Ethyl methacrylate

{{short description|Organic compound}}

{{Chembox

| ImageFile = Ethyl methacrylate.svg

| ImageSize = 200px

| ImageAlt =

| PIN = Ethyl 2-methylprop-2-enoate

| OtherNames = Ethyl 2-methylpropenoate, Acryester E, Acryester BMA

|Section1={{Chembox Identifiers

| CASNo = 97-63-2

| ChemSpiderID = 7066

| PubChem = 7343

| EC_number = 202-597-5

| RTECS = OZ4550000

| UNNumber = 2277

| UNII = 80F70CLT4O

| ChEMBL = 3182984

| DTXSID = DTXSID1025308

| StdInChI=1S/C6H10O2/c1-4-8-6(7)5(2)3/h2,4H2,1,3H3

| StdInChIKey = SUPCQIBBMFXVTL-UHFFFAOYSA-N

| SMILES = CCOC(=O)C(=C)C

}}

|Section2={{Chembox Properties

| C=6|H=10|O=2

| MolarMass =

| Appearance = Colorless liquid

| Density = 0.9135 g/cm³

| MeltingPtC =

| BoilingPtC = 117

| Solubility = }}

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS02}}{{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|225|315|317|319|335}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|272|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|333+313|337+313|362|363|370+378|403+233|403+235|405|501}}

| NFPA-H = 2

| NFPA-F = 3

| NFPA-R = 2

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Ethyl methacrylate is the organic compound with the formula C₂H₅O₂CC(CH₃)=CH₂. A colorless liquid, it is a common monomer for the preparation of acrylate polymers.{{Ullmann|first1=William|last1=Bauer, Jr.|title=Methacrylic Acid and Derivatives|year=2002|doi=10.1002/14356007.a16_441}}. It is typically polymerized under free-radical conditions.{{cite journal|title=Controlled Radical Polymerization of Methacrylic Monomers in the Presence of a Bis(ortho-chelated) Arylnickel(II) Complex and Different Activated Alkyl Halides|last1=Granel, C.|last2=Dubois |first2=Ph.|last3=Jérôme |first3=R.|last4=Teyssié |first4=Ph.|journal=Macromolecules|year=1996|volume=29|issue=27|pages=8576–8582|doi=10.1021/ma9608380|bibcode=1996MaMol..29.8576G}}

Ethyl methacrylate was first obtained by treating ethyl 2-hydroxyisobutyrate with phosphorus pentachloride in a dehydration reaction.{{cite journal|journal=Justus Liebigs Annalen der Chemie|volume= 136|page= 12|title=Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe|author=E. Frankland, B. F. Duppa|year=1865|doi=10.1002/jlac.18651360102|url= https://zenodo.org/record/1427247}}