2,4-dimethylpentan-3-one

Structural formula
General
Surname	2,4-dimethylpentan-3-one
other names	2,4-dimethyl-3-pentanone Diisopropyl ketone Tetramethylacetone 3-oxo-2,4-dimethylpentane Isobutyron
Molecular formula	C 7 H 14 O
Brief description	colorless liquid with an odor similar to acetone
External identifiers / databases
CAS number 565-80-0 EC number 209-294-7 ECHA InfoCard 100.008.450 PubChem 11271 ChemSpider 10797 Wikidata Q27159900
properties
Molar mass	114.19 g mol −1
Physical state	liquid
density	0.81 g cm −3
Melting point	−34 ° C
boiling point	124 ° C
Vapor pressure	27 hPa (30 ° C)
solubility	sparingly soluble in water (5.7 g l −1 at 25 ° C) soluble in ethanol, acetone and chloroform
Refractive index	1.3990 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-332 P: 210-304 + 340 + 312
Toxicological data	3540 mg kg −1 ( LD 50 ,  rat ,  oral ) > 16100 mg kg −1 ( LD 50 ,  rat ,  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-Dimethylpentan-3-one ( diisopropyl ketone ) is a chemical compound from the group of alkanones .

Extraction and presentation

2,4-Dimethylpentan-3-one can be obtained by passing 2,2,4-trimethyl-1,3-pentanediol over an aluminum oxide catalyst.

2,4-Dimethylpentan-3-one is also produced by oxidation of the corresponding secondary carbinol, which is an important by-product of methanol.

It can also be made from isobutyric acid and by the reaction of sodium amide and iodomethane with acetone , methyl ethyl ketone , diethyl ketone and methyl isopropyl ketone .

properties

2,4-Dimethylpentan-3-one is an easily flammable colorless liquid with an acetone-like odor that is sparingly soluble in water.

use

2,4-Dimethylpentan-3-one is used as an intermediate in the production of α-aryl ketones and in Grignard reactions .

safety instructions

The vapors of 2,4-dimethylpentan-3-one can form an explosive mixture with air ( flash point 18 ° C, ignition temperature 478 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m} Entry on 2,4-dimethylpentan-3-one in the GESTIS substance database of the IFA , accessed on January 14, 2020(JavaScript required) .
2. ↑ ^{a b c} data sheet diisopropyl ketone, 98% from AlfaAesar, accessed on August 12, 2018 ( PDF )(JavaScript required) .
3. ^ William M. Haynes: CRC Handbook of Chemistry and Physics, 96th Edition . CRC Press, 2015, ISBN 978-1-4822-6097-7 , pp. 218 ( limited preview in Google Book search).
4. ↑ Entry on 2,4-dimethylpentan-3-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 31, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Google Patents: US3660492A - Synthesis of diisopropyl ketone - Google Patents , accessed August 12, 2018.
6. ^ ^{A b} Frank C. Whitmore: Organic Chemistry, Volume One Part I: Aliphatic Compounds Part II: Alicyclic Compounds . Courier Corporation, 2012, ISBN 978-0-486-60700-9 , pp. 222 ( limited preview in Google Book search).