Ethyl diazoacetate

Ethyl diazoacetate Basic information
Synthesis
Product Name:Ethyl diazoacetate
Synonyms:Acetic acid, diazo-, ethyl ester;Daae;Diazoacetic acid ethyl ester;Diazoacetic ester;diazoaceticacid,ethylester;diazo-aceticaciethylester;diazoaceticester;Diazoessigsaeure-aethylester
CAS:623-73-4
MF:C4H6N2O2
MW:114.1
EINECS:210-810-8
Product Categories:Azo/Diazo Compounds;Building Blocks;Carboxylic;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Azo/Diazo Compounds;Nitrogen Compounds;Organic Building Blocks
Mol File:623-73-4.mol
Ethyl diazoacetate Structure
Ethyl diazoacetate Chemical Properties
Melting point -22 °C (lit.)
Boiling point 140-141 °C/720 mmHg (lit.)
density 1.085 g/mL at 25 °C (lit.)
refractive index n20/D 1.46(lit.)
Fp 115 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), DMSO (Soluble), Hexane (Slightly), Methanol (Slightly)
form Oil
color Light Yellow to Orange
Merck 13,3021
BRN 107654
NIST Chemistry ReferenceEthyl diazoacetate(623-73-4)
Safety Information
Hazard Codes Xn,F
Risk Statements 5-10-22-40-67-65-48/20-38-11-63
Safety Statements 36/37-62-16
RIDADR UN 1993 3/PG 3
WGK Germany 3
RTECS AG5775000
HazardClass 3.2
PackingGroup III
HS Code 29270000
MSDS Information
ProviderLanguage
SigmaAldrich English
Ethyl diazoacetate Usage And Synthesis
SynthesisGlycine 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
Chemical PropertiesLiquid.
UsesReagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.1
UsesNew Diazoacetate Formulations
HazardFlammable liquid that explodes when heated.
Safety ProfilePoison 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 MethodsIt 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.]
TERT-BUTYL DIAZOACETATE ETHYL DIAZOACETOACETATE Trinexapac-ethyl (E,E) DIAZOTRIFLUOROPROPIONYLOXY GERANIOL, [1-3H] Ethanol AZASERINE-HYPOXANTHINE thrazarine AZASERINE Ethyl 2-(4-bromophenyl)-2-diazoacetate ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE ISOXADIFEN-ETHYL Ethyl acetate Ethyl propiolate Ethyl diazophenylacetate Ethyl acrylate (E,E)-(2-DIAZO-TRIFLUOROPROPIONYLOXY) GERANYL DIPHOSPHATE, [1-3H] Ethyl diazoacetate Ethyl cyanoacetate

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