Basic information
- Standard SMILES
CCOC(=O)C(C)C(C)=O- InChIKey
FNENWZWNOPCZGK-UHFFFAOYSA-N- Molecular formula
- C7H12O3
- Average molar mass
- 144.17 g/mol
- Monoisotopic mass
- 144.07864424
Overview
structure in first source
Names & identifiers
- Preferred name
- Ethyl 2-methylacetoacetate
- IUPAC
- ethyl 2-methyl-3-oxobutanoate
- English name
- Ethyl 2-methylacetoacetate
- Molecular formula
- C7H12O3
- Molecular weight
- 144.17
Names & synonyms
Ethyl 2-methylacetoacetateEthyl 2-methyl-3-oxobutanoate609-14-3Ethyl 2-acetylpropionateEthyl methylacetoacetateEthyl 2-methyl-3-oxobutyrateButanoic acid, 2-methyl-3-oxo-, ethyl esterEthyl alpha-methylacetylacetateNE9WOZ20JEEthyl alpha-acetylpropionateAcetoacetic acid, 2-methyl-, ethyl esteralpha-Methylacetoacetic ester
Show more names
2-MethylacetoacetateEthyl 2-methylacetacetateNSC 1102Ethyl 2-acetylpropanoateETHYL 2-METHYL-AETACETATE
NSC-1102RefChem:921256210-179-9Ethyl-2-methyl acetoacetateEthyl2-methylacetoacetate2-Methylacetoacetic acid ethyl esterMFCD000091642-methyl-3-oxobutanoic acid ethyl ester
Database identifiers
- CAS
609-14-3- PubChem CID
- 701
- DTXSID
DTXSID2033493- ChEMBL
CHEMBL31596- UNII
- NE9WOZ20JE
- EC Number
- 210-179-9
- Nikkaji
- J101.360B
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 140
Physicochemical properties
- Melting point
- -45 °C · -45 °C
- Boiling point
- 187 °C · 187 °C (lit.)
- Density
- 1.019 g/mL · 1.019 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.418(lit.)
- Flash point
- 145 °F · 145 °F
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 11.98 · 11.98±0.46(Predicted)
- form
- Liquid
- Specific Gravity
- 1.019 · 1.019
- color
- Clear colorless to yellow
- Water Solubility
- IMMISCIBLE
- BRN
- 1071742 · 1071742
- InChI
- 1S/C7H12O3/c1-4-10-7(9)5(2)6(3)8/h5H,4H2,1-3H3
- InChIKey
- FNENWZWNOPCZGK-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C(C)C(C)=O
- LogP
- 1.063 · 1.063 (est)
- CAS DataBase Reference
- 609 · 609-14-3(CAS DataBase Reference)
- FDA UNII
- 9 WOZ20JE · NE9WOZ20JE
- NIST Chemistry Reference
- 2 · Butanoic acid, 2-methyl-3-oxo-, ethyl ester(609-14-3)
- EPA Substance Registry System
- 2 · Butanoic acid, 2-methyl-3-oxo-, ethyl ester (609-14-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 227 · H227
- Precautionary statements
- 210 e-P280a-P370+P378a-P403+P235-P501a · P210e-P280a-P370+P378a-P403+P235-P501a
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Safety Statements
- 24 · 24/25
- RIDADR
- 1993 · 1993
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29182300 · 29182300
- Storage Class
- 10 · 10 - Combustible liquids
Safety & regulation
GHS classification
GHS Classification
Warning
H227 (25%): Combustible liquid [Warning Flammable liquids]
P210, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Butanoic acid, 2-methyl-3-oxo-, ethyl ester
Hazard Classes and CategoriesFlam. Liq. 4 (25%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 1993
- hs_code
- 29182300
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H227
- Precautionary statements
- P210e-P280a-P370+P378a-P403+P235-P501a
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationButanoic acid, 2-methyl-3-oxo-, ethyl ester: ACTIVE
Applications
UsesEthyl 2-methylacetoacetate is used in Japp-Klingemann reaction to prepare hydrazones from beta-keto acid and aryl diazonium salts. It is used as a precursor involved in the synthesis of ethylpyruvate phenylhydrazone via reaction with benzenediazonium chloride.
UsesEthyl 2-methylacetoacetate is used as a substrate in the rhenium-catalyzed synthesis of multisubstituted aromatic compounds.It can be employed in the synthesis of coumarin derivatives via Pechmann condensation.It undergoes dehydration to yield conjugated alkynyl and allenyl esters.It is also used in the total synthesis of chlorotonil A, yangjinhualine A, (+)- and ()-saudin.
Upstream & downstream products
Upstream raw materials
Downstream products
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