Ethyl isocyanatoacetate

Base Information

• Chemical Name: Ethyl isocyanatoacetate
• CAS No.: 2949-22-6
• Deprecated CAS: 1025436-14-9
• Molecular Formula: C5H7 N O3
• Molecular Weight: 129.115
• Hs Code.: 2929109000
• European Community (EC) Number: 220-967-4
• NSC Number: 56429,6276
• DSSTox Substance ID: DTXSID3062738
• Nikkaji Number: J208.648D
• Mol file: 2949-22-6.mol

Synonyms:Ethyl isocyanatoacetate;2949-22-6;ethyl 2-isocyanatoacetate;Isocyanatoacetic acid ethyl ester;Acetic acid, isocyanato-, ethyl ester;Ethoxycarbonylmethyl isocyanate;Carbethoxymethyl isocyanate;ethylisocyanatoacetate;Isocyanatoethyl acetate;Ethyl 2-isocyanotoacetate;Ethyl glycolate isocyanate;NSC 6276;EINECS 220-967-4;NSC 56429;Acetic acid, 2-isocyanato-, ethyl ester;AI3-52377;ethyl N-(oxomethylidene)glycinate;isocyanato-acetic acid ethyl ester;MFCD00002040;ethoxycarbonylmethylisocyanate;ethyl N-(oxomethylene)glycinate;Acetic acid,2-isocyanato-, ethyl ester;ethyl isocyanato-acetate;SCHEMBL48624;Ethyl isocyanatoacetate, 95%;DTXSID3062738;isocyanato-acetic acid-ethy ester;AMY3222;NSC6276;glycine, N-carbonyl-, ethyl ester;NSC-6276;NSC56429;AC9274;BBL027369;GEO-03266;NSC-56429;STK502574;Acetic acid,2-isocyanato-,ethyl ester;AKOS000120133;AB00195;ACETIC ACID,ISOCYANATO,ETHYL ESTER;AS-64026;SY050586;BB 0259393;FT-0627391;I0386;EN300-20639;J-017547;J-521261

Chemical Property of Ethyl isocyanatoacetate

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 67-68 °C11 mm Hg(lit.)
• Flash Point: 163 °F
• PSA: 55.73000
• Density: 1.151 g/mL at 25 °C(lit.)
• LogP: -0.11470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

99.5% ^*data from raw suppliers

Ethyl isocyanatoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion and inhalation.
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42
• Safety Statements: 23-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN=C=O
• Uses: Ethyl isocyanate is a carboxylate organic compound and can be used in various chemial synthesis.Ethyl isocyanatoacetate has been used in the preparation of:6-(carboxymethylureido)-(±)-nicotine (CMUNic), nicotine immunogenethyl 8-carbamoyl-4-oxo-3,4-dihydroimidazo[5,1-d]-1,2,3,5-tetrazin-3-ylacetateimidazo[1,2-c]-quinazoline-2,5-(3H,6H)dione

Technology Process of Ethyl isocyanatoacetate

There total 13 articles about Ethyl isocyanatoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Ethyl isocyanoacetate (2999-46-4) → Glycine ethyl ester isocyanate (2949-22-6)

Guidance literature:

With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -78 - 20 ℃; for 1.25h; Inert atmosphere; Cooling with acetone-dry ice;

DOI:10.15227/orgsyn.089.0404

Reference yield: 90.0%

oxalyl dichloride (79-37-8) + Ethyl oxamate (617-36-7) → Glycine ethyl ester isocyanate (2949-22-6)

Guidance literature:

In dichloromethane; Reflux;

DOI:10.1021/jm201348t

Reference yield:

hydrogen ethyl malonate (1071-46-1) → Glycine ethyl ester isocyanate (2949-22-6)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine;

DOI:10.1016/S0960-894X(01)00264-5

upstream raw materials:

phosgene

glycine ethyl ester hydrochloride

GlyOEt*HCl

trichloromethyl chloroformate

Downstream raw materials:

Z-(Bzl)-L-Cys-Gly-OEt

5-[4-(4-nitro-phenylsulfanyl)-phenyl]-hydantoic acid ethyl ester

N-benzyloxycarbonyl-glycyl=>glycyl=>-glycine ethyl ester

N,N'(N-benzyloxycarbonyl-glutamoyl)-bis-glycine diethyl ester

Refernces

• 1、 Le, Hoang V.,Ganem, Bruce. "A practical synthesis of isocyanates from isonitriles: Ethyl 2-isocyanatoacetate". . p. 404 - 408. Retrieved 2014/04/17.
• 2、 Le, Hoang V.,Ganem, Bruce. "Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: A rapid, convenient synthesis of isocyanates". supporting information; experimental part. p. 2584 - 2585. Retrieved 2011/06/25.