2-Chloroethanol

2-Chloroethanol
Ball and stick model of 2-chloroethanol	Spacefill model of 2-chloroethanol
Names
	Preferred IUPAC name 2-Chloroethan-1-ol
	Other names 2-Chloroethanol; beta-Chloroethanol; 2-Chloro-1-ethanol; β-Chloroethanol; δ-Chloroethanol; 2-Chloroethyl alcohol; Ethyl chlorhydrin; Ethylene chlorohydrin; Glycol chlorohydrin; Glycol monochlorohydrin; 2-Hydroxyethyl chloride; β-Hydroxyethyl chloride; 2-Monochloroethanol;
Identifiers
CAS Number	107-07-3 ;
3D model (JSmol)	Interactive image ;
3DMet	B01042 ;
Beilstein Reference	878139
ChEBI	CHEBI:28200 ;
ChEMBL	ChEMBL191244 ;
ChemSpider	21106015 ;
ECHA InfoCard	100.003.146
EC Number	203-459-7;
Gmelin Reference	25389
KEGG	C06753 ;
MeSH	Ethylene+Chlorohydrin
PubChem CID	34 ;
RTECS number	KK0875000;
UNII	753N66IHAN ;
UN number	1135
CompTox Dashboard (EPA)	DTXSID1021877 ;
	InChI InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N ;
	SMILES OCCCl;
Properties
Chemical formula	C2H5ClO
Molar mass	80.51 g·mol−1
Appearance	Colourless liquid
Odor	ether-like
Density	1.201 g/mL
Melting point	−62.60 °C; −80.68 °F; 210.55 K
Boiling point	127–131 °C; 260–268 °F; 400–404 K
Solubility in water	Miscible
log P	−0.107
Vapor pressure	700 Pa (at 20 °C)
Refractive index (nD)	1.441
Thermochemistry
Std enthalpy of; combustion (ΔcH⦵298)	−1.1914 MJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic and flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H300+H310+H330
Precautionary statements	P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)	4 2 0
Flash point	55 °C (131 °F; 328 K)
Autoignition; temperature	425 °C (797 °F; 698 K)
Explosive limits	5–16%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	67 mg/kg (dermal, rabbit)[ citation needed ]; 72 mg/kg (rat, oral); 81 mg/kg (mouse, oral); 71 mg/kg (rat, oral); 110 mg/kg (guinea pig, oral);
LC50 (median concentration)	7.5 ppm (rat, 1 h); 32 ppm (rat, 4 h); 260 ppm (guinea pig); 33 ppm (rat, 4 h); 87 ppm (rat); 115 ppm (mouse);
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (16 mg/m3) [skin]
REL (Recommended)	C 1 ppm (3 mg/m3) [skin]
IDLH (Immediate danger)	7 ppm
Related compounds
Related compounds	Chloromethane ; Chloroiodomethane ; Bromochloromethane ; Dibromochloromethane ; Isobutyl chloride ; 2-Bromo-1-chloropropane ;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Last updated January 26, 2023

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).^[6] 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.^[7]

Synthesis and applications

2-Chloroethanol is produced by treating ethylene with hypochlorous acid:^[7]

2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:

HOCH₂CH₂Cl + NaOH → C₂H₄O + NaCl + H₂O

This application has been supplanted by the more economic direct oxidation of ethylene. Otherwise chloroethanol is still used in the production of pharmaceuticals, biocides, and plasticizers.^[7] Many of these applications entail its use in installing 2-hydroxyethyl groups.^[8] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.^[9] It is also used for manufacture of thiodiglycol.

It is a solvent for cellulose acetate and ethyl cellulose, textile printing dyes, in dewaxing, refining of rosin, extraction of pine lignin, and the cleaning of machines.

Environmental aspects

Chloroethanol is a metabolite in the degradation of 1,2-dichloroethane. The alcohol is then further oxidized via chloroacetaldehyde to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor to vinyl chloride.^[10]

Safety

2-Chloroethanol is toxic with an LD₅₀ of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol releases hydrochloric acid and phosgene when burned.

In regards to dermal exposure to 2-chloroethanol, the Occupational Safety and Health Administration has set a permissible exposure limit of 5 ppm (16 mg/m³) over an eight-hour time-weighted average, while the National Institute for Occupational Safety and Health has a more protective recommended exposure limit of a 1 ppm (3 mg/m³) exposure ceiling.^[11]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[12]^{[ failed verification ]}

Related Research Articles

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (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 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.

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C^₂H^₄Br^₂. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

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). About 13 million metric tonne are produced annually. VCM is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States currently remains the largest VCM 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 VCM. Vinyl chloride is a gas with a sweet odor. It is highly toxic, flammable, and 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. In the past VCM was used as a refrigerant.

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C₆H₄(NH₂)₂. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

<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.

Methylamine is an organic compound with a formula of CH₃NH₂. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

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

Phosphorus trichloride is an inorganic compound with the chemical formula PCl₃. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

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

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.

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<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH₂=CHCH₂OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<span class="mw-page-title-main">Propan-1-ol</span> Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH₃CH₂CH₂OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

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

Crotonaldehyde is a chemical compound with the formula CH₃CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

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Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

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Methyl cyanoacrylate (MCA) is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

<span class="mw-page-title-main">Clopidol</span>

Clopidol is an organic compound that is used as in veterinary medicine as a coccidiostat. It is prepared industrially by a multistep process from dehydroacetic acid.

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

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.

References

1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 29. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. For example, the omission of the locant '1' in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.
1 2 3 4 5 6 7 8 9 10 11 12 Depositor-supplied synonyms for CID 34.
1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).
1 2 "Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
"NFPA Chemicals". New Environment Inc.
↑ Ethylene chlorohydrin: properties
1 2 3 Liu, Gordon Y. T.; Richey, W. Frank; Betso, Joanne E.; et al. (2014). "Chlorohydrins". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_565.pub2.
↑ Butler J; Kellogg R (1987). "Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane". Organic Syntheses. 65 (150): 150. doi:10.15227/orgsyn.065.0150.
↑ Raue, Roderich; Corbett, John F. (2002). "Nitro and Nitroso Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383.
↑ Janssen, D. B.; van der Ploeg, J. R.; Pries, F. (1994). "Genetics and Biochemistry of 1,2-Dichloroethane Degradation" (PDF). Biodegradation. 5 (3–4): 249–57. doi:10.1007/BF00696463. PMID 7765836. S2CID 475768.
↑ CDC - NIOSH Pocket Guide to Chemical Hazards
↑ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.

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[iupac2013-1] 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 29. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. For example, the omission of the locant '1' in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.

[pubchem-2] 1 2 3 4 5 6 7 8 9 10 11 12 Depositor-supplied synonyms for CID 34.

[PGCH-3] 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] 1 2 "Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[5] "NFPA Chemicals". New Environment Inc.

[6] Ethylene chlorohydrin: properties

[Ullmann-7] 1 2 3 Liu, Gordon Y. T.; Richey, W. Frank; Betso, Joanne E.; et al. (2014). "Chlorohydrins". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_565.pub2.

[8] Butler J; Kellogg R (1987). "Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane". Organic Syntheses. 65 (150): 150. doi:10.15227/orgsyn.065.0150.

[9] Raue, Roderich; Corbett, John F. (2002). "Nitro and Nitroso Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383.

[10] Janssen, D. B.; van der Ploeg, J. R.; Pries, F. (1994). "Genetics and Biochemistry of 1,2-Dichloroethane Degradation" (PDF). Biodegradation. 5 (3–4): 249–57. doi:10.1007/BF00696463. PMID 7765836. S2CID 475768.

[11] CDC - NIOSH Pocket Guide to Chemical Hazards

[12] "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.

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