Cyclopropylmethanol

Base Information

• Chemical Name: Cyclopropylmethanol
• CAS No.: 2516-33-8
• Molecular Formula: C4H8O
• Molecular Weight: 72.1069
• Hs Code.: 29061990
• European Community (EC) Number: 219-735-5
• NSC Number: 85925
• DSSTox Substance ID: DTXSID2051922
• Nikkaji Number: J175I
• Wikidata: Q13506987
• Mol file: 2516-33-8.mol

Synonyms:cyclopropylcarbinol;cyclopropylmethanol

Chemical Property of Cyclopropylmethanol

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 6mmHg at 25°C
• Melting Point: -60 °C
• Refractive Index: 1.429-1.433
• Boiling Point: 124.3 °C at 760 mmHg
• PKA: 15.10±0.10(Predicted)
• Flash Point: 35 °C
• PSA: 20.23000
• Density: 1.004 g/cm³
• LogP: 0.38870
• Storage Temp.: Flammables area
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: miscible
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 72.057514874
• Heavy Atom Count: 5
• Complexity: 30.6

Purity/Quality:

98% ^*data from raw suppliers

Cyclopropylmethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, C, F
• Hazard Codes: Xn,Xi,C,F
• Statements: 10-22-36-34
• Safety Statements: 16-26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C1CC1CO
• Description: Cyclopropyl 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.
• Uses: Cyclopropylmethanol used to increase selectivity of pyridyl-cinnoline phosphodiesterase 10A, inhibitors against phosphodiesterase 3 (PDE3). Also used in the synthesis of benzodiazapin-2-ones Cyclopropanemethanol is used as an organic chemical synthesis intermediate.

Technology Process of Cyclopropylmethanol

There total 37 articles about Cyclopropylmethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

cyclopropanecarboxylic acid (1759-53-1) → Cyclopropylmethanol (2516-33-8)

Guidance literature:

With sodium tetrahydroborate; In tert-butyl methyl ether; at 0 - 50 ℃; for 24h;

Reference yield: 90.0%

2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1344115-77-0) → Cyclopropylmethanol (2516-33-8)

Guidance literature:

With rose bengal; triethylamine; In ethanol; at 25 ℃; for 12h; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.8b02095

Reference yield: 88.0%

methyl cyclopropylcarboxylate (2868-37-3) → Cyclopropylmethanol (2516-33-8)

Guidance literature:

With sodium; In methanol; at 45 - 65 ℃; for 2h; Inert atmosphere; Large scale;

upstream raw materials:

cyclopropanecarboxylic acid

diazomethane

allyl alcohol

(2-bromoethyl)oxirane

Downstream raw materials:

chloro(cyclopropyl)methane

1,4-dibromo-butane

3-butenyl chloride

cyclobutanone

Refernces

• 1、 Tomilov, Yu. V.,Kostitsyn, A. B.,Nefedov, O. M.. "CATALYTIC CYCLOPROPANATION OF OXYGEN- AND NITROGEN-CONTAINING ALLYL DERIVATIVES USING DIAZOMETHANE". . p. 2678. Retrieved 1987.
• 2、 Roberts,D.D.. "-". . p. 294 - 297. Retrieved 1964.
• 3、 -. "Synthesis method of cyclobutanone". Paragraph 0015. . Retrieved 2020/06/02.
• 4、 -. "Metal complex catalysts and method for catalytically reducing carboxylic acids". Paragraph 0156; 0159; 0160; 0178; 0179. . Retrieved 2020/06/20.