|Jmol interactive 3D||Image|
|Molar mass||92.14 g·mol−1|
|Odor||sweet, pungent, benzene-like|
|Density||0.87 g/mL (20 °C)|
|Melting point||−95 °C (−139 °F; 178 K)|
|Boiling point||111 °C (232 °F; 384 K)|
|0.52 g/L (20 °C)|
|Vapor pressure||21 mmHg (20°C)|
Refractive index (nD)
|1.497 (20 °C)|
|Viscosity||0.590 cP (20 °C)|
|Main hazards||highly flammable|
|Safety data sheet||See: data page
|R-phrases||R11, R38, R48/20, R63, R65, R67|
|S-phrases||(S2), S36/37, S29, S46, S62|
|Flash point||6 °C (43 °F; 279 K)|
|50 mL m−3, 190 mg m−3|
|Lethal dose or concentration (LD, LC):|
LC50 (Median concentration)
|>26700 ppm (rat, 1 hr)
400 ppm (mouse, 24 hr)
LCLo (Lowest published)
|55,000 ppm (rabbit, 40 min)|
|US health exposure limits (NIOSH):|
|TWA 200 ppm C 300 ppm 500 ppm (10-minute maximum peak)|
|TWA 100 ppm (375 mg/m3) ST 150 ppm (560 mg/m3)|
IDLH (Immediate danger
Related aromatic hydrocarbons
|Supplementary data page|
|Refractive index (n),
Dielectric constant (εr), etc.
|UV, IR, NMR, MS|
|what is ?)(|
Toluene //, formerly known as toluol //, is a colourless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a CH3 group attached to a phenyl group. As such, its IUPAC systematic name is methylbenzene. It is an aromatic hydrocarbon.
Toluene is widely used as an industrial feedstock and as a solvent. Like other solvents, toluene is sometimes also used as an inhalant drug for its intoxicating properties; however, inhaling toluene has potential to cause severe neurological harm. Toluene is an important organic solvent. Its economic significance is considerable: In 2013, worldwide about 24.5 billion US-dollars were generated with the sale of toluene. 
The compound was first isolated in 1837 through a distillation of pine oil by a Polish chemist named Filip Walter, who named it rétinnaphte. In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree Myroxylon balsamum), which Deville recognized as similar to Walter's rétinnaphte and to benzene; hence he called the new hydrocarbon benzoène.  In 1843, Jöns Jacob Berzelius recommended the name toluin. In 1850, French chemist Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville's benzoène and which Cahours named toluène.
Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution. Owing to greater electron-releasing properties of the methyl group vs hydrogen, toluene is more reactive than benzene to electrophiles. It undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene.
Importantly the methyl side chain in toluene is susceptible to oxidation. Potassium permanganate converts toluene to benzoic acid, whereas chromyl chloride leads to benzaldehyde (Étard reaction). The methyl group undergoes halogenation can be performed under free radical conditions. For example, N-bromosuccinimide (NBS) heated with toluene in the presence of AIBN leads to benzyl bromide. The same conversion can be effected with elemental bromine in the presence of UV light or even sunlight. Toluene may also be brominated by treating it with HBr and H2O2 in the presence of light.
- C6H5CH3 + Br2 → C6H5CH2Br + HBr
- C6H5CH2Br + Br2 → C6H5CHBr2 + HBr
The methyl group in toluene undergoes deprotonation only with very strong bases, its pKa is approximately 45. Catalytic hydrogenation of toluene gives methylcyclohexane. The reaction requires a high pressure of hydrogen and a catalyst.
Toluene occurs naturally at low levels in crude oil and is usually produced in the production of gasoline via a catalytic reformer, in an ethylene cracker, or the production coke from coal. Final separation, either via distillation or solvent extraction, takes place in one of the many available processes for extraction of the BTX aromatics (benzene, toluene, and xylene isomers).
Toluene is so inexpensively produced industrially that it is not prepared in the laboratory. In principle it could be prepared by a variety of methods. For example, although only of didactical interest, benzene reacts with methyl chloride in presence of a Lewis acid such as aluminium chloride to give toluene:
- C6H5H + CH3Cl → C6H5CH3 + HCl
Such reactions are complicated by polymethylation because toluene is more susceptible to alkylation than is benzene.
Toluene is mainly used as a precursor to benzene. The process involves hydrodealkylation:
- C6H5CH3 + H2 → C6H6 + CH4
Precursor to other chemicals
Aside from being converted to benzene and xylene, toluene is a raw material for toluene diisocyanate (used in the manufacture of polyurethane foam) and TNT. Also an important precursor in the production of synthetic drugs.
Toluene can be used as an octane booster in gasoline fuels used in internal combustion engines. Toluene at 86% by volume fuelled all the turbo Formula 1 teams in the 1980s, first pioneered by the Honda team. The remaining 14% was a "filler" of n-heptane, to reduce the octane to meet Formula 1 fuel restrictions. Toluene at 100% can be used as a fuel for both two-stroke and four-stroke engines; however, due to the density of the fuel and other factors, the fuel does not vaporise easily unless preheated to 70 degrees Celsius (Honda accomplished this in their Formula 1 cars by routing the fuel lines through the exhaust system to heat the fuel).
In Australia, in 2003, toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel. Toluene attracts no fuel excise, whereas other fuels are taxed at over 40%, so fuel suppliers are able to profit from substituting the cheaper toluene for petrol. The extent of toluene substitution has not been determined.
In the laboratory, toluene is used as a solvent for carbon nanomaterials, including nanotubes and fullerenes, and it can also be used as a fullerene indicator. The colour of the toluene solution of C60 is bright purple. It is also used as a cement for fine polystyrene kits (by dissolving and then fusing surfaces) as it can be applied very precisely by brush and contains none of the bulk of an adhesive. Toluene can be used to break open red blood cells in order to extract haemoglobin in biochemistry experiments.
Toluene has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops.
Toxicology and metabolism
Inhalation of toluene in low to moderate levels can cause tiredness, confusion, weakness, drunken-type actions, memory loss, nausea, loss of appetite, and hearing and color vision loss. These symptoms usually disappear when exposure is stopped. Inhaling high levels of toluene in a short time may cause light-headedness, nausea, or sleepiness, unconsciousness - and even death. Toluene is, however, much less toxic than benzene, and has, as a consequence, largely replaced it as an aromatic solvent in chemical preparation. The EPA considers that there is inadequate information to assess the carcinogenic potential of toluene.
Similar to many other solvents such as 1,1,1-trichloroethane and some alkylbenzenes, toluene has been shown to act as a non-competitive NMDA receptor antagonist and GABAA receptor positive allosteric modulator. Additionally, toluene has been shown to display antidepressant-like effects in rodents in the forced swim test (FST) and the tail suspension test (TST).
Several types of fungi including Cladophialophora, Exophiala, Leptodontium, Pseudeurotium zonatum, and Cladosporium sphaerospermum, and certain species of bacteria can degrade toluene using it as a source of carbon and energy.
Toluene is an intoxicative inhalant and its possession and use are regulated in many jurisdictions. As of 2007, 24 U.S. states had laws penalizing use, possession with intent to use, and/or distribution of inhalants such as toluene.
- Record in the GESTIS Substance Database of the IFA
- "NIOSH Pocket Guide to Chemical Hazards #0619". National Institute for Occupational Safety and Health (NIOSH).
- "Toluene". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- Streicher, H. Z.; Gabow, P. A.; Moss, A.H.; Kono, D.; Kaehny, W. D. (1981). "Syndromes of toluene sniffing in adults". Annals of Internal Medicine 94 (6): 758–62. doi:10.7326/0003-4819-94-6-758. PMID 7235417.
- Devathasan, G.; Low, D.; Teoh, P. C.; Wan, S. H.; Wong, P. K. (1984). "Complications of chronic glue (toluene) abuse in adolescents". Aust N Z J Med 14 (1): 39–43. doi:10.1111/j.1445-5994.1984.tb03583.x. PMID 6087782.
- Hogan, C. Michael (2011), "Sulfur", in Jorgensen, A.; Cleveland, C. J., Encyclopedia of Earth, Washington DC: National Council for Science and the Environment, retrieved 26 October 2012,
Sulfur is insoluble in water, but soluble in carbon disulfide, somewhat soluble in other non-polar organic solvents such as the aromatics benzene and toluene.
- Market Study on Toluene (January 2015), by Ceresana Research
- Pelletier and Walter (1837) "Examen des produits provenant du traitement de la résine dans la fabrication du gaz pour l'éclairage" (Examination of products arising from the treatment of resin during the production of illuminating gas), Comptes rendus, 4 : 898–899.
- Pelletier and Philippe Walter (1838) "Examen des produits provenant du traitement de la résine dans la fabrication du gaz pour l'éclairage," Annales de Chimie et de Physique, 2nd series, 67 : 269-303. Toluene is named on pp. 278-279: "Nous désignerons la substance qui nous occupe par le nom de rétinnaphte, qui rappelle son origine et ses propriétés physiques (ρητίνη-νάφτα)." (We will designate the substance that occupies us by the name of rétinnaphte, which recalls its origin and its physical properties (ρητίνη-νάφτα [resin-naphtha]).
- Deville (1841) "Recherches sur les résines. Étude du baume de Tolu" (Investigations of resins. Study of Tolu balsam), Comptes rendus, 13 : 476–478.
- H. Deville (1841) "Recherches chimiques sur les résines; Premier mémoire" (Chemical investigations of resins; first memoir), Annales de Chimie et de Physique, 3rd series, 3 : 151-195. Deville names toluene on p. 170: "J'ai adopté, pour le corps qui m'occupe dans ce moment, le nom de benzoène, qui rappelle, dans les baumes dont il provient, ce caractère presque générique qui est de contenir de l'acide benzoïque." (I've adopted, for this substance that occupies me at the moment, the name benzoène, which recalls, in the balsams from which it comes, that character which is contained in benzoic acid.)
- Wisniak, Jaime (2004). "Henri Étienne Sainte-Claire Deville: A physician turned metallurgist". Journal of Materials Engineering and Performance 13 (2): 117–118. doi:10.1361/10599490418271.
- Jacob Berzelius (1843) Jahres Berichte, 22 : 353-354..
- Cahours, Auguste (1850) "Recherches sur les huiles légéres obtenues dans la distillation du bois" (Investigations of light oils obtained by the distillation of wood), Compte rendus, 30 : 319-323 ; see page 320.
- Jaime Wisniak (October 2013) "Auguste André Thomas Cahours," Educación Química, 24 (4) : 451–460.
- B. S. Furniss et al., Vogel's Textbook of Practical Organic Chemistry, 5th edition, Longman/Wiley, New York, 1989
- L. G. Wade, Organic Chemistry, 5th ed., p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003
- J. March, Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992
- Podgoršek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej (2006). "Free radical bromination by the H2O2–HBr system on water". Tetrahedron Letters 47 (40): 7245. doi:10.1016/j.tetlet.2006.07.109.
- Jörg Fabri, Ulrich Graeser, Thomas A. Simo "Toluene" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a27_147.pub2
- Dual cure, low-solvent silicone pressure-sensitive adhesives – Patent 6387487
- Ji, C.; Egolfopoulos, F. N. (2011). "Hydrogen Flame propagation of mixtures of air with binary liquid fuel mixtures". Proc. Comb. Inst. 33: 955–961. doi:10.1016/j.proci.2010.06.085.
- Merory, Joseph (1968). Food Flavorings: Composition, Manufacture and Use (2nd ed.). Westport, CT: AVI Publishing Company, Inc..
- "Health Effects of Toluene", Canadian Centre for Occupational Health and Safety.
- "Toluene Toxicity Physiologic Effects", Agency for Toxic Substances and Disease Registry.
- , EPA
- Cruz, S. L.; Soberanes-Chávez, P.; Páez-Martinez, N.; López-Rubalcava, C. (June 2009). "Toluene has antidepressant-like actions in two animal models used for the screening of antidepressant drugs". Psychopharmacology 204 (2): 279–86. doi:10.1007/s00213-009-1462-2. PMID 19151967.
- Prenafeta-Boldu, Francesc X.; Kuhn, Andrea; Luykx, Dion M. A. M.; Anke, Heidrun; van Groenestijn, Johan W.; de Bont, Jan A. M. (April 2001). "Isolation and characterisation of fungi growing on volatile aromatic hydrocarbons as their sole carbon and energy source". Mycological Research (Elsevier) 105 (4): 477–484. doi:10.1017/S0953756201003719.
- "State Laws on Inhalant Use".
|Wikimedia Commons has media related to toluene.|
|Wikiquote has quotations related to: Toluene|
- ATSDR – Case Studies in Environmental Medicine: Toluene Toxicity U.S. Department of Health and Human Services (public domain)
- Toluene CDC – NIOSH Workplace Safety and Health Topic (DHHS)