Chloral hydrate is a geminal diol with the formula C2H3Cl3O2. It is a colorless solid. It has limited use as a sedative and hypnotic pharmaceutical drug. It is also a useful laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of precursors to nylon.
The Fischer oxazole synthesis is a chemical synthesis of an oxazole from a cyanohydrin and an aldehyde in the presence of anhydrous hydrochloric acid. This method was discovered by Emil Fischer in 1896. The cyanohydrin itself is derived from a separate aldehyde. The reactants of the oxazole synthesis itself, the cyanohydrin of an aldehyde and the other aldehyde itself, are usually present in equimolar amounts. Both reactants usually have an aromatic group, which appear at specific positions on the resulting heterocycle.
A cyanohydrin reaction is an organic chemical reaction in which an aldehyde or ketone reacts with a cyanide anion or a nitrile to form a cyanohydrin. This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. The cyanide source can be potassium cyanide, sodium cyanide or trimethylsilyl cyanide. With aromatic aldehydes such as benzaldehyde, the benzoin condensation is a competing reaction. The reaction is used in carbohydrate chemistry as a chain extension method for example that of D-xylose.
Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.
Dichloralphenazone is a 1:2 mixture of antipyrine with chloral hydrate. In combination with paracetamol and isometheptene, it is the active ingredient of medications for migraine and tension headaches, including Epidrin and Midrin. Performance impairments are common with this drug and caution is advised, for example when driving motor vehicles. Additional uses of dichloralphenazone include sedation for the treatment of short-term insomnia, although there are probably better drug choices for the treatment of insomnia.
Melzer's reagent is a chemical reagent used by mycologists to assist with the identification of fungi, and by phytopathologists for fungi that are plant pathogens.
The Kiliani–Fischer synthesis, named for German chemists Heinrich Kiliani and Emil Fischer, is a method for synthesizing monosaccharides. It proceeds via synthesis and hydrolysis of a cyanohydrin, followed by reduction of the intermediate acid to the aldehyde, thus elongating the carbon chain of an aldose by one carbon atom while preserving stereochemistry on all the previously present chiral carbons. The new chiral carbon is produced with both stereochemistries, so the product of a Kiliani–Fischer synthesis is a mixture of two diastereomeric sugars, called epimers. For example, D-arabinose is converted to a mixture of D-glucose and D-mannose.
Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil, cassava, lima bean, roseroot and white clover, among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.
Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.
Sulfonmethane is a chemical compound first synthesized by Eugen Baumann in 1888 and introduced as a hypnotic drug by Alfred Kast later on, but now superseded by newer and safer sedatives. Its appearance is either in colorless crystalline or powdered form. In United States, it is scheduled as a Schedule III drug in the Controlled Substance Act.
Acetylglycinamide chloral hydrate is a hypnotic/sedative. It is a combination of acetylglycinamide and chloral hydrate.
In enzymology, a hydroxynitrilase is an enzyme that catalyzes the chemical reaction
In enzymology, a cyanohydrin beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction
Petrichloral is a sedative and hypnotic chloral hydrate prodrug. It is a Schedule IV drug in the USA.
Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde. It is a colourless liquid that dissolves in water and ether. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.
Chloral betaine, also known as cloral betaine (INN), is a sedative-hypnotic drug. It was introduced by Mead Johnson in the United States in 1963. It is a betaine complex with chloral hydrate, which acts as an extended-acting formulation of chloral hydrate which is then metabolized into trichloroethanol, which is responsible for most or all of its effects.
Lactonitrile is the organic compound with the formula CH3CH(OH)CN. It is an intermediate in the industrial production of ethyl lactate and lactic acid. It is the cyanohydrin of acetaldehyde. It is a colorless liquid, although degraded samples can appear yellow.
(S)-hydroxynitrile lyase is an enzyme with systematic name (S)-cyanohydrin lyase . This enzyme catalyses the interconversion between cyanohydrins and the carbonyl compounds derived from the cyanohydrin with free cyanide, as in the following two chemical reactions:
