Cyclopropyl carbinol

Cyclopropyl carbinol Basic information
Description Referrence
Product Name:Cyclopropyl carbinol
Synonyms:Cyclopropylmethanol for synthesis;CPC-OL;CP-CARBINOL;CPMO;CYCLOPROPYL CARBINOL;CYCLOPROPYLMETHANOL;CYCLPOPROPANEMETHANOL;CYCLOPROPANEMETHANOL
CAS:2516-33-8
MF:C4H8O
MW:72.11
EINECS:219-735-5
Product Categories:Alcohols;Building Blocks;C2 to C6;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Cyclopropanes;Simple 3-Membered Ring Compounds;Cycloalkanes;Organic solvents;Pyridines ,Halogenated Heterocycles
Mol File:2516-33-8.mol
Cyclopropyl carbinol Structure
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.)
Fp 95 °F
storage temp. Flammables area
solubility Chloroform, Ethyl Acetate
pka15.10±0.10(Predicted)
form Liquid
color Clear colorless
Specific Gravity0.890
Water Solubility miscible
BRN 1846846
InChIKeyGUDMZGLFZNLYEY-UHFFFAOYSA-N
CAS DataBase Reference2516-33-8(CAS DataBase Reference)
NIST Chemistry ReferenceCyclopropyl carbinol(2516-33-8)
EPA Substance Registry SystemCyclopropanemethanol (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 Information
ProviderLanguage
CPMO English
ACROS English
SigmaAldrich English
ALFA English
Cyclopropyl carbinol Usage And Synthesis
DescriptionCyclopropyl 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.
ReferrenceMarshall, 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 PropertiesClear colorless liquid
UsesCyclopropylmethanol used to increase selectivity of pyridyl-cinnoline phosphodiesterase 10A, inhibitors against phosphodiesterase 3 (PDE3). Also used in the synthesis of benzodiazapin-2-ones
UsesCyclopropanemethanol is used as an organic chemical synthesis intermediate.
PreparationThe 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%.

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General DescriptionCyclopropanemethanol (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.
Cyclopropane Cyclopropyl methyl ketone Cyclopropyl acetylene Trimethylolpropane ETHYL 1-METHYLCYCLOPROPANE-1-CARBOXYLATE Methyl cyclopropane carboxylate 2-Hydroxyethyl methacrylate N,N-Diisopropylethylamine Hydroxymethyl ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE Methanol (Bromomethyl)cyclopropane METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE Ethyl cyclopropanecarboxylate Tris(hydroxymethyl)aminomethane Cyclopropyl bromide Diethyl 1,1-cyclopropanedicarboxylate Cyclopropanecarbonitrile

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