Benzyl (2-iodoethyl)carbamate

Base Information

• Chemical Name: Benzyl (2-iodoethyl)carbamate
• CAS No.: 68373-12-6
• Molecular Formula: C10H12INO2
• Molecular Weight: 305.115
• DSSTox Substance ID: DTXSID90461747
• Wikidata: Q82286152
• Mol file: 68373-12-6.mol

Synonyms:Benzyl (2-iodoethyl)carbamate;68373-12-6;Benzyl N-(2-iodoethyl)carbamate;(2-IODO-ETHYL)-CARBAMIC ACID BENZYL ESTER;BENZYL 2-IODOETHYLCARBAMATE;Benzyl(2-iodoethyl)carbamate;SCHEMBL707687;benzyloxycarbonyl-2-iodoethylamine;DTXSID90461747;BBNJIQPJPQOWDM-UHFFFAOYSA-N;MFCD09951822;N-benzyloxycarbonyl-2-iodo-ethylamine;AKOS016005125;AB55270;BS-29346;CS-0208775;FT-0765876;F88120;EN300-4266719

Chemical Property of Benzyl (2-iodoethyl)carbamate

Chemical Property:

• PSA: 41.82000
• LogP: 2.55220
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 304.99128
• Heavy Atom Count: 14
• Complexity: 170

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2-Iodo-ethyl)-carbamicacidbenzylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCCI

Technology Process of Benzyl (2-iodoethyl)carbamate

There total 6 articles about Benzyl (2-iodoethyl)carbamate 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: 92.0%

benzyl 2-hydroxyethylcarbamate (77987-49-6) → N-benzyloxycarbonyl-2-iodo-ethylamine (68373-12-6)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1039/b405575f

Reference yield:

N-(Benzyloxycarbonyl)glycine (1138-80-3) → N-benzyloxycarbonyl-2-iodo-ethylamine (68373-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methyl-morpholine / tetrahydrofuran / -15 °C

2: sodium tetrahydroborate

3: triphenylphosphine; iodine / dichloromethane / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-2-iodo-ethylamine (68373-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous NaOH

2: acetone; NaI

With sodium hydroxide; acetone; sodium iodide;

upstream raw materials:

benzyl N-(2-bromoethyl)carbamate

2-iodoethylamine

benzyl chloroformate

benzyl 2-hydroxyethylcarbamate

Downstream raw materials:

S-(2-benzyloxycarbonylamino-ethyl)-L-cysteine

C₁₃H₁₄N₄O₄

Refernces

• 1、 Becerra-Cely, Laura,Rueda-Espinosa, Juan,Ojeda-Porras, Andrea,Gamba-Sánchez, Diego. "Insights into the Pummerer synthesis of oxazolines". . p. 8474 - 8485. Retrieved 2016/09/28.
• 2、 De Cola, Chiara,Manicardi, Alex,Corradini, Roberto,Izzo, Irene,De Riccardis, Francesco. "Carboxyalkyl peptoid PNAs: Synthesis and hybridization properties". experimental part. p. 499 - 506. Retrieved 2012/01/14.