2-methyl-1-butanol

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	2-methyl-1-butanol
other names	2-methylbutan-1-ol; 2-methylbutyl alcohol; sec-butylcarbinol; (±) -2-methyl-1-butanol; 2-methylbutanol (ambiguous);
Molecular formula	C 5 H 12 O
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
ECHA InfoCard	100.004.809
PubChem	8723
Wikidata	Q209425
properties
Molar mass	88.15 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	−70 ° C
boiling point	129 ° C
Vapor pressure	3.28 mbar (20 ° C)
solubility	soluble in water (31 g l −1 at 25 ° C); miscible with ethanol and diethyl ether ;
Refractive index	1.4107 (20 ° C, 589 nm)
safety instructions
H and P phrases	H: 226-332-315-319-335
	EUH: 066
	P: 210-280-303 + 361 + 353-304 + 340-312
Toxicological data	2890 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 4170 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

2-Methyl-1-butanol is a chemical compound from the group of alcohols . It is one of eight structural isomers of pentanols . The compound occurs in two enantiomeric forms (or as a racemate ).

Occurrence

( S ) - (-) - 2-Methyl-1-butanol occurs naturally in practically all fruits (e.g. apples ), wine , beer and other spirits . It arises from the alcoholic fermentation as by-products from the amino acids leucine and isoleucine .

( S ) - (-) - 2-Methy-1-butanol
( R ) - (+) - 2-methyl-1-butanol

( R ) - (+) - 2-methyl-1-butanol can be detected as a component of the mold odor.

Extraction and presentation

( RS ) -2-methyl-1-butanol can be hydroformylated from n - butenes with a mixture of carbon monoxide and hydrogen in the presence of a cobalt hydrocarbonyl catalyst , a mixture of isomeric C5 aldehydes which are then hydrogenated to the associated amyl alcohol . A chlorination of pentanes is also possible.

( S ) - (-) - 2-methyl-1-butanol by fractionation of fusel oils recovered.

properties

( S ) - (-) - 2-Methyl-1-butanol is a flammable, volatile, colorless liquid with an unpleasant musty odor that is soluble in water. It has an odor threshold of 45 µg · m ⁻³ .

use

( S ) - (-) - 2-Methyl-1-butanol is assigned to the Chiral Pool and is used in organic syntheses (introduction of an active amyl group ). In the USA it is used as a biochemical agent as a lure for hornets and wasps in traps.

safety instructions

The vapors of 2-methyl-1-butanol can form an explosive mixture with air ( flash point 40 ° C, ignition temperature 340 ° C). They also have a narcotic effect.

Web links

( RS ) -Racemat: Beilstein (System No. 24), Volume 1 H 388
( S ) - (-): Beilstein (Syst. No. 24), Volume 1 H 385
( R ) - (+): Beilstein (Syst. No. 24), Volume 1 H 388

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 2-methyl-1-butanol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Entry on (S) - (-) - 2-methyl-1-butanol at TCI Europe, accessed on April 2, 2012.
↑ ^a ^b Data sheet 2-methyl-1-butanol (PDF) from Merck , accessed on April 2, 2012.
↑ ^a ^b EPA: 2-Methyl-1-butanol (431602) Fact Sheet , accessed January 27, 2018.
↑ Günter Jeromin: Organic chemistry: A practical textbook . 2005, ISBN 978-3-8171-1732-1 , pp. 261 ( limited preview in Google Book search).
↑ Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 67 ( limited preview in Google Book search).
↑ ^a ^b ^c Entry on 2-methyl-1-butanol in the Hazardous Substances Data Bank , accessed on July 27, 2012.
↑ Wolfgang Mücke, Christa Lemmen: Bioaerosols and health . ecomed medicine, 2008, ISBN 978-3-609-16371-0 , p. 42 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 2-methyl-1-butanol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[TCI-2] Entry on (S) - (-) - 2-methyl-1-butanol at TCI Europe, accessed on April 2, 2012.

[Merck-3] Data sheet 2-methyl-1-butanol (PDF) from Merck , accessed on April 2, 2012.

[EPA-4] EPA: 2-Methyl-1-butanol (431602) Fact Sheet , accessed January 27, 2018.

[Jeromin-5] Günter Jeromin: Organic chemistry: A practical textbook . 2005, ISBN 978-3-8171-1732-1 , pp. 261 ( limited preview in Google Book search).

[Legrum-6] Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 67 ( limited preview in Google Book search).

[hsdb-7] Entry on 2-methyl-1-butanol in the Hazardous Substances Data Bank , accessed on July 27, 2012.

[Mücke-8] Wolfgang Mücke, Christa Lemmen: Bioaerosols and health . ecomed medicine, 2008, ISBN 978-3-609-16371-0 , p. 42 ( limited preview in Google Book search).