octane

Octane
Identifiers
CAS number	111-65-9
PubChem	356
RTECS number	RG8400000
SMILES	CCCCCCCC
InChI	1/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3
ChemSpider ID	349
Properties
Molecular formula	C8H18
Molar mass	114.2285 g/mol
Appearance	colorless liquid
Density	0.703 g/ml, liquid
Melting point	−57 °C (216 K)
Boiling point	125.52 °C (398.7 K)
Solubility in water	Immiscible
Viscosity	0.542 cP at 20 °C
Thermochemistry
Std enthalpy of formation ΔfHo298	−250 kJ/mol
Std enthalpy of combustion ΔcHo298	−5430 kJ/mol
Hazards
EU classification	Flammable (F) Harmful (Xn) Dangerous for the environment (N)
R-phrases	R11, R38, R50/53, R65, R67
S-phrases	(S2), S9, S16, S29, S33, S60, S61, S62
Flash point	13 °C
Autoignition temperature	220 °C
Related compounds
Related alkanes	Heptane 2,2,4-Trimethylpentane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Octane is a straight-chain alkane with the chemical formula CH₃(CH₂)₆CH₃.

Octane has 18 structural isomers (25 including stereoisomers):

• Octane (n-octane)
• 2-Methylheptane
• 3-Methylheptane (2 enantiomers)
• 4-Methylheptane
• 3-Ethylhexane
• 2,2-Dimethylhexane
• 2,3-Dimethylhexane (2 enantiomers)
• 2,4-Dimethylhexane (2 enantiomers)
• 2,5-Dimethylhexane
• 3,3-Dimethylhexane
• 3,4-Dimethylhexane (2 enantiomers + 1 meso compound)
• 3-Ethyl-2-methylpentane (2 enantiomers)
• 3-Ethyl-3-methylpentane
• 2,2,3-Trimethylpentane (2 enantiomers)
• 2,2,4-Trimethylpentane (isooctane)
• 2,3,3-Trimethylpentane
• 2,3,4-Trimethylpentane
• 2,2,3,3-Tetramethylbutane

Metaphorical use

Octane became well-known in American popular culture in the mid- and late-sixties, when gasoline companies boasted of "high octane" levels in their gasoline on television commercials. These commercials are referring to the octane rating, which is a measure for the anti-knocking properties of gasoline. The octane rating is not related to the amount of octane contained in the gasoline.

These commercials had disappeared by the time of the 1973 Oil Crisis, which spared gasoline companies the need to compete via advertising. "Octane" was rarely cited in non-technical contexts over the next two decades.

The compound adjective "high-octane" was apparently first used in its figurative sense (i.e. without reference to gasoline) in a book review of Michael Crichton's novel Jurassic Park (1990), which appeared in the newspaper New York Newsday. The review, by Gregory Feeley, called the novel "intellectually provocative, high-octane entertainment," and was quoted the following year in the front matter of the novel's paperback edition, which sold more than 15 million copies in the United States. By the mid-nineties, the phrase was commonly being used to as an intensifier, and (despite the paucity of references to octane in any other context) has apparently found a place in modern English vernacular.

References

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External links

• International Chemical Safety Card 0933
• NIOSH Pocket Guide to Chemical Hazards 0470
• Material Safety Data Sheet for Octane
• Phytochemical database entry
• Chemical and physical properties table
• "High octane" in the urban dictionary