Methyl acetoacetate

{{chembox

|ImageFile = Methylacetoacetaat structuur.png

|ImageAlt =

| IUPACName = methyl 3-oxobutanoate

|OtherNames = {{ubl|Acetoacetic acid methyl ester|Methyl acetylacetate|3-Oxobutanoic acid methyl ester}}

|Section1={{Chembox Identifiers

|SMILES = COC(=O)CC(C)=O

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

|ChemSpiderID = 13874867

| EC_number = 203-299-8

| UNII = CW4I82QAX1

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

|KEGG =

|PubChem = 7757

|UNNumber = 1993

| ChEBI = 166454

| ChEMBL = 3186053

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

|StdInChI = 1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

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

|StdInChIKey = WRQNANDWMGAFTP-UHFFFAOYSA-N

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

|CASNo = 105-45-3

|RTECS =

}}

|Section2={{Chembox Properties

|C=5|H=8|O=3

|MolarMass =

|Appearance = Colourless liquid

|Odour = Fruit or rum

|Density = 1.076 g/cm³

|Solubility = 40 g/100 mL (20 °C)

|MeltingPtC =

|BoilingPtC = 166

|pKa =

|MagSus =

| RefractIndex = 1.411

}}

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS07}}

| GHSSignalWord = warning

| HPhrases = {{HPhrases|H319}}

| PPhrases = {{PPhrases|P305+P351+P338}}

| GHS_ref = {{GESTIS|ZVG=10400|Date=2021-12-19}}

|NFPA-H = 2

|NFPA-F = 2

|NFPA-R =

|FlashPtC = 70

}}

|Section8={{Chembox Related

|OtherFunction_label = esters

|OtherFunction = {{ubl|Ethyl acetoacetate|Ethyl acetate|Diethyl malonate}}

|OtherCompounds = {{ubl|Acetone|Acetylacetone|Diketene}}

}}

}}

The organic compound methyl acetoacetate is the methyl ester of acetoacetic acid. It is a colorless liquid. It is used as a chemical intermediate. Many of its properties are similar to those for ethyl acetoacetate, which is more common.

At large scale, methyl acetoacetate is industrially produced by treatment of diketene with methanol.{{cite book|doi=10.1002/14356007.a09_565.pub2|chapter=Esters, Organic|year=2005|last1=Riemenschneider|first1=Wilhelm|last2=Bolt|first2=Hermann M.|isbn=3527306730|title=Ullmann's Encyclopedia of Industrial Chemistry|location=Weinheim|publisher=Wiley-VCH}}