n-Butylbenzene

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n-Butylbenzene
Butylbenzene.svg
Names
Preferred IUPAC name
Butylbenzene
Other names
1-Butylbenzene
1-Phenylbutane
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.002.918 Edit this at Wikidata
EC Number
  • 203-209-7
UNII
UN number 2709
  • InChI=1S/C10H14/c1-2-3-7-10-8-5-4-6-9-10/h4-6,8-9H,2-3,7H2,1H3
    Key: OCKPCBLVNKHBMX-UHFFFAOYSA-N
  • CCCCC1=CC=CC=C1
Properties
C10H14
Molar mass 134.222 g·mol−1
Appearance Colorless liquid
Density 0.8601 g/cm3 at 20 °C
Melting point −87.9 °C (−126.2 °F; 185.2 K)
Boiling point 183.3 °C (361.9 °F; 456.4 K)
11.8 mg/L
Solubility alcohol, ether, benzene
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Warning
H226, H315, H319, H410
P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P313, P337+P313, P362, P370+P378, P391, P403+P235, P501
Flash point 71 °C; 160 °F; 344 K
410 °C (770 °F; 683 K)
Related compounds
Related compounds
iso-Butylbenzene, sec-Butylbenzene, tert-Butylbenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

n-Butylbenzene is the organic compound with the formula C6H5C4H9. Of two isomers of butylbenzene, n-butylbenzene consists of a phenyl group attached to the 1 position of a butyl group. It is a slightly greasy, colorless liquid.

The synthesis of n-butylbenzene by the reaction of chlorobenzene and butylmagnesium bromide was one of the first demonstrations of the Kumada coupling using nickel diphosphine catalysts.[1] This mild and efficient process contrasted with older methods.[2]

See also[edit]

References[edit]

  1. ^ Tamao, Kohei; Sumitani, Koji; Kumada, Makoto (1972). "Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine Complexes". Journal of the American Chemical Society. 94 (12): 4374–6. doi:10.1021/ja00767a075.{{cite journal}}: CS1 maint: uses authors parameter (link)
  2. ^ R. R. Read, L. S. Foster, Alfred Russell, V. L. Simril (1945). "n-Butylbenzene". Org. Synth. 25: 11. doi:10.15227/orgsyn.025.0011.{{cite journal}}: CS1 maint: uses authors parameter (link)