939-89-9

Basic information

• Product Name: cis-2-Phenylcyclopropanecarboxylicacid
• Synonyms: cis-2-Phenylcyclopropanecarboxylicacid;(1R,2S)‐rel-2‐phenylcyclopropane‐1‐carboxylic acid;(1R,2S)-rel-2-Phenylcyclopropanecarboxylic acid;CYCLOPROPANECARBOXYLIC ACID,2-PHENYL-,(1R,2S)-REL-;-rel-2-Phenylcyclopropanecarboxylic acid;cis-2-phenylcyclopropane-1-carboxylic acid
• CAS NO: 939-89-9
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• Mol File: 939-89-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 317.1°Cat760mmHg
• Flash Point: 144.3°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 0.000165mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.57±0.10(Predicted)
• CAS DataBase Reference: cis-2-Phenylcyclopropanecarboxylicacid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2-Phenylcyclopropanecarboxylicacid(939-89-9)
• EPA Substance Registry System: cis-2-Phenylcyclopropanecarboxylicacid(939-89-9)

Safety Data

• Hazardous Substances Data: 939-89-9(Hazardous Substances Data)

Usage

Description

cis-2-Phenylcyclopropanecarboxylic acid, also known as rel-(1R,2S)-2-Phenylcyclopropanecarboxylic acid, is an organic compound that serves as a crucial reagent in the synthesis of various pharmaceutical compounds. It is characterized by its unique cyclopropane ring fused with a phenyl group and a carboxylic acid functional group, which contributes to its reactivity and potential applications in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
cis-2-Phenylcyclopropanecarboxylic acid is used as a key reagent for the synthesis of tranylcypromine compounds, which are potent and efficacious 5-HT2C receptor agonists. These agonists play a significant role in the treatment of various psychiatric and neurological disorders, such as depression, anxiety, and obsessive-compulsive disorder, by modulating the activity of the serotonin receptor.
Additionally, the unique structural features of cis-2-Phenylcyclopropanecarboxylic acid may also allow it to be used in the development of other pharmaceutical compounds with diverse therapeutic applications. Its ability to form stable intermediates and participate in various chemical reactions makes it a valuable building block in the synthesis of complex organic molecules with potential medicinal properties.

InChI:InChI=1/C10H10O2/c11-10(12)9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6H2,(H,11,12)/t8-,9-/m1/s1

Upstream product

• 100-42-5 styrene 
• 623-73-4 diazoacetic acid ethyl ester 
• 766-94-9 vinyl phenyl ether 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 124-38-9 carbon dioxide 
• 36617-02-4 1-bromo-2-phenylcyclopropane 
• 75-47-8 iodoform 
• 140-10-3 cis-cinnamic acid 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 201230-82-2 carbon monoxide 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 

Downstream Products

• 939-87-7 2-phenyl-1-cyclopropanecarbonyl chloride 
• 3977-92-2 cis-2-phenylcyclopropanecarboxylic acid diethylamide 
• 17955-08-7 ((1S,2S)-2-Vinyl-cyclopropyl)-benzene 
• 42916-17-6 ((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanaminium (1R,2S)-2-phenylcyclopropane-1-carboxylate 
• 1265913-09-4 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-16-3 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-25-4 (1S,5R)-5-(3-methoxyphenyl)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265913-30-1 (1R,5S)-5-(3-methoxyphenyl)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265968-40-8 3-((1S,5R)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1265968-43-1 3-((1R,5S)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 48126-51-8 (1R,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 67528-62-5 cis-methyl 2-phenylcyclopropane-1-carboxylate 
• 23020-18-0 (1S,2R)-2-phenylcyclopropanecarboxylic acid 
• 936-98-1 rac-((1S,2R)-2-phenylcyclopropyl)methanol 

Relevant articles and documents

Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide

A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.