Cyclopropanemethanol
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Basic information
- CAS
2516-33-8- Standard SMILES
OCC1CC1- InChIKey
GUDMZGLFZNLYEY-UHFFFAOYSA-N- Molecular formula
- C4H8O
- Average molar mass
- 72.11 g/mol
- Monoisotopic mass
- 72.05751488
Overview
potential anti-amoebic agent; inhibits alcohol dehydrogenase 2 from Entamoeba histolytica
Names & identifiers
- Preferred name
- Cyclopropanemethanol
- IUPAC
- cyclopropylmethanol
- English name
- Cyclopropyl carbinol
- Molecular formula
- C4H8O
- Molecular weight
- 72.11
Names & synonyms
CyclopropylmethanolCyclopropanemethanol2516-33-8Cyclopropyl carbinolCyclopropylcarbinolCyclopropylmethyl alcoholCyclopropanemethyl alcoholCyclopropylcarbinyl alcoholNSC-85925AQJ99GBE9FDTXSID2051922RefChem:129955
Show more names
CPMOCP-CARBINOLCPC-OLCyclopropylmethaneRARECHEM AK ML 0580Cyelopropyl carbinol
DTXCID7030484219-735-5(Hydroxymethyl)cyclopropaneHydroxymethylcyclopropaneMFCD00001309cyclopropylmethan-1-olCyclopropyl-MethanolEINECS 219-735-5
Database identifiers
- CAS
2516-33-8- PubChem CID
- 75644
- DTXSID
DTXSID2051922- UNII
- AQJ99GBE9F
- EC Number
- 219-735-5
- Nikkaji
- J175I
Properties
Computed structural propertiesFilling in
- XLogP
- 0.3
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 30.6
Experimental & physicochemical properties
PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesAtomic environment
Physical Description
Liquid
Clear light yellow liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -60 °C · -60 °C
- Boiling point
- 123 · 123-124 °C738 mm Hg(lit.)
- Density
- 0.89 g/mL · 0.89 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.431(lit.)
- Flash point
- 95 °F · 95 °F
- storage temp.
- Flammables area
- solubility
- Chloroform, Ethyl Acetate
- pka
- 15.1 · 15.10±0.10(Predicted)
- form
- Liquid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H226 (99.2%): Flammable liquid and vapor [Warning Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P318, P319, P321, P330, P337+P317, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 120 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Cyclopropanemethanol
Cyclopropanemethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopropanemethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 17-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23682
Cyclopropanemethanol: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Potentially neurotoxic effects observed in oral lethal-dose study of rats; Corrosive to rabbit skin; Histopathological changes of the heart (myocarditis with myocardial fiber necrosis) observed in 4-week inhalation study of rats at all tested concentrations (0.003 mg/L the lowest tested concentration); [EPA - TSCATS] A strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See Cyclohexanol.
Hazard Classes and CategoriesFlam. Liq. 3 (99.2%)
Toxicology
Chemistry & industry
Uses & manufacturing
Uses
Used as an intermediate for pharmaceuticals and other chemicals; [EPA - TSCATS]
Last manufactured by the Eastman Chemical Company in 1998; [EPA - TSCATS]
U.S. Production2023: <50,000 lb
Industry UsesIntermediate
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
Cyclopropanemethanol: ACTIVE
Applications
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.
UsesCyclopropanemethanol is used as an organic chemical synthesis intermediate.
UsesCyclopropylmethanol used to increase selectivity of pyridyl-cinnoline phosphodiesterase 10A, inhibitors against phosphodiesterase 3 (PDE3). Also used in the synthesis of benzodiazapin-2-ones
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.
Preparation methods
Related reactions
462 records
Compound notes
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