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| 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 | |||
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3D model (JSmol) | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.000.288 | ||
| EC Number |
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| KEGG |
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| UNII | |||
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| Properties | |||
| C4H7Cl3O | |||
| Molar mass | 177.45 g·mol−1 | ||
| Appearance | White solid | ||
| Odor | Camphor-like | ||
| Melting point | 95–99 °C (203–210 °F; 368–372 K) | ||
| Boiling point | 167 °C (333 °F; 440 K) | ||
| Slightly soluble[vague] | |||
| Solubility in acetone | Soluble | ||
| Pharmacology | |||
| A04AD04 (WHO) | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Xn[clarification needed] | ||
| NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Chlorobutanol (trichloro-2-methyl-2-propanol) is anorganic compound with the formulaCCl3C(OH)(CH3)2. It is ahalohydrin—specifically a chlorohydrin. Chlorobutanol acts as apreservative,sedative,hypnotic, and weaklocal anesthetic similar in nature tochloral hydrate; it also 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 the anesthesia and euthanasia of aquatic invertebrates and various fishes.[2][3] It is a white, volatile solid with acamphor-like odor.
Chlorobutanol was first synthesized in 1881 by the German chemistConrad Willgerodt (1841–1930).[4]
Chlorobutanol is formed by the reaction ofchloroform andacetone in the presence ofpotassium orsodium hydroxide. It may be purified by sublimation or recrystallisation.[5]
Chlorobutanol has proven effective at stimulatingparthenogenesis insea urchin eggs up to the pluteus stage, possibly by increasing irritability to cause stimulation. For the eggs of the fishOryzias latipes, however, chlorobutanol only acted as an anesthetic.[6]
It is an anesthetic agent with effects somewhat likeisoflurane andhalothane when ingested[7]
Chlorobutanol is also toxic to the liver, skin and eyes.[8]
