2,5 hexanediol

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	2,5 hexanediol
other names	Hexane-2,5-diol; Diisopropanol;
Molecular formula	C 6 H 14 O 2
Brief description	colorless liquid
External identifiers / databases
ECHA InfoCard	100.019.010
PubChem	18049
Wikidata	Q27158159
properties
Molar mass	118.18 g mol −1
Physical state	liquid
density	0.96 g cm −3
Melting point	53–54 ° C (2 R , 5 R ); 52–53 ° C (2 S , 5 S ); 43–44.5 ° C (2 RS , 5 RS ); 40–41 ° C (2 R * , 5 S * );
boiling point	221 ° C
solubility	easily soluble in water; soluble in ethanol;
Refractive index	1.447 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	15,700 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 2000 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

2,5-Hexanediol is a chemical compound from the group of diols . There are three stereoisomers:

(2 R , 5 R ) -2,5-hexanediol,
(2 S , 5 S ) -2,5-hexanediol and
meso -2,5-hexanediol.

Extraction and presentation

(2 R , 5 R ) -hexanediol can be obtained from 2,5-hexanedione .

properties

2,5-Hexanediol is a flammable, hardly inflammable, colorless liquid that is easily soluble in water.

use

2,5-hexanediol can be used for the production of other chemical compounds e.g. B. 2,4-hexadiene can be used. ( 2S , 5S ) -2,5-hexanediol is a precursor of chiral phosphine - catalysts and chiral pharmaceutical intermediates.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry for CAS no. 2935-44-6 in the GESTIS substance database of the IFA , accessed on October 8, 2016(JavaScript required) .
↑ ^a ^b ^c ^d J. Buckingham: Dictionary of Organic Compounds . CRC Press, 1986, ISBN 978-0-412-54090-5 , pp. 3511 ( limited preview in Google Book search).
^ William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 298 ( limited preview in Google Book search).
↑ Data sheet 2,5-hexanediol, 99% (mixture of isomers) from Sigma-Aldrich , accessed on October 8, 2016 ( PDF ).
↑ Jürgen Haberland, Werner Hummel, Thomas Daussmann, Andreas Liese: New Continuous Production Process for Enantiopure (2,5) -Hexanediol. In: Organic Process Research & Development. 6, 2002, p. 458, doi : 10.1021 / op020023t .
↑ J. Haberland, A. Kriegesmann, E. Wolfram, W. Hummel, A. Liese: Diastereoselective synthesis of optically active (2R, 5R) -hexanediol. In: Applied Microbiology and Biotechnology. 58, 2002, p. 595, doi : 10.1007 / s00253-002-0936-5 .
↑ Eberhard Breitmaier, Günther Jung: Organic chemistry basics, substance classes, reactions, concepts, molecular structures; 129 tables . Georg Thieme Verlag, 2005, ISBN 978-3-13-541505-5 , p. 86 ( limited preview in Google Book search).
↑ M. Bertau, M. Katzberg, W. Hummel, T. Daußmann, J. Stohrer: Biocatalytic synthesis of (S, S) -2,5-hexanediol. In: Chemical Engineer Technology. 78, 2006, p. 1437, doi : 10.1002 / cite.200650458 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry for CAS no. 2935-44-6 in the GESTIS substance database of the IFA , accessed on October 8, 2016(JavaScript required) .

[J._Buckingham-2] J. Buckingham: Dictionary of Organic Compounds . CRC Press, 1986, ISBN 978-0-412-54090-5 , pp. 3511 ( limited preview in Google Book search).

[William_M._Haynes-3] William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 298 ( limited preview in Google Book search).

[Sigma-4] Data sheet 2,5-hexanediol, 99% (mixture of isomers) from Sigma-Aldrich , accessed on October 8, 2016 ( PDF ).

[DOI10.1021/op020023t-5] Jürgen Haberland, Werner Hummel, Thomas Daussmann, Andreas Liese: New Continuous Production Process for Enantiopure (2,5) -Hexanediol. In: Organic Process Research & Development. 6, 2002, p. 458, doi : 10.1021 / op020023t .

[DOI10.1007/s00253-002-0936-5-6] J. Haberland, A. Kriegesmann, E. Wolfram, W. Hummel, A. Liese: Diastereoselective synthesis of optically active (2R, 5R) -hexanediol. In: Applied Microbiology and Biotechnology. 58, 2002, p. 595, doi : 10.1007 / s00253-002-0936-5 .

[Eberhard_Breitmaier,_Günther_Jung-7] Eberhard Breitmaier, Günther Jung: Organic chemistry basics, substance classes, reactions, concepts, molecular structures; 129 tables . Georg Thieme Verlag, 2005, ISBN 978-3-13-541505-5 , p. 86 ( limited preview in Google Book search).

[DOI10.1002/cite.200650458-8] M. Bertau, M. Katzberg, W. Hummel, T. Daußmann, J. Stohrer: Biocatalytic synthesis of (S, S) -2,5-hexanediol. In: Chemical Engineer Technology. 78, 2006, p. 1437, doi : 10.1002 / cite.200650458 .