83458-10-0

Basic information

• Product Name: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, trans- (9CI)
• Synonyms: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, trans- (9CI)
• CAS NO: 83458-10-0
• Molecular Formula: C6H6Cl2O2
• Molecular Weight: 181.01664
• Product Categories: ACIDHALIDE
• Mol File: 83458-10-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, trans- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, trans- (9CI)(83458-10-0)
• EPA Substance Registry System: 1,2-Cyclopropanedicarbonyl dichloride, 1-methyl-, trans- (9CI)(83458-10-0)

Safety Data

• Hazardous Substances Data: 83458-10-0(Hazardous Substances Data)

Usage

Isomer

trans-isomer of 1-methyl-1,2-cyclopropanedicarbonyl dichloride

Application

used in organic synthesis and pharmaceutical research

Structure

dichloride derivative of a cyclopropane compound

Functional groups

two carbonyl (C=O) groups

Reactivity

highly reactive due to the presence of two chlorine atoms

Usage

building block in the synthesis of complex organic compounds

Role

used as a reagent to introduce the cyclopropane ring into other molecules

Upstream product

• 702-92-1 1-Methyl-r-1,t-2-cyclopropandicarbonsaeure-dimethylester 
• 697-49-4 trans-1-methyl-1,2-cyclopropanedicarboxylic acid 
• 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

Synthesis and mode of action of 1-substituted trans-cyclopropane 1,2-dicarboxylic acids: Inhibitors of the methylaspartase reaction

A range of 1-substituted cyclopropane 1,2-dicarboxylic acids are synthesised using short efficient routes and are found to be good to potent inhibitors of 3-methylaspartase; the crystallographically determined absolute stereochemistry and the mode of acti

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.