Ethyl benzoylacetate (HCID 7170)

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 properties

XLogP: 1.9
Topological polar surface area: 43.4 Å²
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 · 2 items

1.87

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.107-1.120

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

GHS classification

GHS Classification · 3 items

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 · 4 items

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 · 3 items

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationBenzenepropanoic acid, .beta.-oxo-, ethyl ester: ACTIVE

Applications · 4 items

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

NORDALBERGIN ETHYL 2-HYDROXY-4-PHENYLPYRIMIDINE-5-CARBOXYLATE ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE RUFLOXACIN PHENOXYACETIC ACID Ciprofloxacin hydrochloride 3-(4-OXO-6-PHENYL-1,4-DIHYDRO-PYRIMIDIN-2-YLSULFANYL)-PROPIONIC ACID Ethyl 2-amino-4-phenyl-5-thiazolecarboxylate ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE 2,4-DIPHENYL-1,3-THIAZOLE-5-CARBALDEHYDE ETHYL 2-HYDRAZINYL-4-PHENYLPYRIMIDINE-5-CARBOXYLATE 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBONYL CHLORIDE

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: Ethyl 3-oxo-3-phenylpropanoate is an aromatic ketone.

Related reactions

274 records

New reaction record

HRID 8347As reactantuspto-grants-2006_08

HRID 17825As reactantuspto-grants-2010_06

HRID 17880As reactantuspto-grants-2010_06

HRID 18656As reactantuspto-grants-2010_06

HRID 21571As reactantuspto-grants-1995_06

HRID 23307As reactantuspto-grants-2005_02

HRID 25872As reactantuspto-grants-1979_04

HRID 29888As reactantuspto-grants-2008_09

Linked notes

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Basic information