5659-93-8

Basic information

• Product Name: DIMETHYLMALONYL CHLORIDE
• Synonyms: DIMETHYLMALONYL CHLORIDE;DIMETHYLMALONYL DICHLORIDE;2,2-diMethylMalonyl dichloride;DiMethylMalonyl chloride 98%
• CAS NO: 5659-93-8
• Molecular Formula: C₅H₆Cl₂O₂
• Molecular Weight: 169.01
• Product Categories: Carboxylic Acid Monomers;Monomers;Polymer Science;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 5659-93-8.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 60 °C10 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 1.278 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.45mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 774374
• CAS DataBase Reference: DIMETHYLMALONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLMALONYL CHLORIDE(5659-93-8)
• EPA Substance Registry System: DIMETHYLMALONYL CHLORIDE(5659-93-8)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5659-93-8(Hazardous Substances Data)

Usage

General Description

Dimethylmalonyl Chloride is a chemical compound that functions as an acylating agent, typically used in organic chemistry. This chemical is colorless to light yellow in appearance with a pungent odor, and it is reactive and often used to create complex molecules, particularly in pharmaceuticals. Its molecular formula is C5H7ClO2. However, dimethylmalonyl chloride should be handled with caution as it may cause burns to the skin and eyes in addition to being harmful if swallowed or inhaled. Therefore, protective gear and proper ventilation are essential while using this chemical compound.

InChI:InChI=1/C5H6Cl2O2/c1-5(2,3(6)8)4(7)9/h1-2H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 79-30-1 isobutyryl chloride 
• 503-38-8 trichloromethyl chloroformate 
• 595-46-0 2,2-dimethylmalonic acid 
• 1619-62-1 2,2-dimethylmalonic acid diethyl ester 

Downstream Products

• 34917-91-4 4-hydroxyisobutyrophenone 
• 58655-59-7 2,2-dimethyl-N,N’-diphenylmalonic diamide 
• 24448-94-0 5,5-dimethylbarbituric acid 
• 96730-45-9 N-(3,3-dimethyl-2,4-dioxo-azetidin-1-yl)-N-methyl-N'-phenyl-thiourea 
• 854885-20-4 2-methoxy-5,5-dimethyl-4,6-dioxo-cyclohex-2-ene-1,1,3-tricarboxylic acid trimethyl ester 
• 41169-42-0 2,2-dimethyl-1,3-diphenylpropane-1,3-dione 
• 26595-27-7 dimethyl-malonic acid diphenyl ester 
• 19136-93-7 α-deuterio-isobutyric acid 
• 595-46-0 2,2-dimethylmalonic acid 
• 60901-30-6 2-benzylsulfanyl-5,5-dimethyl-[1,3]thiazine-4,6-dione 
• 56945-86-9 6,6-dimethyl-3-phenyl-pyrazolo[5,1-b][1,3]oxazine-2,5,7-trione 
• 56945-79-0 3-cyclohexyl-6,6-dimethyl-pyrazolo[5,1-b][1,3]oxazine-2,5,7-trione 
• 56673-24-6 2-[1-(1-cyclohexyl-1H-tetrazol-5-yl)-cyclohexyl]-4,4-dimethyl-isoxazolidine-3,5-dione 
• 56673-23-5 1-(4,4-dimethyl-3,5-dioxo-isoxazolidin-2-yl)-cyclohexanecarboxylic acid cyclohexylamide 

Relevant articles and documents

A Convenient Synthesis of a Macrocyclic Dioxo Pentaamine and X-ray Crystal Structure of Its Monohydrazoic Acid Salt

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Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes

The enantioselective hydroarylation of vinylarenes catalyzed by a chiral, non-racemic nickel catalyst is presented as a facile method to generate chiral 1,1-diarylethanes. These reactions proceed via formation of a chiral, non-racemic nickel benzyl intermediate. Transmetalation with arylboron nucleophiles and subsequent reductive elimination enable the formation of a variety of chiral 1,1-diarylethanes. The 1,1-diarylethane products from reactions of arylboronic acids containing electron-donating substituents are formed with typically greater than 90% ee, while the 1,1-diarylethanes generated from reactions of arylboronic acids containing electron-withdrawing groups are generated with typically less than 80% ee. These results are consistent with the rate of transmetalation with an arylboron nucleophile playing a key role in the enantioselectivity of these hydroarylation reactions. This mechanistic insight has led to the development of reactions of neo-pentylglycolate esters of arylboronic acids with vinylarenes that occur with higher enantioselectivities based on increased rates of transmetalation.

Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification

A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.