2-methylcyclohexanol

Structural formula
	Simplified structural formula without stereochemistry; (* = stereocenter)
General
Surname	2-methylcyclohexanol
other names	Methylhexalin; Heptalin; Hexahydro-2-hydroxytoluene; Hexahydro-2-methylphenol; 1-hydroxy-2-methylcyclohexane; 2-methylanol;
Molecular formula	C 7 H 14 O
Brief description	colorless liquid with a camphor-like odor
External identifiers / databases
EC number	209-512-0
ECHA InfoCard	100.008.649
PubChem	11418
ChemSpider	10938
Wikidata	Q2456972
properties
Molar mass	114.19 g mol −1
Physical state	liquid
density	0.936 g cm −3 ( cis form); 0.924 g cm −3 ( trans form); 0.93 g cm −3 (mixture of isomers);
Melting point	8 ° C ( cis -form); −4 ° C ( trans form); −38 ° C (mixture of isomers);
boiling point	165 ° C ( cis -form); 166.5 ° C ( trans form); 163–166 ° C (mixture of isomers);
Vapor pressure	3.5 hPa (20 ° C)
solubility	poorly soluble in water; very soluble with ethanol;
Refractive index	1.462 (20 ° C)
safety instructions
H and P phrases	H: 226-302-332-319
	P: 210-280-301 + 330 + 331-303 + 361 + 353-304 + 340-337 + 313
Toxicological data	1660 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Methylcyclohexanol is a chemical compound from the group of cyclohexanol derivatives , so it is one of the alcohols .

Stereoisomerism

2-Methylcyclohexanol has two stereocenters, so there are four stereoisomers :

(1 S , 2 R ) -2-methylcyclohexanol
(1 R , 2 S ) -2-methylcyclohexanol
(1 R , 2 R ) -2-methylcyclohexanol
(1 S , 2 S ) -2-methylcyclohexanol

Isomers of 2-methylcyclohexanol
Exact name	(1 S , 2 R ) -2-methylcyclohexanol	(1 R , 2 S ) -2-methylcyclohexanol	(1 R , 2 R ) -2-methylcyclohexanol	(1 S , 2 S ) -2-methylcyclohexanol
Structural formula

A mixture of (1 S , 2 R ) -2-methylcyclohexanol and (1 R , 2 S ) -2-methylcyclohexanol is called cis -2-methylcyclohexanol. trans -2-methylcyclohexanol is a mixture of (1 R , 2 R ) -2-methylcyclohexanol and (1 S , 2 S ) -2-methylcyclohexanol.

Extraction and presentation

trans -2-methylcyclohexanol can be obtained by hydroboration of methylcyclohexene . A mixture of 75% cis -2-methylcyclohexanol and 25% trans -2-methylcyclohexanol can be obtained by reducing 2-methylcyclohexanone with lithium triethylborohydride .

properties

The compound is a colorless liquid with a camphor-like odor that is sparingly soluble in water.

use

2-Methylcyclohexanol is used to study the effect of organic solvents on epoxide hydrolase. It is also used in the production of acetic acid (2-methyl-cyclohexyl ester ) by reaction with acetic anhydride .

safety instructions

The vapors of 2-methylcyclohexanol can form an explosive mixture with air ( flash point 58 ° C, ignition temperature 295 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on 2-methylcyclohexanol in the GESTIS substance database of the IFA , accessed on January 12, 2019(JavaScript required) .
↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 378 ( limited preview in Google Book search).
↑ ^a ^b Data sheet 2-Methylcyclohexanol, mixture of cis and trans, 99% from Sigma-Aldrich , accessed on January 12, 2019 ( PDF ).
↑ Entry on 2-methylcyclohexanol, mixed isomers in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 12, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ BAuA: Explanation on methylcyclohexanol in TRGS 900 , June 2008, accessed on January 12, 2019.
↑ ScienceDirect Topics: Hydroboration - an overview | ScienceDirect Topics , accessed January 12, 2019.
^ Marye Anne Fox, James K. Whitesell: Organic Chemistry . Jones & Bartlett Learning, 2004, ISBN 978-0-7637-2197-8 , pp. 498 ( limited preview in Google Book search).
^ Herbert C. Brown, SC Kim, S. Krishnamurthy: Selective reductions. 26. Lithium triethylborohydride as an exceptionally powerful and selective reducing agent in organic synthesis. Exploration of the reactions with selected organic compounds containing representative functional groups. In: The Journal of Organic Chemistry. 45, 1980, p. 1, doi : 10.1021 / jo01289a001 .
↑ Data sheet 2-methylcyclohexanol, cis + trans, 97% from AlfaAesar, accessed on January 12, 2019 ( PDF )(JavaScript required) .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on 2-methylcyclohexanol in the GESTIS substance database of the IFA , accessed on January 12, 2019(JavaScript required) .

[David_R._Lide-2] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 378 ( limited preview in Google Book search).

[Sigma-3] Data sheet 2-Methylcyclohexanol, mixture of cis and trans, 99% from Sigma-Aldrich , accessed on January 12, 2019 ( PDF ).

[CLP_100.008.649-4] Entry on 2-methylcyclohexanol, mixed isomers in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 12, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[BAuA-5] BAuA: Explanation on methylcyclohexanol in TRGS 900 , June 2008, accessed on January 12, 2019.

[sciencedirect.com-6] ScienceDirect Topics: Hydroboration - an overview | ScienceDirect Topics , accessed January 12, 2019.

[Marye_Anne_Fox,_James_K._Whitesell-7] Marye Anne Fox, James K. Whitesell: Organic Chemistry . Jones & Bartlett Learning, 2004, ISBN 978-0-7637-2197-8 , pp. 498 ( limited preview in Google Book search).

[DOI10.1021/jo01289a001-8] Herbert C. Brown, SC Kim, S. Krishnamurthy: Selective reductions. 26. Lithium triethylborohydride as an exceptionally powerful and selective reducing agent in organic synthesis. Exploration of the reactions with selected organic compounds containing representative functional groups. In: The Journal of Organic Chemistry. 45, 1980, p. 1, doi : 10.1021 / jo01289a001 .

[Alfa-9] Data sheet 2-methylcyclohexanol, cis + trans, 97% from AlfaAesar, accessed on January 12, 2019 ( PDF )(JavaScript required) .