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CAS No.: | 71-43-2 |
---|---|
Name: | Benzene |
Article Data: | 3748 |
Molecular Structure: | |
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: | F,T |
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
cyclohexa-1,4-diene
benzene
Conditions | Yield |
---|---|
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% |
cyclohexa-1,3-diene
benzene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
5-cyclopentylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
A
butatriene
B
ethene
C
carbon dioxide
D
cyclohexa-1,3-diene
E
acetone
F
benzene
Conditions | Yield |
---|---|
With variation of temp. at 550℃; Product distribution; | A 4% B 11.9% C 100% D 39.2% E 101.9 % F 3.3% |
Conditions | Yield |
---|---|
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% |
1,1-dicyano-2,2-bis(trifluoromethyl)ethene
A
2,2-Bis(trifluoromethyl)ethane-1,1-dicarbonitrile
B
benzene
Conditions | Yield |
---|---|
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% |
C22H17ClN6O
A
4-Chloro-1-(4-methoxy-phenyl)-[1,2,4]triazolo[4,3-a]quinoxaline
B
benzene
Conditions | Yield |
---|---|
In chloroform-d1 at 60℃; for 0.0333333h; Product distribution; Thermodynamic data; Rate constant; other temperature, time; | A 100% B 80% |
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%.
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. |