Cyclopropanemethanol

HCID 75644CAS 2516-33-8
Substructure searchFind similar structures

Basic information

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 properties

XLogP
0.3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesAtomic environment
Physical Description · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 4 items

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 · 1 item

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

Adverse EffectsDermatotoxin - Skin burns.
Toxicity DataLC50 (rat) = 3,300 mg/m3/6hr

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
GZ2212250
ridadr
UN 1987 3/PG 3
hs_code
29061990

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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 · 2 items

Pharmaceutical and Medicine Manufacturing

Cyclopropanemethanol: ACTIVE

Applications · 4 items

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 · 1 item

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%.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

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Linked notes

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