Chlorobutanol

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.

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
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1439973
ChemSpider	13842993
ECHA InfoCard	100.000.288
EC Number	200-317-6
KEGG	D01942
PubChem CID	5977
UNII	HM4YQM8WRC
CompTox Dashboard (EPA)	DTXSID1041217
InChI InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3 Key: OSASVXMJTNOKOY-UHFFFAOYSA-N 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 (WHO)
Hazards
Main hazards	Xn
NFPA 704 (fire diamond)	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Sublimed crystals of chlorobutanol

Chlorobutanol was first synthesized in 1881 by the German chemist Conrad Willgerodt (1841–1930).[3]

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.[4]

Toxicity

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

Pharmacology

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

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. doi:10.1093/ilar.52.2.196. PMID 21709312.
3. 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.
4. "Chlorobutanol". Sciencemadness Wiki. Retrieved 14 August 2020.
5. MSDS
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.

External links

• Chlorobutanol MSDS
• A04AD04 (WHO)