2-Bromnaphthalin - 2-Bromnaphthalin

Structural formula
Structure of 2-bromonaphthalene
General
Name 2-Bromnaphthalin
other names

β-Naphthylbromid

Sum formula C 10 H 7 Br
Brief description

yellow solid with characteristic odor [1]

External identifiers / databases
CAS number 580-13-2
EC number 209-452-5
ECHA-InfoCard 100.008.594
PubChem 11372
Wikidata Q27289466
characteristics
Molar mass 207.07 g · mol −1
Physical state

fest[1]

Melting point

52–55 °C[1]

boiling point

281–283 °C[1]

solubility

practically insoluble in water (8 mg · l −1 at 25 ° C) [1]

safety instructions
GHS hazard labeling [1]
07 - Warning

Caution

H and P phrases H: 302​‐​319
P: 305+351+338 [1]
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Bromonaphthalene (β-naphthyl bromide) is a chemical compound that belongs to the substance class of substituted naphthalenes . It is isomeric to 1-bromonaphthalene .

Extraction and presentation

2-Bromonaphthalene can be prepared in a Sandmeyer reaction from 2-aminonaphthalene (β-naphthylamine) with copper (I) bromide as a reagent. The reaction takes place via the diazonium salt as an intermediate. [2]

Sandmeyer reaction for the synthesis of 2-bromonaphthalene

characteristics

2-Bromonaphthalene is a yellow solid.

use

2-Bromonaphthalene can be used for the synthesis of biaryls in a Suzuki cross-coupling reaction [3] and for the preparation of a pentacarbonyl [methoxy (2-naphthyl) carbene] chromium complex. [4]

Individual evidence

  1. a b c d e f g Entry on 2-bromonaphthalene in the GESTIS substance database of the IFA , accessed on February 24, 2017(JavaScript required) .
  2. H. Meislich, H. Nechamkin, J. Sharefkin: Organic Chemistry. (= Foam's outline ). McGraw Hill, Düsseldorf 1980, ISBN 978-0-070-63425-1 , p. 341.
  3. Data sheet 2-bromonaphthalene from Sigma-Aldrich , accessed on February 25, 2017 ( PDF ).
  4. Hans Joachim Stendel: Highly substituted hydrochinoid tricarbonyl (phenanthrene) chromium and tricarbonyl (triphenylene) chromium complexes: syntheses, structures and haptotropic metal migrations . Bonn 2005, DNB 974188557 , urn : nbn: de: hbz: 5N-04972 (dissertation, University of Bonn).