CasNo: 302-17-0
Molecular Formula: C2H3Cl3O2
Appearance: colourless crystals with a pentrating odour
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Chemical Description |
Chloral hydrate and chloral alcoholate are derivatives of chloral used in the synthesis of DDT. |
Biological Functions |
Chloral hydrate (Noctec, Somnos) was developed in the late 1800s and is still used as a sedative–hypnotic agent. It is a hydrated aldehyde with a disagreeable smell and taste that is rapidly reduced in vivo to trichloroethanol, which is considered to be the active metabolite. It produces a high incidence of gastric irritation and allergic responses, occasionally causes cardiac arrhythmias, and is unreliable in patients with liver damage. |
Air & Water Reactions |
Water soluble. |
Reactivity Profile |
Chloral hydrate is incompatible with alkalis, alkaline earth metals, alkali carbonates and soluble barbiturates. Chloral hydrate is decomposed by sodium hydroxide. Chloral hydrate reduces ammoniacal silver nitrate. Chloral hydrate liquefies when triturated with an equal quantity of menthol, camphor or thymol. . Reaction of Chloral hydrate with hydroxylamine produces toxic hydrogen cyanide gas, Org. Synth., 1941, Vol. 1, 377. |
Hazard |
Overdose toxic, hypnotic drug, dangerous to eyes. Probable carcinogen. |
Fire Hazard |
Flash point data for Chloral hydrate are not available; however, Chloral hydrate is probably combustible. |
Flammability and Explosibility |
Nonflammable |
Biochem/physiol Actions |
Chloral hydrate is a sedative/hypnotic. |
Safety Profile |
A human poison by ingestion and possibly other routes. Poison experimentally by ingestion, intravenous, and rectal routes. Moderately toxic by subcutaneous, parenteral, and intraperitoneal routes, Experimental reproductive effects. Human systemic effects by ingestion: general anesthetic, cardiac arrhythmias, blood pressure depression, eye effects, coma, pulse rate increase, arrhythmias. Human mutation data reported. Questionable carcinogen with experimental carcinogenic and tumorigenic data by skin contact. A sedative, anesthetic, and narcotic. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-. |
Synthesis |
Chloral hydrate, 2,2,2-trichloro-1,1-ethandiol (4.3.1), is synthesized either by chlorination of ethanol or chlorination of acetaldehyde and the subsequent addition of water molecules to the resulting trichloroacetic aldehyde [31]. |
Potential Exposure |
Chloral is used as an intermediate in the manufacture of such pesticides as DDT, methoxychlor, DDVP, naled, trichlorfon, and TCA. Chloral is also used in the production of chloral hydrate; used as a therapeutic agent with hypnotic, sedative, and narcotic effects; used in a time prior to the introduction of barbiturates |
Drug interactions |
Potentially hazardous interactions with other drugs Anticoagulants: may transiently enhance effect of coumarins. Antipsychotics: enhanced sedative effects. Antivirals: concentration possibly increased by ritonavir. |
Carcinogenicity |
Chloral hydrate has not been adequately tested for teratogenicity, reproductive effects, or chronic toxicity. Similarly, no histological evaluations have been conducted. |
Environmental Fate |
Chloral hydrate is a CNS depressant, but its mechanism of action is not well known. Coingestion with ethanol produces enhanced effects by several mechanisms. First, ethanol competes for alcohol and aldehyde dehydrogenase, which then prolongs the half-life of ethanol. The metabolism of ethanol generates the reduced form of NADH, which is a cofactor for the metabolism of chloral hydrate to its active metabolite trichloroethanol. Finally, ethanol inhibits the conjugation of trichloroethanol to its inactive form urochloralic acid. This results in enhanced CNS depression. |
Metabolism |
Chloral hydrate is rapidly metabolised to trichloroethanol (the active metabolite) and trichloroacetic acid in the erythrocytes, liver, and other tissues. It is excreted partly in the urine as trichloroethanol and its glucuronide (urochloralic acid) and as trichloroacetic acid. Some is also excreted in the bile. |
Shipping |
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. |
Toxicity evaluation |
Chloral hydrate has been detected at 5 mg l-1 in the US drinking water supply. Although chloral hydrate does not exist naturally, it can be produced as a by-product of chlorination of water at water treatment facilities, specifically in exposed water with high amounts of humic and fulvic substances. |
Incompatibilities |
Chloral hydrate reacts with strong bases forming chloroform. Contact with acids, or exposure to light may cause polymerization. Reacts with water, forming chloral hydrate. Reacts with oxidizers, with a risk of fire or explosions. |
Waste Disposal |
Incineration after mixing with another combustible fuel; care must be taken to assure complete combustion to prevent phosgene formation; an acid scrubber is necessary to remove the halo acids produced. |
Definition |
ChEBI: An organochlorine compound that is the hydrate of trichloroacetaldehyde. |
General Description |
Chloral hydrate, trichloroacetaldehydemonohydrate, CCl3CH(OH)2 (Noctec), is analdehyde hydrate stable enough to be isolated. The relativestability of this gem-diol is largely a result of an unfavorabledipole–dipole repulsion between the trichloromethyl carbonand the carbonyl carbon present in the parent carbonylcompound.Chloral hydrate is unstable in alkaline solutions, undergoingthe last step of the haloform reaction to yield chloroformand formate ion. In hydroalcoholic solutions, it formsthe hemiacetal with ethanol. Whether or not this compoundis the basis for the notorious and potentially lethal effect of the combination of ethanol and chloral hydrate (the “MickeyFinn”) is controversial. Synergism between two differentCNS depressants also could be involved. Additionally,ethanol, by increasing the concentration of nicotinamideadenine dinucleotide (NADH), enhances the reduction ofchloral to the more active metabolite trichloroethanol, andchloral can inhibit the metabolism of alcohol because it inhibitsalcohol dehydrogenase. Chloral hydrate is a weak acidbecause its CCl3 group is very strong electron withdrawing.A 10% aqueous solution of chloral hydrate has pH 3.5 to4.4, which makes it irritating to mucous membranes in thestomach. As a result, GI upset commonly occurs for thedrug if undiluted or taken on an empty stomach. Chloral hydrateas a capsule, syrup, or suppository is currently available. |
InChI:InChI=1/C2HCl3O.H2O/c3-2(4,5)1-6;/h1H;1H2
In this study, UV irradiation combined w...
In the Maillard reaction, independent de...
Trichloroethylene (TRI), a common ground...
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
chloral hydrate
chloroform
1,1-Dichloroacetone
1,1,1-trichloroacetone
Conditions | Yield |
---|---|
With chlorine; In aq. phosphate buffer; pH=7; pH-value; Kinetics; UV-irradiation;
|
L-alanin
α-picoline
chloral hydrate
2-ethylideneamino propanoic acid
cyclo(-DL-Ala-DL-Ala-)
Conditions | Yield |
---|---|
With copper dichloride; at 250 ℃; for 0.00555556h; Pyrolysis; Inert atmosphere;
|
ethanol
chloroacetylene
benzoic acid hydrazide
acetaldehyde
1,1,1-trichloro-2,3-epoxypropane
Dimethyl ether
N-Formylpiperidine
1,1,1-trichloro-2,2-di-[2]thienyl-ethane
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