3-methyl-1-butanol

Structural formula
General
Surname	3-methyl-1-butanol
other names	i-amyl alcohol, prim; i -butyl carbinol; Isopentyl alcohol; Isoamyl alcohol; Isopentanol; 3-methylbutan-1-ol ( IUPAC ); 3-methylbutanol-1; iso- amyl alcohol; ISOAMYL ALCOHOL ( INCI ) ;
Molecular formula	C 5 H 12 O
Brief description	flammable, colorless liquid
External identifiers / databases
EC number	204-633-5
ECHA InfoCard	100.004.213
PubChem	31260
DrugBank	DB02296
Wikidata	Q223101
properties
Molar mass	88.15 g mol −1
Physical state	liquid
density	0.81 g cm −3 (20 ° C)
Melting point	−117 ° C
boiling point	131 ° C
Vapor pressure	3 hPa (20 ° C)
solubility	poor in water (28 g l −1 at 20 ° C); soluble in organic solvents such as ethanol , acetone , benzene , chloroform , petroleum ether and glacial acetic acid ;
Refractive index	1.406 (20 ° C)
safety instructions
H and P phrases	H: 226-332-315-318-335
	EUH: 066
	P: 210-261-280-305 + 351 + 338 + 310-370 + 378
Toxicological data	1300 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-Methyl-1-butanol (also called isoamyl alcohol ) is an organic chemical compound from the group of alcohols . It is one of eight structural isomers of pentanols .

Occurrence

3-Methyl-1-butanol is the main component of fusel oil , but also a characteristic accompanying substance in alcoholic beverages such as whiskey and brandy as well as wine and beer. It is formed by breaking down the amino acid leucine through fermentation with yeasts via a-keto- isocaproic acid , whereby the ammonia released is required for the yeast cell growth.

Extraction and presentation

3-Methyl-1-butanol is obtained by hydroformylation of butene isomers.

properties

3-Methyl-1-butanol is a flammable, colorless liquid and has a dynamic viscosity of 5.09 m Pa · s at 20 ° C.

Safety-related parameters

3-Methyl-1-butanol forms highly flammable vapor-air mixtures. The compound has a flash point of 42 ° C. The explosion range is between 1.2% by volume (44 g / m ³ ) as the lower explosion limit (LEL) and 10.5% by volume (385 g / m ³ ) as the upper explosion limit (UEL). The limit gap width was determined to be 0.91 mm. This results in an assignment to explosion group IIA. The ignition temperature is 440 ° C. The substance therefore falls into temperature class T2.

use

3-Methyl-1-butanol is used as a solvent for fats, oils and resins and (in combination with chloroform ) for the extraction of nucleic acids . It also serves as an intermediate for the production of other chemical compounds (such as bis (3-methylbutyl) ether), which are used as fragrances and flavorings and as herbicides .

safety instructions

In 2016, 3-methyl-1-butanol was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of 3-methyl-1-butanol were concerns about consumer use and exposure of workers as well as the possible dangers of carcinogenic, reproductive toxicity and sensitizing properties. The re-evaluation should be carried out by Poland from 2020 .

Individual evidence

↑ Entry on ISOAMYL ALCOHOL in the CosIng database of the EU Commission, accessed on March 21, 2020.

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 3-methyl-1-butanol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

↑ ^a ^b ^c Toxicological assessment of 3-methylbutanol-1 (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

↑ 3-Methyl-1-butanol data sheet from Sigma-Aldrich , accessed on December 15, 2010 ( PDF ).

^ Isoamyl alcohol ( Memento from September 6, 2016 in the Internet Archive ).

↑ Data sheet 3-methyl-1-butanol (PDF) from Merck , accessed on December 15, 2010.

^ ^A ^b ^c ^d ^e E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

↑ Isoamyl alcohol data sheet (PDF) from Carl Roth , accessed on July 13, 2015.

↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 3-methylbutan-1-ol , accessed on March 26, 2019.

[CosIng-1] Entry on ISOAMYL ALCOHOL in the CosIng database of the EU Commission, accessed on March 21, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 3-methyl-1-butanol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[bgchemie-3] Toxicological assessment of 3-methylbutanol-1 (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.