82979-45-1

Basic information

• Product Name: methyl 2-chloro-2-cyclopropylideneacetate
• Synonyms: methyl 2-chloro-2-cyclopropylideneacetate;3-((2R,3S)-1-(2-tert-butoxy-2-oxoethyl)-3-(tert-butoxycarbonyl)-;Methyl 2-chloro-2-cyclopropylidenacetate
• CAS NO: 82979-45-1
• Molecular Formula: C₆H₇ClO₂
• Molecular Weight: 147
• Mol File: 82979-45-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: methyl 2-chloro-2-cyclopropylideneacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-chloro-2-cyclopropylideneacetate(82979-45-1)
• EPA Substance Registry System: methyl 2-chloro-2-cyclopropylideneacetate(82979-45-1)

Safety Data

• Hazardous Substances Data: 82979-45-1(Hazardous Substances Data)

Usage

General Description

Methyl 2-chloro-2-cyclopropylideneacetate is a chemical compound with the molecular formula C6H7ClO2. It is a cyclopropyl-containing methyl ester that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. methyl 2-chloro-2-cyclopropylideneacetate is widely used in organic synthesis as a versatile building block for the preparation of various pharmaceutical compounds and bioactive molecules. It is a colorless liquid with a pungent odor and is soluble in organic solvents such as ethanol and diethyl ether. Methyl 2-chloro-2-cyclopropylideneacetate is also known for its potential as a chiral ligand in asymmetric catalysis and as a key raw material in the production of active pharmaceutical ingredients.

Upstream product

• 832142-16-2 methyl 2-chloro-(1-methanesulfonyloxy-cyclopropyl)acetate 
• 82979-27-9 1-chloro-1-(trichloroethenyl)cyclopropane 
• 82979-34-8 trimethyl 2-chloro-2-cyclopropylidenorthoacetate 
• 832142-14-0 2-{1-[(methylsulfonyl)oxy]cyclopropyl}acetic acid 
• 832142-17-3 1-(2,2-diethoxyethyl)cyclopropane-1-ol 
• 832142-15-1 1-(2,2-dimethoxyethyl)cyclopropan-1-ol 

Downstream Products

• 125506-36-7 Methyl 2-<1-(diphenylmethylene)aminocyclopropyl>-2-chloroacetate 
• 116084-52-7 methyl 2'-benzyloxy-6'-oxospiro2,7>octane>-1'-carboxylate 
• 110793-85-6 Methyl 2-chloro-2-(1'-phenylselenocyclopropyl)acetate 
• 287728-65-8 methyl 2-(4-bromophenyl)spiro(cyclopropane-1',4-oxazoline)-5-carboxylate 
• 552832-50-5 methyl spiro([2H][1,4]benzoxazine-2,1'-cyclopropane)-3-carboxylate 
• 408321-74-4 3-phenyl-2,4-diazabicyclo[4.2.0]octa-1⁽⁶⁾,2-dien-5-one 

Relevant articles and documents

Cyclopropyl building blocks for organic synthesis, part 100.[?] Advanced syntheses of cyclopropylideneacetates - Versatile multifunctional building blocks for organic synthesis

A well reproducible and inexpensive preparation of the cyclopropylideneacetates 2-4 has been developed. The key intermediate 2-(1′-mesyloxycyclopropyl)acetic acid (8), produced either from methyl phenylacetate (1) or 3,3-dimethoxypropionate (5-Me) and 3,3-diethoxypropionate (5-Et) in a sequence of Kulinkovich reductive cyclopropanation, mesylation and oxidative cleavage or cleavage and oxidation, respectively, was either converted to the benzyl ester 11b, or chlorinated (brominated) via the in situ formed acid chloride. The α-chloro- 12a and α-bromo ester 12b were dehydromesylated by treatment with triethylamine to furnish methyl 2-chloro-2-cyclopropylideneacetate (3-Me) and the 2-bromo analogue 4-Me with an overall yield of 68% (65%, 68%) and 52% (49%, 51%) respectively, starting from 1 (5-Me, 5-Et). The parent benzyl cyclopropylideneacetate 2-Bn was obtained by dehydromesylation of 11b with potassium t-butoxide in t-butyl methyl ether with an overall yield of 60% (57%, 9%) from 1 (5-Me, 5-Et).

A Convenient General Access to Methyl 2-Chloro-2-cyclopropylidenacetates, Reactive Michael Acceptors and Cycloaddends

The reaction of 1-chloro-1-(trichlorovinyl)cyclopropanes 1 with potassium hydroxide/methanol or sodium methoxide/methanol yields trimethyl 2-chloro-2-cyclopropylidenorthoacetates 7, which can be quantitatively converted to the corresponding esters 8 by ac