Benzyl 2-isocyanoacetate

Base Information

• Chemical Name: Benzyl 2-isocyanoacetate
• CAS No.: 41995-26-0
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• European Community (EC) Number: 830-812-8
• DSSTox Substance ID: DTXSID40340119
• Nikkaji Number: J624.579J
• Wikidata: Q82109586
• Mol file: 41995-26-0.mol

Synonyms:Benzyl 2-isocyanoacetate;41995-26-0;Acetic acid, isocyano-, phenylmethyl ester;Isocyanoacetic acid benzyl ester;SCHEMBL2903810;DTXSID40340119;AC8601;MFCD27950648;GS-0397;SY249703;EN300-4521969

Chemical Property of Benzyl 2-isocyanoacetate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: [C-]#[N+]CC(=O)OCC1=CC=CC=C1

Technology Process of Benzyl 2-isocyanoacetate

There total 8 articles about Benzyl 2-isocyanoacetate 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: 100.0%

[N-formyl(O-benzyl)]glycinate (51354-16-6) → benzyl isocyanoacetate (41995-26-0)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; at -50 - 20 ℃; for 0.833333h;

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl isocyanoacetate (41995-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / 5 h / 110 - 120 °C

2: 65 percent / Et₃N / 20 h / Heating

3: 80 percent / Et₃N, POCl₃ / CH₂Cl₂ / 1 h / 0 °C

With triethylamine; trichlorophosphate; In dichloromethane;

DOI:10.1002/jhet.5570310402

Reference yield:

Gly-OBz (1738-68-7) → benzyl isocyanoacetate (41995-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 70 °C

2: POCl₃, Et₃N / CH₂Cl₂ / Ambient temperature

With triethylamine; trichlorophosphate; In dichloromethane; toluene;

DOI:10.1021/jm00076a018

upstream raw materials:

benzyl bromide

potassium 2-isocyanoacetate

[N-formyl(O-benzyl)]glycinate

benzyl alcohol

Downstream raw materials:

5,5-diethyl-4,5-dihydro-thiazole-4-carboxylic acid benzyl ester

3,4-dimethyl-pyrrole-2-carboxylic acid benzyl ester

benzyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate

benzyl 3-(2'-methoxycarbonylethyl)-4-methylpyrrole-2-carboxylate

Refernces

• 1、 Borase, Bhushan B.,Godbole, Himanshu M.,Singh, Girij P.,Upadhyay, Pritesh R.,Trivedi, Anurag,Bhat, Varadaraj,Shenoy, Gautham G.. "Application of Ugi three component reaction for the synthesis of quinapril hydrochloride". supporting information. p. 48 - 55. Retrieved 2019/11/19.
• 2、 Liang, Wenbin,Nakajima, Kazunari,Sakata, Ken,Nishibayashi, Yoshiaki. "Copper-Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3-Azaphospholes". supporting information. p. 1168 - 1173. Retrieved 2019/01/04.