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Chlorobutanol

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Chlorobutanol
Names
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, 1,1,1-trichloro-2-methyl-2-propanol; tert-Trichlorobutyl alcohol; Trichloro-tert-butanol; Trichlorisobutylalcohol; 2,2,2-Trichloro-1,1-dimethylethanol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.288 Edit this at Wikidata
EC Number
  • 200-317-6
KEGG
UNII
  • InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3 checkY
    Key: OSASVXMJTNOKOY-UHFFFAOYSA-N checkY
  • InChI=1/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
    Key: OSASVXMJTNOKOY-UHFFFAOYAO
  • ClC(Cl)(Cl)C(C)(C)O
Properties
C4H7Cl3O
Molar mass 177.45 g·mol−1
Appearance White solid
Odor Menthol
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chlorobutanol (trichloro-2-methyl-2-propanol) is a preservative, sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It has antibacterial and antifungal properties. 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.[1][2] It is a white, volatile solid with a menthol-like odor.

Synthesis

Chlorobutanol is formed by the reaction of chloroform and acetone in the presence of potassium or sodium hydroxide.

Toxicity

Chlorobutanol is highly toxic to the liver, is a skin irritant and a severe eye irritant.[3]

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.[4]

Pharmacology

It is an anesthetics with effects related to isoflurane and halothane.[5]

References

  1. ^ W. N. McFarland & G. W. Klontz (1969). "Anesthesia in fishes". Federation Proceedings. 28 (4): 1535–1540. PMID 4894939.
  2. ^ John E. Cooper (2011). "Anesthesia, analgesia, and euthanasia of invertebrates". ILAR Journal. 52 (2): 196–204. PMID 21709312.
  3. ^ MSDS
  4. ^ Embryologia 1956
  5. ^ Nicholas P. Franks (2006). "Molecular targets underlying general anaesthesia". British Journal of Pharmacology. 147 Suppl 1: S72–S81. doi:10.1038/sj.bjp.0706441. PMC 1760740. PMID 16402123.
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