n-Butylbenzene

n-Butylbenzene
Names
	Preferred IUPAC name Butylbenzene
	Other names 1-Butylbenzene; 1-Phenylbutane
Identifiers
CAS Number	104-51-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:44194;
ECHA InfoCard	100.002.918
EC Number	203-209-7;
PubChem CID	7705;
UNII	S8XZ2901RZ;
UN number	2709
CompTox Dashboard (EPA)	DTXSID6022472 ;
	InChI 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;
	SMILES CCCCC1=CC=CC=C1;
Properties
Chemical formula	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)
Solubility in water	11.8 mg/L
Solubility	alcohol, ether, benzene
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H315, H319, H400, H410
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+352, P303+361+353, P305+351+338, P321, P332+313, P337+313, P362, P370+378, P391, P403+235, P501
Flash point	71 °C; 160 °F; 344 K
Autoignition; temperature	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).
	Infobox references

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]

References

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: 4374–6. doi:10.1021/ja00767a075.CS1 maint: uses authors parameter (link)
R. R. Read, L. S. Foster, Alfred Russell, V. L. Simril (1945). "n-Butylbenzene". Org. Synth. 25: 11. doi:10.15227/orgsyn.025.0011.CS1 maint: uses authors parameter (link)

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[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: 4374–6. doi:10.1021/ja00767a075.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.CS1 maint: uses authors parameter (link)