Ethyl benzoylacetate
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Basic information
- CAS
94-02-0- Standard SMILES
CCOC(=O)CC(=O)c1ccccc1- InChIKey
GKKZMYDNDDMXSE-UHFFFAOYSA-N- Molecular formula
- C11H12O3
- Average molar mass
- 192.21 g/mol
- Monoisotopic mass
- 192.07864424
Overview
Ethyl 3-oxo-3-phenylpropanoate is an aromatic ketone.
Names & identifiers
- Preferred name
- Ethyl benzoylacetate
- IUPAC
- ethyl 3-oxo-3-phenylpropanoate
- English name
- Ethyl benzoylacetate
- Molecular formula
- C11H12O3
- Molecular weight
- 192.21
Names & synonyms
ETHYL BENZOYLACETATE94-02-0Ethyl benzoyl acetateBenzoylacetic acid ethyl esterAcetic acid, benzoyl-, ethyl esterBenzenepropanoic acid, beta-oxo-, ethyl esterFEMA No. 2423DTXSID4047094K8CHJ4MKM0NSC-6774NSC-227214DTXCID2027094
Show more names
FEMA 2423AKOS 92622AKOS BBS-00004233Ethylbenzoylacetatthyl benzoylacetate
RefChem:1085027202-295-3Ethyl 3-oxo-3-phenylpropanoateEthyl beta-oxobenzenepropanoateBenzoylacetic acid, ethyl esterEthyl 3-oxo-3-phenylpropionateEthyl 3-phenyl-3-oxopropanoateMFCD00009196
Database identifiers
- CAS
94-02-0- PubChem CID
- 7170
- DTXSID
DTXSID4047094- ChEMBL
CHEMBL3182719- ChEBI
CHEBI:173927- UNII
- K8CHJ4MKM0
- EC Number
- 202-295-3
- Nikkaji
- J60.326K
Properties
Computed structural propertiesFilling in
- XLogP
- 1.9
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 205
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Ethyl benzoylacetate) -> IFRA transparency List
LogP
1.87
1.87
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.107-1.120
Flavoring AgentsEU Flavoring substances
Solubility
insoluble in water; soluble in organic solvents, oils
miscible at room temperature (in ethanol)
Boiling Point
265.00 to 270.00 °C. @ 760.00 mm Hg
147 °C (11 mm Hg)
Melting Point< 0 °C
Refractive Index1.524-1.533
Physical Description
Liquid with a pleasant odor; Turns yellow from light and air; [Merck Index] Colorless or yellow liquid; [Alfa Aesar MSDS]
Liquid
colourless to light yellow liquid with a brandy-like, woody, cherry, phenolic odour
Physicochemical properties
- Melting point
- 0 °C · <0 °C
- Boiling point
- 265 · 265-270 °C (lit.)
- Density
- 1.11 g/mL · 1.11 g/mL at 25 °C (lit.)
- vapor density
- 6.6 · 6.6 (vs air)
- vapor pressure
- 1 hPa · 1 hPa (108 °C)
- FEMA
- 2423 · 2423 | ETHYL BENZOYLACETATE
- refractive index
- 20 · n20/D 1.52(lit.)
- FLAVIS Number
- 9.476 · 09.476 | Ethyl 3-phenyl-3-oxopropionate
- Flash point
- 147 °F · 147 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- alcohol: miscible
- form
- Powder
- pka
- 9.85 · 9.85±0.23(Predicted)
- color
- Brown
- Odor
- 100 % · at 100.00 %. fruity cherry naphthyl hawthorn cumin phenolic almond spicy woody maraschino cherry
- Odor Type
- fruity
- Water Solubility
- INSOLUBLE
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,3767
- JECFA Number
- 834 · 834
- BRN
- 389944 · 389944
- Dielectric constant
- 12.8 · 12.8(20℃)
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3
- InChIKey
- GKKZMYDNDDMXSE-UHFFFAOYSA-N
- SMILES
- CCOC(=O)CC(=O)c1ccccc1
- LogP
- 1.87 · 1.87
- CAS DataBase Reference
- 94 · 94-02-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ETHYL BENZOYLACETATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8 CHJ4MKM0 · K8CHJ4MKM0
- NIST Chemistry Reference
- Ethyl benzoylacetate(94-02-0)
- EPA Substance Registry System
- Benzenepropanoic acid, .beta.-oxo-, ethyl ester (94-02-0)
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Safety Statements
- 24 · 24/25
- WGK Germany
- 2 · 2
- RTECS
- 4878000 · AF4878000
- Autoignition Temperature
- 375 °C · 375 °C DIN 51794
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29183000 · 29183000
- Storage Class
- 10 · 10 - Combustible liquids
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 5000 mg/kg
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 98.2% (107 of 109) of all reports.
Not Classified
Aggregated GHS information provided per 109 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Benzenepropanoic acid, .beta.-oxo-, ethyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 19-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33015
Benzenepropanoic acid, .beta.-oxo-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzenepropanoic acid, .beta.-oxo-, ethyl ester: Environment tier I assessment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AF4878000
- hs_code
- 29183000
- Toxicity
- LD50 orally in Rabbit: > 5000 mg/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- hazard_class
- IRRITANT
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302-H315-H319-H332-H335
- REACH Registrations
- Active
- Autoignition Temperature
- 375 °C DIN 51794
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzenepropanoic acid, .beta.-oxo-, ethyl ester: ACTIVE
Applications
UsesEthyl benzoylacetate (Best) is used as intermediate for different organic synthesis. Product Data Sheet
UsesEthyl benzoylacetate (Best) is used as an intermediate for different organic synthesis Product Data Sheet
UsesEthyl benzoylacetate (Benzoylacetic acid ethyl ester) was used to prepare ethyl 2-fluoro-2-benzolyacetate. It was also used to synthesize iodonium ylides.
General DescriptionEthyl benzoylacetate is an ester. It undergoes microbial reduction by bakers′ yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum to afford ethyl (S)-3-hydroxy-3-phenylpropionate. It undergoes Claisen condensation reaction with malononitrile to afford 2-cyano-5-phenyl-3,5-dioxopentanonitrile which on cyclization followed by coupling with diazonium salts yields azo derivatives.
Preparation methods
PreparationBy condensation of ethyl benzoate with ethyl acetate (via Claisen condensation) using sodium ethoxide; another method also known.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Ethyl 3-oxo-3-phenylpropanoate is an aromatic ketone.
Related reactions
274 records
Compound notes
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