2,4-pentanediol

Structural formula
Simplified structural formula without stereochemistry
General
Surname	2,4-pentanediol
other names	Pentane-2,4-diol 2,4-dihydroxypentane 2,4-amylene glycol
Molecular formula	C 5 H 12 O 2
Brief description	colorless to yellowish odorless liquid
External identifiers / databases
CAS number 625-69-4 42075-32-1 [ (R, R) -enantiomer] 72345-23-4 [ (S, S) -enantiomer] 3950-21-8 [meso form] EC number 210-907-5 ECHA InfoCard 100.009.916 PubChem 12262 Wikidata Q27271503
properties
Molar mass	104.15 g mol −1
Physical state	liquid
density	0.96 g cm −3
Melting point	48-50 ° C ( R ) 44-48 ° C ( S )
boiling point	201 ° C 111-113 ° C (19 mmHg, R )
solubility	miscible with water easily soluble in ethanol
Refractive index	1.435 (20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	6860 mg kg −1 ( LD 50 ,  rat ,  oral ) 13700 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
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

2,4-Pentanediol is a chemical compound from the group of alkanediols that occurs in three isomeric forms. It can still be in the meso form and as a racemate .

Isomerism

2,4-Pentanediol is a chiral compound with two stereocenters . Consequently, there are the two enantiomeric forms ( R, R ) -2,4-pentanediol and ( S, S ) -2,4-pentanediol and the achiral meso compound ( R, S ) -2,4-pentanediol.

Isomers of 2,4-pentanediol
Surname	( R, R ) -2,4-pentanediol	( S, S ) -2,4-pentanediol	meso-2,4-pentanediol
other names	(-) - 2,4-pentanediol	(+) - 2,4-pentanediol	( R *, S * ) -2,4-pentanediol
Structural formula
CAS number	42075-32-1	72345-23-4	3950-21-8
	625-69-4 (unspec.)
PubChem	2723683	6950200	6950199
	12262 (unspec.)
Wikidata	Q72499966	Q97731988	Q27287604
	Q27271503 (unspec.)

Extraction and presentation

2,4-Pentanediol can be obtained by asymmetric hydrogenation of 2,4-pentanedione .

properties

2,4-Pentanediol is a flammable, hardly inflammable, colorless to yellowish, odorless liquid that is miscible with water.

use

2,4-Pentanediol can be used to synthesize chelated polynuclear complexes. The R form is used as an acetalizing reagent for ketones and β-ketoesters, in the synthesis of optically active polyesters and as a diol with a wide range of possible uses as a chiral auxiliary, building block and chiral ligand.

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on 2,4-pentanediol in the GESTIS substance database of the IFA , accessed on December 2, 2018(JavaScript required) .
2. ↑ ^{a b} Data sheet (R, R) - (-) - 2,4-Pentanediol, 99% from Sigma-Aldrich , accessed on December 2, 2018 ( PDF ).
3. ↑ Data sheet (2S, 4S) - (+) - Pentanediol, 99% from Sigma-Aldrich , accessed on December 2, 2018 ( PDF ).
4. ↑ 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. 454 ( limited preview in Google Book search).
5. ↑ ^{a b c} data sheet 2,4-pentanediol, 98% from Sigma-Aldrich , accessed on December 2, 2018 ( PDF ).
6. ^ JG Pritchard, RL Vollmer: The meso and Racemic Forms of 2,4-Pentanediol and Certain of Their Derivatives. In: The Journal of Organic Chemistry. 28, 1963, p. 1545, doi : 10.1021 / jo01041a025 .
7. ↑ J. Michael Chong: (2R, 4R) -2,4-pentanediol . In: Encyclopedia of Reagents for Organic Synthesis, 2001. doi : 10.1002 / 047084289X.rp029