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B73104

Sigma-Aldrich

1-Bromonaphthalene

97%

Synonym(s):

1-Naphthyl bromide

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About This Item

Empirical Formula (Hill Notation):
C10H7Br
CAS Number:
90-11-9
Molecular Weight:
207.07
Beilstein:
1906414
EC Number:
201-965-2
MDL number:
MFCD00003868
UNSPSC Code:
12352100
PubChem Substance ID:
24891985
NACRES:
NA.22
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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.[1][2]

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.[1]
  • The preparation of indeno annelated polycyclic aromatic hydrocarbons by reacting with o-bromobenzeneboronic acid and oligocyclic bromoarenes via Suzuki-Heck type coupling.[3]
  • Ni catalyzed Kumada–Tamao–Corriu cross-coupling reaction with PhMgBr.[2]
  • The preparation of arylnaphthalenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with aryl boronic acid.[4]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4240
BCCK3446
BCCL2355
BCCH3693
BCCH9438

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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)
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)
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
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)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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