Chlorobutanol (trichloro-2-methyl-2-propanol) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula . The compound is a

chlorohydrin In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol ...

. The compound is a

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

hypnotic A hypnotic (from Ancient Greek, Greek ''Hypnos'', sleep), also known as a somnifacient or soporific, and commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to sleep induction, induce sleep and to trea ...

and weak

local anesthetic A local anesthetic (LA) is a medication that causes absence of all sensation (including pain) in a specific body part without loss of consciousness, providing local anesthesia, as opposed to a general anesthetic, which eliminates all sensati ...

similar in nature to

chloral hydrate Chloral hydrate is a geminal diol with the formula . It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in use in the United States until at ...

. 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. It is a white, volatile solid with a

camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...

-like odor.

Synthesis

Chlorobutanol was first synthesized in 1881 by the German chemist

Conrad Willgerodt Conrad Heinrich Christoph Willgerodt (2 November 1841 – 19 December 1930) was a German chemist who first described the Willgerodt rearrangement, Willgerodt reaction. Alongside the Willgerodt reaction, he had also discovered Iodosobenzene and chlo ...

(1841–1930). Chlorobutanol is formed by the reaction of

chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

and

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

in the presence of

potassium Potassium is a chemical element; it has Symbol (chemistry), symbol K (from Neo-Latin ) and atomic number19. It is a silvery white metal that is soft enough to easily cut with a knife. Potassium metal reacts rapidly with atmospheric oxygen to ...

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

. It may be purified by sublimation or recrystallisation.

Parthenogenesis

Chlorobutanol has proven effective at stimulating parthenogenesis in

sea urchin Sea urchins or urchins () are echinoderms in the class (biology), class Echinoidea. About 950 species live on the seabed, inhabiting all oceans and depth zones from the intertidal zone to deep seas of . They typically have a globular body cove ...

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.

Pharmacology and toxicity

It is an anesthetic with effects related to

isoflurane Isoflurane, sold under the brand name Forane among others, is a halogenated ether used as a general anesthetic. It can be used to start or maintain anesthesia; however, other medications are often used to start anesthesia, due to airway irritat ...

and

halothane Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful ...

. Chlorobutanol is toxic to the liver, a skin irritant and a severe eye irritant.MSDS
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References

External links

* {{Authority control Hypnotics Sedatives Trichloromethyl compounds Tertiary alcohols GABAA receptor positive allosteric modulators Glycine receptor agonists Halohydrins Substances discovered in the 19th century