Dimethylmalonyl chloride

Base Information

• Chemical Name: Dimethylmalonyl chloride
• CAS No.: 5659-93-8
• Molecular Formula: C5H6Cl2O2
• Molecular Weight: 169.007
• Hs Code.: 2917190090
• European Community (EC) Number: 628-043-6
• DSSTox Substance ID: DTXSID60403917
• Nikkaji Number: J980.522B
• Wikidata: Q82207811
• Mol file: 5659-93-8.mol

Synonyms:Dimethylmalonyl chloride;5659-93-8;Dimethylmalonyl Dichloride;2,2-dimethylpropanedioyl Dichloride;MFCD00192081;dimethylmalonylchloride;Propanedioyl dichloride, dimethyl-;2,2-Dimethylmalonic acid dichloride;Dimethylmalonylchlorid;DimethylmalonylDichloride;2,2-Dimethylmalonyl chloride;dimethylmalonic acid dichloride;SCHEMBL808933;2,2-dimethylmalonyl dichloride;Dimethylmalonyl chloride, 98%;DTXSID60403917;AKOS024015164;BS-17140;SY052671;D2723;InChI=1/C5H6Cl2O2/c1-5(2,3(6)8)4(7)9/h1-2H

Chemical Property of Dimethylmalonyl chloride

Chemical Property:

• Vapor Pressure: 1.45mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 170.7 °C at 760 mmHg
• Flash Point: 58.5 °C
• PSA: 34.14000
• Density: 1.319 g/cm³
• LogP: 1.54340
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 167.9744848
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

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

Dimethylmalonyl Dichloride ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethylmalonyl chloride

There total 5 articles about Dimethylmalonyl 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: 90.0%

2,2-dimethylmalonic acid (595-46-0) → 2,2-Dimethylmalonyl chloride (5659-93-8)

Guidance literature:

With oxalyl dichloride; In N,N-dimethyl-formamide; at 25 ℃; for 18h;

DOI:10.1021/jo980296f

Reference yield:

2,2-dimethylmalonic acid diethyl ester (1619-62-1) → 2,2-Dimethylmalonyl chloride (5659-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol

2: pyridine; oxalyl dichloride

With pyridine; oxalyl dichloride; sodium hydroxide; In ethanol;

DOI:10.1016/j.tet.2014.11.016

Reference yield:

isobutyryl chloride (79-30-1) + trichloromethyl chloroformate (503-38-8) → 2,2-Dimethylmalonyl chloride (5659-93-8)

Guidance literature:

at 225 ℃;

upstream raw materials:

oxalyl dichloride

isobutyryl chloride

trichloromethyl chloroformate

2,2-dimethylmalonic acid

Downstream raw materials:

N-(3,3-dimethyl-2,4-dioxo-azetidin-1-yl)-N-methyl-N'-phenyl-thiourea

2-methoxy-5,5-dimethyl-4,6-dioxo-cyclohex-2-ene-1,1,3-tricarboxylic acid trimethyl ester

2,2-dimethyl-1,3-diphenylpropane-1,3-dione

dimethyl-malonic acid diphenyl ester

Refernces

• 1、 Tang, Li-Wei,Dong, Xiao,Zhou, Zhi-Ming,Liu, Ying-Qiang,Dai, Li,Zhang, Man. "The first 4,4′-imidazolium-tagged C2-symmetric bis(oxazolines): Application in the asymmetric Henry reaction". . p. 4758 - 4765. Retrieved 2015.
• 2、 Tran, Hai N.,Stanley, Levi M.. "Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes". supporting information. p. 395 - 399. Retrieved 2021/12/27.
• 3、 Polat, Emrah,Turbedaroglu, Ozge,Cakici, Murat. "Synthesis of bis(benzoxazole) frameworks chiralized by planar chiral [2.2]Paracyclophane". . . Retrieved 2021/02/22.