3709-20-4

Basic information

• Product Name: 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester
• CAS NO: 3709-20-4
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• Mol File: 3709-20-4.mol
• Article Data: 59

Chemical Properties

• CAS DataBase Reference: 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester(3709-20-4)
• EPA Substance Registry System: 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester(3709-20-4)

Safety Data

• Hazardous Substances Data: 3709-20-4(Hazardous Substances Data)

Usage

Structure

Dimethyl ester derivative of 1,1-Cyclopropanedicarboxylic acid, 2-phenyl

Physical state

Colorless to pale yellow liquid

Odor

Slightly sweet, fruity

Solubility

Soluble in most organic solvents

Applications

a. Organic synthesis
b. Precursor for various pharmaceutical compounds
c. Research and pharmaceutical industries
d. Synthesis of drugs and therapeutic agents

Usage

Primarily used in the synthesis of various drugs and therapeutic agents in the research and pharmaceutical industries.

Upstream product

• 100-42-5 styrene 
• 145838-86-4 bis(methoxycarbonyl)(phenyliodinio)methanide 
• 124-41-4 sodium methylate 
• 62360-06-9 methyl 1-bromo-2-phenylcyclopropane-1-carboxylate 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 62360-06-9 rac-(1R,2R)-methyl 1-bromo-2-phenylcyclopropanecarboxylate 
• 100-47-0 benzonitrile 
• 6626-84-2 dimethyl 2-benzylidenepropanedioate 
• 868-26-8 dimethyl 2-bromomalonate 
• 100-52-7 benzaldehyde 
• 1379474-27-7 bis(methoxycarbonyl)-2-butoxyphenyliodinio-methanide 
• 1379474-26-6 bis(methoxycarbonyl)-2-isopropoxyphenyliodinio-methanide 
• 1379474-25-5 bis(methoxycarbonyl)-2-propoxyphenyliodinio-methanide 
• 1379474-24-4 dimethyl 2-((2-methoxyphenyl)-λ³-iodanylidene)malonate 

Downstream Products

• 72397-56-9 (2R)-dimethyl 2-phenylcyclopropane-1,1-dicarboxylate 
• 158800-60-3 dimethyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate 

Relevant articles and documents

Ni-Catalyzed [8+3] cycloaddition of tropones with 1,1-cyclopropanediesters

A variety of cycloheptapyrane derivatives were prepared via Ni-catalyzed formal [8+3] cycloaddition of tropones with 1,1-cyclopropanediesters. The asymmetric version of the process can be achieved using either an enantiomerically enriched cyclopropane as the starting material or a racemic cyclopropane and a chiral Lewis acid.

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding- 1,2-zwitterionic intermediates or (2-arylethyl-idene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

(3+2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiocyanate: A Facile and Efficient Synthesis of 2-Amino-4,5-dihydrothiophenes

An easy and efficient route to obtain 2-amino-4,5-dihydrothiophenes is presented. A formal (3+2)-cycloaddition of donor-acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf) 3delivers the desired products in good to excellent yields. A broad range of functional groups is tolerated during this process.

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.