Chlorobutanol

Last updated
Chlorobutanol
Chlorobutanol Structural Formula V.2.svg
Chlorobutanol3d.png
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.288 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-317-6
KEGG
PubChem CID
UNII
  • InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3 Yes check.svgY
    Key: OSASVXMJTNOKOY-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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 acetoneSoluble
Pharmacology
A04AD04 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Xn
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis

Sublimed crystals of chlorobutanol Chlorobutanol crystals.jpg
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]

Pharmacology and toxicity

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]

Related Research Articles

<span class="mw-page-title-main">Resorcinol</span> Chemical compound

Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.

<span class="mw-page-title-main">Erythorbic acid</span> Chemical compound

Erythorbic acid is a stereoisomer of ascorbic acid. It is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature. It is denoted by E number E315, and is widely used as an antioxidant in processed foods.

The Japp–Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The reaction is named after the chemists Francis Robert Japp and Felix Klingemann.

The Bischler–Möhlau indole synthesis, also often referred to as the Bischler indole synthesis, is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline; it is named after August Bischler and Richard Möhlau .

<span class="mw-page-title-main">Johannes Thiele (chemist)</span> German chemist (1865–1918)

Friedrich Karl Johannes Thiele was a German chemist and a prominent professor at several universities, including those in Munich and Strasbourg. He developed many laboratory techniques related to isolation of organic compounds. In 1907 he described a device for the accurate determination of melting points, since named Thiele tube after him.

<span class="mw-page-title-main">Reimer–Tiemann reaction</span> Chemical reaction for ortho-formylation of phenols

The Reimer–Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. with the simplest example being the conversion of phenol to salicylaldehyde. The reaction was first reported by Karl Reimer and Ferdinand Tiemann.

<span class="mw-page-title-main">Bromoacetone</span> Chemical compound

Bromoacetone is an organic compound with the formula CH3COCH2Br. It is a colorless liquid although impure samples appear yellow or even brown. It is a lachrymatory agent and a precursor to other organic compounds.

<span class="mw-page-title-main">Organomercury chemistry</span> Group of chemical compounds containing mercury

Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.

<span class="mw-page-title-main">Hans von Pechmann</span> German chemist (1850–1902)

Hans Freiherr von Pechmann was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pechmann pyrazole synthesis. He also first prepared 1,2-diketones, acetonedicarboxylic acid, methylglyoxal and diphenyltriketone; established the symmetrical structure of anthraquinone.

<span class="mw-page-title-main">Fischer glycosidation</span>

Fischer glycosidation refers to the formation of a glycoside by the reaction of an aldose or ketose with an alcohol in the presence of an acid catalyst. The reaction is named after the German chemist, Emil Fischer, winner of the Nobel Prize in chemistry, 1902, who developed this method between 1893 and 1895.

The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone, alkyne, or alkene to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt. The formation of the corresponding carboxylic acid is a side reaction resulting from hydrolysis of the amide. When the alkyl group is an aliphatic chain, multiple reactions take place with the amide group always ending up at the terminal end. The net effect is thus migration of the carbonyl group to the end of the chain and oxidation.

In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen. It can be considered as a specific variation of the aldol condensation. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J. Gustav Schmidt, who independently published on this topic in 1880 and 1881. An example is the synthesis of dibenzylideneacetone ( -1,5-diphenylpenta-1,4-dien-3-one).

<span class="mw-page-title-main">Carl Theodore Liebermann</span> German chemist (1842–1914)

Carl Theodore Liebermann was a German chemist and student of Adolf von Baeyer.

Conrad Heinrich Christoph Willgerodt was a German chemist who first described the Willgerodt reaction. Alongside the Willgerodt reaction, he had also discovered Iodosobenzene and chlorobutanol.

<span class="mw-page-title-main">Oskar Piloty</span> German chemist (1866–1915)

Oskar Piloty was a German chemist.

Richard Wolffenstein was a German chemist.

<span class="mw-page-title-main">Friedrich Oskar Giesel</span> German organic chemist (1852–1927)

Friedrich Oskar Giesel was a German organic chemist. During his work in a quinine factory in the late 1890s, he started to work on the at-that-time-new field of radiochemistry and started the production of radium. In the period between 1902 and 1904, he was able to isolate a new element emanium. In a now controversially reviewed process, it was stated that emanium is identical to actinium, which was discovered by André-Louis Debierne in 1899.

<span class="mw-page-title-main">Conhydrine</span> Chemical compound

Conhydrine is a poisonous alkaloid found in poison hemlock in small quantities.

Ernest Tytus Bandrowski was a Polish chemist.

<span class="mw-page-title-main">Sulfuryl diazide</span> Chemical compound

Sulfuryl diazide or sulfuryl azide is a chemical compound with the molecular formula SO2(N3)2. It was first described in the 1920s when its reactions with benzene and p-xylene were studied by Theodor Curtius and Karl Friedrich Schmidt. The compound is reported as having "exceedingly explosive, unpredictable properties" and "in many cases very violent explosions occurred without any apparent reason".

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