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Chlorobutanol
Names
Preferred IUPAC name
1,1,1-Trichloro-2-methylpropan-2-ol
Other names
1,1,1-Trichloro-2-methyl-2-propanol; Chlorbutol; Chloreton; Chloretone; Chlortran; Trichloro-tert -butyl alcohol; 1,1,1-Trichloro-tert -butyl alcohol; 2-(Trichloromethyl)propan-2-ol; tert -Trichlorobutyl alcohol; Trichloro-tert -butanol; Trichlorisobutylalcohol; 2,2,2-Trichloro-1,1-dimethylethanol
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.000.288
EC Number
KEGG
UNII
InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
Y Key: OSASVXMJTNOKOY-UHFFFAOYSA-N
Y InChI=1/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
Key: OSASVXMJTNOKOY-UHFFFAOYAO
Properties
C 4 H 7 Cl 3 O
Molar mass
177.45 g·mol−1
Appearance
White solid
Odor
Camphor
Melting point
95–99 °C (203–210 °F; 368–372 K)
Boiling point
167 °C (333 °F; 440 K)
Slightly soluble
Solubility in acetone
Soluble
Pharmacology
A04AD04 (
WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Xn
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Chlorobutanol (trichloro-2-methyl-2-propanol ) is an
organic compound with the formula CCl3 C(OH)(CH3 )2 . The compound is an example of a
chlorohydrin . The compound is a
preservative ,
sedative ,
hypnotic and weak
local anesthetic similar in nature to
chloral hydrate . It has antibacterial and antifungal properties.
[1] Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes.
[2]
[3] It is a white, volatile solid with a
camphor -like odor.
Synthesis
Sublimed crystals of chlorobutanol
Chlorobutanol was first synthesized in 1881 by the German chemist
Conrad Willgerodt (1841–1930).
[4]
Chlorobutanol is formed by the reaction of
chloroform and
acetone in the presence of
potassium or
sodium hydroxide . It may be purified by sublimation or recrystallisation.
[5]
Parthenogenesis
Chlorobutanol has proven effective at stimulating parthenogenesis in
sea urchin eggs up to the pluteus stage, possibly by increasing irritability to cause stimulation. For the eggs of the fish
Oryzias latipes , however, chlorobutanol only acted as an anesthetic.
[6]
Pharmacology and toxicity
It is an anesthetic with effects related to
isoflurane and
halothane .
[7]
Chlorobutanol is toxic to the liver, a skin irritant and a severe eye irritant.
[8]
References
External links
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