bis(chloroethyl) ether

{{Chembox

|Verifiedfields=changed

|Watchedfields=changed

|verifiedrevid=

|Name=Bis(chloroethyl) ether

|ImageFile=Bis(chloroethyl) ether.svg

|PIN = 1-Chloro-2-(2-chloroethoxy)ethane

|OtherNames=Oxygen mustard; Bis(2-chloroethyl) ether; 2,2'-Dichlorodiethyl ether; Chlorex; Khloreks; DCEE; 2-Chloroethyl ether; 1,1'-oxybis[2-chloroethane]

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21106016

| SMILES = ClCCOCCCl

| InChI = 1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2

| InChIKey = ZNSMNVMLTJELDZ-UHFFFAOYAN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZNSMNVMLTJELDZ-UHFFFAOYSA-N

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1613350

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 111-44-4

| PubChem = 8115

| EC_number = 203-870-1

| RTECS = KN0875000

| UNNumber = 1916

| UNII = 6K7D1G5M5N

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C14688

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 34573

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|Section2={{Chembox Properties

| C=4 | H=8 | Cl=2 | O=1

| Appearance = Clear liquid

| Odor = Chlorinated solvent-like

| Density = 1.22 g/mL

| Solubility = 10,200 mg/L

| MeltingPtF = -58

| MeltingPt_ref =

| BoilingPtF = 352

| BoilingPt_ref =

| BoilingPt_notes = decomposes

| VaporPressure = 0.7 mmHg (20 °C)

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|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards = Very toxic (T+)
Dangerous for the environment (N)
Vesicant

| NFPA-H = 4

| NFPA-F = 1

| NFPA-R = 1

| FlashPtF = 131

| PEL = TWA 15 ppm (90 mg/m³) [skin]{{PGCH|0196}}

| ExploLimits = 2.7%-?

| IDLH = Ca [100 ppm]

| REL = Ca TWA 5 ppm (30 mg/m³) ST 10 ppm (60 mg/m³) [skin]

| LC50 = 77 ppm (rat, 4 hr)
152 ppm (mouse, 2 hr)
500 ppm (guinea pig, 1 hr){{IDLH|111444|Dichloroethyl ether}}

| LCLo = 250 ppm (rat, 4 hr)
500 ppm (guinea pig, 5 hr)

| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|300|310|315|319|330|351}}

| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|262|264|270|271|280|281|284|301+310|302+350|302+352|303+361+353|304+340|305+351+338|308+313|310|320|321|322|330|332+313|337+313|361|362|363|370+378|403+233|403+235|405|501}}

}}

|Section8={{Chembox Related

| OtherCompounds = Sulfur mustard
Nitrogen mustard
2-Bromoethyl ether

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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.{{cite journal|last1=Wang|first1=Q. Q.|last2=Begum|first2=R. A.|last3=Day|first3=V. W.|last4=Bowman-James|first4=K.|author-link4=Kristin Bowman-James|year=2012|title=Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Wang, Qi-Qiang; Begum, Rowshan Ara; Day, Victor W.; Bowman-James, Kristin|journal=Organic & Biomolecular Chemistry|volume=10|issue=44|pages=8786–8793|doi=10.1039/c2ob26482j|pmid=23070251|s2cid=9721325}}