Names | |||
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Preferred IUPAC name Chloroacetaldehyde | |||
Systematic IUPAC name Chloroethanal | |||
Other names 2-Chloroacetaldehyde 2-Chloroethanal | |||
Identifiers | |||
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3D model (JSmol) | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.003.158 | ||
EC Number |
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PubChem CID | |||
UNII |
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CompTox Dashboard (EPA) | |||
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Properties | |||
C2H3ClO | |||
Molar mass | 78.50 g mol−1 | ||
Appearance | Colourless liquid | ||
Odor | acrid, penetrating [1] | ||
Density | 1.117 g/mL | ||
Melting point | −16.3 °C (2.7 °F; 256.8 K) hydrate melts at 43–50 °C [1] | ||
Boiling point | 85 to 85.5 °C (185.0 to 185.9 °F; 358.1 to 358.6 K) | ||
soluble [1] | |||
Solubility | organic solvents | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | alkylating agent | ||
GHS labelling: | |||
Danger | |||
H301, H311, H314, H330, H351, H400 | |||
Flash point | 87.7 °C (189.9 °F) (closed cup) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 89 mg/kg (oral, rat) 82 mg/kg (oral, mouse) [2] | ||
LC50 (median concentration) | 200 ppm (rat, 1 hr) [3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | C 1 ppm (3 mg/m3) [4] | ||
REL (Recommended) | C 1 ppm (3 mg/m3) [4] | ||
IDLH (Immediate danger) | 45 ppm [4] | ||
Related compounds | |||
Related compounds | 2-chloroethanol, Chloroacetic acid | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.
Chloroacetaldehyde is a metabolite of the antineoplastic ifosfamide and believed to be responsible for some of the toxicity observed with ifosfamide.
Hydrated chloroacetaldehyde is produced by the chlorination of aqueous vinyl chloride:
It can also be prepared from vinyl acetate [5] or by careful chlorination of acetaldehyde. [1] The related bromoacetaldehyde is prepared via bromination of vinyl acetate. It also rapidly forms an acetals in the presence of alcohols. [6]
Water free chloroacetaldehyde is prepared from the hydrate by azeotropic distillation with chloroform, toluene, or carbon tetrachloride. Anhydrous chloroacetaldehyde reversibly converts to polyacetals. [7] [1] Less reactive chloroacetaldehyde derivatives might be used instead to obtain chloroacetaldehyde or bypass its intermediate formation completely: e.g. chloroacetaldehyde dimethyl acetal (2-chloro-1,1-dimethoxyethane) hydrolyzes in acidic conditions to give chloroacetaldehyde, which may then quickly react with the other reagents [7] instead of polymerizing.
Relevant to its occurrence in humans, it arises via the isomerization of chloroethylene oxide, a metabolite of vinyl chloride. [8]
Chloroacetaldehyde readily hydrates:
Being bifunctional, chloroacetaldehyde is a precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once used in the preparation of sulfathiazole, one of the first sulfa drugs. [5] Chloroacetaldehyde is a building block in the synthesis of the pharmaceuticals altizide, polythiazide, brotizolam, and ciclotizolam. [7] Chloroacetaldehyde is an alkylating agent. It reacts with adenosine and cytidine to give cyclic products containing a fused imidazole group. This reaction is related to the possible mutagenic properties of chloroacetaldehyde. [9]
Chloroacetaldehyde is a metabolite in the degradation of 1,2-dichloroethane, which initially converts to chloroethanol. This metabolic pathway is topical because 1,2-dichloroethane is produced on a large scale as a precursor to vinyl chloride. [10]
Chloroacetaldehyde is corrosive to mucous membranes. It irritates eyes, skin and respiratory tract. [1]
Based on data collected from human studies in 1962, exposures to 45 ppm of chloroacetaldehyde were found to be disagreeable and caused conjunctival irritation to the subjects. [11] The Occupational Safety and Health Administration established a permissible exposure limit at a ceiling of 1 ppm (3 mg/m3) for exposures to chloroacetaldehyde. [12]
Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc" (or "PERC"), and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor, similar to the smell of chloroform, detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985.
Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.
Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant.
Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer, poly(vinyl chloride) (PVC). Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride. Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. Before the 1970s, vinyl chloride was used as an aerosol propellant and refrigerant.
The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.
Iron(III) chloride describes the inorganic compounds with the formula FeCl3(H2O)x. Also called ferric chloride, these compounds are available both in anhydrous and hydrated forms which are both hygroscopic. They are common sources of iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while the hydrate is a mild oxidizing agent. It is used as a water cleaner and as an etchant for metals.
Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.
Barium chloride is an inorganic compound with the formula BaCl2. It is one of the most common water-soluble salts of barium. Like most other water-soluble barium salts, it is a white powder, highly toxic, and imparts a yellow-green coloration to a flame. It is also hygroscopic, converting to the dihydrate BaCl2·2H2O, which are colourless crystals with a bitter salty taste. It has limited use in the laboratory and industry.
Chromium(III) chloride (also called chromic chloride) is an inorganic chemical compound with the chemical formula CrCl3. It forms several hydrates with the formula CrCl3·nH2O, among which are hydrates where n can be 5 (chromium(III) chloride pentahydrate CrCl3·5H2O) or 6 (chromium(III) chloride hexahydrate CrCl3·6H2O). The anhydrous compound with the formula CrCl3 are violet crystals, while the most common form of the chromium(III) chloride are the dark green crystals of hexahydrate, CrCl3·6H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.
Nickel(II) chloride (or just nickel chloride) is the chemical compound NiCl2. The anhydrous salt is yellow, but the more familiar hydrate NiCl2·6H2O is green. Nickel(II) chloride, in various forms, is the most important source of nickel for chemical synthesis. The nickel chlorides are deliquescent, absorbing moisture from the air to form a solution. Nickel salts have been shown to be carcinogenic to the lungs and nasal passages in cases of long-term inhalation exposure.
Cadmium chloride is a white crystalline compound of cadmium and chloride, with the formula CdCl2. This salt is a hygroscopic solid that is highly soluble in water and slightly soluble in alcohol. The crystal structure of cadmium chloride (described below), is a reference for describing other crystal structures. Also known are CdCl2•H2O and the hemipenahydrate CdCl2•2.5H2O.
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.
2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2. They are both colorless liquids with a sweet odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent. In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.
1,1-Dichloroethene, commonly called 1,1-dichloroethylene or vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, but soluble in organic solvents. 1,1-DCE was the precursor to the original clingwrap, Saran, for food, but this application has been phased out.
1,1,2-Trichloroethane, or 1,1,2-TCA, is an organochloride solvent with the molecular formula C2H3Cl3 and the structural formula CH2Cl—CHCl2. It is a colourless, sweet-smelling liquid that does not dissolve in water, but is soluble in most organic solvents. It is an isomer of 1,1,1-trichloroethane.
1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.
Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.
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