Chlorobutanol

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
CAS Number	57-15-8 Y
ChEMBL	ChEMBL1439973 N
ChemSpider	13842993 Y
Jmol 3D model	Interactive image
KEGG	D01942 Y
UNII	HM4YQM8WRC Y
InChI 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
SMILES ClC(Cl)(Cl)C(C)(C)O
Properties
Chemical formula	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)
Solubility in water	Slightly soluble
Solubility in acetone	Soluble
Pharmacology
ATC code	A04AD04
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Chlorobutanol, or trichloro-2-methyl-2-propanol, is a chemical preservative, sedative hypnotic and weak local anaesthetic 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. In pure state it's a white, volatile solid with a menthol-like odor.

Chemical synthesis

Chlorobutanol is formed by the simple nucleophilic addition of chloroform and acetone. The reaction is base driven by potassium or sodium hydroxide.

Toxicity

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

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 anaesthetic.

External links

• Chlorobutanol MSDS
• A04AD04