6970-72-5

Basic information

• Product Name: 1-(hydroxymethyl)cyclobutanol
• Synonyms: Cyclobutanemethanol, 1-hydroxy-
• CAS NO: 6970-72-5
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.1317
• Mol File: 6970-72-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 225.7°C at 760 mmHg
• Flash Point: 110.4°C
• Density: 1.201g/cm³
• Vapor Pressure: 0.017mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 1-(hydroxymethyl)cyclobutanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(hydroxymethyl)cyclobutanol(6970-72-5)
• EPA Substance Registry System: 1-(hydroxymethyl)cyclobutanol(6970-72-5)

Safety Data

• Hazardous Substances Data: 6970-72-5(Hazardous Substances Data)

Usage

Type of compound

Cyclobutane derivative

Functional groups

Hydroxyl group and methyl group

Physical state

Colorless liquid

Odor

Characteristic odor

Boiling point

Relatively high boiling point

Usage

Intermediate in the synthesis of other organic compounds

Industries

Pharmaceutical and agrochemical industries

Potential uses

Building block for the synthesis of various compounds

Safety precautions

Harmful if ingested or inhaled, causes skin and eye irritation upon contact

Upstream product

• 1120-56-5 methylidenecyclobutane 

Downstream Products

• 1191-95-3 cyclobutanone 
• 1347638-66-7 6-(4-chlorophenyl)-3-(4-((1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one 
• 1140917-94-7 N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-[(1-hydroxycyclobutyl)methoxy]-5-(trifluoromethyl)benzamide 
• 64-18-6 formic acid 
• 110-94-1 1,5-pentanedioic acid 
• 2889-31-8 2-hydroxyglutaric acid 
• 110-15-6 succinic acid 

Relevant articles and documents

Thermolytic Rearrangements of 1,1-Cyclopropanedimethanol Disulfonates: Cyclopropylcarbinyl Cations Revisited

1,1-Cyclopropanedimethanol dimethanesulfonate (1a) and the corresponding ditosylate 1b underwent thermal rearrangement at 110-140 deg C after melting.Short reaction time resulted in the formation of mixtures containing 1-(sulfonyloxy)cyclobutanemethanol sulfonates 5a,b (major), starting material, and 2-methylene-1,4-butanediol disulfonates 6a,b.Longer reaction times afforded complete conversion to disulfonates 6a,b, isolated in 49 and 62 percent yield, respectively.These reactions are postulated to proceed via initial carbocation formation, presumably interconverting bicyclobutonium and cyclopropylcarbinyl cations, which exist as ion pairs in the melt.Crossover experiments with dimesylate 1a and ditosylate 1b offer support for the presence of ion pairs in the melt: internal return competed with external trapping of the intermediate cations.Reaction of 1a and 2-methylene-1,4-butanediol ditosylate (6b) gave a mixture in which 2-methylene-1,4-butanediol 1-mesylate 4-tosylate (8) predominated over the isomeric 4-mesylate 1-tosylate 7 by a 5:1 ratio.Crossover experiments with 6a and 6b indicated that partial allylic substitution was occurring for the open-chain products under the thermolysis conditions.Reaction of 1a with excess tetrabutylammonium tosylate at 114-15 deg C afforded mixed 1-(sulfonyloxy)cyclobutanemethanol sulfonates and 2-methylene-1,4-butanediol disulfonates formed competitively by internal return and tosylate interception.Acetolysis of 1a at 42-43 deg C afforded predominately products of internal return early on the reaction profile.Longer reaction times afforded predominately monoacetates while reactions run at 108-10 deg C afforded substantial amounts of diacetates.Acetolysis of 1-acetoxycyclobutanemethanol mesylate (12a) resulted in the substitution of the mesyloxy group with substantial rearrangement.