Basic information
- CAS
41051-15-4- Standard SMILES
COCC(=O)CC(=O)OC- InChIKey
QGBPKJFJAVDUNC-UHFFFAOYSA-N- Molecular formula
- C6H10O4
- Average molar mass
- 146.14 g/mol
- Monoisotopic mass
- 146.0579088
Names & identifiers
- Preferred name
- Methyl 4-methoxyacetoacetate
- IUPAC
- methyl 4-methoxy-3-oxobutanoate
- English name
- Methyl 4-methoxyacetoacetate
- Molecular formula
- C6H10O4
- Molecular weight
- 146.14
Names & synonyms
Methyl 4-methoxyacetoacetate41051-15-4Butanoic acid, 4-methoxy-3-oxo-, methyl esterMethyl 4-methoxy-3-oxobutyrateEINECS 255-188-9DTXSID1068273RefChem:816503DTXCID5039854255-188-9Methyl 4-methoxy-3-oxobutanoateMFCD00010183Methyl methoxyacetoacetate
Show more names
4-MethoxyacetoacetateMethyl4-methoxyacetateMethyl 4-methoxy-3-oxobuMethyl 4-MethoxyacetoacetatDolutegravir Intermediates2METHYL 4-METHOXYACETOXYACETATEMethyl 3-oxo-4-methoxybutyrate
4-Methoxyacetoacetic Acid Methyl EsterMethyl 4-methoxy-3-oxo-butanoatemethyl-4-methoxyacetoacetate4-methoxy-3-oxo-butyric acid methyl ester4-methoxy-3-oxobutanoic acid methyl estermethyl 4-methoxy-acetoacetateSCHEMBL126506methyl gamma-methoxyacetoacetate
Database identifiers
- CAS
41051-15-4- PubChem CID
- 123500
- DTXSID
DTXSID1068273- EC Number
- 255-188-9
- Nikkaji
- J256.618D
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 130
Physicochemical properties
- Melting point
- -80 ℃ · -80℃
- Boiling point
- 89 °C/8.5 · 89 °C/8.5 mmHg (lit.)
- Density
- 1.129 g/mL · 1.129 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.431(lit.)
- Flash point
- 193 °F · 193 °F
- storage temp.
- Sealed in dry,Room Temperature
- form
- clear liquid
- pka
- 9.88 · 9.88±0.46(Predicted)
- color
- Colorless to Light yellow to Light orange
- Specific Gravity
- 1.129 · 1.129
- BRN
- 1761215 · 1761215
- InChI
- 1S/C6H10O4/c1-9-4-5(7)3-6(8)10-2/h3-4H2,1-2H3
- InChIKey
- QGBPKJFJAVDUNC-UHFFFAOYSA-N
- SMILES
- COCC(=O)CC(=O)OC
- LogP
- 0.34 · 0.340 (est)
- CAS DataBase Reference
- 41051 · 41051-15-4(CAS DataBase Reference)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (96.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Butanoic acid, 4-methoxy-3-oxo-, methyl ester
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesSkin Irrit. 2 (96.4%)
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29189900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationButanoic acid, 4-methoxy-3-oxo-, methyl ester: INACTIVE
Applications
UsesMethyl 4-Methoxyacetoacetate is a reactant in the formation of an abiotic poorphyrinogen in aqueous solution.
UsesMethyl 4-methoxyacetoacetate has been used in generation of a small focused library of diversely functionalized dihydropyrimidine derivatives via one-pot three-component Biginelli cyclocondensation of β-ketoesters, aldehydes and (thio)ureas.
Preparation methods
PreparationThe preparation method of a 4-methoxyl group methyl acetoacetate: add solvents tetrahydrofurane in a kettle. and pass into rare gas element, the temperature in the kettle arranging reactor is 15-25℃, industrial sodium hydride and metal alkaline compound is added under whipped state, add solvents tetrahydrofurane again, the mixed solution reaction 4-6h of methyl alcohol and 4-chloro methyl acetoacetate is dripped in less than 20℃, then be warming up to 20-25℃ and continue reaction 4-15h, TLC detection reaction is complete, reduce system temperature to 6-10℃, add the hydrochloric acid soln regulation system pH=5-7 that volumetric molar concentration is 2mol/L, stratification, after separatory, upper strata is concentrated is spin-dried for removing solvents tetrahydrofurane, then colorless product 4-methoxyl group methyl acetoacetate is obtained by wiped film molecular distillation.
Upstream & downstream products
Upstream raw materials
Related reactions
170 records
Compound notes
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