TCI America

  • (A1246)  Diisopropyl Azodicarboxylate (40% in Toluene, ca. 1.9mol/L)  

  • 2446-83-5

  • 250g

  • 690.00CNY

  • Detail
  • Alfa Aesar

  • (L10386)  Diisopropyl azodicarboxylate, 94%   

  • 2446-83-5

  • 25g

  • 480.0CNY

  • Detail
  • Alfa Aesar

  • (L10386)  Diisopropyl azodicarboxylate, 94%   

  • 2446-83-5

  • 100g

  • 1053.0CNY

  • Detail
  • Aldrich

  • (225541)  Diisopropylazodicarboxylate  98%

  • 2446-83-5

  • 225541-5G

  • 347.49CNY

  • Detail
  • Aldrich

  • (225541)  Diisopropylazodicarboxylate  98%

  • 2446-83-5

  • 225541-25G

  • 409.50CNY

  • Detail
  • Aldrich

  • (225541)  Diisopropylazodicarboxylate  98%

  • 2446-83-5

  • 225541-100G

  • 1,115.01CNY

  • Detail

2446-83-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Diisopropyl azodicarboxylate

1.2 Other means of identification

Product number -
Other names diisopropyl azodicarbonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2446-83-5 SDS

2446-83-5Synthetic route

ethyl acetate n-hexane

ethyl acetate n-hexane

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine
103057-44-9

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

thioacetic acid
507-09-5

thioacetic acid

tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate

tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran100%
1-(3,5-dimethylbenzyl)-3-isothiocyanatoindolin-2-one

1-(3,5-dimethylbenzyl)-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-(3,5-dimethylbenzyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-(3,5-dimethylbenzyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
1-benzyl-4-bromo-3-isothiocyanatoindolin-2-one

1-benzyl-4-bromo-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-4-bromo-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-4-bromo-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-methylindolin-2-one
1287715-28-9

3-isothiocyanato-1-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at -20℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-propylindolin-2-one
1422555-11-0

3-isothiocyanato-1-propylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 2-oxo-1-propyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 2-oxo-1-propyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at -20℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-phenylindolin-2-one
1354636-91-1

3-isothiocyanato-1-phenylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 2-oxo-1-phenyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 2-oxo-1-phenyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
1-benzyl-3-isothiocyanatoindolin-2-one
1287715-31-4

1-benzyl-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Solvent; Temperature; Inert atmosphere; enantioselective reaction;99%
3-tolyl isocyanate
621-29-4

3-tolyl isocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-(3-methylphenyl)-5-oxo-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-(3-methylphenyl)-5-oxo-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-5-oxo-4-phenyl-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-5-oxo-4-phenyl-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;98%
1-oxoindane-2-carboxylic acid ethyl ester
6742-25-2

1-oxoindane-2-carboxylic acid ethyl ester

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C20H26N2O7

C20H26N2O7

Conditions
ConditionsYield
chiral palladium complex In methanol at 20℃; for 0.5h;98%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<1,10>dioxacyclooctadecin-23,25-dione
145986-91-0

2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<1,10>dioxacyclooctadecin-23,25-dione

C60H80N4O12

C60H80N4O12

Conditions
ConditionsYield
In toluene at 110℃; for 6h;98%
C19H14ONCl

C19H14ONCl

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C27H28ClN3O4
1004974-38-2

C27H28ClN3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
C15H12O3N2

C15H12O3N2

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C23H26N4O6
1004974-44-0

C23H26N4O6

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
phenyl (3-phenylaziridin-2-yl) methanone
51659-21-3

phenyl (3-phenylaziridin-2-yl) methanone

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C23H27N3O4
1004974-16-6

C23H27N3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(4-Methoxy-phenyl)-[3-(4-nitro-phenyl)-aziridin-2-yl]-methanone

(4-Methoxy-phenyl)-[3-(4-nitro-phenyl)-aziridin-2-yl]-methanone

C24H28N4O7
1004974-32-6

C24H28N4O7

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-(naphthalen-2-ylmethyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-(naphthalen-2-ylmethyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 5'-((1,2-bis(isopropoxycarbonyl)hydrazinyl)thio)-1-(naphthalen-2-ylmethyl)-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 5'-((1,2-bis(isopropoxycarbonyl)hydrazinyl)thio)-1-(naphthalen-2-ylmethyl)-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
1-benzyl-3-isothiocyanato-5-methoxyindolin-2-one

1-benzyl-3-isothiocyanato-5-methoxyindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-5-methoxy-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-5-methoxy-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
propionaldehyde
123-38-6

propionaldehyde

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-propionylhydrazine-1,2-dicarboxylate

diisopropyl 1-propionylhydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
dirhodium tetraacetate In ethyl acetate at 25℃; for 12h;97%
1-benzyl-3-isothiocyanato-5-methylindolin-2-one
1450988-91-6

1-benzyl-3-isothiocyanato-5-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;97%
1-benzyl-3-isothiocyanato-6-methylindolin-2-one

1-benzyl-3-isothiocyanato-6-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-6-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-6-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;97%
(E)-3-(anthracen-10-yl)-1-(4-chlorophenyl)prop-2-en-1-one
57076-91-2

(E)-3-(anthracen-10-yl)-1-(4-chlorophenyl)prop-2-en-1-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C31H29ClN2O4

C31H29ClN2O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 3h; Heating;96%
3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester
445490-67-5

3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester
445490-68-6

3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran96%
N,N-di(tert-butoxycarbonyl)hydroxylamine
85006-25-3

N,N-di(tert-butoxycarbonyl)hydroxylamine

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(E)-3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-en-1-ol
174258-43-6

(E)-3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-en-1-ol

(E)-N-tert-Butoxycarbonyloxy-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-carbamic acid tert-butyl ester
174258-44-7

(E)-N-tert-Butoxycarbonyloxy-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran96%
C17H17ON

C17H17ON

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C25H31N3O4
1004974-22-4

C25H31N3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;96%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

4,4'-Dichlorobenzophenone
90-98-2

4,4'-Dichlorobenzophenone

diisopropyl 2-[bis(4-chlorophenyl)methylene]hydrazine-1,1-dicarboxylate
1041432-63-6

diisopropyl 2-[bis(4-chlorophenyl)methylene]hydrazine-1,1-dicarboxylate

Conditions
ConditionsYield
With triphenylphosphine In toluene at 110℃; for 12h;96%
1-benzyl-6-chloro-3-isothiocyanatoindolin-2-one

1-benzyl-6-chloro-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-6-chloro-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-6-chloro-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;96%
1-benzyl-3-isothiocyanatoindolin-2-one
1287715-31-4

1-benzyl-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With C31H32N2O2 In tetrahydrofuran at 20℃; for 0.0833333h; Reagent/catalyst; Solvent; Inert atmosphere;96%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-phenyl-5-thioxo-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-phenyl-5-thioxo-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;95%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(E)-1-(4-chlorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

(E)-1-(4-chlorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

C27H27ClN2O4

C27H27ClN2O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 3h; Heating;95%

2446-83-5Relevant articles and documents

Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

M?rz,Chudoba,Kohout,Cibulka

supporting information, p. 1970 - 1975 (2017/03/11)

The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.

Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions

Jung, Dahyeon,Kim, Min Hye,Kim, Jinho

supporting information, p. 6300 - 6303 (2016/12/23)

A new class of co-catalytic system was developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular oxygen as a terminal oxidant. A variety of quinolines were efficiently synthesized by the developed Cu and di-tert-butyl azodicarboxylate co-catalytic system.

Method of manufacturing Azodicarboxylic acid diester compd. (by machine translation)

-

Paragraph 0029-0031, (2017/04/28)

PROBLEM TO BE SOLVED: To provide a manufacturing method in which an azodicarboxylate diester compound can be efficiently obtained in a high yield and which is industrially advantageous.SOLUTION: There is provided a manufacturing method for azodicarboxylate diester compound including: a process (a) of obtaining a 1,2-hydrazine dicarboxylate diester compound through reaction between hydrazine and a halocarbonate ester; and a process (b) of obtaining an azodicarboxylate diester compound represented by general formula (2) (where A represents a hydrocarbon or a hydrocarbon which may have an ether bond) by oxidizing the 1,2-hydrazine dicarboxylate diester compound obtained in the process (a), the 1,2-hydrazine dicarboxylate diester compound being neither isolated nor refined.

QUINAZOLINE-2,4-DIONE DERIVATIVES

-

, (2014/06/25)

The invention relates to antibacterial compounds of formula (I), wherein R1 is H, halogen, (C1-C3)alkyl or (C1-C3)alkoxy; R2 is H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or pyrrolidin-1-yl; R3 is H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy, vinyl or 2-methoxycarbonyvinyl or R2 and R3 together with the two carbon atoms which bear them form a phenyl ring; R4 is H, halogen, (C1-C3)alkyl or (C1-C3)alkoxy; and R5 is H, (C1-C3)alkyl or cyclopropyl, or R4 and R5 form together a —CH2CH2CH2— group; A is the divalent group —CH2—, —CH2CH2—, #—CH(OH)CH2—*, #—CH2N(R6)—* and —CH2NHCH2—, wherein # indicates the point of attachment to the optionally substituted (quinazoline-2,4-dione-3-yl)methyl residue and * represents the point of attachment to the substituted (oxazolidinon-4-yl)methyl residue; R6 is H or acetyl; Y is CH or N; and Q is O or S; and salts of such compounds.

HEPATITIS C VIRUS NS3 PROTEASE INHIBITORS

-

, (2013/03/26)

The present invention relates to macrocyclic compounds of Formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

New phenylalanine derivatives

-

, (2008/06/13)

Specified phenylalanine derivatives and analogues thereof have an antagonistic activity to α4 integrin. They are used as therapeutic agents for various diseases concerning α4 integrin.

1,1- and 1,2-disubstituted cyclopropane compounds

-

, (2008/06/13)

A compound selected from those of formula (I): wherein: p represents an integer of from 0 to 6 inclusive, n represents an integer of from 0 to 6 inclusive, R1, and R2 represent a group selected from hydrogen, alkyl, aryl and arylalkyl, or R1+R2 form together with nitrogen carrying them saturated, monocyclic, or bicyclic system, X represents a group selected from oxygen, sulphur, a group —CH═CH—, methylene, a group of formula —HC═N—O— and a group of formula —O—CH2—CH═CH—, in which groups oxygen is linked to Y of the compounds of formula (I), Y represents a group selected from aryl, heteroaryl, arylalkyl, heteroarylalkyl, —C(O)—A, and —C(S)—A, A represents a group selected from alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, and NR3R4 wherein R3, and R4 represent a group selected from hydrogen, alkyl, aryl, and arylalkyl, or R3+R4 form together with nitrogen carrying them monocyclic, or bicyclic (C3-C10) system, its isomers and addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same are useful as specific nicotinic ligand of (α4β2 receptors.

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