Chlorobutanol

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Chlorobutanol
Chlorobutanol Structural Formula V.2.svg
Chlorobutanol3d.png
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
57-15-8 YesY
ChEMBL ChEMBL1439973 N
ChemSpider 13842993 YesY
Jmol 3D model Interactive image
KEGG D01942 YesY
UNII HM4YQM8WRC YesY
  • InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3 YesY
    Key: OSASVXMJTNOKOY-UHFFFAOYSA-N YesY
  • 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
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 YesYN ?)
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.[1]

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.[2]

References

External links