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Toluene

Toluene
Sample of toluene
Names
Preferred IUPAC name
Toluene[2]
Systematic IUPAC name
Methylbenzene
Other names
Methyl benzene[1]
Methylcyclohexa-1,3,5-triene
Benzylane
Phenylmethane
Toluol
Anisen
Identifiers
3D model (JSmol)
Abbreviations PhMe
MePh
BnH
Tol
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.297 Edit this at Wikidata
KEGG
RTECS number
  • XS5250000
UNII
UN number 1294
  • InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 checkY
    Key: YXFVVABEGXRONW-UHFFFAOYSA-N checkY
  • InChI=1/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
    Key: YXFVVABEGXRONW-UHFFFAOYAT
  • Cc1ccccc1
Properties
C6H5CH3
Molar mass 92.141 g·mol−1
Appearance Colorless liquid[3]
Odor sweet, pungent, benzene-like[4]
Density 0.8623 g/mL (25 °C)[1]
Melting point −95.0 °C (−139.0 °F; 178.2 K)[1]
Boiling point 110.60 °C (231.08 °F; 383.75 K)[1]
0.54 g/L (5 °C)
0.519 g/L (25 °C)
0.63 g/L (45 °C)
1.2 g/L (90 °C)[5]
log P 2.73[6]
Vapor pressure 2.8 kPa (20 °C)[4]
−66.1·10−6 cm3/mol[7]
Thermal conductivity 0.1310 W/(m·K) (25 °C)[8]
1.4941 (25 °C)[1]
Viscosity 0.560 mPa·s (25 °C)[9]
Structure
0.375 D[10]
Thermochemistry[11]
157.3 J/(mol·K)
12.4 kJ/mol
3.910 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 highly flammable
GHS labelling:
GHS02: FlammableGHS08: Health hazardGHS07: Exclamation mark
Danger
H225, H304, H315, H336, H361d, H373
P210, P240, P301+P310, P302+P352, P308+P313, P314, P403+P233
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 4 °C (39 °F; 277 K)[12]
480[12] °C (896 °F; 753 K)
Explosive limits 1.1–7.1%[12]
50 mL/m3, 190 mg/m3
Lethal dose or concentration (LD, LC):
>26700 ppm (rat, 1 h)
400 ppm (mouse, 24 h)[13]
55,000 ppm (rabbit, 40 min)[13]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 200 ppm C 300 ppm 500 ppm (10-minute maximum peak)[4]
REL (Recommended)
 TWA 100 ppm (375 mg/m3) ST 150 ppm (560 mg/m3)[4]
IDLH (Immediate danger)
 500 ppm[4]
Safety data sheet (SDS) SIRI.org
Related compounds
benzene
xylene
naphthalene
Related compounds
 methylcyclohexane
Supplementary data page
Toluene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Toluene (/ˈtɒl.juiːn/), also known as toluol (/ˈtɒl.ju.ɒl, -ɔːl, -oʊl/), is a substituted aromatic hydrocarbon[15] with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant[16] and has the potential of causing severe neurological harm.[17][18]

  1. ^ a b c d e Haynes, p. 3.514
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 139. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4. Toluene and xylene are preferred IUPAC names, but are not freely substitutable; toluene is substitutable under certain conditions, but only for general nomenclature (see P-15.1.8 for a general substitution rules for retained names).
  3. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0619". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Haynes, p. 5.164
  6. ^ Haynes, p. 5.176
  7. ^ Haynes, p. 3.579
  8. ^ Haynes, p. 6.258
  9. ^ Haynes, p. 6.246
  10. ^ Haynes, p. 9.66
  11. ^ Haynes, pp. 5.39, 5.67
  12. ^ a b c Haynes, p. 16.30
  13. ^ a b "Toluene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  14. ^ "NFPA Chemicals". New Environment, Inc. Archived from the original on November 14, 2021. Retrieved March 13, 2015.
  15. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  16. ^ McKeown NJ (February 1, 2015). Tarabar A (ed.). "Toluene Toxicity, Background, Pathophysiology, Epidemiology". WebMD Health Professional Network. Archived from the original on March 9, 2016. Retrieved March 22, 2016.
  17. ^ Streicher HZ, Gabow PA, Moss AH, Kono D, Kaehny WD (June 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.
  18. ^ Devathasan G, Low D, Teoh PC, Wan SH, Wong PK (February 1984). "Complications of chronic glue (toluene) abuse in adolescents". Australian and New Zealand Journal of Medicine. 14 (1): 39–43. doi:10.1111/j.1445-5994.1984.tb03583.x. PMID 6087782.