Cyclopropyl carbinol Chemical Properties

Melting point:

-60 °C

Boiling point:

123-124 °C738 mm Hg(lit.)

Density 

0.89 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.431(lit.)

Flash point:

95 °F

storage temp. 

Flammables area

solubility 

Chloroform, Ethyl Acetate

pka

15.10±0.10(Predicted)

form 

Liquid

color 

Clear colorless

Specific Gravity

0.890

Water Solubility 

miscible

BRN 

1846846

InChIKey

GUDMZGLFZNLYEY-UHFFFAOYSA-N

CAS DataBase Reference

2516-33-8(CAS DataBase Reference)

NIST Chemistry Reference

Cyclopropyl carbinol(2516-33-8)

EPA Substance Registry System

Cyclopropanemethanol (2516-33-8)

Safety Information

Hazard Codes 

Xn,Xi,C,F

Risk Statements 

10-22-36-34

Safety Statements 

16-26-36-45-36/37/39

RIDADR 

UN 1987 3/PG 3

WGK Germany 

1

RTECS 

GZ2212250

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29061990

MSDS

• Language:English Provider:CPMO
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Cyclopropyl carbinol Usage And Synthesis

Description

Cyclopropyl carbinol (also known as Cyclopropanemethanol) is an anaesthetic. Cyclopropyl Carbinol is used as an intermediate for pharmaceuticals, agrochemical, and other organic synthesis such as for the applications for electronics chemicals, polymer additives, coatings, adhesives, surfactants, and other applications3. It can also be used for the preparation of cyclopropanecarbaldehyde, cyclopropylmethylsulfonate and dibenzyl cyclopropylmethyl phosphate1. It is also quite useful to for stereoselective synthesis of cycloalkene-fused butyrolactones via cyclopropylcarbinol solvolysis.

Referrence

Marshall, James A., and R. H. Ellison. "Stereoselective synthesis of cycloalkene-fused butyrolactones via cyclopropylcarbinol solvolysis." Journal of Organic Chemistry 40.14(1975):2070-2073.

Chemical Properties

Clear colorless liquid

Uses

Cyclopropanemethanol is used as an organic chemical synthesis intermediate.

Uses

Cyclopropylmethanol used to increase selectivity of pyridyl-cinnoline phosphodiesterase 10A, inhibitors against phosphodiesterase 3 (PDE3). Also used in the synthesis of benzodiazapin-2-ones

Preparation

The preparation of Cyclopropyl carbinol is as follows:A 1L three-necked flask was charged with 100 g (1mol) of methyl cyclopropanoate. 57g (1.5mol) of sodium borohydride, 500 mL of methanol, and then cooled to 2°C, 66.67g (0.5mol) of aluminum trichloride was added in batches and reacted overnight. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride, filtered, and the filtrate was concentrated and evaporated. The product was collected in a yield of 53.49g, a yield of 74.3%.

General Description

Cyclopropanemethanol (Cyclopropyl carbinol, CPMO), a cycloalkanemethanol, is an anaesthetic. The coupling reaction of cyclopropanemethanol with alkynes to form substituted allylic alcohols has been reported. The microwave spectrum of CPMO has been recorded. Its rotational constants and dipole moment have been determined.

Cyclopropyl carbinol(2516-33-8)Related Product Information

• Allyl chloride
• Propylthiouracil
• Cyclopropanesulfonyl chloride
• methylol cellulose
• Methyl 2-hydroxyethyl cellulose
• Tris(hydroxymethyl)nitromethane
• Tris(hydroxymethyl)aminomethane
• Cyclopropyl bromide
• Cyclopropyl acetylene
• Cyclopropane
• Cyclopropanecarbonitrile
• (Bromomethyl)cyclopropane
• Trimethylolpropane
• 2-Hydroxyethyl methacrylate
• N,N-Diisopropylethylamine
• Cyclopropyl methyl ketone
• Methanol
• Dicyclopropane methylamine