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71-43-2

Basic Information
CAS No.: 71-43-2
Name: Benzene
Article Data: 3748
Cas Database
Molecular Structure:
Molecular Structure of 71-43-2 (Benzene)
Formula: C6H6
Molecular Weight: 78.1136
Synonyms: 1,3,5-Cyclohexatriene;Benzol;Benzole;Coal naphtha;Cyclohexatriene;NSC 67315;Phene;Phenylhydride;Pyrobenzol;Pyrobenzole;[6]Annulene;crude benzene;
EINECS: 200-753-7
Density: 0.873 g/cm3
Melting Point: 5.5 °C
Boiling Point: 78.834 °C at 760 mmHg
Flash Point: -11 °C
Solubility: 0.18 g/100 mL in water
Appearance: clear colorless liquid with a petroleum-like odor
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 45-46-11-36/38-48/23/24/25-65-39/23/24/25-23/24/25
Safety: 53-45-36/37
Transport Information: UN 1114 3/PG 2
PSA: 0.00000
LogP: 1.68660
Synthetic route
108-86-1

bromobenzene

71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h;100%
With 9-borabicyclo[3.3.1]nonane dimer; triphenylstannane In toluene at 0℃;100%
With TiCpCl2; diisobutylaluminium hydride In 1,4-dioxane at 80℃; for 4h; Product distribution; further reagents(Zr, Hf complexes), solvents, and temperatures; further halobenzenes, alkyl, alkenyl and cyclopropyl halides;100%
591-50-4

iodobenzene

71-43-2

benzene

Conditions
ConditionsYield
With tetrabutoxytitanium; diisobutylaluminium hydride In diethyl ether for 6h; Heating;100%
With sodium hydroxide; ethanol; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 1h;100%
With potassium tert-butylate; benzaldehyde In N,N-dimethyl-formamide at 90℃; for 1h; Schlenk technique; Inert atmosphere;99%
1165952-92-0

cyclohexa-1,4-diene

71-43-2

benzene

Conditions
ConditionsYield
With [Mn(IV)(O)(BQCN)(H2O)](2+) In water; acetonitrile at 0℃; Kinetics; Concentration; Inert atmosphere;100%
With Fe2(OH)0.6(2,5-dioxido-1,4-benzenedicarboxylate) at 24℃;100%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;99%
1165952-91-9

cyclohexa-1,3-diene

71-43-2

benzene

Conditions
ConditionsYield
With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 12h; Product distribution; Heating; var. aromatic species; var. reaction times;100%
With iron(III) trifluoromethanesulfonate; C65H77N5O4S2 In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 8h; Inert atmosphere;78%
With [[HC-(CMeNC6H3(iPr)2)2]NiIII(O2)CuIII(N(indane)(2-pyridyl(ethylamine))2)](OTf) In dichloromethane at -60℃; Kinetics; Reagent/catalyst; Inert atmosphere;49%
108-90-7

chlorobenzene

71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h; Product distribution; effect of bases and solvents on the hydrodechlorination;100%
With potassium hydroxide; hydrogen; palladium on activated charcoal; Aliquat 336 In 2,2,4-trimethylpentane at 50℃; for 4.5h;100%
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h;100%
106-39-8

bromochlorobenzene

71-43-2

benzene

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; palladium on activated charcoal; Aliquat 336 In water at 50℃; for 0.833333h;100%
With di-tert-butyl peroxide; caesium carbonate; isopropyl alcohol at 120℃; for 3h; Inert atmosphere;93 %Chromat.
With ammonium formate In methanol at 20℃; for 16h;
3968-30-7

5-cyclopentylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

A

2873-50-9

butatriene

B

74-85-1

ethene

C

124-38-9

carbon dioxide

D

1165952-91-9

cyclohexa-1,3-diene

E

67-64-1

acetone

F

71-43-2

benzene

Conditions
ConditionsYield
With variation of temp. at 550℃; Product distribution;A 4%
B 11.9%
C 100%
D 39.2%
E 101.9 %
F 3.3%
106-46-7

para-dichlorobenzene

71-43-2

benzene

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water at 50℃; for 0.25h;100%
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 6h;100%
With Ni[1,10-phenanthroline]2(PF6)2; water; zinc at 70℃; for 7h; Ionic liquid;51.2%
1113-69-5

1,1-dicyano-2,2-bis(trifluoromethyl)ethene

A

82947-39-5

2,2-Bis(trifluoromethyl)ethane-1,1-dicarbonitrile

B

71-43-2

benzene

Conditions
ConditionsYield
With cyclohexa-1,4-diene In chloroform-d1 Mechanism; Ambient temperature; or 1,3-cyclohexadiene, 2,5-dihydrofuran;A 100%
B 97%
With cyclohexa-1,4-diene In chloroform-d1 Ambient temperature; also with 1,3-cyclohexadiene, 2,5-dihydrofuran;A 100%
B 97%

A

97111-56-3

4-Chloro-1-(4-methoxy-phenyl)-[1,2,4]triazolo[4,3-a]quinoxaline

B

71-43-2

benzene

Conditions
ConditionsYield
In chloroform-d1 at 60℃; for 0.0333333h; Product distribution; Thermodynamic data; Rate constant; other temperature, time;A 100%
B 80%
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Specification

Benzene, also kanow as (6)Annulene, is clear colorless, highly flammable liquid with a petroleum-like odor. It evaporates into the air very quickly. Benzene is a natural constituent of crude oil, and is one of the most basic petrochemicals. It is widely used as solvent and precursor in a range of products. By substitution, addition reaction and benzene ring rupture reaction, many important chemical intermediates can be derived.

Benzene is insoluble in water. In addition to glycerol, ethylene glycol, diethylene glycol, 1,4 - butanediol and other polyols, Benzene can be miscible with alcohol, chloroform, ether, carbon tetrachloride, carbon disulfide, glacial acetic acid, acetone, toluene, xylene, aliphatic hydrocarbon and most organic solvents. With the exception of slightly dissolved iodine and sulfur, the inorganic substance is insoluble in benzene.

Preparation: The production and supply of benzene in different countries and regions are not the same. The United States is mainly get the benzene from the restructuring gasoline. The Western Europe is mainly from pyrolysis gasoline. And China is mainly from the restructuring gasoline and coking by-product.

1. Coking by-product: There is part of benzene in the high temperature tar of coking by-product. After some treamtent, benzene is obtained.

2. Pyrolysis gasoline: Benzene The pyrolysis gasoline generally contains about 40% -70% aromatic hydrocarbon. About 37% of aromatic hydrocarbon is benzene, about 14% is toluene, and about 5% is xylene. Benzene can be extracted by hydrogenation and dealkylation.

3. Benzene also can be prepared by toluene from hydrodealkylation. In this hydrogen-intensive process, toluene is mixed with hydrogen. Then in the presence of catalysts Chromium, Molybdenum or Platinum oxide, the reaction happens at 500–600 °C and 40–60 atm pressure. A typical reaction yield exceeds 95 %.
C6H5CH3 + H2 → C6H6 + CH4

Uses: 1. Benzene is used as important raw material of synthetic dye, synthetic rubbers, synthetic resin, synthetic fiber, synthetic grain, plastics, pharmaceuticals, pesticides, photographic film and petrochemical products. Benzene has good solubility, so it is widely used as adhesive and industrial solvent such as lacquer thinner of varnish and nitrocellulose, paint remover, lubricant, grease, wax, celluloid, resin, leather.

2. Benzene is also used as standard sample in the measurment of refractive index. And it can be used as solvent and cleaning agent in precision optical instruments, electronics and so on.

3. It is used as solvent of cosmetics, paint, rubber, glue, etc. Today, benzene is used mainly as an intermediate to make other chemicals. For example: it can react with azidobenzene to get diphenylamine. This reaction needs reagent at temperature of 55 °C. The reaction time is 1 hours. The yield is 82%.

Benzene can react with azidobenzene to get diphenylamine

Safty: Benzene is toxic by inhalation, in contact with skin and if swallowed. Moreover, it is harmful that may cause lung damage if swallowed. In addition, Benzene has danger of very serious irreversible effects and serious damage to health by prolonged exposure that may cause heritable genetic damage. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Please avoid exposure - obtain special instructions before use.

Structure Descriptors:
1. Smiles:c1ccccc1
2. InChI:InChI=1/C6H6/c1-2-4-6-5-3-1/h1-6H

Toxicity:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 170000mg/m3 (170000mg/m3)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 324, 1955.
dog LCLo inhalation 146000mg/m3 (146000mg/m3)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 324, 1955.
dog LDLo oral 2gm/kg (2000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1313, 1935.
frog LDLo subcutaneous 1400mg/kg (1400mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1313, 1935.
guinea pig LD50 skin > 9400uL/kg (9.4mL/kg)   Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.
guinea pig LDLo intraperitoneal 527mg/kg (527mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 42, 1955.
human LCLo inhalation 65mg/m3/5Y (65mg/m3) BLOOD: OTHER CHANGES Archiv fuer Geschwulstforschung. Vol. 44, Pg. 145, 1974.
human LCLo inhalation 2pph/5M (20000ppm)   Tabulae Biologicae. Vol. 3, Pg. 231, 1933.
human TCLo inhalation 100ppm (100ppm) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: NAUSEA OR VOMITING
Industrial Medicine. Vol. 17, Pg. 199, 1948.
mammal (species unspecified) LCLo inhalation 20000ppm/5M (20000ppm)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 138, Pg. 65, 1928.
mammal (species unspecified) LD50 oral 5700mg/kg (5700mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mammal (species unspecified) LDLo intraperitoneal 1500mg/kg (1500mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: IRRITABILITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
American Journal of Hygiene. Vol. 7, Pg. 276, 1927.
man LDLo oral 50mg/kg (50mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 883, 1980.
man LDLo unreported 194mg/kg (194mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TCLo inhalation 150ppm/1Y-I (150ppm) BLOOD: OTHER CHANGES Blut. Vol. 28, Pg. 293, 1974.
mouse LC50 inhalation 9980ppm (9980ppm) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 366, 1943.
mouse LD50 intraperitoneal 340mg/kg (340mg/kg)   Annals of the New York Academy of Sciences. Vol. 243, Pg. 104, 1975.
mouse LD50 oral 4700mg/kg (4700mg/kg)   Hygiene and Sanitation Vol. 32(3), Pg. 349, 1967.
mouse LD50 skin 48mg/kg (48mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 5, 1974.
rabbit LCLo inhalation 45000ppm/30M (45000ppm)   Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 69, 1944.
rabbit LD50 skin > 9400uL/kg (9.4mL/kg)   Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.
rabbit LDLo intravenous 88mg/kg (88mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

GASTROINTESTINAL: GASTRITIS

SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE
Journal of Toxicology and Environmental Health. Vol. (Suppl,
rat LC50 inhalation 10000ppm/7H (10000ppm)   "Toxicology and Biochemistry of Aromatic Hydrocarbons," Gerarde, H., New York, Elsevier, 1960Vol. -, Pg. 113, 1960.
rat LD50 intraperitoneal 1100ug/kg (1.1mg/kg)   Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961.
rat LD50 oral 930mg/kg (930mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 7, Pg. 767, 1965.