30491-95-3

Usage

Physical state

Colorless liquid at room temperature

Usage

Intermediate in the synthesis of various pharmaceuticals and agrochemicals

Structural components

Hydroxymethyl group and a cyclopropane ring

Versatility

Building block in organic synthesis

Reactivity

Known for its reactivity, used in the production of heterocyclic compounds and other complex organic molecules

Industry applications

Potential applications in the pharmaceutical and chemical industries, making it an important compound in organic chemistry

Upstream product

• 3999-56-2 trans-racemic ethyl 2-cyanocyclopropane-1-carboxylate 
• 592-51-8 4-Pentenenitrile 
• 30491-94-2 3-oxiran-2-ylpropanenitrile 

Downstream Products

• 39891-86-6 trans-2-Cyanocyclopropylmethyl-p-toluolsulfonat 
• 82480-47-5 (1R,2R)-2-Benzenesulfonylmethyl-cyclopropanecarbonitrile 
• 115373-45-0 2-Phenylsulfanylmethyl-cyclopropanecarbonitrile 
• 1615-70-9 penta-2,4-dienenitrile 
• 1372118-36-9 (R)-2-{4-chloro-N-{[(1R,2R)-2-cyanocyclopropyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide 
• 1372118-35-8 (R)-2-{4-chloro-N-{[(1S,2S)-2-cyanocyclopropyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide 

Relevant academic research and scientific papers

Cyclopropane-containing polyamine analogues are efficient growth inhibitors of a human prostate tumor xenograft in nude mice

Polyamine analogues 7, 10, 18, 27, and 32 containing cyclopropane rings were obtained by chemical synthesis. Their antineoplastic activities were assessed against the cultured human prostate tumor cell lines DU-145, DuPro, and PC-3. Decamines 32 and 27 ex

Acidic Isomerization of Vicinally Substituted (cis)-Acceptor-Donor Cyclopropanes via an Open Ring Mechanism

Many (cis)-cyclopropanes bearing 1-electronwithdrawing and 2-hydroxymethylene groups were synthesized under mild acidic conditions to afford the corresponding trans isomers.The mechanism is reported.

Elimination and Addition Reactions. Part 41. Nucleophilic Eliminative Fission of Cyclopropanes: the Coiled Spring Effect of Ring Strain on Nucleofugality and its Evaluation

Rates have been measured of sulphonyl-activated eliminative ring fissions of a series of six cyclopropanes in which the leaving group is stabilised by alkoxycarbonyl, cyano, or sulphonyl groups.The measurements allow assignment of ranks (nucleofugalities) to carbon leaving groups in systems in which the connection to the leaving group is strained by incorporation in a cyclopropane ring.The values obtained are compered with those obtained for a unstrained (acyclic) analogues.Rank enhancements of about 9(log) units are obtained; these enhancements suggests that free energies of activation for leaving-group expulsion are reduced by about 53 kJmol-1, or about 46 percent of these excess of enthalpy of the strained ring, notwithstanding the small degree of ring fission in the transition structure.The effect of phenyl substitution at the leaving group suggests that cleavage of the ring is very little advanced in the transition structure, although this is variable with the nature of the leaving-group stabilisation.This is the first direct determination of the effect of strain on nucleofugality.