2,2-Dimethylbutyryl chloride

Base Information

• Chemical Name: 2,2-Dimethylbutyryl chloride
• CAS No.: 5856-77-9
• Molecular Formula: C6H11ClO
• Molecular Weight: 134.606
• Hs Code.: 29159000
• European Community (EC) Number: 227-478-5
• UNII: XKZ78Q3WJ3
• DSSTox Substance ID: DTXSID00207274
• Nikkaji Number: J218.104E
• Wikidata: Q72469604
• Mol file: 5856-77-9.mol

Synonyms:2,2-Dimethylbutyryl chloride;5856-77-9;2,2-dimethylbutanoyl chloride;2,2-dimethyl butyryl chloride;2,2-Dimethylbutyrylchloride;Butanoyl chloride, 2,2-dimethyl-;2,2-dimethyl-butyryl chloride;2,2-dimethylbutyric acid chloride;EINECS 227-478-5;EC 227-478-5;XKZ78Q3WJ3;SCHEMBL388297;DTXSID00207274;AMY25715;MFCD03093071;AKOS009158285;BS-22425;2,2-Dimethylbutanoyl chloride, AldrichCPR;A8288;D3987;FT-0609270;FT-0667341;EN300-224794;W-105385

Chemical Property of 2,2-Dimethylbutyryl chloride

Chemical Property:

• Appearance/Colour: clear to yellowish liquid
• Vapor Pressure: 9.14mmHg at 25°C
• Refractive Index: 1.4240
• Boiling Point: 131.8 °C at 760 mmHg
• Flash Point: 30.2 °C
• PSA: 17.07000
• Density: 0.988 g/cm³
• LogP: 2.18800
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Reacts with water. Soluble in chloroform and ethyl acetate.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.0498427
• Heavy Atom Count: 8
• Complexity: 96.7

Purity/Quality:

99%min, ^*data from raw suppliers

2,2-DimethylbutanoylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-34-43
• Safety Statements: 26-36/37/39-45-36/37-20

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)Cl
• Uses: ,2-Dimethylbutanoyl chloride is a reagent that is used in the synthesis of 4α,5-Dihydro Simvastatin, the drug, is sold under the trade name Zocor. A competitive inhibitor of HMG-CoA reductase. A synthetic analog of Lovastatin. Antilipemic.

Technology Process of 2,2-Dimethylbutyryl chloride

There total 5 articles about 2,2-Dimethylbutyryl chloride 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: 76.0%

2,2-dimethylbutyric acid (595-37-9) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Guidance literature:

With thionyl chloride; at 100 ℃; for 2h;

DOI:10.1021/jm00155a040

Reference yield:

2,2-dimethyl-butanoic acid methyl ester (813-67-2) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / methanol / 65 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 17 h / 0 - 20 °C

With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In methanol; dichloromethane;

DOI:10.1016/j.cclet.2017.06.007

Reference yield:

tert-Butylacetic acid (1070-83-3) + benzoyl chloride (98-88-4) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Guidance literature:

DOI:10.1021/ja01205a034

upstream raw materials:

tert-Butylacetic acid

benzoyl chloride

2,2-dimethylbutyric acid

2,2-dimethyl-butanoic acid methyl ester

Downstream raw materials:

2,2-Dimethyl-1-butanol

isopropyl-tert-pentyl-carbinol

2,2-dimethyl-butyric acid cyclohexylamide

tert-butyl 2,2-dimethylperoxybutyrate

Refernces

• 1、 Correia, José Tiago M.,Piva Da Silva, Gustavo,Kisukuri, Camila M.,André, Elias,Pires, Bruno,Carneiro, Pablo S.,Paixa?, Márcio W.. "Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex". . p. 9820 - 9834. Retrieved 2020/09/03.
• 2、 Xiao, Han-Zhi,Wang, Wen-Shu,Sun, Yu-Song,Luo, Hao,Li, Bo-Wen,Wang, Xiao-Dong,Lin, Wei-Li,Luo, Fei-Xian. "Pd/Cu-Catalyzed Cascade C(sp3)-H Arylation and Intramolecular C-N Coupling: A One-Pot Synthesis of 3,4-2 H-Quinolinone Skeletons". supporting information. p. 1668 - 1671. Retrieved 2019/03/11.