heptane

n-Heptane
Identifiers
CAS number	142-82-5 Y
PubChem	8900
RTECS number	MI7700000
SMILES	CCCCCCC
InChI	1/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3
ChemSpider ID	8560
Properties
Molecular formula	C7H16
Molar mass	100.21 g/mol
Appearance	colourless liquid
Density	0.684 g/ml, liquid
Melting point	−90.61 °C (182.55 K)
Boiling point	98.42 °C (371.58 K)
Solubility in water	Immiscible
Viscosity	0.386 cP at 25 °C
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
NFPA 704	3 1 0
Flash point	−4 °C
Autoignition temperature	285 °C
Related compounds
Related alkanes	Hexane Octane
Related compounds	Methylcyclohexane Cycloheptane
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

n-Heptane is the straight-chain alkane with the chemical formula H₃C(CH₂)₅CH₃ or C₇H₁₆. It is the zero point of the octane rating scale (the 100 point is iso-octane).

Uses

Heptane (and its many isomers) is widely applied in laboratories as a totally non-polar solvent. A liquid, it is ideal for transport and storage. In the grease spot test, heptane is used to dissolve the oil spot to show the previous presence of organic compounds on a stained paper. This is done by shaking the stained paper in a heptane solution for about half a minute.^{[citation needed]}

Extraction into heptane is a means by which aqueous bromine may be distingiushed from aqueous iodine. In water, both bromine and iodine appear brown. However, iodine turns purple when dissolved in heptane, whereas the bromine solution remains brown.

Heptane is commercially available as the rubber cement solvent "Bestine" and the outdoor stove fuel "Powerfuel" by Primus.

Octane rating scale

n-Heptane is the zero point of the octane rating scale. It is undesirable in petrol, because it burns explosively, causing engine knocking, as opposed to branched-chain octane isomers, which burn more slowly and give better performance. It was chosen as the zero point of the scale because of the availability of very high purity n-heptane, unmixed with other isomers of heptane or other alkanes, distilled from the resin of Jeffrey Pine and from the fruit of Pittosporum resiniferum. Other sources of heptane and octane, produced from crude oil, contain a mixture of different isomers with greatly differing ratings and do not give as precise a zero point.

Isomers and enantiomers

Heptane has nine isomers, or eleven if enantiomers are counted:

• Heptane (n-heptane), H₃C–CH₂–CH₂–CH₂–CH₂–CH₂–CH₃,
• 2-Methylhexane (isoheptane), H₃C–CH(CH₃)–CH₂–CH₂–CH₂–CH₃,
• 3-Methylhexane, H₃C–CH₂–C^*H(CH₃)–CH₂–CH₂–CH₃ (chiral),
• 2,2-Dimethylpentane (neoheptane), (H₃C)₃–C–CH₂–CH₂–CH₃,
• 2,3-Dimethylpentane, (H₃C)₂–CH–C^*H(CH₃)–CH₂–CH₃ (chiral),
• 2,4-Dimethylpentane, (H₃C)₂–CH–CH₂–CH–(CH₃)₂,
• 3,3-Dimethylpentane, H₃C–CH₂–C(CH₃)₂–CH₂–CH₃,
• 3-Ethylpentane, H₃C–CH₂–CH(CH₂CH₃)–CH₂–CH₃,
• 2,2,3-Trimethylbutane, CH₃–C(CH₃)₂–CH(CH₃)–CH₃, this isomer is also known as pentamethylethane and triptane.^[1]

References

External links

• International Chemical Safety Card 0657 (n-heptane)
• International Chemical Safety Card 0658 (2-methylhexane)
• NIOSH Pocket Guide to Chemical Hazards
• European Chemicals Bureau
• Material Safety Data Sheet for Heptane
• Phytochemical database entry