Benzene

HCID 178746954CAS 54682-86-9

Basic information

Standard SMILES
c1ccccc1
InChIKey
UHOVQNZJYSORNB-UHFFFAOYSA-N
Molecular formula
C6H6
Average molar mass
78.11 g/mol

Overview

Benzene is a colorless liquid with a sweet odor. It evaporates into the air very quickly and dissolves slightly in water. It is highly flammable and is formed from both natural processes and human activities. Benzene is widely used in the United States; it ranks in the top 20 chemicals for production volume. Some industries use benzene to make other chemicals which are used to make plastics, resins, and nylon and synthetic fibers. Benzene is also used to make some types of rubbers, lubricants, dyes, detergents, drugs, and pesticides. Natural sources of benzene include volcanoes and forest fires. Benzene is also a natural part of crude oil, gasoline, and cigarette smoke.

Names & identifiers

Preferred name
Benzene
IUPAC
benzene
English name
Benzene
Molecular formula
C6H6
Molecular weight
78.11184

Names & synonyms

benzene71-43-2benzolCyclohexatrienebenzolePyrobenzoleBenzineCoal naphthaPyrobenzolBenzenPhenePhenyl hydride
Show more names
Mineral naphthaBenzoleneBicarburet of hydrogenMotor benzolBenzeenBenzoloFenzen(6)Annulene

Database identifiers

CAS
54682-86-9
ChEMBL
CHEMBL277500
ChEBI
CHEBI:16716
UNII
J64922108F
EC Number
200-753-7
Nikkaji
J1.749.610G、J2.375B

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 5 items

Hazardous Air Pollutants (HAPs)

Urban Hazardous Air Pollutants (HAPs) - EPA specified greatest potential health threat in urban areas

Carcinogens

-> NIOSH Emergency Response Categories

Volatile Organic Compound (VOC)

SolventsSolvents -> Aromatic Solvents
CosmeticsCosmetics ingredient -> Fragrance; Other (Specify)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance substance (Benzene) -> IFRA amendment 38
PesticidesPesticide -> EPA IRIS

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P318, P319, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1934) of reports.

Danger

H225 (99.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: Benzene

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Developmental Toxicity; Genotoxicity; Hematotoxicity; Immunotoxicity; Neurodevelopmental Toxicity; Neurotoxicity; Reproductive Toxicity; Respiratory Toxicity

Regulation (EC) No 1333/2008 (amended)

Benzene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene 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)

Status: Active Update: 09-12-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/1466

Restricted substance: Benzene

Other Safety Information · 2 items

PEC / SN / Other assessments - Benzene: Health and Environment

- Indoor Air: Benzene can be released into indoor air as a liquid spray (aerosol), mist, or vapor.

DOT LabelFlammable Liquid
Fire Hazards · 3 items

Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. (USCG, 1999)

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

Highly flammable. Vapour/air mixtures are explosive. Risk of fire and explosion. See Chemical Dangers.

Fire PotentialA dangerous fire hazard when exosed to heat or flame. ... Ignites on contact with sodium peroxide + water, dioxygenyl tetrafluoroborate, iodine heptafluoride, and dioxygen difluoride.
Health Hazards · 2 items

Dizziness, excitation, pallor, followed by flushing, weakness, headache, breathlessness, chest constriction, nausea, and vomiting. Coma and possible death. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Safety & protection

Fire Fighting · 3 items

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use foam, water spray, carbon dioxide, powder. In case of fire: keep drums, etc., cool by spraying with water.

- Benzene is highly flammable.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

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 · 3 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from food and feedstuffs, oxidants and halogens. Store in an area without drain or sewer access.
Firefighting Hazards · 2 items

Vapors are heavier than air and may travel to a source of ignition & flash back. Liquid floats on water and may travel to a source of ignition and spread fire.

Special hazards arising from the substance or mixture: Carbon oxides Flash back possible over considerable distance. Container explosion may occur under fire conditions.

Toxicology

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 2 items

Benzene was detected in all 8 samples of mothers' milk from women living in 4 USA urban areas(1). Breath samples from persons without specific exposure to benzene ranged from 8 to 20 ppb(2). Whole blood samples from 250 subjects (121 males, 129 females) ranged from not detected to 5.9 ppb, (mean 0.8 ppb)(3). In FY82, the National Human Adipose Tissue Survey specimens found that of 46 composite samples, 96% tested positive to benzene (concentrations were >4 ppb for wet tissue) with a max concentration of 97 ppb max(4).

In a 1980's study of non-occupational benzene exposure, it was found that smokers had an average benzene body burden about 6 to 10 times that of nonsmokers, and received about 90% of their benzene exposure from smoking(1). The mean benzene concentration found in the breath and blood of 1,683 individuals was 13.1 and 131 ng/L, respectively(1).

Treatment · 1 item

There is no known antidote for benzene and poisoning is first treated by preventing further exposure. If inhaled, respiratory assist may be necessary. If ingested, gastric lavage may be performed, or activated charcoal can be administered. (T8)

Cancer Sites · 2 items

Hematologic

[leukemia]

Interactions · 5 items

Dimethyl sulfoxide (DMSO) enhanced the hypertaurinuria produced by benzene, chlorobenzene, and toluene in rats. Undiluted DMSO was more effective than DMSO diluted with water in potentiating the toxicity of benzene in both rats and mice. Supernatants (9000g) prepared from livers of rats treated with DMSO 24 hours earlier metabolized more benzene than those from control rats.

Benzene & ethanol induced a common cytochrome P450 species in rabbit liver specifically effective in hydroxyl radical-mediated oxygenation of ethanol. Benzene oxidation by the benzene-inducible form of cytochrome P450 was almost completely inhibited by catalase, superoxide dismutase, DMSO, & mannitol.

Simultaneous treatments with both benzene and toluene, or benzene and piperonyl butoxide, increased the excretion of unchanged benzene in the expired air. These compounds apparently act by inhibiting benzene metabolism.

Toluene, Aroclor 1254, phenobarbital, acetone, and ethanol are known to alter the metabolism and toxicity of benzene.

For more Interactions (Complete) data for BENZENE (13 total), please visit the HSDB record page.

Target Organs · 3 items

Cancer, Gastrointestinal (Stomach and Intestines, part of the digestive system), Hematological (Blood Forming), Immunological (Immune System), Neurological (Nervous System)

Immune

Eyes, skin, respiratory system, blood, central nervous system, bone marrow

Regulatory information

FDA RequirementsBenzene is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 3 items

D018; A solid waste containing benzene may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

F005; When benzene is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F005), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.

U019; As stipulated in 40 CFR 261.33, when benzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Atmospheric Standards · 4 items

National emission standard for equipment leaks (fugitive emission sources) of benzene prohibit detectable benzene emissions from processing equipment (eg, pumps, valves) that contains materials which have a benzene concn of 10% or more by wt.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzene is produced, as an intermediate or a final product, by process units covered under this subpart.

Benzene has been designated as a hazardous air pollutant under section 112 of the Clean Air Act.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Benzene is included on this list.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Clean Water Act Requirements · 2 items

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations.

Benzene is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

State Drinking Water Standards · 3 items

(CA) CALIFORNIA 1 ug/L

(FL) FLORIDA 1 ug/L

(NJ) NEW JERSEY 1 ug/L

Chemistry & industry

Pharmacology

Mechanism of Action · 5 items

Covalent interaction of a benzene metabolite with dna was shown in vivo, but no information was given about the chem nature of this metabolite. A likely intermediate in benzene metabolism is benzene oxide. In neutral aq media it rearranges only slowly to the phenol so that its lifetime could be long enough for diffusion from the site of activation to the dna. Alternatively, the metabolic appearance of polyhydroxy derivatives suggests the formation of a phenol epoxide, so that the reactive molecule could be a secondary metabolite.

The available evidence supports the concept that benzene toxicity is caused by one or more metabolites of benzene. ... Benzene metabolites containing 2 or 3 hydroxyl groups inhibited mitosis. Toluene, which inhibits benzene metabolism, protected animals against benzene-induced myelotoxicity. Benzene toxicity could be correlated with the appearance of benzene metabolites in bone marrow. Although it is clear that benzene can be metabolized in bone marrow, the observation that partial hepatectomy protects against benzene toxicity suggests that a metabolite formed in liver is essential for benzene toxicity.

... Importance of polyhydroxylated derivatives of benzene & their semiquinones. ... /It has been/ shown that hydroquinone inhibits rat brain microtubule polymerization; that hydroquinone & para-benzoquinone are the most potent inhibitors of T- & B-lymphocyte function, as measured in mouse spleen cells in culture; that hydroquinone inhibits lectin-stimulated lymphocyte agglutination in rat spleen prepn in vitro; & that para-benzoquinone is the metabolite most likely to be responsible for suppression of lymphocyte transformation & microtubule assembly in rat spleen cells in culture. However, admin of these cmpd to animals does not produce the typical picture of benzene toxicity ... admin /of/ major metabolites of benzene to mice ... failed to ... decr ... red blood cell production, using the (59)Fe uptake technique ... /it's been/ suggested that ring-opening products may play a role in benzene toxicity. ... In mice benzene treatment suppressed subsequent colony forming unit-C formation from bone-marrow cells in vitro. Treating the animals with phenol, hydroquinone or benzene dihydrodiol failed to suppress colony forming unit-C. Thus, the toxic metabolites of benzene have yet to be identified.

... Radioactivity /has been demonstrated/ in a nucleic acid fraction from rat liver following admin of either (3)h- or (14)C-labelled benzene. It has been shown that benzene binds covalently to protein in liver, bone marrow, kidney, lung, spleen, blood, & muscle. Less covalent binding was observed to the protein of bone marrow, blood, & spleen of C57Bl/6 mice, which are more resistant to the benzene-induced effects on red cell production, than to that of sensitive DBA/2 mice. ... Covalent binding of benzene to protein in perfused bone-marrow prepn /has been demonstrated/. ... A metabolite of phenol binds to liver protein more efficiently than does benzene oxide, & they have electrophoretically separated hepatic proteins to which benzene preferentially binds. ... Covalent binding to mitochondria is a prominent feature of benzene metabolism. ... There is relatively more radioactivity in a nucleic acid-rich fraction of a benzene metabolite isolated from mouse bone-marrow cells than in a similar fraction from liver.

For more Mechanism of Action (Complete) data for BENZENE (12 total), please visit the HSDB record page.

Biological Half-Life · 3 items

Whole body: 9-24 hours; however, up to 90 hours due to distribution in fat; [TDR, p. 154]

The excretion of unchanged benzene from the lung of rats was reported to be biphasic, suggesting a two-compartment model for distribution and a half-life of 0.7 hr. This agreed with experimental half-life values for various tissues that ranged from 0.4 to 1.6 hr.

... The half-time of benzene in /high lipid content/ tissues is approximately 24 hours.

Metabolism/Metabolites · 6 items

The major metabolitesof benzene metabolism are phenol, hydroquinone, and catechol. These metabolites are interactive and can affect the rate of each other's metabolism because they are substrates for the P-450 enzyme system. The route of exposure has little effect on the subsequent metabolism of benzene to hemotoxic metabolites.

Metabolic products in rat ... are phenol, hydroquinone, catechol, hydroxyhydroquinone, & phenylmercapturic acid. Conjugated phenols have been reported ... except for a small amt of free phenol, all the phenolic metabolites were excreted in conjugated form. When (3)H-benzene was admin to mice, (3)H2O was also recovered from urine.

Yields N-acetyl-S-phenyl-cysteine in rat. Yields benzyl alcohol in guinea pigs. ... Yields cis-1,2-dihydro-1,2-dihydroxybenzene in pseudomonas. Phenol in pseudomonas & achromobacter. Yields cis,cis-muconic acid in rabbit. /From table/

In the rabbit, the major hydroxylation product of benzene was phenol, which along with some catechol and hydroquinone, was found in the urine conjugated with ethereal sulfate or glucuronic acid.

For more Metabolism/Metabolites (Complete) data for BENZENE (26 total), please visit the HSDB record page.

Benzene has known human metabolites that include phenol.

Absorption, Distribution and Excretion · 5 items

Benzene is readily absorbed via lung, & about 40-50% is retained. ... It is taken up preferentially by fatty & nervous tissues, & about 30-50% ... is excreted unchanged via lung; a 3-phase excretion pattern is seen at ... /approx/ 0.7-1.7 hr, 3-4 hr, & 20-30 hr.

When benzene was placed on skin under closed cup it was absorbed at rate of 0.4 mg/sq cm/hr (Hanke et al 1961) ...

Mice treated SC with 2 mL (3)H-labeled benzene/kg contained irreversibly bound radioactivity with decreasing binding magnitude in the following organs: liver, brain, kidney, spleen, fat. Mice treated with 2 daily SC doses of 0.5 mL (3)H-benzene/kg for 1-10 days showed a radioactivity binding with liver & bone marrow residues which increased with treatment duration, except in the case of binding to bone marrow which decreased after day 6.

When administered to mice subcutaneously, 72% of dose is recovered in expired air.

For more Absorption, Distribution and Excretion (Complete) data for BENZENE (14 total), please visit the HSDB record page.

Tissue LocationsBone Marrow

Uses & manufacturing

Uses · 6 items

Benzene is used as a constituent in motor fuels; as a solvent for fats, waxes, resins, oils, inks, paints, plastics, and rubber; in the extraction of oils from seeds and nuts; and in photogravure printing. It is also used as a chemical intermediate. Benzene is also used in the manufacture of detergents, explosives, pharmaceuticals, and dyestuffs.

Benzene was used in the past as a solvent in inks, rubber, lacquers, and paint removers. Today, it is used mainly in closed processes to synthesize organic chemicals. Gasoline in some countries contains a high concentration of benzene (as high as 30%); the U.S. average is 1-3%. Workers who remove or clean underground storage tanks may be exposed to significant levels. [ACGIH] Gasoline in North America now contains about 1% benzene. [AIHAJ 2002;63(2):225-30] The European Union (EU) reduced in 2000 the maximum allowed benzene content in gasoline from 5% to 1% by volume. Mean exposures in the Swedish petroleum industry are well below the Swedish occupational exposure limits. [PMID 28578463]

EPA restricts benzene emission from specific point sources; maximum contaminant level in drinking water is 5 ppb; FDA prohibits the use of benzene in food; [ATSDR Case Studies]

Metal Preparation and Pouring [Category: Foundry]

Smoking cigarettes [Category: Food & Drugs]

For benzene (USEPA/OPP Pesticide Code: 008801) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

ImpuritiesMajor impurities are toluene and xylene, others: phenol, thiophene, carbon disulfide, acetylnitrile, and pyridine.
U.S. Exports · 5 items

(1978) 1.52X10+11 G

(1983) 3.66X10+10 G

(1979) 1.3 million lb

(1985) 3.77X10+10 g

Exports were thought to be less than 10 million gallons.

U.S. Imports · 5 items

(1978) 2.26X10+11 G

(1979) 1.6 billion kg

(1983) 4.93X10+11 G

(1985) 4.96X10+11 g

For more U.S. Imports (Complete) data for BENZENE (6 total), please visit the HSDB record page.

U.S. Production · 6 items

2023: 15,000,000,000 - <20,000,000,000 lb

(1967) 9.6X10+8 gal (data reported by tar distillers are not included)

(1977) 4.80X10+12 G

(1980) 1.5X10+9 gal (data reported by tar distillers are not included)

(1981) 4.3X10+11 GRAMS

For more U.S. Production (Complete) data for BENZENE (24 total), please visit the HSDB record page.

Consumption Patterns · 5 items

Consumption by chemical industry in USA, 1977: 1.4 billion gallons annually.

Chem int for ethylbenzene, 49.1%; chem int for cumene, 18.4%; chem int for cyclohexane, 15.1%; chem int for nitrobenzene, 4.5%; chem int for maleic anhydride, 2.8%; chem int for chlorobenzenes, 2.5%; chem int for detergent alkylate, 2.4%; exports, 2.7%; other uses, 2.5% (1981 non-gasoline uses)

Demand: (1980) 1,586 Million Gal; /Projected demand for/ (1984): 1,708 Million Gal

BENZENE RANKED 17TH IN 1981 & 1982 IN THE TOP 50 CHEMICAL PRODUCTION: BILLIONS OF LB: 7.87 (1982), 9.61 (1981).

For more Consumption Patterns (Complete) data for BENZENE (10 total), please visit the HSDB record page.

Suppliers1 total

Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Benzene is a six-carbon aromatic annulene in which each carbon atom donates one of its two 2p electrons into a delocalised pi system. A toxic, flammable liquid byproduct of coal distillation, it is used as an industrial solvent. Benzene is a carcinogen that also damages bone marrow and the central nervous system. It has a role as a non-polar solvent, a carcinogenic agent and an environmental contaminant. It is an aromatic annulene, a volatile organic compound and a member of benzenes.

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