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Merck

B73104

Sigma-Aldrich

1-Bromonaphthalene

97%

Sinónimos:

1-Naphthyl bromide

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About This Item

Fórmula empírica (notación de Hill):
C10H7Br
Número de CAS:
Peso molecular:
207.07
Beilstein/REAXYS Number:
1906414
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.6570 (lit.)

bp

133-134 °C/10 mmHg (lit.)

mp

−2-−1 °C (lit.)

density

1.48 g/mL at 20 °C (lit.)

SMILES string

Brc1cccc2ccccc12

InChI

1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

InChI key

DLKQHBOKULLWDQ-UHFFFAOYSA-N

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General description

1-Bromonaphthalene serves as an intermediate for the synthesis of biaryl compounds via cross-coupling reactions.

Application

1-Bromonaphthalene is a bromoarene that can be used in:
  • Palladium-catalyzed Suzuki–Miyaura coupling reaction with potassium aryltrifluoroborates without the use of phase-transfer catalysts or phosphine ligands.
  • The preparation of indeno annelated polycyclic aromatic hydrocarbons by reacting with o-bromobenzeneboronic acid and oligocyclic bromoarenes via Suzuki-Heck type coupling.
  • Ni catalyzed Kumada–Tamao–Corriu cross-coupling reaction with PhMgBr.
  • The preparation of arylnaphthalenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with aryl boronic acid.

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Exploring the selectivity of the Suzuki-Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes
Lima CFRAC, et al.
Tetrahedron, 67(4), 689-697 (2011)
Microwave-accelerated Suzuki-Miyaura coupling reactions using potassium aryltrifluoroborates
Harker RL and Crouch RD
Synthesis, 2007(01), 25-27 (2007)
High efficiency of cavity-based triaryl-phosphines in nickel-catalysed Kumada-Tamao-Corriu cross-coupling
Monnereau L, et al.
Chemical Communications (Cambridge, England), 47(23), 6626-6628 (2011)
M Arivazhagan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 83(1), 553-560 (2011-10-01)
In this work, the experimental and theoretical vibrational spectra of 1-bromonaphthalene (1-BN) were studied. FTIR and FT Raman spectra were recorded in the region 4000-400 cm(-1) and 3500-50 cm(-1), respectively. The structural and spectroscopic data of the molecule in the
Xinzhen Du et al.
Journal of colloid and interface science, 274(2), 645-651 (2004-05-18)
The binding of polyethylene glycol (10) n-octylphenyl ether (OPE) and polyethylene glycol (10) tert-octylphenyl ether (Triton X-100, TX) to beta-cyclodextrin (beta-CD) and heptakis(2,3- beta-dimethyl)- beta-CD (DM- beta-CD) was described in detail by surface tension, steady-state fluorescence of OPE and TX

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