Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)-

Base Information

• Chemical Name: Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)-
• CAS No.: 701223-12-3
• Molecular Formula: C5H5 Cl3 O
• Molecular Weight: 187.453
• DSSTox Substance ID: DTXSID60426787
• Nikkaji Number: J2.211.382H
• Wikidata: Q82239599
• Mol file: 701223-12-3.mol

Synonyms:701223-12-3;Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)-;DTXSID60426787;1-Methyl-2,2-dichlorocyclopropane-1beta-carbonyl chloride

Chemical Property of Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)-

Chemical Property:

• PSA: 17.07000
• LogP: 2.33570
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 185.940598
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC1(Cl)Cl)C(=O)Cl
• Isomeric SMILES: C[C@]1(CC1(Cl)Cl)C(=O)Cl

Technology Process of Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)-

There total 2 articles about Cyclopropanecarbonylchloride, 2,2-dichloro-1-methyl-, (1S)- 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: 86.0%

(1S)-2,2-dichloro-1-methylcyclopropanecarboxylic acid (264194-30-1) → (1S)-2,2-dichloro-1-methylcyclopropanecarbonyl chloride (701223-12-3)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In hexane; for 1h; Heating;

DOI:10.1021/ja0319442

Reference yield:

2,2-dichloro-1-methylcyclopropanecarboxylic acid (1447-14-9) → (1S)-2,2-dichloro-1-methylcyclopropanecarbonyl chloride (701223-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 29 percent / via salt with (+)-cinchonine

2: 86 percent / SOCl₂; DMF / hexane / 1 h / Heating

With thionyl chloride; N,N-dimethyl-formamide; In hexane;

DOI:10.1021/ja0319442

Reference yield: 88.0%

(1S)-2,2-dichloro-1-methylcyclopropanecarbonyl chloride (701223-12-3) + phenol (108-95-2,27073-41-2) → phenyl (1S)-2,2-dichloro-1-methylcyclopropanecarboxylate

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In toluene; at 20 ℃; for 2h;

DOI:10.1021/ja0319442

upstream raw materials:

(1S)-2,2-dichloro-1-methylcyclopropanecarboxylic acid

2,2-dichloro-1-methylcyclopropanecarboxylic acid

Downstream raw materials:

(-)-(1S)-2,2-dichloro-1-methylcyclopropyl(2-chlorophenyl)methanone

(-)-(1S)-2,2-dichloro-1-methylcyclopropyl(o-tolyl)methanone

(-)-(S)-[(1S)-2,2-dichloro-1-methylcyclopropyl](phenyl)(o-tolyl)methanol

(-)-(R)-[(1S)-2,2-dichloro-1-methylcyclopropyl](phenyl)(o-tolyl)methanol