Chloral hydrate CAS 302-17-0
Introduction：Basic information about Chloral hydrate CAS 302-17-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Chloral hydrate Basic information
| Product Name: | Chloral hydrate |
| Synonyms: | 2,2,2-Trichloro-1,1-ethanediol;2,2,2-TRICHLOROETHANE-1,1-DIOL;2,2,2-TRICHLOROETHANE-1,1-DIOL HYDRATE;TRICHLOROACETALDEHYDE HYDRATE;TRICHLOROACETALDEHYDE MONOHYDRATE;'SCHLIFF-AUF';CHLORAL HYDRATE, CRYSTALLIZED;CHLORAL HYDRATE SOLUTION (1 G/ML) REAG. DAB |
| CAS: | 302-17-0 |
| MF: | C2H3Cl3O2 |
| MW: | 165.4 |
| EINECS: | 206-117-5 |
| Product Categories: | Aldehydes;Method 551EPA;Method 8240;500 Series Drinking Water Methods;8000 Series Solidwaste Methods;EPA;Organics;Miscellaneous;Bioactive Small Molecules;Building Blocks;C1 to C6;Carbonyl Compounds;C-CH;Cell Biology;Chemical Synthesis;Organic Building Blocks;302-17-0 |
| Mol File: | 302-17-0.mol |
Chloral hydrate Chemical Properties
| Melting point | 57 °C(lit.) |
| Boiling point | 97 °C |
| density | 1.43 g/mL at 20 °C |
| vapor pressure | 19.998hPa at 25℃ |
| refractive index | 1.4603 (estimate) |
| Fp | 16 °C |
| storage temp. | 0-6°C |
| solubility | Very soluble in water, freely soluble in ethanol (96 per cent). |
| pka | 10(at 25℃) |
| form | A crystalline solid |
| Specific Gravity | 1.91 |
| PH | 3.5-5.5 (20℃, 10%) |
| Water Solubility | 660 g/100 mL |
| Merck | 13,2080 |
| BRN | 1698497 |
| Dielectric constant | 5.5（15℃） |
| Stability: | Stable, but may be air or light sensitive. Incompatible with alcohols, cyanides, iodine, strong bases, carbonates. |
| Major Application | environmental |
| InChI | 1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H |
| InChIKey | RNFNDJAIBTYOQL-UHFFFAOYSA-N |
| SMILES | OC(O)C(Cl)(Cl)Cl |
| LogP | 1.092 at 25℃ |
| CAS DataBase Reference | 302-17-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Chloral hydrate(302-17-0) |
| IARC | 2A (Vol. 63, 84, 106) 2014 |
| EPA Substance Registry System | Chloral hydrate (302-17-0) |
Safety Information
| Hazard Codes | T,F,Xn |
| Risk Statements | 25-36/38-39/23/24/25-23/24/25-11-36/37/38-36-20/21/22 |
| Safety Statements | 26-45-25-23-36/37-16-27 |
| RIDADR | UN 3286 3/PG 2 |
| WGK Germany | 2 |
| RTECS | FM8750000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29055900 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 |
| Hazardous Substances Data | 302-17-0(Hazardous Substances Data) |
| Toxicity | LD50 oral in rat: 479mg/kg |
| Description | Chloral hydrate is one of the oldest sedatives used for dental sedation. It was first synthesized in 1832 by Justus von Liebig and was the first synthetic central nervous system (CNS) depressant. It was used to treat delirium tremens, insomnia, and anxiety, although it is considered an unapproved drug by the US Food and Drug Administration. Initially considered to be a safer alternative to opium, it was noted to produce rapid unconsciousness when combined with ethanol. Physical dependence can occur with chronic use. Chloral hydrate is classified as a sedative-hypnotic and is known to induce sleep in children. It has been very popular in pediatric dentistry since the mid-1950s. Chloral hydrate is rapidly absorbed following oral administration and is converted through its first pass in the liver to trichloroethanol，its active form. Trichloroethanol is conjugated in the liver and excreted in the urine. Like other agents that are metabolized in the liver, chloral hydrate may interact with other drugs, herbs, or foods resulting in clinically significant alterations of the agents (e.g.,warfarin). |
| Chemical Properties | Chloral is a combustible, oily liquid with apungent irritating odor. |
| Uses | Chloral hydrate is used as an intermediate in the production of insecticides, herbicides and hypnotic drugs. It has also been widely used as a sedative or hypnotic drug in humans at oral doses of up to about 750-1000 mg/day. Chloral hydrate is used as a sedative hypnotic, more commonly in pediatrics. With the advent of newer sedative hypnotics, its use has significantly decreased. It is also a drug of abuse, particularly in combination with ethanol to produce an amnestic effect in an individual who ingests it unknowingly. |
| Uses | Trichloroacetaldehyde Hydrate is a useful chemical reagent used as a sedative/hypnotic agent for the short-term treatment of insomnia. First developed in 1832, chloral hydrate is the oldest sleep medication still in use today. This medication is also used to calm you just before surgery or other procedures. It works by affecting certain parts of the brain to cause calmness. Studies have shown that when used in pediatric sedation side effects such as hallucination, excessive sleep and seizures were observed. Drowsiness and trouble waking up in the morning, nausea, vomiting, stomach pain, diarrhea, and headache may occur. Stomach problems can be reduced by taking chloral hydrate with a full glass of water. It is sometimes administered to patients being treated with cyclophosphamide and it is known to inhibit some aldehyde dehydrogenases. Besides, Chloral hydrate is a starting point for the synthesis of other organic compounds. It is the starting material for the production of chloral, which is produced by the distillation of a mixture of chloral hydrate and sulfuric acid, which serves as the desiccant. |
| Definition | ChEBI: Chloral hydrate is an organochlorine compound that is the hydrate of trichloroacetaldehyde. It has a role as a sedative, a general anaesthetic, a mouse metabolite and a xenobiotic. It is an organochlorine compound, an aldehyde hydrate and an ethanediol. |
| Biological Functions | Chloral hydrate (Noctec, Somnos) was developed inthe late 1800s and is still used as a sedative–hypnoticagent. It is a hydrated aldehyde with a disagreeablesmell and taste that is rapidly reduced in vivo totrichloroethanol, which is considered to be the activemetabolite. It produces a high incidence of gastric irritationand allergic responses, occasionally causes cardiacarrhythmias, and is unreliable in patients with liverdamage. |
| 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. |
| 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, dangerousto eyes. Probable carcinogen. |
| Fire Hazard | Flash point data for Chloral hydrate are not available; however, Chloral hydrate is probably combustible. |
| Flammability and Explosibility | Non flammable |
| reaction suitability | reagent type: cross-linking reagent |
| Biochem/physiol Actions | Chloral hydrate is a sedative/hypnotic. |
| Clinical Use | Although it is suggested that chloral hydrate per semay act as a hypnotic,chloral hydrate is very quickly convertedto trichloroethanol, which is generally assumed toaccount for almost all of the hypnotic effect. Thetrichloroethanol is metabolized by oxidation to chloral andthen to the inactive metabolite, trichloracetic acid, which is also extensively metabolized to acylglucuronidesvia conjugation with glucuronic acid. It appears tohave potent barbiturate-like binding to GABAAreceptors.Although an old drug, it still finds use as a sedative in nonoperatingroom procedures for the pediatric patient. |
| 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 synthesizedeither 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 intermediatein the manufacture of such pesticides as DDT, methoxychlor, DDVP, naled, trichlorfon, and TCA. Chloral isalso used in the production of chloral hydrate; used asa therapeutic agent with hypnotic, sedative, and narcoticeffects; used in a time prior to the introduction ofbarbiturates |
| 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, nohistological evaluations have been conducted. |
| Environmental Fate | Chloral hydrate is a CNS depressant, but its mechanism ofaction is not well known. Coingestion with ethanol producesenhanced effects by several mechanisms. First, ethanolcompetes for alcohol and aldehyde dehydrogenase, which thenprolongs the half-life of ethanol. The metabolism of ethanolgenerates the reduced form of NADH, which is a cofactor forthe metabolism of chloral hydrate to its active metabolitetrichloroethanol. Finally, ethanol inhibits the conjugation oftrichloroethanol to its inactive form urochloralic acid. Thisresults 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., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required. |
| Toxicity evaluation | Chloral hydrate has been detected at 5 mg l-1 in the US drinkingwater supply. Although chloral hydrate does not exist naturally,it can be produced as a by-product of chlorination of water atwater treatment facilities, specifically in exposed water withhigh amounts of humic and fulvic substances. |
| Incompatibilities | Chloral hydrate reacts with strong basesforming chloroform. Contact with acids, or exposure tolight may cause polymerization. Reacts with water, formingchloral hydrate. Reacts with oxidizers, with a risk of fire orexplosions. |
| Waste Disposal | Incineration after mixing withanother combustible fuel; care must be taken to assure complete combustion to prevent phosgene formation; an acidscrubber is necessary to remove the halo acids produced. |
Chloral hydrate Preparation Products And Raw materials
| Raw materials | Ethanol-->Chlorine-->Calcium carbonate-->Hydroquinone-->Chloral |
| Preparation Products | Chloral-->Trichloroacetic acid-->5-Methoxy-3-indazolecarboxylic acid-->1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE-->Tenidap-->5-Methoxyisatin-->6-Bromoisatin-->2-AMINO-5,6-DICHLOROBENZOIC ACID-->Etodolac-->4,4'-DDT-->2-Oxiranecarboxylicacid, 3-(trichloromethyl)-, ethyl ester-->5-Chloroisatin-->DCU-->1H,1H,9H-Hexadecafluoro-1-nonanol-->4,7-DIFLUOROISATIN-->5,6-difluoro-indoline-2,3-dione-->2,2,3,3,4,4,4-Heptafluoro-1-butanol |
