1-Phenyl-1-propanone

HCID 7148CAS 93-55-0

Basic information

Standard SMILES
CCC(=O)c1ccccc1
InChIKey
KRIOVPPHQSLHCZ-UHFFFAOYSA-N
Molecular formula
C9H10O
Average molar mass
134.17 g/mol
Monoisotopic mass
134.07316494

Overview

Propiophenone is an aromatic ketone in which the two substituents on the carbonyl C atom are phenyl and ethyl. It has a role as a fragrance.

Names & identifiers

Preferred name
1-Phenyl-1-propanone
IUPAC
1-phenylpropan-1-one
English name
1 -Phenyl-1 -propanone
Molecular formula
C9H10O
Molecular weight
134.1751

Names & synonyms

1-Phenyl-1-propanoneRefChem:1056285Propiophenone93-55-01-phenylpropan-1-oneEthyl phenyl ketonePropionylbenzenePHENYL ETHYL KETONE1-Propanone, 1-phenyl-Ketone, ethyl phenylUSAF EK-1235Propionphenone
Show more names
1-Phenyl-propan-1-oneFEMA No. 3469NSC 169372-methyl-acetophenoneDTXSID2044470MFCD00009309E599A8OKQHNSC-16937

Database identifiers

CAS
93-55-0
PubChem CID
7148
DTXSID
DTXSID2044470
ChEMBL
CHEMBL193446
ChEBI
CHEBI:425902
UNII
E599A8OKQH
EC Number
202-257-6
Nikkaji
J22.071J

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 items

Log Kow = 2.19

2.19

2.3

OdorSTRONG, PERSISTENT, AGREEABLE, FLOWERY ODOR
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 items

1.0105 @ 20 °C/4 °C, LIQ

1.004-1.014

Physicochemical properties

Melting point
21 °C · 21 °C
Boiling point
218 °C · 218.0 °C
Density
1.008 g/cm3 · 1.008 g/cm3(Temp: 16 °C)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 70.8% (92 of 130) of all reports.

Warning

H319 (29.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 130 reports by companies from 5 notifications to the ECHA C&L Inventory.

Danger

Hazard information

Regulatory Information · 4 items

Chemical: 1-Propanone, 1-phenyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 15-12-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/11044

1-Propanone, 1-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME. CAN REACT WITH OXIDIZING MATERIALS
Hazards SummarySafe when used as a flavoring agent; [JECFA] An eye and respiratory tract irritant; [HSDB] May cause irritation; [MSDSonline] See Acetophenone.
Hazard Classes and Categories · 2 items

Eye Irrit. 2A (29.2%)

Flammable liquids - Category 4

Skin, Eye, and Respiratory IrritationsVAPORS ARE IRRITATING TO EYES & RESPIRATORY SYSTEM

Safety & protection

Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEM.
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 2 items

ALL OPERATIONS INVOLVING USE OF KETONES SHOULD BE CONDUCTED IN WELL-VENTILATED CONDITIONS, EG BY PROVISION OF EFFICIENT EXHAUST VENTILATION. /KETONES/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Toxicology

Body BurdenPhenyl ethyl ketone is a component (mean concentration from 54 urban nonsmoking subjects was 0.261 ng/L) of normal human expired air(1).
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 370(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phenyl ethyl ketone will have moderate mobility in soil(SRC). Volatilization of phenyl ethyl ketone may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), calculated from an experimental vapor pressure(5) and water solubility(5) values, and from dry soil surfaces(SRC) based on an experimental vapor pressure of 1.5 mm Hg(5). Phenyl ethyl ketone will not be susceptible to direct photolysis on soil surfaces based upon its lack of absorption of light at wavelengths >290 nm(6). Insufficient data are available to determine the rate or importance of biodegradation of phenyl ethyl ketone in soil(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 370(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phenyl ethyl ketone may adsorb to suspended solids and sediment(SRC) in the water. Phenyl ethyl ketone may volatilize from water surfaces based on an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), calculated from experimental vapor pressure(4) and water solubility(4) values. Estimated half-lives for a model river and model lake are 11 hours and 7 days, respectively(3,SRC). An estimated BCF value of 27(3,SRC), from an experimental log Kow(2), suggests that phenyl ethyl ketone will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Phenyl ethyl ketone will not be susceptible to direct photolysis on water surfaces based upon its lack of absorption of light at wavelengths >290 nm(6). Insufficient data are available to determine the rate or importance of biodegradation of phenyl ethyl ketone in water(SRC).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 1.5 mm Hg at 25 °C(2,SRC) indicates that phenyl ethyl ketone will exist in the vapor in the ambient atmosphere. Vapor-phase phenyl ethyl ketone is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 5 days(3,SRC). Phenyl ethyl ketone will not be susceptible to direct photolysis based upon its lack of absorption of light at wavelengths >290 nm(4).

Food Survey ValuesPhenyl ethyl ketone has been qualitatively identified as a volatile component of roasted filberts(1).
Effluent Concentrations · 1 item

Phenyl ethyl ketone has been detected in one sample of wastewater from the organic chemicals industry at 29 ng/ul extract(1). Phenyl ethyl ketone was also found at concentrations of 20, 200, 220, and 120 ug/mL in a test blank, and three different samples, respectively, of combustion products from different incineration test sites(2).

Soil Adsorption/Mobility · 1 item

The Koc of phenyl ethyl ketone is estimated as approximately 370(SRC), using an experimental log Kow of 2.19(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that phenyl ethyl ketone has medium mobility in soil(SRC).

TSCA Test Submissions · 1 item

A case study for propiophenone (CAS # 93-55-0) was reported regarding a spill that occurred at Union Carbide Corp's, South Charleston, West Virginia Plant. Two male and one female maintenance employees reported urinary dysfunction (bladder fullness, bladder pain, urgency, urinary frequency, and small volume of urine upon voiding) after cleaning up the propiophenone spill. Urinary dysfunction symptoms manifested several hours after exposure. The route of exposure was presumed to be via inhalation, because the employees were protected from ingestion and skin absorption of the chemical. The air concentration was above the threshold odor level and the levels of chemical exposure are not known.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

YIELDS 1-PHENYL-1-PROPANOL IN RABBIT. /FROM TABLE/

PROPIOPHENONE...REDUCED IN RABBIT TO CORRESPONDING CARBINOLS, IE, (-)-ETHYLPHENYLCARBINOL...

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 3 items

Used in perfumery; to make ephedrine, other pharmaceuticals, and organic chemicals; as laboratory reagent; [HSDB]

IN PERFUMERY; IN SYNTHESIS OF EPHEDRINE & RELATED COMPOUNDS

SYNTHESIS OF PHARMACEUTICALS & ORG CHEMICALS; LABORATORY REAGENT

Methods of Manufacturing · 3 items

PREPARED FROM PROPIONYL CHLORIDE AND BENZENE IN PRESENCE OF ANHYDROUS ALUMINUM CHLORIDE. NUMEROUS OTHER SYNTHESES. ... USUALLY SUPPLIED AS A LIQ.

From the Hock process for the production of phenol from isopropylbenzene; it is isolated from the residue of this process.

Oxidation of ethylbenzene with air or oxygen at 130 °C and 0.5 MPa. Catalysts include cobalt salts or manganese salts of naphthenic or fatty acids.

Use Classification · 5 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 items

1-Propanone, 1-phenyl-: ACTIVE

ORGANOLEPTIC CHARACTERISTICS: ACETOPHENONE CHERRY, WATERMELON AROMA & TASTE BELOW 5 PPM; REGULATORY STATUS: 3469; FLAVORS USEFUL IN: TRACES IN CHERRY, HONEY.

Friedel-Crafts acetylation of benzene with acetic anhydride (of no industrial importance).

Related reactions

150 records

Linked notes

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