1972-28-7 Usage
Chemical Description
Diethyl azodicarboxylate is a reagent used in organic synthesis to introduce azo groups.
Chemical Description
Diethyl azodicarboxylate is another oxidant used in the preparation of compound 32.
Description
Diethyl azodicarboxylate, also known as diethyl diazene-1,2-dicarboxylate, is an organic compound with the chemical formula C6H10N2O4. It is a clear orange to orange-red liquid and is known for its use as a reagent and building block in various chemical reactions and applications.
Uses
Diethyl azodicarboxylate is used as a fluorescent CDK inhibitor for the treatment of cancer. It plays a crucial role in modulating cellular processes and inhibiting the growth of cancer cells.
Used in Pharmaceutical Industry:
Diethyl azodicarboxylate is used as a reactant for the preparation of immunostimulants, specifically α-Galactosylceramides. These immunostimulants help enhance the immune response in the body and are used in the development of vaccines and other therapeutic agents.
Used in Biochemical Research:
Diethyl azodicarboxylate is used as a reactant for the preparation of cellotriose and cellotetraose analogues, which serve as transition state mimics for mechanistic studies of cellulases. These analogues help researchers understand the enzymatic processes involved in the breakdown of cellulose, a crucial component in the bioenergy and biofuel industries.
Used in Enzyme Inhibition Studies:
Diethyl azodicarboxylate is used as a reactant for the synthesis of bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase (COMT). These inhibitors are essential in studying the enzyme's role in various biological processes and its potential as a therapeutic target for diseases.
Used in Cannabinoid Research:
Diethyl azodicarboxylate is used as a reactant for the preparation of derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities. These derivatives are crucial in understanding the interactions between cannabinoids and their receptors, which can lead to the development of new therapeutic agents for various conditions.
Used in Organic Synthesis:
Diethyl azodicarboxylate is used as a reactant for the synthesis of Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes. This reaction is an essential step in the development of novel pharmaceutical compounds and other organic molecules with potential applications.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for the annulation of N-protected imines, which are crucial intermediates in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for α-thiocyanation of enolizable ketones with ammonium thiocyanate. This reaction is an important step in the synthesis of various organic compounds with potential applications in the pharmaceutical and chemical industries.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for Diels-Alder reactions, which are fundamental in organic chemistry for the synthesis of complex organic molecules, including pharmaceuticals, natural products, and other specialty chemicals.
General Description:
The DOT Special Approval Submission for Diethyl azodicarboxylate is under review, with an estimated availability in March 2012. As a clear orange to orange-red liquid, it possesses unique chemical properties that make it a versatile reagent and building block in various applications across different industries.
Purification Methods
Dissolve DEAD in toluene, wash it with 10% NaHCO3 till neutral (may require several washes if too much hydrolysis had occurred: check IR for OH bands), then wash with H2O (2x), dry over Na2SO4, filter, evaporate the toluene and distil it through a short Vigreux column (p 11) at as high a vacuum as possible. The main portion boils at 107-111o/15mm. 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. [Rabjohn Org Synth Coll Vol III 375 1955, see Kauer Org Synth Coll Vol IV 412 1963]. [Beilstein 3 III 233.] It is commercially available as a 40% solution in toluene. 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 above and DIAD below]. § A polystyrene supported DEAD version is commercially available with a loading of ~1.2mmol/g.
Check Digit Verification of cas no
The CAS Registry Mumber 1972-28-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,7 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1972-28:
(6*1)+(5*9)+(4*7)+(3*2)+(2*2)+(1*8)=97
97 % 10 = 7
So 1972-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H10N2O4/c1-5(9)11-3-7-8-4-12-6(2)10/h3-4H2,1-2H3/b8-7+
1972-28-7Relevant articles and documents
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Buechi et al.
, p. 37,39, 40 (1962)
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Synthesis and neuroprotective properties of isosteric analogs of nicotine
Matveeva,Podrugina,Morozkin,Tkachenko,Zefirov
, p. 1149 - 1153 (2000)
A method has been developed for the synthesis of isosteric analogs of nicotine involving ethers of S(-)-1-2-pyrrolidinemethanol and S(-)-1-2-pyrrolidineethanol based on the Mitsunobu reaction. The results of testing the synthesized compounds as calcium channel blockers are presented.
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Reynolds,Hauser
, p. Warnungsbeilage (1958)
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METHOD FOR PRODUCING AZO COMPOUNDS
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Paragraph 0050; 0051, (2018/08/22)
PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of at least one compound selected from the group consisting of vanadium and cerium compounds, the oxidation reaction to be performed without using a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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.
