2-Bromonaphthalene

2-Bromonaphthalene
Identifiers
CAS Number	580-13-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL192643;
ChemSpider	10894;
ECHA InfoCard	100.008.594
EC Number	209-452-5;
PubChem CID	11372;
UNII	SYU33I753N;
CompTox Dashboard (EPA)	DTXSID3060378 ;
	InChI InChI=1S/C10H7Br/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H Key: APSMUYYLXZULMS-UHFFFAOYSA-N;
	SMILES C1=CC=C2C=C(C=CC2=C1)Br;
Properties
Chemical formula	C10H7Br
Molar mass	207.070 g·mol−1
Appearance	white solid
Melting point	45–50 °C (113–122 °F; 318–323 K)
Boiling point	281–283 °C (538–541 °F; 554–556 K)
Vapor pressure	0.00347 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H319
Precautionary statements	P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Bromonaphthalene is an organic compound with the formula C₁₀H₇Br. It is one of two isomeric monobromonaphthalenes, the other being 1-bromonaphthalene. Under normal conditions, the substance is a colorless solid.

Synthesis and reactions

It is prepared by treatment of 2-naphthol with triphenylphosphine dibromide:^[2]

C₁₀H₇(OH) + (C₆H₅)₃PBr₂ → C₁₀H₇Br + (C₆H₅)₃PO + HBr

It can also be prepared by a Sandmeyer reaction from 2-aminonaphthalene.^[3]

It forms a Grignard reagent.^[4]

References

↑ PubChem. "2-Bromonaphthalene". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-04-14.
↑ Schaefer, J. P.; Higgins, Jerry; Shenoy, P. K. (1969). "2-Bromonaphthalene". Organic Syntheses. 49: 6. doi:10.15227/orgsyn.049.0006.
↑ H. Meislich, H. Nechamkin, J. Sharefkin: Organische Chemie. (= Schaum's outline). McGraw Hill, Düsseldorf 1980, ISBN 978-0-070-63425-1, S. 341.
↑ Beck, Albert K.; Gysi, Peter; La Vecchia, Luigi; Seebach, Dieter (1999). "(4R,5R)-2,2-Dimethyl-α,α,α',α'-Tetra(naphth-2-yl)-1,3-Dioxolane-4,5-Dimethanol from Dimethyl Tartrate and 2-Naphthyl Magnesium Bromide". Organic Syntheses. 76: 12. doi:10.15227/orgsyn.076.0012.

[1] PubChem. "2-Bromonaphthalene". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-04-14.

[2] Schaefer, J. P.; Higgins, Jerry; Shenoy, P. K. (1969). "2-Bromonaphthalene". Organic Syntheses. 49: 6. doi:10.15227/orgsyn.049.0006.

[3] H. Meislich, H. Nechamkin, J. Sharefkin: Organische Chemie. (= Schaum's outline). McGraw Hill, Düsseldorf 1980, ISBN 978-0-070-63425-1, S. 341.

[4] Beck, Albert K.; Gysi, Peter; La Vecchia, Luigi; Seebach, Dieter (1999). "(4R,5R)-2,2-Dimethyl-α,α,α',α'-Tetra(naphth-2-yl)-1,3-Dioxolane-4,5-Dimethanol from Dimethyl Tartrate and 2-Naphthyl Magnesium Bromide". Organic Syntheses. 76: 12. doi:10.15227/orgsyn.076.0012.

[1]

[2]

[3]

[4]