Propylbenzene

HCID 7668CAS 103-65-1

Basic information

Standard SMILES
CCCc1ccccc1
InChIKey
ODLMAHJVESYWTB-UHFFFAOYSA-N
Molecular formula
C9H12
Average molar mass
120.19 g/mol
Monoisotopic mass
120.09390038

Overview

N-propyl benzene appears as a clear colorless liquid. Insoluble in water and less dense than water. Flash point 86 °F. Mildly toxic by ingestion and inhalation. Used to make other chemicals.

Names & identifiers

Preferred name
Propylbenzene
IUPAC
propylbenzene
English name
N-PROPYLBENZENE
Molecular formula
C9H12
Molecular weight
120.19

Names & synonyms

PropylbenzeneN-PROPYLBENZENE103-65-11-PhenylpropanePhenylpropaneIsocumeneBenzene, propyl-1-PropylbenzeneDTXSID30422190WR86ZHG2ZNSC-16941DTXCID1022219
Show more names
IsocomenePropylbenzolbenzene,propyl-propylbenzene solutionpropyl-benzen
CHEBI:42630benzene, propylRefChem:6174203-132-9n-Propyl benzenePropylbenzene, n-Propyl-benzeneNSC 16941

Database identifiers

CAS
103-65-1
PubChem CID
7668
DTXSID
DTXSID3042219
ChEMBL
CHEMBL286062
ChEBI
CHEBI:42630
UNII
0WR86ZHG2Z
EC Number
203-132-9
Nikkaji
J5.516F

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
9

Experimental & physicochemical properties

Chemical Classes · 2 items

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

SolventsSolvents -> Aromatic Solvents
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 items

log Kow= 3.69

3.79

Density · 3 items

0.862 (USCG, 1999) - Less dense than water; will float

Specific gravity: 0.8620 @ 20 °C/4 °C

0.8593 @25 °C

Color/Form · 2 items

Colorless liquid

Liquid

Physicochemical properties

Melting point
-99 °C · -99 °C (lit.)
Boiling point
159 °C · 159 °C (lit.)
Density
0.862 g/mL · 0.862 g/mL at 25 °C (lit.)
vapor density
4.14 · 4.14 (vs air)
vapor pressure
2 mm · 2 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.491(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P301+P316, P303+P361+P353, P304+P340, P319, P331, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1188) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: Benzene, propyl-

Hazard Traits - Nephrotoxicity and Other Toxicity to the Urinary System

Benzene, propyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, propyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Propylbenzene: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 2 items

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire Potential · 2 items

Flammable, moderate fire risk.

A very dangerous fire hazard when exposed to heat, flame, or oxidizers ...

Health Hazards · 2 items

May be harmful by inhalation, ingestion, or skin absorption. May cause eye and skin irritation. (USCG, 1999)

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Hazards Summary · 2 items

In animal studies, it acts as a CNS depressant and general anesthetic. [HSDB] If left on clothes, can cause reddening of skin; [CHRIS]

The major hazards encountered in the use and handling of n-propylbenzene stem from its toxicologic properties and flammability. Toxic by all routes (ie, inhalation, ingestion, dermal contact), exposure to this colorless liquid may occur from its use in textile dyeing and printing, as a solvent for cellulose acetate, and in the manufacture of methylstyrene. Effects from exposure may include burns to the skin and eyes, nausea, headache, dizziness, central nervous system depression, and unconsciousness. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus and protective clothing. If contact should occur, immediately irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed and left at the site. This substance is flammable and may be ignited by heat, sparks, or flames. Its heavier-than-air vapor may travel to a source of ignition and flash back, or accumulate to explosive concentrations in enclosed spaces, such as sewers. Also, containers of n-propylbenzene may explode in the heat of a fire. For fires involving this substance, extinguish with dry chemical, CO2, water spray, fog, or alcohol-resistant foam. Isolate for 1/2 mile in all directions if tank, rail car or tank truck is involved in the fire. For small spills of n-propylbenzene, take up with sand or other noncombustible absorbent, and place into container for later disposal. Dike far ahead of large spills to contain for later disposal.

Safety & protection

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

INHALATION: Call for medical aid. Remove the victim to fresh air. If not breathing give artificial respiration. If breathing is difficult, give oxygen.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 2 items

To fight fire, use foam, carbon dioxide, dry chemical.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Toxicology

Body Burdenn-Propylbenzene was qualitatively detected in 8 of 46 samples of human adipose tissue analyzed during the EPA National Human Adipose Tissue Survey in fiscal year 1982(1).
Ecotoxicity Values · 2 items

WEC50 Mytilus edulis (mussels) 0.86 mg/l (0.69-1.07 mg/l) (toxicant concn in water required to reduce feeding rate by 50%).

TEC50 Mytilus edulis (mussels) 27.0 mg/kg (22.7-32.1 mg/kg) (toxicant conc in mussel tissue required to reduce feeding rate by 50%).

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 955(SRC), determined from molecular connectivity indices(2), and measured values of 495 to 725(3,4) indicates that n-propylbenzene is expected to have low mobility in soil(SRC). Volatilization of n-propylbenzene from moist soil surfaces is expected to be an important fate process(7) given a Henry's Law constant of 1.05X10-2 atm-cu m/mole(5). The potential for volatilization of n-propylbenzene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 3.42 mm Hg(6). Biodegradation from soil may occur based on results from activated sludge studies(8).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 955(SRC), determined from molecular connectivity indices(2), as well as measured Koc values ranging from 495 to 725(3,4), indicate that n-propylbenzene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(5) based upon a Henry's Law constant of 1.05X01-2 atm-cu m/mole(6). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 1 hr and 4 days, respectively(SRC). Volatilization half-lives of 1.3 to 19 days have been predicted for the Narraganset Bay near RI where volatilization is expected to be the major removal process(10). Aquatic hydrolysis is not an important fate process(SRC) due to the lack of hydrolyzable functional groups(5). According to a classification scheme(7), an estimated BCF of 138(SRC), from its log Kow of 3.69(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is moderate. Biodegradation from water may occur based on activated sludge studies, with theoretical BODs ranging from 21.8 to 43.7%(11,12).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-propylbenzene, which has a vapor pressure of 3.42 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-propylbenzene 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 2 days(SRC), calculated from its rate constant of 5.0X10-12 cu cm/molecule-sec at 25 °C(3). The detection of n-propylbenzene in rainwater samples(4) suggests that physical removal from the atmosphere by wet deposition is possible(SRC).

Food Survey Valuesn-Propylbenzene has been qualitatively identified as a volatile constituent of chickpea flour(1), roasted filbert nuts(2) and scrambled eggs(3). Level in peanut oil was less than 2% of the total volatiles(4).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Average Daily IntakeAIR: Assuming an avg n-propylbenzene concn of 0.605-0.822 ug/cu m in urban-suburban outdoor air(1) and an inhalation rate of 20 cu m/day, the AVDI is 12.1-16.44 ug/day(SRC).

Regulatory information

State Drinking Water Guidelines · 3 items

(CA) CALIFORNIA 260 ug/l

(FL) FLORIDA 280 ug/l

(NH) NEW HAMPSHIRE 260 ug/L

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
DA8750000
ridadr
UN 2364
hs_code
29029090

Chemistry & industry

Pharmacology

Metabolism/MetabolitesIN RATS, THERE APPEARS TO BE A DUAL METABOLIC PATHWAY: SIDE-CHAIN OXIDATION & RING HYDROXYLATION, WITH FORMER PREFERRED.
Absorption, Distribution and Excretion... PROBABLY READILY ABSORBED FROM GI TRACT & LUNG & EXCRETED MAINLY IN URINE OF HUMANS.
Cellular LocationsMembrane

Uses & manufacturing

Uses · 3 items

Used as a chemical intermediate and solvent for printing and textile dyeing; a constituent of asphalt and naphtha; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Mfg methylstyrene; textile dyeing; printing solvent for cellulose acetate; asphalt and naphtha constituent.

U.S. Production · 2 items

2023: <25,000 lb

(1977) AT LEAST 4.54X10+10 GRAMS

Consumer UsesSolvent
Industry UsesFuel agents
Methods of Manufacturing · 5 items

Prepd by the action of diethyl sulfate on benzyl magnesium chloride.

... IS PRODUCED IN PETROLEUM REFINING & AS BYPRODUCT OF CUMENE MFR.

PROBABLY BY ALKYLATION OF BENZENE WITH N-PROPYL CHLORIDE IN THE PRESENCE OF ALUMINUM CHLORIDE; FRACTIONAL DISTILLATION OF PETROLEUM REFORMATE.

Reaction of benzylmagnesium chloride and diethyl sulfate.

Petroleum refining; by-product of cumene mfg.

Household ProductsInformation on 13 consumer products that contain Propylbenzene in the following categories is provided:
Applications · 4 items

Descriptionn-Propylbenzene (phenylpropane) is an aromatic hydrocarbon. It is in the form of a colorless liquid. n-Propylbenzene is found in petroleum and bituminous coal. It can used to produce cumene and methylstyrene. It is used as an organic solvent in textile dyeing and printing.

UsesIn textile dyeing and printing; as solvent for cellulose acetate.

Usesn-Propylbenzene is used to prepare benzoic acid. It is employed as a solvent for gas chromatography. It is also used as a solvent and an intermediate in organic synthesis. Further, it is used in fuels and fuel additives.

General DescriptionA clear colorless liquid. Insoluble in water and less dense than water. Flash point 86°F. Mildly toxic by ingestion and inhalation. Used to make other chemicals.

Additional notes

DefinitionChEBI: An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.

Related reactions

22 records

Linked notes

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