Chlorobutanol
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 444584652
|Name = Chlorobutanol
|ImageFileL1 = Chlorobutanol Structural Formula V.2.svg
|ImageClassL1 = skin-invert-image
|ImageFileR1 = Chlorobutanol3d.png
|ImageClassR1 = bg-transparent
|PIN = 1,1,1-Trichloro-2-methylpropan-2-ol
|OtherNames = 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
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 13842993
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = HM4YQM8WRC
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = D01942
|InChI = 1/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
|InChIKey = OSASVXMJTNOKOY-UHFFFAOYAO
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = OSASVXMJTNOKOY-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 57-15-8
|PubChem = 5977
|EINECS = 200-317-6
|ChEMBL_Ref = {{ebicite|changed|EBI}}
|ChEMBL = 1439973
|SMILES = ClC(Cl)(Cl)C(C)(C)O
}}
|Section2={{Chembox Properties
|C=4 | H=7 | Cl=3 | O=1
|Appearance = White solid
|Odor= Camphor
|MeltingPtC = 95-99
|BoilingPtC = 167
|SolubleOther = Soluble
|Solvent = acetone
|Solubility = Slightly soluble
}}
|Section3={{Chembox Pharmacology
|ATCCode_prefix = A04
|ATCCode_suffix = AD04
}}
|Section4={{Chembox Hazards
|MainHazards = Xn
|NFPA-H = 2
|NFPA-F = 1
|NFPA-R = 0
}}
}}
Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula {{chem2|CCl3C(OH)(CH3)2}}. The compound is 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.{{cite journal |doi=10.1007/bf02853166 |title=Effects of common ophthalmic preservatives on ocular health |date=2001 |last1=Noecker |first1=Robert |journal=Advances in Therapy |volume=18 |issue=5 |pages=205–215 |pmid=11783457 |s2cid=1455107 }} 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.{{Cite journal | author = W. N. McFarland & G. W. Klontz | title = Anesthesia in fishes | journal = Federation Proceedings | volume = 28 | issue = 4 | pages = 1535–1540 | year = 1969 | pmid = 4894939}}{{Cite journal | author = John E. Cooper | title = Anesthesia, analgesia, and euthanasia of invertebrates | journal = ILAR Journal | volume = 52 | issue = 2 | pages = 196–204 | year = 2011 | pmid = 21709312| doi = 10.1093/ilar.52.2.196 | doi-access = free }} It is a white, volatile solid with a camphor-like odor.
Synthesis
File:Chlorobutanol crystals.jpg
Chlorobutanol was first synthesized in 1881 by the German chemist Conrad Willgerodt (1841–1930).See:
- {{cite journal |last1=Willgerodt |first1=C. |title=Ueber die Einwirkung ätzender Alkalien auf halogenirte Verbindungen in Acetonlösungen |journal=Berichte der Deutschen Chemischen Gesellschaft |date=1881 |volume=14 |issue=2 |pages=2451–2460 |doi=10.1002/cber.188101402191 |url=https://babel.hathitrust.org/cgi/pt?id=hvd.cl1hzb&view=1up&seq=873 |trans-title=On the action of caustic alkalies on halogenated compounds in acetone solutions |language=de}}
- {{cite journal |last1=Willgerodt |first1=C. |title=Ueberführung des Acetonchloroforms in die Oxyisobuttersäure |journal=Berichte der Deutschen Chemischen Gesellschaft |date=1882 |volume=15 |issue=2 |pages=2305–2308 |doi=10.1002/cber.188201502176 |url=https://babel.hathitrust.org/cgi/pt?id=uiug.30112025692838&view=1up&seq=1205 |trans-title=Conversion of chlorobutanol into 2-hydroxyisobutyric acid |language=de}}
- {{cite journal |last1=Willgerodt |first1=C. |title=Zur Kenntniss des Acetonchloroforms |journal=Berichte der Deutschen Chemischen Gesellschaft |date=1883 |volume=16 |issue=2 |page=1585 |doi=10.1002/cber.18830160218 |url=https://babel.hathitrust.org/cgi/pt?id=osu.32435060218708&view=1up&seq=469 |trans-title=[Contribution] to [our] knowledge of chlorobutanol |language=de}}
- {{cite journal |last1=Willgerodt |first1=C. |last2=Genieser |first2=Ad. |title=Beiträge zur Kenntniss des Acetonchloroforms |journal=Journal für praktische Chemie |date=1888 |volume=37 |issue=8 |pages=361–374 |doi=10.1002/prac.18880370131 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015026393622&view=1up&seq=377 |trans-title=Contributions to [our] knowledge of chlorobutanol |language=de}}
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.{{Cite journal |last1=Ho |first1=Chih-Kuo |last2=Wang |first2=Tsan-Ching |date=September 1959 |title=Synthesis of Chlorobutanol |url=https://onlinelibrary.wiley.com/doi/10.1002/jccs.195900009 |journal=Journal of the Chinese Chemical Society |language=en |volume=6 |issue=1 |pages=80–83 |doi=10.1002/jccs.195900009 |issn=0009-4536}}
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.[http://onlinelibrary.wiley.com/store/10.1111/j.1440-169X.1956.tb00062.x/asset/j.1440-169X.1956.tb00062.x.pdf?v=1&t=ie95071c&s=493f4ab23ad771e4d05dcc297f7bba0b3bcdebd0 Embryologia 1956]
Pharmacology and toxicity
It is an anesthetic with effects related to isoflurane and halothane.{{Cite journal | author = Nicholas P. Franks | title = Molecular targets underlying general anaesthesia | journal = British Journal of Pharmacology | volume = 147 | pages = S72–S81 | year = 2006 | issue = Suppl 1 | doi = 10.1038/sj.bjp.0706441 | pmid = 16402123| pmc = 1760740 }}
Chlorobutanol is toxic to the liver, a skin irritant and a severe eye irritant.[https://web.archive.org/web/20131106022221/https://www.spectrumchemical.com/MSDS/C4046.PDF MSDS]
References
{{Reflist}}
External links
- [https://web.archive.org/web/20110716024512/http://siri.org/msds/f2/cgc/cgchj.html Chlorobutanol MSDS]
- {{ATC|A04|AD04}}
{{Sedatives}}
{{GABAAR PAMs}}
{{Glycinergics}}
{{Authority control}}
Category:Trichloromethyl compounds
Category:GABAA receptor positive allosteric modulators