623-73-4 Usage
Description
Ethyl diazoacetate, also known as EDA, is an organic compound with the chemical formula C4H6N2O2. It is a liquid and serves as a reagent in various chemical reactions, particularly in the field of organic synthesis.
Uses
Used in Chemical Synthesis:
Ethyl diazoacetate is used as a reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes. This application is significant because it allows for the selective formation of cyclopropane derivatives, which are important structural motifs in many biologically active compounds and pharmaceuticals.
In the field of organic chemistry, Ethyl diazoacetate is used as a reagent for the synthesis of various complex organic molecules due to its unique reactivity and the ability to form cyclopropane rings under specific catalytic conditions. This makes it a valuable tool in the development of new drugs and materials.
Synthesis
Glycine ethyl ester hydrochloride can be dissolved in a buffer solution composed of acetic acid and sodium acetate, and then dichloroethane is added as a solvent, and sodium nitrite solution is added dropwise at 10 to 15 ° C. After the dropwise addition, continue stirring for 15min. The separated organic layer is a dichloroethane solution of ethyl diazoacetate.NH2CH2COOC2H5·HCl+NaNO2+HCl→N2CHCOOC2H5+NaCl+H2O
Hazard
Flammable liquid that explodes when
heated.
Safety Profile
Poison by ingestion and
intravenous routes. Questionable carcinogen
with experimental carcinogenic and
tumorigenic data. Can explode. Explodes on
contact with tris(dimethy1amino) antimony.
When heated to decomposition it emits
toxic fumes of NOx. See also ESTERS.
Purification Methods
It is a very volatile yellow oil with a strong pungent odour. EXPLOSIVE [distillation even under reduced pressure is dangerous and may result in an explosion — TAKE ALL THE NECESSARY PRECAUTIONS IF DISTILLATION IS TO BE CARRIED OUT]. It explodes in contact with conc H2SO4-trace acid causes rapid decomposition. It is slightly soluble in H2O, but is miscible with EtOH, *C6H6, pet ether and Et2O. To purify, dissolve it in Et2O [using CH2Cl2 instead of Et2O, protects the ester from acid], wash it with 10% aqueous Na2CO3, dry (MgSO4), filter and repeat as many times as possible until the Et2O layer loses its yellow colour, then remove the solvent below 20o (vacuum). Note that prolonged heating may lead to rapid decomposition and low yields. It can also be purified by steam distillation under reduced pressure but with considerable loss in yield. Place the residual oil in a brown bottle, keep below 10o, and use as soon as possible without distilling. For preparing esters usually the ethereal solution is used directly without purification. [Womack & Nelson Org Synth Coll Vol III 392 1955, UV: Miller & White J Am Chem Soc 79 5974 1957, Fieser 1 367 1967, Beilstein 3 IV 1495.]
Check Digit Verification of cas no
The CAS Registry Mumber 623-73-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 3 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 623-73:
(5*6)+(4*2)+(3*3)+(2*7)+(1*3)=64
64 % 10 = 4
So 623-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3/b4-3+
623-73-4Relevant articles and documents
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La Forge et al.
, p. 391 (1952)
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Clusius,Luehti
, p. 445 (1957)
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A pilot-scale synthesis of (1R)-trans-2-(2,3-dihydro-4-benzofuranyl) cyclopropanecarboxylic acid: A practical application of asymmetric cyclopropanation using a styrene as a limiting reagent
Simpson, James H.,Godfrey, Jollie,Fox, Rita,Kotnis, Atul,Kacsur, David,Hamm, Jason,Totelben, Michael,Rosso, Victor,Mueller, Richard,Delaney, Edward,Deshpande, Rajendra P.
, p. 3569 - 3574 (2003)
Asymmetric cyclopropanation of styrene 1 (as the limiting reagent) was demonstrated using excess ethyl diazoacetate and catalytic Ru(ip-Pybox). Selective hydrolysis of the resulting 90:10 trans:cis mixture of cyclopropane 4 generated cyclopropyl acid 2 as a 96:4 trans:cis mixture with 84% e.e. for the trans-cyclopropane. Further purification and enantiomeric enrichment was achieved by diastereoselective crystallization with (+)-dehydroabeitylamine to afford the (R,R)-isomer with ≥99.9% e.e in 60-65 M% yield starting from styrene 1.
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Womack,Nelson
, p. 392 (1955)
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METHOD OF PRODUCING NITRO COMPOUND
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Paragraph 0041, (2021/06/25)
PROBLEM TO BE SOLVED: To provide a production method which can efficiently provide a nitro compound in an industrial scale. SOLUTION: A method of producing a compound represented by formula (2) comprises using nitric acid to nitrate a compound represented by formula (1) in the presence of concentrated sulfuric acid that weighs 1.5-5.0 times more than the compound represented by formula (1). [In formulas (1) and (2), X1 and X2 are identical or different and represent halogen atoms, and R represents an optionally substituted 6-membered heterocyclic group.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization
Kim, Jiyoung,Yoo, Eun Jeong
supporting information, p. 4256 - 4260 (2021/06/28)
Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.
