Methyl hypochlorite

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 458444954

| ImageFile = Methyl hypochlorite.svg

| ImageFileR1 = Methyl hypochlorite Space Fill 3D.png

| ImageSizeR1 = 150px

| ImageFileL1 = Methyl hypochlorite Ball and Stick 3D.png

| ImageSizeL1 = 150px

| PIN = Methyl hypochlorite

| OtherNames = (Chlorooxy)methane; Hypochlorous acid methyl ester; Methoxy chloride

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 593-78-2

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

| StdInChI = 1S/CH3ClO/c1-3-2/h1H3

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

| StdInChIKey = UCFFGYASXIPWPD-UHFFFAOYSA-N

| PubChem = 79056

| ChemSpiderID = 71388

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

| SMILES = COCl

| InChI = 1S/CH3ClO/c1-3-2/h1H3

| InChIKey = UCFFGYASXIPWPD-UHFFFAOYSA-N}}

|Section2={{Chembox Properties

| C=1 | H=3 | Cl=1 | O=1

| Appearance = Gas

| Odor = Pungent

| Solubility = Decomposes

| Solvent1 = Water

| Solubility1 =

| Solvent2 =

| Solubility2 =

| SolubleOther =

| Density = 1.058 g/cm³

| MeltingPtC = -120.4

| BoilingPtC = 9.18

| RefractIndex = 1.343

| pKa =

}}

|Section7={{Chembox Hazards

| ExternalSDS =

| NFPA-H = 4

| NFPA-F =

| NFPA-R = 4

| FlashPt =

| GHSPictograms = {{GHS01}}{{GHS02}}{{GHS05}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|}}

| PPhrases = {{P-phrases|}}

| LD50 =

}}

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Methyl hypochlorite is the simplest of the organic alkyl hypochlorites. It is an unstable compound that can be produced by the reaction of methanol with hypochlorous acid.{{cite journal |last1=Taylor |first1=M. C. |last2=MacMullin |first2=R. B. |last3=Gammal |first3=C. A. |title=Hypochlorous Acid and the Alkyl Hypochlorite |journal=Journal of the American Chemical Society |date=February 1925 |volume=47 |issue=2 |pages=395–403 |doi=10.1021/ja01679a017}} It was first synthesized by Traugott Sandmeyer in the 1880s.{{cite journal |last1=Sandmeyer |first1=Traugott |title=Ueber Aethyl- und Methylhypochlorit |journal=Berichte der Deutschen Chemischen Gesellschaft |date=January 1886 |volume=19 |issue=1 |pages=857–861 |doi=10.1002/cber.188601901196|url=https://zenodo.org/record/1425421}}

Methyl hypochlorite forms in the Earth's atmosphere by a reaction between ClO and CH₃OO and is thought to be an important species in ozone destruction over the Arctic and Antarctic regions.{{cite journal |last1=Helleis |first1=Frank |last2=Crowley |first2=John |last3=Moortgat |first3=Geert |title=Temperature dependent CH₃OCl formation in the reaction between CH₃O₂ and ClO |journal=Geophysical Research Letters |date=15 August 1994 |volume=21 |issue=17 |pages=1795–1798 |doi=10.1029/94GL01280|bibcode=1994GeoRL..21.1795H}}