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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:
Molecular Weight:
72.11
Beilstein:
1846846
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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.)

functional group

hydroxyl

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

Signal Word

Warning

Hazard Statements

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

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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)
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)
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)
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

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