3,3-dimethyl-2-butanone

Structural formula
General
Surname	3,3-dimethyl-2-butanone
other names	Pinacolon; Pinacolon; Pinacolin; Methyl tert-butyl ketone; 1,1,1-trimethylacetone;
Molecular formula	C 6 H 12 O
Brief description	colorless liquid with a camphor to peppermint odor
External identifiers / databases
EC number	200-920-4
ECHA InfoCard	100,000,838
PubChem	6416
Wikidata	Q222983
properties
Molar mass	100.16 g mol −1
Physical state	liquid
density	0.8 g cm −3
Melting point	−50 ° C
boiling point	106 ° C
Vapor pressure	32.6 h Pa (20 ° C)
solubility	little in water (17.7 g l −1 at 20 ° C)
Refractive index	1.3960
safety instructions
H and P phrases	H: 225-302
	P: 210
Toxicological data	610 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

3,3-Dimethyl-2-butanone (also called pinacolone ) is a chemical compound that serves as an intermediate in the manufacture of pivalic acid and other chemical compounds. It is used, among other things, as a starting material for the manufacture of pharmaceuticals , fungicides and herbicides (via triazolylpinacolone to triadimefon or metribuzin ). It is derived from the compound pinacol (or the substance group of the same name).

history

The structure of pinacolon was clarified by Charles Friedel in the 19th century .

Extraction and presentation

Pinacolone can be made in a number of ways. One way runs through the pinacol rearrangement .

safety instructions

Pinacolon is highly flammable ( flash point at 3 ° C, self-ignition at 520 ° C) and is on the export control list because it can be used to manufacture chemical weapons.

literature

Ullmann's Encyclopedia of Technical Chemistry , Volume 14, 4th Edition

Web links

Manufacturing process ( Memento from February 21, 2014 in the Internet Archive )

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 3,3-dimethyl-2-butanone in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
↑ Data sheet 3,3-dimethyl-2-butanone (PDF) from Merck , accessed on March 20, 2011.
^ Nerve Agent Precursors ( Memento of July 24, 2007 in the Internet Archive )
↑ Data sheet Pinacolone at chemicalland21 , accessed on March 2, 2019.
↑ GA Hill, EW Flosdorf: Pinacolone In: Organic Synthesis . 5, 1925, p. 91, doi : 10.15227 / orgsyn.005.0091 ; Coll. Vol. 1, 1941, p. 462 ( PDF ).
↑ Category 1 export control list ( Memento of December 8, 2012 in the Internet Archive ) (PDF; 296 kB).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 3,3-dimethyl-2-butanone in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CRC-2] CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .

[Merck-3] Data sheet 3,3-dimethyl-2-butanone (PDF) from Merck , accessed on March 20, 2011.

[a-4] Nerve Agent Precursors ( Memento of July 24, 2007 in the Internet Archive )

[5] Data sheet Pinacolone at chemicalland21 , accessed on March 2, 2019.

[6] GA Hill, EW Flosdorf: Pinacolone In: Organic Synthesis . 5, 1925, p. 91, doi : 10.15227 / orgsyn.005.0091 ; Coll. Vol. 1, 1941, p. 462 ( PDF ).

[7] Category 1 export control list ( Memento of December 8, 2012 in the Internet Archive ) (PDF; 296 kB).