エーテル
WordNet
- any of a class of organic compounds that have two hydrocarbon groups linked by an oxygen atom
- a colorless volatile highly inflammable liquid formerly used as an inhalation anesthetic (同)ethoxyethane, divinyl ether, vinyl_ether, diethyl_ether, ethyl_ether
- a medium that was once supposed to fill all space and to support the propagation of electromagnetic waves (同)aether
PrepTutorEJDIC
- エーテル(麻酔などに用いる) / (またaether)《詩》天空,青空
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/09 20:18:15」(JST)
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Bis(chloromethyl) ether
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| Names |
| IUPAC name
bis(chloromethyl) ether
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| Other names
bis-CME, chloro-(chloromethoxy)methane, oxybis(chloromethane), bis-Chloromethyl ether, Chloromethyl ether, Dichlorodimethyl ether, Dichloromethyl ether
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| Identifiers |
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CAS Number
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542-88-1 |
| Abbreviations |
BCME |
| ChemSpider |
21106500 |
| EC Number |
208-832-8 |
| Jmol 3D model |
Interactive image |
| KEGG |
C19158 Y |
| PubChem |
10967 |
InChI
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InChI=1/C2H4Cl2O/c3-1-5-2-4/h1-2H2
Key: HRQGCQVOJVTVLU-UHFFFAOYAN
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| Properties |
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Chemical formula
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C2H4Cl2O |
| Molar mass |
114.95 g·mol−1 |
| Density |
1.33 g/cm3 |
| Melting point |
−41.5 °C (−42.7 °F; 231.7 K) |
| Boiling point |
106 °C (223 °F; 379 K) |
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Solubility in water
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reacts[1] |
| Vapor pressure |
30 mmHg (22°C)[1] |
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Refractive index (nD)
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1.4421[2] |
| Hazards |
| Main hazards |
carcinogen, reacts with water[1] |
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GHS hazard statements
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H225, H302, H311, H330, H350 |
| Flash point |
38 °C (100 °F; 311 K) |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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OSHA-regulated carcinogen[1] |
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REL (Recommended)
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potential occupational carcinogen[1] |
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IDLH (Immediate danger)
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N.D.[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references |
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Bis(chloromethyl) ether is an organic compound with the chemical formula (CH2Cl)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale, but was found to be highly carcinogenic and thus such production has all but ceased.
Contents
- 1 Synthesis
- 2 Uses
- 3 Safety
- 4 See Also
- 5 References
Synthesis
It was produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid.[3] It is also produced as a by-product in the Blanc chloromethylation reaction and is a known impurity in technical grade chloromethyl methyl ether.
Because of their carcinogenic potency, the industrial production of chloromethyl ethers ended in most countries in the early 1980s. Bis(chloromethyl) ether was no exception to this with production in the U.S.A. ending in 1982.
Uses
Bis(chloromethyl) ether has been extensively used in chemical synthesis, primarily as a crosslinking agent in the manufacture of ion-exchange resins and in the textile industry. It was also used as a linker in the synthesis of certain nerve agent antidotes (asoxime chloride, obidoxime). Bis(chloromethyl) was also effective for chloromethylation of aromatic substrates.[4]
Safety
Bis(chloromethyl) ether is carcinogenic.[5][6] It is one of 13 chemicals considered an OSHA-regulated occupational carcinogen.[7] Chronic exposure has been linked to in increased risk of lung cancer.[5]
See Also
- chloromethyl methyl ether - CH2ClOMe
- Bis(chloroethyl) ether - (CH2ClCH2)2O
References
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0128". National Institute for Occupational Safety and Health (NIOSH).
- ^ Evans, L.; Gray, R. (May 1958). "Notes - Preparation of Certain Polychlorodimethyl Ethers". The Journal of Organic Chemistry 23 (5): 745–746. doi:10.1021/jo01099a602.
- ^ Wilhelm Heitmann, Günther Strehlke, Dieter Mayer “Ethers, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a10_023
- ^ Olah, George A.; Beal, David A.; Olah, Judith A. (April 1976). "Aromatic substitution. XXXVIII. Chloromethylation of benzene and alkylbenzenes with bis(chloromethyl)ether, 1,4-bis(chloromethoxy)butane, 1-chloro-4-chloromethoxybutane, and formaldehyde derivatives". The Journal of Organic Chemistry 41 (9): 1627–1631. doi:10.1021/jo00871a032.
- ^ a b "Bis(chloromethyl)ether (BCME) (CASRN 542-88-1)". U.S. environmental protection agency. Retrieved 26 November 2014.
- ^ Van Duuren, BL (August 1989). "Comparison of potency of human carcinogens: vinyl chloride, chloromethylmethyl ether and bis(chloromethyl)ether.". Environmental research 49 (2): 143–51. doi:10.1016/s0013-9351(89)80059-3. PMID 2526731.
- ^ "NIOSH Pocket Guide to Chemical Hazards: bis-Chloromethyl ether". Centers for Disease Control and Prevention. Retrieved 26 November 2014.
UpToDate Contents
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English Journal
- Risk of Lung Cancer in Workers Exposed to Benzidine and/or Beta-Naphthylamine: A Systematic Review and Meta-Analysis.
- Tomioka K1, Saeki K, Obayashi K, Kurumatani N.
- Journal of epidemiology.J Epidemiol.2016 Sep 5;26(9):447-58. doi: 10.2188/jea.JE20150233. Epub 2016 Mar 5.
- PMID 26947956
- Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651.
- El-Brollosy NR1, Loddo R2.
- Drug research.Drug Res (Stuttg).2016 Apr;66(4):181-8. doi: 10.1055/s-0035-1559683. Epub 2015 Aug 27.
- PMID 26313923
- Increased risk of lung cancer associated with occupational exposure to benzidine and/or beta-naphthylamine.
- Tomioka K1, Obayashi K, Saeki K, Okamoto N, Kurumatani N.
- International archives of occupational and environmental health.Int Arch Occup Environ Health.2015 May;88(4):455-65. doi: 10.1007/s00420-014-0974-1. Epub 2014 Aug 24.
- PMID 25151432
Japanese Journal
- Risk of Lung Cancer in Workers Exposed to Benzidine and/or Beta-Naphthylamine: A Systematic Review and Meta-Analysis
- Synthesis and Photoinitiated Cationic Polymerization of Polyfunctional 1-Propenyl Ether Monomers and Polymers Containing Phosphonate Linkage in the Main Chain
- タニデムクライゼン転位 : 新規機能性フェノール誘導体の構築
Related Links
- OSHA Permissible Exposure Limit (PEL): General Industry: 29 CFR 1910.1008 bis(Chloromethyl) ether requirements identical to 29 CFR 1910.1003 -- 13 Carcinogens (4-Nitrobiphenyl, etc.)-- Cancer-Suspect Agent Construction ...
- This page contains information on the chemical bis-Chloromethyl ether including: 34 synonyms/identifiers; U.S. Code of Federal Regulations Title 49 Section 172 shipping regulations and proper shipping name; USDOT 2008 ...