2,2-dichloro-N-phenethylacetamide

Base Information

• Chemical Name: 2,2-dichloro-N-phenethylacetamide
• CAS No.: 39106-18-8
• Molecular Formula: C10H11Cl2NO
• Molecular Weight: 232.109
• European Community (EC) Number: 660-814-2
• NSC Number: 52557
• UNII: Y4GNB8GAQ4
• DSSTox Substance ID: DTXSID10959914
• Nikkaji Number: J3.376.980F
• Wikidata: Q82940871
• Mol file: 39106-18-8.mol

Synonyms:2,2-dichloro-N-phenethylacetamide;2,2-dichloro-N-(2-phenylethyl)acetamide;39106-18-8;NSC-52557;acetamide, 2,2-dichloro-n-(2-phenylethyl)-;2,2-Dichloro-n-phenethyl-acetamide;NSC52557;Y4GNB8GAQ4;Cambridge id 5336015;DTXSID10959914;STK019503;AKOS003277462;2,2-Dichloro-N-(2-phenylethyl)ethanimidic acid;SR-01000205415;SR-01000205415-1

Chemical Property of 2,2-dichloro-N-phenethylacetamide

Chemical Property:

• Vapor Pressure: 4.53E-06mmHg at 25°C
• Boiling Point: 383°Cat760mmHg
• Flash Point: 185.5°C
• Density: 1.259g/cm³
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 231.0217694
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCNC(=O)C(Cl)Cl

Technology Process of 2,2-dichloro-N-phenethylacetamide

There total 6 articles about 2,2-dichloro-N-phenethylacetamide 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: 82.0%

phenethyl isocyanate (1943-82-4) + dichloromethane (75-09-2) → 2,2-dichloro-N-(2-phenylethyl)acetamide (39106-18-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; methyllithium; lithium bromide; In tetrahydrofuran; at -78 ℃; for 1h; chemoselective reaction;

DOI:10.1055/s-0034-1379209

Reference yield: 65.0%

5,5-dichloro-meldrum’s acid + phenethylamine (64-04-0) → 2,2-dichloro-N-(2-phenylethyl)acetamide (39106-18-8)

Guidance literature:

In ethyl acetate; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.1c00850

Reference yield:

dichloroacetic acid methyl ester (116-54-1) + phenethylamine (64-04-0) → 2,2-dichloro-N-(2-phenylethyl)acetamide (39106-18-8)

Guidance literature:

DOI:10.1021/ja01152a030 DOI:10.1021/ja01143a524

upstream raw materials:

dichloroacetic acid methyl ester

phenethylamine

ethyl 1,1-dichloroacetate

2-chloro-N-phenethylacetamide

Downstream raw materials:

2-dichloroacetyl-1,2,3,4-tetrahydroisoquinoline

dichloro-acetic acid-(4-nitro-phenethylamide)

Refernces

• 1、 Pace, Vittorio,Castoldi, Laura,Mamuye, Ashenafi Damtew,Holzer, Wolfgang. "Homologation of isocyanates with lithium carbenoids: A straightforward access to α-halomethyl- and α,α-dihalomethylamides". . p. 2897 - 2909. Retrieved 2015/01/16.