696-16-2

Basic information

• Product Name: (+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride
• CAS NO: 696-16-2
• Molecular Weight: 126.112
• Mol File: 696-16-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 47 °C
• Boiling Point: 96 °C(Press: 0.8 Torr)
• Density: 1.461±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride(696-16-2)
• EPA Substance Registry System: (+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride(696-16-2)

Safety Data

• Hazardous Substances Data: 696-16-2(Hazardous Substances Data)

Usage

Description

(+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride is a cyclic anhydride derived from 1-methylcyclopropane-1r,2c-dicarboxylic acid, synthesized through the reaction of maleic anhydride with 3-methyl-1,3-butadiene. It is a chemical compound known for its unique reactivity and is commonly used in organic synthesis for the preparation of various pharmaceuticals and agricultural chemicals.

Uses

Used in Pharmaceutical Industry:
(+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride is used as an intermediate in the production of various drugs. Its unique reactivity allows it to undergo a variety of chemical transformations, making it an essential compound in the development of new pharmaceuticals.
Used in Agricultural Chemical Industry:
(+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid-anhydride is also used as an intermediate in the production of various agrochemicals. Its ability to undergo different chemical reactions makes it a valuable compound in the creation of new agricultural chemicals.

Upstream product

• 697-48-3 cis (±)-1-methylcyclopropane-1,2-dicarboxylic acid 
• 119908-65-5 C₆H₆O₄^(2-)*2K⁽¹⁺⁾ 

Downstream Products

• 852359-83-2 3-benzyl-1-methyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 852359-88-7 3-benzyl-1-methyl-3-aza-bicyclo[3.1.0]hexane 

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.