Chlorobutanol

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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.288
EC Number
  • 200-317-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • ClC(Cl)(Cl)C(C)(C)O
Properties
Chemical formula
 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)
Solubility in water
 Slightly soluble
Solubility in acetone Soluble
Pharmacology
ATC code
 A04AD04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Xn
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
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 ?)
Infobox references

Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula CCl3C(OH)(CH3)2. It is a halohydrin‍—‍‌specifically a chlorohydrin. Chlorobutanol acts as a preservative, sedative, hypnotic, and weak local anesthetic similar in nature to chloral 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 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]

Safety

It is an anesthetic agent with effects somewhat like isoflurane and halothane when ingested[7]

Chlorobutanol is also toxic to the liver, skin and eyes.[8]

References

  1. ^ Noecker, Robert (2001). "Effects of common ophthalmic preservatives on ocular health". Advances in Therapy. 18 (5): 205–215. doi:10.1007/bf02853166. PMID 11783457. S2CID 1455107.
  2. ^ W. N. McFarland & G. W. Klontz (1969). "Anesthesia in fishes". Federation Proceedings. 28 (4): 1535–1540. PMID 4894939.
  3. ^ John E. Cooper (2011). "Anesthesia, analgesia, and euthanasia of invertebrates". ILAR Journal. 52 (2): 196–204. doi:10.1093/ilar.52.2.196. PMID 21709312.
  4. ^ See:
  5. ^ Ho, Chih-Kuo; Wang, Tsan-Ching (September 1959). "Synthesis of Chlorobutanol". Journal of the Chinese Chemical Society. 6 (1): 80–83. doi:10.1002/jccs.195900009. ISSN 0009-4536.
  6. ^ Embryologia 1956
  7. ^ 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.
  8. ^ MSDS
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.