2446-83-5 Usage
Description
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.
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+
2446-83-5Relevant 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.
Method of manufacturing Azodicarboxylic acid diester compd. (by machine translation)
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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.
HEPATITIS C VIRUS NS3 PROTEASE INHIBITORS
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, (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.