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Sigma-Aldrich

2-Bromonaphthalene

97%

Synonym(s):

β-Bromonaphthalene, β-Naphthyl bromide, 2-Naphthyl bromide

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About This Item

Empirical Formula (Hill Notation):
C10H7Br
CAS Number:
580-13-2
Molecular Weight:
207.07
Beilstein:
1858110
EC Number:
209-452-5
MDL number:
MFCD00004051
UNSPSC Code:
12352100
PubChem Substance ID:
24851065
NACRES:
NA.22

Assay

97%

form

solid

impurities

≤3% 1-bromonaphthalene

bp

281-282 °C (lit.)

mp

52-55 °C (lit.)

solubility

methanol: soluble 50 mg/mL, clear, colorless to yellow

SMILES string

Brc1ccc2ccccc2c1

InChI

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

InChI key

APSMUYYLXZULMS-UHFFFAOYSA-N

Gene Information

human ... CYP2A6(1548)
mouse ... Cyp2a5(13087)

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General description

Reaction of 2-bromonaphthalene with cuprous cyanide in N-methylpyrrolidone has been investigated. Nanosecond time-resolved resonance Raman spectra of the T1→Tn transition of 2-bromonaphthalene in methanol solvent has been investigated.

Application

2-Bromonaphthalene was used in the synthesis of biaryls via Suzuki cross coupling reaction in water under microwave irradiation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rapid microwave-promoted Suzuki cross coupling reaction in water.
Bai L, et al.
Green Chemistry, 5(5), 615-617 (2003)
Nanosecond time-resolved resonance Raman investigation of the T1→ Tn transition of 2-bromonaphthalene.
Shoute LCT, et al.
Chemical Physics Letters, 290(1), 24-28 (1998)
Isaiah R Speight et al.
Molecules (Basel, Switzerland), 25(3) (2020-02-06)
Owing to the strength of the C-F bond, the 'direct' preparation of Grignard reagents, i.e., the interaction of elemental magnesium with an organic halide, typically in an ethereal solvent, fails for bulk magnesium and organofluorine compounds. Previously described mechanochemical methods
Notes-A Convenient Synthesis of Water-Soluble Carbodiimides.
Sheehan J, et al.
The Journal of Organic Chemistry, 26(7), 2525-2528 (1961)
J M Shoulder et al.
SAR and QSAR in environmental research, 30(4), 229-245 (2019-03-22)
Persistent organic contaminants in the environment pose an environmental risk due to widespread occurrence and toxic properties. Advanced oxidation processes (AOPs) are treatment methods that have been used to successfully degrade organic contaminants in water, soil, sediments and sludge. Reaction
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