1-Bromonaphthalene

1-Bromonaphthalene
Names
	Preferred IUPAC name 1-Bromonaphthalene
	Other names α-Bromonaphthalene
Identifiers
CAS Number	90-11-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	6735;
ECHA InfoCard	100.001.787
EC Number	201-965-2;
MeSH	C108222
PubChem CID	7001;
UNII	976Y53P08P ;
CompTox Dashboard (EPA)	DTXSID30861681 ;
	InChI InChI=1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H Key: DLKQHBOKULLWDQ-UHFFFAOYSA-N; InChI=1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H Key: DLKQHBOKULLWDQ-UHFFFAOYAA;
	SMILES c1ccc2c(c1)cccc2Br;
Properties
Chemical formula	C10H7Br
Molar mass	207.070 g·mol−1
Appearance	Colorless liquid
Density	1.48 g/mL
Melting point	1–2 °C (34–36 °F; 274–275 K)
Boiling point	132–135 °C at 12 mm; 145–148 °C at 20 mm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Bromonaphthalene is an organic compound with the formula C₁₀H₇Br.

It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid.

Synthesis and reactions

It is prepared by treatment of naphthalene with bromine:^[1]

C₁₀H₈ + Br₂ → C₁₀H₇Br + HBr

The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile.

It forms a Grignard reagent^[2] and organolithium compound.

Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithium–halogen exchange:

C₁₀H₇Br + BuLi → C₁₀H₇Li + BuBr (Bu = butyl)

The resulting 1-lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. The 1,8-dilithio derivative is a precursor to a host of peri-naphthalene derivatives.^[3]

Applications

The compound is also used as a precursor to various substituted naphthalenes, but substituted bromonaphthalenes are more important commercially.^[4]

Because of its high refractive index (1.656-1.659_nD),^[5] 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.

References

↑ Clarke, H. T.; Brethen, M. R. (1921). "α-Bromonaphthalene". Organic Syntheses. 1: 35. doi:10.15227/orgsyn.001.0035.
↑ Gilman, Henry; St. John, Nina B.; Schulze., F. (1931). "α-Naphthoic Acid". Organic Syntheses. 11: 80. doi:10.15227/orgsyn.011.0080.
↑ van Soolingen J, de Lang RJ, den Besten R, et al. (1995). "A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene". Synthetic Communications. 25 (11): 1741–1744. doi:10.1080/00397919508015858.
↑ Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and Hydronaphthalenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2..
↑ "1-Bromonaphthalene".

[1] Clarke, H. T.; Brethen, M. R. (1921). "α-Bromonaphthalene". Organic Syntheses. 1: 35. doi:10.15227/orgsyn.001.0035.

[2] Gilman, Henry; St. John, Nina B.; Schulze., F. (1931). "α-Naphthoic Acid". Organic Syntheses. 11: 80. doi:10.15227/orgsyn.011.0080.

[3] van Soolingen J, de Lang RJ, den Besten R, et al. (1995). "A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene". Synthetic Communications. 25 (11): 1741–1744. doi:10.1080/00397919508015858.

[Ullmann-4] Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and Hydronaphthalenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2..

[5] "1-Bromonaphthalene".

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1-Bromonaphthalene

Contents

Synthesis and reactions

Applications

See also

References