1-Phenyl-1-cyclopropanecarboxylic acid Chemical Properties

Melting point:

85-87 °C (lit.)

Boiling point:

248.88°C (rough estimate)

Density 

1.0613 (rough estimate)

refractive index 

1.5782 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

4.30±0.20(Predicted)

form 

Crystals, Crystalline Powder or Chunks

color 

White to beige

InChI

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

InChIKey

IWWCCNVRNHTGLV-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)(C(O)=O)CC1

CAS DataBase Reference

6120-95-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:1-Phenyl-1-cyclopropanecarboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-Phenyl-1-cyclopropanecarboxylic acid Usage And Synthesis

Chemical Properties

white to beige crystals, crystalline powder

Uses

1-Phenyl-1-cyclopropanecarboxylic Acid, is an intermediate in the synthesis of pharmaceutical products including inhibitors and anticancer compounds. It is also used as the starting material in the synthesis of 2-(1-Phenylcyclopropyl)-4-oxazolecarboxylic Acid (P319785).

Synthesis

Step (vi): synthesis of 1-phenylcyclopropanecarboxylic acid Experimental Procedure: to a solution of 1-phenylcyclopropanecarbonitrile (7 g, mmol) was added water (15 mL), acetic acid (15 mL), and concentrated sulfuric acid (15 mL) sequentially. The reaction mixture was refluxed at 110 °C overnight. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with saturated sodium chloride solution (2 x 50 mL) and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (230-400 mesh) with 5% ethyl acetate/hexane mixture as eluent, the target component was collected, and 1-phenylcyclopropanecarboxylic acid was obtained as a colorless solid after concentration under reduced pressure (4.35 g, 50% yield).

References

[1] Pharmaceutical Chemistry Journal, 1980, vol. 14, # 2, p. 114 - 118
[2] Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 2, p. 40 - 45
[3] European Journal of Medicinal Chemistry, 1991, vol. 26, # 2, p. 125 - 128
[4] Patent: WO2012/12410, 2012, A2. Location in patent: Page/Page column 46-47
[5] Journal of Organic Chemistry, 1959, vol. 24, p. 616,618, 619

1-Phenyl-1-cyclopropanecarboxylic acid(6120-95-2)Related Product Information

• Cyclopropanecarbonitrile
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• Cyclohexylbenzene
• Folic acid
• 1,1-Bis(hydroxymethyl)cyclopropane
• Cyclopropylboronic acid
• Cyclopropanecarboxylic acid
• Aminomethylcyclopropane
• Cyclopropyl methyl ketone
• Ciprofloxacin hydrochloride
• Cyclohexanecarboxylic acid
• Ciprofloxacin
• Ethyl 2-(Chlorosulfonyl)acetate
• DIPHENYLCYCLOPROPENONE
• PHENYL VALERATE
• Dicyclopropane methylamine
• 1-Phenyl-2-nitropropene
• Citric acid