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482099

Sigma-Aldrich

Cyclopropanemethanol

≥99.5%

Synonym(s):

(Hydroxymethyl)cyclopropane, CPMO, Cyclopropyl carbinol, Cyclopropylmethanol

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About This Item

Linear Formula:
C3H5CH2OH
CAS Number:
2516-33-8
Molecular Weight:
72.11
Beilstein:
1846846
EC Number:
219-735-5
MDL number:
MFCD00001309
UNSPSC Code:
12352100
PubChem Substance ID:
24871809
NACRES:
NA.22

Assay

≥99.5%

refractive index

n20/D 1.431 (lit.)

bp

123-124 °C/738 mmHg (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

OCC1CC1

InChI

1S/C4H8O/c5-3-4-1-2-4/h4-5H,1-3H2

InChI key

GUDMZGLFZNLYEY-UHFFFAOYSA-N

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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.

Application

Cyclopropanemethanol may be used in the preparation of:
  • cyclopropanecarbaldehyde
  • cyclopropylmethylsulfonate
  • dibenzyl cyclopropylmethyl phosphate

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

95.0 °F - closed cup

Flash Point(C)

35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The microwave spectrum, dipole moment, and structure of cyclopropyl carbinol.
Bhaumik A, et al.
Canadian Journal of Chemistry, 48(19) , 2949-2954 (1970)
Surbhi Soni et al.
Chirality, 30(1), 85-94 (2017-10-25)
A profoundly time-efficient chemoenzymatic method for the synthesis of (S)-3-(4-chlorophenoxy)propan-1,2-diol and (S)-1-chloro-3-(2,5-dichlorophenoxy)propan-2-ol, two important pharmaceutical intermediates, was successfully developed using Pseudomonas fluorescens lipase (PFL). Kinetic resolution was successfully achieved using vinyl acetate as acylating agent, toluene/hexane as solvent, and reaction
D E Raines et al.
Anesthesiology, 78(5), 918-927 (1993-05-01)
N-alkanols containing up to 12 carbons are anesthetic; however, those with more than 12 carbons are not. This phenomenon has been termed cutoff. Lipid disordering theories of anesthesia suggest that cutoff occurs because the alkyl chains of long-chain alcohols approach
Cyclopropylmethyl dihydrogen phosphate. Preparation and use in the phosphorylation of nucleosides.
Schoffstall AM.
The Journal of Organic Chemistry, 40(23), 3444-3445 (1975)
Nickel-Catalyzed Redox-Economical Coupling of Alcohols and Alkynes to Form Allylic Alcohols.
Nakai K, et al.
Journal of the American Chemical Society, 136(22), 7797-7800 (2014)
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