4-methyl-1-pentanol

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Structural formula
Structural formula of 4-methyl-1-pentanol
General
Surname 4-methyl-1-pentanol
other names
  • 4-methylpentan-1-ol
  • Isohexyl alcohol
Molecular formula C 6 H 14 O
Brief description

colorless liquid

External identifiers / databases
CAS number 626-89-1
ECHA InfoCard 100.009.973
PubChem 12296
ChemSpider 11793
Wikidata Q3278329
properties
Molar mass 102.17 g mol −1
Physical state

liquid

density

0.821 g cm −3 (25 ° C)

boiling point

160-165 ° C

Refractive index

1.414 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable

Caution

H and P phrases H: 226
P: no P-phrases
Toxicological data

170 mg kg −1 ( LD 50 ,  mouse ,  iv )

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

4-methyl-1-pentanol is a chemical compound from the group of alkanols .

Occurrence

Longan fruits ( Dimocarpus longan )

4-methyl-1-pentanol occurs naturally in tobacco . The connection has also been demonstrated in wine and longan fruit .

Extraction and presentation

4-methyl-1-pentanol can be obtained by hydroboration of 4-methyl-1-pentene with diborane in THF as solvent (borane-THF complex) and subsequent oxidation with basic hydrogen peroxide solution.

Hydroboration of 4-methyl-1-pentene with borane in tetrahydrofuran as solvent and subsequent oxidation of the trialkylborane formed with hydrogen peroxide and sodium hydroxide in water to give 4-methyl-1-pentanol in good yield

Due to the pronounced regioselectivity of the hydroboration, the anti-Markovnikov alcohol is almost exclusively formed. The desired product is obtained in about 80% yield .

The compound can also be prepared by the reaction of isoamyl magnesium bromide with formaldehyde and other synthetic methods.

properties

4-methyl-1-pentanol is a colorless liquid.

Individual evidence

  1. ↑ a b c d e f g h i data sheet 4-methyl-1-pentanol, 97% from Sigma-Aldrich , accessed on January 14, 2019 ( PDF ).
  2. ↑ Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke, Second Edition . CRC Press, 2013, ISBN 978-1-4665-1548-2 , pp. 2107 ( limited preview in Google Book search).
  3. ↑ Guo Cheng, Y. e. Liu, Tai-Xin Yue, Zhen-Wen Zhang: Comparison between aroma compounds in wines from four Vitis vinifera grape varieties grown in different shoot positions. In: Food Science and Technology. 35, 2015, p. 237, doi : 10.1590 / 1678-457X.6438 .
  4. ↑ ET Contis, C.-T. Ho, CJ Mussinan, TH Parliment, Fereidoon Shahidi, AM Spanier: Food Flavors: Formation, Analysis and Packaging Influences . Elsevier, 1998, ISBN 978-0-08-053183-0 , pp. 362 ( limited preview in Google Book search).
  5. ↑ a b K. Peter C. Vollhardt, Neil E. Schore, Katrin-M. Roy: Organic chemistry . Ed .: Holger Butenschön. 5th edition. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2011, ISBN 978-3-527-32754-6 , p. 572 ( limited preview in Google Book search).
  6. ^ 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. 125 ( limited preview in Google Book Search).