Chlorobutanol

Summary

Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula CCl3C(OH)(CH3)2. The compound is an example of a chlorohydrin. The compound is a preservative, sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It 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 anesthesia and euthanasia of invertebrates and fishes.[2][3] It is a white, volatile solid with a camphor-like odor.

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
  • 57-15-8 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1439973 ☒N
ChemSpider
  • 13842993 checkY
ECHA InfoCard 100.000.288 Edit this at Wikidata
EC Number
  • 200-317-6
KEGG
  • D01942 checkY
  • 5977
UNII
  • HM4YQM8WRC checkY
  • DTXSID1041217 Edit this at Wikidata
  • 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 Camphor
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 ?)
Infobox references

Synthesis edit

 
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 edit

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]

Pharmacology and toxicity edit

It is an anesthetic with effects related to isoflurane and halothane.[7]

Chlorobutanol is toxic to the liver, a skin irritant and a severe eye irritant.[8]

References edit

  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:
    • Willgerodt, C. (1881). "Ueber die Einwirkung ätzender Alkalien auf halogenirte Verbindungen in Acetonlösungen" [On the action of caustic alkalies on halogenated compounds in acetone solutions]. Berichte der Deutschen Chemischen Gesellschaft (in German). 14 (2): 2451–2460. doi:10.1002/cber.188101402191.
    • Willgerodt, C. (1882). "Ueberführung des Acetonchloroforms in die Oxyisobuttersäure" [Conversion of chlorobutanol into 2-hydroxyisobutyric acid]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15 (2): 2305–2308. doi:10.1002/cber.188201502176.
    • Willgerodt, C. (1883). "Zur Kenntniss des Acetonchloroforms" [[Contribution] to [our] knowledge of chlorobutanol]. Berichte der Deutschen Chemischen Gesellschaft (in German). 16 (2): 1585. doi:10.1002/cber.18830160218.
    • Willgerodt, C.; Genieser, Ad. (1888). "Beiträge zur Kenntniss des Acetonchloroforms" [Contributions to [our] knowledge of chlorobutanol]. Journal für praktische Chemie (in German). 37 (8): 361–374. doi:10.1002/prac.18880370131.
  5. ^ "Chlorobutanol". Sciencemadness Wiki. Retrieved 14 August 2020.
  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

External links edit