2,3,5-trimethylhydroquinone

Structural formula
General
Surname	2,3,5-trimethylhydroquinone
other names	2,3,5-trimethyl-1,4-benzenediol ( IUPAC )
Molecular formula	C 9 H 12 O 2
Brief description	beige odorless solid
External identifiers / databases
EC number	211-838-3
ECHA InfoCard	100.010.764
PubChem	12785
ChemSpider	12260
Wikidata	Q27279264
properties
Molar mass	152.19 g mol −1
Physical state	firmly
density	1.24 g cm −3
Melting point	169-172 ° C
boiling point	295 ° C
solubility	sparingly soluble in water (3.5 g l −1 at 20 ° C)
safety instructions
H and P phrases	H: 332-315-317-318-335-410
	P: 261-273-280-305 + 351 + 338-501
Toxicological data	3200 mg kg −1 ( LD 50 , rat , oral ) ; > 200 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 .

2,3,5-Trimethylhydroquinone is a chemical compound from the group of phenols . It is an alkyl-substituted hydroquinone .

Extraction and presentation

2,3,5-Trimethylhydroquinone is produced industrially by condensation of diethyl ketone and crotonaldehyde or methyl vinyl ketone to give the trimethylcyclohexenones and by subsequent catalytic dehydrogenation to 2,3,6-trimethylphenol , by catalytic oxidation to trimethylquinone and subsequent catalytic hydrogenation. It can also be obtained by catalytic alkylation of m-cresol with methanol in the gas phase to give 2,3,6-trimethylphenol and subsequent oxidation.

properties

2,3,5-Trimethylhydroquinone is a flammable, difficult to ignite, beige, odorless solid that is sparingly soluble in water.

use

2,3,5-Trimethylhydroquinone is an important precursor for the synthesis of tocopherol (vitamin E) and (±) -madindolines.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2,3,5-trimethylhydroquinone in the GESTIS substance database of the IFA , accessed on January 19, 2020(JavaScript required) .
^ The MAK Collection for Occupational Health and Safety . American Cancer Society, 2015, ISBN 978-3-527-60041-0 , trimethylquinone and trimethylhydroquinone [MAK Value Documentation in German Language, 2015], p. 1-5 , doi : 10.1002 / 3527600418.mb93592d0058 .
↑ Data sheet Trimethylhydroquinone, 97% from Sigma-Aldrich , accessed on January 19, 2020 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2,3,5-trimethylhydroquinone in the GESTIS substance database of the IFA , accessed on January 19, 2020(JavaScript required) .

[2] The MAK Collection for Occupational Health and Safety . American Cancer Society, 2015, ISBN 978-3-527-60041-0 , trimethylquinone and trimethylhydroquinone [MAK Value Documentation in German Language, 2015], p. 1-5 , doi : 10.1002 / 3527600418.mb93592d0058 .

[Sigma-3] Data sheet Trimethylhydroquinone, 97% from Sigma-Aldrich , accessed on January 19, 2020 ( PDF ).