119908-67-7

Basic information

• Product Name: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI)
• Synonyms: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI)
• CAS NO: 119908-67-7
• Molecular Formula: C6H6Cl2O2
• Molecular Weight: 181.01664
• Product Categories: ACIDHALIDE
• Mol File: 119908-67-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI)(119908-67-7)
• EPA Substance Registry System: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI)(119908-67-7)

Safety Data

• Hazardous Substances Data: 119908-67-7(Hazardous Substances Data)

Usage

General Description

1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI) is a chemical compound with the molecular formula C5H6Cl2O2. It is a white to light yellow liquid that is commonly used as a reagent in organic synthesis. 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, cis- (9CI) is known for its ability to crosslink proteins and peptides, making it useful in the production of advanced materials and pharmaceuticals. It is also used as a building block for the synthesis of various pharmaceuticals and agrochemicals. However, it is important to handle this chemical with care as it can be harmful if it comes into contact with the skin or if it is inhaled.

Upstream product

• 702-91-0 1-Methyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester 
• 119908-65-5 C₆H₆O₄^(2-)*2K⁽¹⁺⁾ 
• 697-48-3 cis (±)-1-methylcyclopropane-1,2-dicarboxylic acid 

Relevant articles and documents

Cyclopropanediamines, 3. - Pure Diastereomers of 1,2-Cyclopropanedicarboxylic Acids and Derivatives

Efficient preparations of pure diastereomers of dimethyl 1,2-cyclopropanedicarboxylates 2, dicarboxylic acids 3, dicarbonyl dichlorides 4, and dihydrazides 5 are reported.Mixtures of diastereomers of dimethyl dicarboxylates 2a, b, d, e are obtained from α,β-unsaturated methyl carboxylates 7 and methyl α-chlorocarboxylates 8 as well as from 7c, d and the sulfur ylide 10 (2c, d).The diastereomers are separated by fractionating distillations (2a, b, c, e) or crystallization (2d) on a 100-g to 1-kg scale (d.e. >99percent).Only low yields of 2c are obtained in the reaction of methyl crotonate (7c) with methyl α-chloroacetate (8a), since 7c predominantly dimerizes to afford 12.The diesters 2 are converted into the pure diastereomeric diacids 3, dicarbonyl dichlorides 4, and dihydrazides 5. 3,3-Dimethyl-cis-1,2-cyclopropanedicarboxylic acid (cis-3f) is obtained by trans-->cis isomerization of trans-3f with the help of acetic anhydride and sodium acetate as catalyst.The configurations of 2-6 and 12 are confirmed by 1H NMR spectroscopy.Derivatives of cis-1,2-dimethyl-1,2-cyclopropanedicarboxylic acid tend to form bicyclic products.Thus, the reaction of cis-3e with phosphorus pentachloride yields mainly the cyclic anhydride 6e and only small amounts of the dicarbonyl dichloride cis-4e.Furthermore, the dihydrazide cis-5e slowly cyclizes in the solid state to give the N-aminoimide 13 and hydrazine, a reaction which is fast in solution.Pure 13 is obtained by thermolysis of cis-5e at 60-65 deg C under high vacuum.