1-Bromonaphthalene Knowpia

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 edit

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. 1-Lithionaphthalene can be further lithiated to give 1,8-dilithionaphthalene, a precursor to peri-naphthalene compounds.

Applications edit

Because of its high refractive index (1.656-1.659_nD),^[3] 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.

The compound is also used as a precursor to various substituted derivatives of naphthalene.

References edit

^ "α-BROMONAPHTHALENE". Organic Syntheses. 1: 35. 1921. doi:10.15227/orgsyn.001.0035.
^ "α-NAPHTHOIC ACID". Organic Syntheses. 11: 80. 1931. doi:10.15227/orgsyn.011.0080.
^ "1-Bromonaphthalene".

[1] "α-BROMONAPHTHALENE". Organic Syntheses. 1: 35. 1921. doi:10.15227/orgsyn.001.0035.

[2] "α-NAPHTHOIC ACID". Organic Syntheses. 11: 80. 1931. doi:10.15227/orgsyn.011.0080.

[3] "1-Bromonaphthalene".

[1]

[2]

[3]

Summary

Synthesis and reactions edit

Applications edit

See also edit

References edit