Isopropylidene glycerine

Structural formula
	Structural formula without stereochemistry
General
Surname	Isopropylidene glycerine
other names	Solketal; ( RS ) -2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; ( R ) -2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; ( S ) -2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (±) -2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (+) - 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (-) - 2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane; ISOPROPYLIDENEGLYCEROL ( INCI ) ;
Molecular formula	C 6 H 12 O 3
Brief description	colorless liquid (racemate)
External identifiers / databases
EC number	202-888-7
ECHA InfoCard	100.002.626
PubChem	7528
ChemSpider	7247
Wikidata	Q2968854
properties
Molar mass	132.16 g mol −1
Physical state	liquid
density	1.063 g / ml (racemate)
Melting point	−26.4 ° C
boiling point	188-189 ° C (racemate)
Vapor pressure	450 mbar (50 ° C)
solubility	soluble in water
Refractive index	1.434 (20 ° C) (racemate)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 319
	P: 305 + 351 + 338
Toxicological data	7000 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

Isopropylidene glycerine , also known as Solketal , is a chemical compound from the group of acetonides and dioxolanes . The derivative of glycerol with an isopropylidene protective group is liquid at room temperature.

Manufacturing

Solketal is made synthetically from glycerine and acetone in the presence of acids .

Stereochemistry

Isopropylidene glycerol has a stereocenter and there are therefore two different and mutually enantiomeric compounds ( R ) - and ( S ) -Solketal.

Chemical properties

The isopropylidene acetal group is a so-called protective group for two hydroxyl groups , which means that a selective reaction can take place on the third, still free hydroxyl group. Later you can split off the protective group in the acid and get the two hydroxyl groups back.

use

Isopropylidene glycerine is used as a synthesis component in the chemical and pharmaceutical industries.

Individual evidence

↑ Entry on ISOPROPYLIDENEGLYCEROL in the CosIng database of the EU Commission, accessed on June 19, 2020.
↑ ^a ^b ^c ^d data sheet DL-1,2-isopropylideneglycerol, ≥98.0% (GC) from Sigma-Aldrich , accessed on January 16, 2013 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f Entry on 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Mary Renoll, Melvin S. Newman: dl-Isopropylideneglycerol : In Organic Synthesis . 28, 1948, p. 73, doi : 10.15227 / orgsyn.028.0073 ; Coll. Vol. 3, 1955, p. 502 ( PDF ).

[CosIng-1] Entry on ISOPROPYLIDENEGLYCEROL in the CosIng database of the EU Commission, accessed on June 19, 2020.

[Sigma-2] ta sheet DL-1,2-isopropylideneglycerol, ≥98.0% (GC) from Sigma-Aldrich , accessed on January 16, 2013 ( PDF ).

[GESTIS-3] ↑ ^a ^b ^c ^d ^e ^f Entry on 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[4] Mary Renoll, Melvin S. Newman: dl-Isopropylideneglycerol : In Organic Synthesis . 28, 1948, p. 73, doi : 10.15227 / orgsyn.028.0073 ; Coll. Vol. 3, 1955, p. 502 ( PDF ).