4-chlorobutanol

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Structural formula
Structural formula of 4-chlorobutanol
General
Surname 4-chlorobutanol
other names
  • 4-chlorobutan-1-ol ( IUPAC )
  • 4-chloro-1-hydroxybutane
  • 1-chloro-4-hydroxybutane
Molecular formula C 4 H 9 OCl
External identifiers / databases
CAS number 928-51-8
EC number 213-175-5
ECHA InfoCard 100,011,978
PubChem 13569
ChemSpider 12980
Wikidata Q229943
properties
Molar mass 107.56 g mol −1
density

1.090 g cm −3 (20 ° C)

boiling point
  • 86-89 ° C
  • 50–52 ° C (1.3 hPa)
Refractive index

1.4518

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 07 - Warning

Caution

H and P phrases H: 226-302-315-319-335
P: 261-305 + 351 + 338
Toxicological data
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-chlorobutanol is an organic chemical compound . It is a 4-position chlorinated n- butanol and thus belongs to the group of chlorobutanols .

General

4-Chlorobutanol can be obtained by introducing hydrogen chloride into tetrahydrofuran and is an intermediate product in the production of 1,4-dichlorobutane .

Synthesis of 4-chlorobutanol

It can also be made by the reaction of 1,4-butanediol with thionyl chloride in the presence of pyridine .

Reactions

4-Chlorobutanol reacts with hydrogen chloride to form 1,4-dichlorobutane with elimination of water.

Chlorination of 4-chlorobutanol

When reacting with phosphorus tribromide , 1-bromo-4-chlorobutane is formed.

Bromination of 4-chlorobutanol

When 4-chlorobutanol is heated to above 85 ° C., hydrogen chloride is split off and tetrahydrofuran is formed.

safety instructions

4-chlorobutanol was found to be moderately toxic in mice with oral LD 50 values ​​of 990 mg / kg and> 100 mg / kg after intraperitoneal administration. Changes in the liver, muscle twitching and gastric bleeding occurred in the animals at high doses.

Individual evidence

  1. ↑ a b Data sheet 4-chloro-1-butanol (PDF) from Merck , accessed on March 13, 2012.
  2. ↑ Data sheet 4-chloro-1-butanol from AlfaAesar, accessed on March 13, 2012 ( PDF )(JavaScript required) .
  3. ^ A b W. R. Kirner, G. Holmes Richter: Tetramethylene Glycol and Tetramethylene Chlorohydrin . In: Journal of the American Chemical Society . 51, No. 8, 1929, pp. 2503-2506. ISSN  0002-7863 . doi : 10.1021 / ja01383a033 .
  4. ↑ a b Data sheet 4-chloro-1-butanol, technical grade, ~ 85% from Sigma-Aldrich , accessed on March 13, 2012 ( PDF ).
  5. ^ Journal of Organic Chemistry . Vol. 21, Pg. 739, 1956.
  6. ↑ a b Entry on 4-chlorobutanol in the ChemIDplus database of the United States National Library of Medicine (NLM)
  7. ↑ a b Journal for the entire hygiene and its border areas . Vol. 26, Pg. 17, 1980.
  8. ↑ D. Starr, RM Hixon: Tetramethylene Chlorohydrid In: Organic Syntheses . 17, 1937, p. 84, doi : 10.15227 / orgsyn.017.0084 ; Coll. Vol. 2, 1943, p. 571 ( PDF ).
  9. ↑ a b Author collective: Organikum . 22nd edition, Wiley-VCH, 2004, ISBN 978-3-527-31148-4 .
  10. ↑ a b c D. Starr, RM Hixon: Reduction of Furan and the Preparation of Tetramethylene Derivatives in J. Am. Chem. Soc. 1934 , 56 (7), pp. 1595-1596. doi : 10.1021 / ja01322a041