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B73104

Sigma-Aldrich

1-Bromonaphthalene

97%

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Synonym(s):
1-Naphthyl bromide
Empirical Formula (Hill Notation):
C10H7Br
CAS Number:
90-11-9
Molecular Weight:
207.07
Beilstein:
1906414
EC Number:
201-965-2
MDL number:
MFCD00003868
PubChem Substance ID:
24891985
NACRES:
NA.22

Quality Level

200

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 - H319 - H410

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A New Suzuki- Heck-Type Coupling Cascade: Indeno [1, 2, 3]-Annelation of Polycyclic Aromatic Hydrocarbons
Wegner HA, et al.
The Journal of Organic Chemistry, 68(3), 883-887 (2003)
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)
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)
Jun-ze Mu et al.
Guang pu xue yu guang pu fen xi = Guang pu, 25(2), 188-191 (2005-04-28)
Fluorescence and room temperature phosphoresce (CD-RTP) induced by cyclodextrin methods were employed to investigate the effects of steric hindrance of guest molecule on the formation of inclusion complexes of beta-cylcodextrin (beta-CD) and bromonaphthalene (BrN). It has been found that the
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