Chloroacetaldehyde

Last updated
Chloroacetaldehyde
Structural formula Chloroacetald.png
Structural formula
Ball-and-stick model Chloroacetaldehyde-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Chloroacetaldehyde
Systematic IUPAC name
Chloroethanal
Other names
2-Chloroacetaldehyde
2-Chloroethanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.158 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-472-8
PubChem CID
UNII
  • InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
    Key: QSKPIOLLBIHNAC-UHFFFAOYSA-N
  • C(C=O)Cl
Properties
C2H3ClO
Molar mass 78.50 g mol−1
AppearanceColourless 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:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H314, H330, H351, H400
Flash point 87.7 °C (189.9 °F) (closed cup)
Lethal dose or concentration (LD, LC):
89 mg/kg (oral, rat)
82 mg/kg (oral, mouse) [2]
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Chloroacetaldehyde is a metabolite of the antineoplastic ifosfamide and believed to be responsible for some of the toxicity observed with ifosfamide.

Synthesis and occurrence

Hydrated chloroacetaldehyde is produced by the chlorination of aqueous vinyl chloride:

ClCH=CH2 + Cl2 + H2O → ClCH2CHO + 2 HCl

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]

Reactions

Chloroacetaldehyde readily hydrates:

Chloroacetaldehyde reaction01.svg

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]

Environmental aspects

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]

Safety

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]

See also

Related Research Articles

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known as perchloroethylene or under the systematic name tetrachloroethene, and abbreviations such as perc, and PCE, is a chlorocarbon with the formula Cl2C=CCl2. It is a non-flammable, stable, colorless and heavy 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 mild sweet, sharp odor, detectable by most people at a concentration of 50 ppm.

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. Most chloromethane is biogenic.

<span class="mw-page-title-main">Vinyl chloride</span> Chemical compound

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 polyvinyl 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.

Iron(III) chloride describes the inorganic compounds with the formula FeCl3(H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated forms which are both hygroscopic. They feature iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while all forms are mild oxidizing agents. It is used as a water cleaner and as an etchant for metals.

<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

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.

<span class="mw-page-title-main">Barium chloride</span> Chemical compound

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.

<span class="mw-page-title-main">Chromium(III) chloride</span> Chemical compound

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.

<span class="mw-page-title-main">Nickel(II) chloride</span> Chemical compound

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.

<span class="mw-page-title-main">Cadmium chloride</span> Chemical compound

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 hemipentahydrate CdCl2•2.5H2O.

<span class="mw-page-title-main">Chloroprene</span> Chemical compound

Chloroprene (IUPAC name 2-chlorobuta-1,3-diene) is a chemical compound with the molecular formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, better known as neoprene, a type of synthetic rubber.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is 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.

<span class="mw-page-title-main">Heptachlor</span> Chemical compound

Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is regulated.

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.

1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2. The two compounds are isomers, each being 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-Dichloroethylene, commonly called vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula CHCl2CH3. 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.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene 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.

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">Chloroacetyl chloride</span> Chemical compound

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical.

References

  1. 1 2 3 4 5 6 The Merck index. S Budavari, M O'Neil, A Smith (12 ed.). Merck. 1996. p. 2108. ISBN   9780911910124.{{cite book}}: CS1 maint: others (link)
  2. ↑ "Chloroacetaldehyde". National Institute for Occupational Safety and Health. 4 December 2014. Retrieved 20 February 2015.
  3. ↑ "Chloroacetaldehyde". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0118". National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 Jira, Reinhard; Kopp, Erwin; McKusick, Blaine C.; Röderer, Gerhard; Bosch, Axel; Fleischmann, Gerald (2007). "Chloroacetaldehydes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_527.pub2. ISBN   978-3527306732.
  6. ↑ S. M. McElvain and D. Kundiger "Bromoacetal" Organic Syntheses 1943, volume 23, p. 8. doi : 10.15227/orgsyn.023.0008.
  7. 1 2 3 Keiji, T (1992-10-30). "α-Chlorocarbonyl Compounds: Their Synthesis and Applications (Commemoration Issue Dedicated to Professor Shigeo Tanimoto On the Occasion of His Retirement)". Bulletin of the Institute for Chemical Research, Kyoto University. 70 (3): 341. hdl:2433/77455. ISSN   0023-6071.
  8. ↑ Swenberg, J. A.; Lu, K.; Moeller, B. C.; Gao, L.; Upton, P. B.; Nakamura, J.; Starr, T. B. (2011). "Endogenous versus Exogenous DNA Adducts: Their Role in Carcinogenesis, Epidemiology, and Risk Assessment". Toxicological Sciences. 120 (Suppl 1): S130–S145. doi:10.1093/toxsci/kfq371. PMC   3043087 . PMID   21163908.
  9. ↑ Singer, B. (1996). "DNA Damage: Chemistry, Repair, and Mutagenic Potential". Regulatory Toxicology and Pharmacology. 23 (1 Pt 1): 2–13. doi:10.1006/rtph.1996.0002. PMID   8628915.
  10. ↑ Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and Biochemistry of 1,2-Dichloroethane Degradation", Biodegradation, 1994, 5, 249-57. doi : 10.1007/BF00696463
  11. ↑ Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs)
  12. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.