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	57-15-8  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1439973  N
ChemSpider	13842993  Y
ECHA InfoCard	100.000.288
EC Number	200-317-6
KEGG	D01942  Y
PubChem CID	5977
UNII	HM4YQM8WRC  Y
CompTox Dashboard (EPA)	DTXSID1041217
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	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[ vague ]
Solubility in acetone	Soluble
Pharmacology
ATC code	A04AD04 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Xn[ clarification needed ]
NFPA 704 (fire 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  YN ?) 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:
   • 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. 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

External links

• Chlorobutanol MSDS
• A04AD04 ( WHO )