Bis(chloroethyl) ether is an organic compound with the formula O(CH2CH2Cl)2. It is an ether with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a chlorinated solvent.[3]
Bis(chloroethyl) ether can be used in the synthesis of the cough suppressant fedrilate. It is combined with benzyl cyanide and two molar equivalents of sodamide in a ring-forming reaction. When treated with strong base, it gives divinyl ether, an anesthetic:[5]
O(CH2CH2Cl)2 + 2 KOH → O(CH=CH2)2 + 2 KCl + 2 H2O
Toxicity
The LD50 is 74 mg/kg (oral, rat).[3] Bis(chloroethyl) ether is considered as a potential carcinogen.[6]
^"CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): Dichloroethyl ether - NIOSH Publications and Products". www.cdc.gov. 2017-11-07. Retrieved 2018-10-31.
January 29, 2023
chloroethyl, ether, organic, compound, with, formula, ch2ch2cl, ether, with, chloroethyl, substituents, colorless, liquid, with, odor, chlorinated, solvent, namespreferred, iupac, name, chloro, chloroethoxy, ethaneother, names, oxygen, mustard, chloroethyl, et. Bis chloroethyl ether is an organic compound with the formula O CH2CH2Cl 2 It is an ether with two 2 chloroethyl substituents It is a colorless liquid with the odor of a chlorinated solvent 3 Bis chloroethyl ether NamesPreferred IUPAC name 1 Chloro 2 2 chloroethoxy ethaneOther names Oxygen mustard Bis 2 chloroethyl ether 2 2 Dichlorodiethyl ether Chlorex Khloreks DCEE 2 Chloroethyl ether 1 1 oxybis 2 chloroethane IdentifiersCAS Number 111 44 4 N3D model JSmol Interactive imageChEBI CHEBI 34573 YChEMBL ChEMBL1613350 YChemSpider 21106016 YECHA InfoCard 100 003 519EC Number 203 870 1KEGG C14688 YPubChem CID 8115RTECS number KN0875000UNII 6K7D1G5M5NUN number 1916CompTox Dashboard EPA DTXSID9020168InChI InChI 1S C4H8Cl2O c5 1 3 7 4 2 6 h1 4H2 YKey ZNSMNVMLTJELDZ UHFFFAOYSA N YInChI 1 C4H8Cl2O c5 1 3 7 4 2 6 h1 4H2Key ZNSMNVMLTJELDZ UHFFFAOYANSMILES ClCCOCCClPropertiesChemical formula C 4H 8Cl 2OMolar mass 143 01 g mol 1Appearance Clear liquid 1 Odor Chlorinated solvent like 1 Density 1 22 g mL 1 Melting point 50 C 58 F 223 K 1 Boiling point 178 C 352 F 451 K 1 decomposesSolubility in water 10 200 mg LVapor pressure 0 7 mmHg 20 C 1 HazardsOccupational safety and health OHS OSH Main hazards Very toxic T Dangerous for the environment N VesicantGHS labelling PictogramsSignal word DangerHazard statements H226 H300 H310 H315 H319 H330 H351Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P260 P262 P264 P270 P271 P280 P281 P284 P301 P310 P302 P350 P302 P352 P303 P361 P353 P304 P340 P305 P351 P338 P308 P313 P310 P320 P321 P322 P330 P332 P313 P337 P313 P361 P362 P363 P370 P378 P403 P233 P403 P235 P405 P501NFPA 704 fire diamond 411Flash point 55 C 131 F 328 KExplosive limits 2 7 1 Lethal dose or concentration LD LC LC50 median concentration 77 ppm rat 4 hr 152 ppm mouse 2 hr 500 ppm guinea pig 1 hr 2 LCLo lowest published 250 ppm rat 4 hr 500 ppm guinea pig 5 hr 2 NIOSH US health exposure limits PEL Permissible TWA 15 ppm 90 mg m3 skin 1 REL Recommended Ca TWA 5 ppm 30 mg m3 ST 10 ppm 60 mg m3 skin 1 IDLH Immediate danger Ca 100 ppm 1 Related compoundsRelated compounds sulfur mustard nitrogen mustardExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N what is Y N Infobox references Contents 1 Reactions and applications 2 Toxicity 3 See also 4 ReferencesReactions and applications EditBis chloroethyl ether is less reactive than the corresponding sulfur mustard S CH2CH2Cl 2 3 In the presence of base it reacts with catechol to form dibenzo 18 crown 6 4 Bis chloroethyl ether can be used in the synthesis of the cough suppressant fedrilate It is combined with benzyl cyanide and two molar equivalents of sodamide in a ring forming reaction When treated with strong base it gives divinyl ether an anesthetic 5 O CH2CH2Cl 2 2 KOH O CH CH2 2 2 KCl 2 H2OToxicity EditThe LD50 is 74 mg kg oral rat 3 Bis chloroethyl ether is considered as a potential carcinogen 6 See also EditBis chloromethyl ether Sulfur mustardReferences Edit a b c d e f g h i j k NIOSH Pocket Guide to Chemical Hazards 0196 National Institute for Occupational Safety and Health NIOSH a b Dichloroethyl ether Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH a b c Wang Q Q Begum R A Day V W Bowman James K 2012 Sulfur Oxygen and Nitrogen Mustards Stability and Reactivity Wang Qi Qiang Begum Rowshan Ara Day Victor W Bowman James Kristin Organic amp Biomolecular Chemistry 10 44 8786 8793 doi 10 1039 c2ob26482j PMID 23070251 S2CID 9721325 Pedersen C J 1972 Macrocyclic Polyethers Dibenzo 18 Crown 6 Polyether and Dicyclohexyl 18 Crown 6 Polyether Organic Syntheses 52 66 Collective Volume vol 6 p 395 Wollweber Hartmund 2000 Anesthetics General Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 289 CDC Immediately Dangerous to Life or Health Concentrations IDLH Dichloroethyl ether NIOSH Publications and Products www cdc gov 2017 11 07 Retrieved 2018 10 31 Retrieved from https en wikipedia org w index php title Bis chloroethyl ether amp oldid 1080824489, wikipedia, wiki, book, books, library,
