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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/REAXYS Number:
1846846
EC Number:
219-735-5
MDL number:
MFCD00001309
UNSPSC Code:
12352100
PubChem Substance ID:
24871809
NACRES:
NA.22

Quality Level

100

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

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

95.0 °F - closed cup

flash_point_c

35 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Galvanic Deposition of Au on Paperlike Cu Fiber for High-Efficiency, Low-Temperature Gas-Phase Oxidation of Alcohols.
Zhao G, et al.
ChemCatChem, 3(10), 1629-1636 (2011)
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)
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)
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