1-Bromonaphthalene

1-Bromonaphthalene Basic information
Product Name:1-Bromonaphthalene
Synonyms:1-bromo-naphthalen;A-BROMONAPHTHALENE;ALPHA-BROMONAPHTHALENE;ALPHA-MONOBROMONAPHTHALENE;ALPHA-NAPHTHYL BROMIDE;1-BROMONAPHTHALENE;1-BROMO NAPTHALENE;1-Bromonaphthalene solution
CAS:90-11-9
MF:C10H7Br
MW:207.07
EINECS:201-965-2
Product Categories:Naphthalene series;Pyridines ,Heterocyclic Acids;C9 to C12;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Naphthalene derivatives;Aryl;C9 to C12;Halogenated Hydrocarbons;Aromatic Compounds;bc0001;90-11-9
Mol File:90-11-9.mol
1-Bromonaphthalene Structure
1-Bromonaphthalene Chemical Properties
Melting point −2-−1 °C(lit.)
Boiling point 133-134 °C10 mm Hg(lit.)
density 1.48 g/mL at 20 °C(lit.)
vapor pressure 0.013 hPa (20 °C)
refractive index n20/D 1.6570(lit.)
Fp >230 °F
storage temp. Store below +30°C.
solubility H2O: slightly soluble
form Liquid
color slightly yellow to deep brownish-yellow
Water Solubility slightly soluble
Merck 14,1425
BRN 1906414
InChIKeyDLKQHBOKULLWDQ-UHFFFAOYSA-N
LogP4.06
CAS DataBase Reference90-11-9(CAS DataBase Reference)
NIST Chemistry ReferenceNaphthalene, 1-bromo-(90-11-9)
EPA Substance Registry SystemNaphthalene, 1-bromo- (90-11-9)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36-36/37/38-20/21/22
Safety Statements 26-36
RIDADR 2810
WGK Germany 3
RTECS QJ1545000
8
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29036990
ToxicityLD50 orally in Rabbit: 810 mg/kg
MSDS Information
ProviderLanguage
alpha-Bromonaphthalene English
SigmaAldrich English
ACROS English
ALFA English
1-Bromonaphthalene Usage And Synthesis
Chemical PropertiesThick colorless yellow to yellow-brown liquid with a pungent odor. Insoluble in water, miscible with alcohol, ether, benzene and chloroform. 1-Bromonaphthalene is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene.
Uses1-Bromonaphthalene is used in organic synthesis and refractometry of fats. It is used in the preparation of N-aryl imidazoles and diaryl ethers. It is used to determine the refractive index of crystals and the water content of alcohols. It is utilized in the preparation of glutathione peroxidase-like antioxidant activity of diaryl diselenides. Further, it serves as a solvent for the exfoliation and dispersion of hexabenzocoronene. In addition to this, it is used as a refrigerant and a solvent molecular weight substance.
Application1-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.
Preparation1-Bromonaphthalene is synthesized by the reaction of naphthalene with bromine: C10H8+ Br2→ C10H7Br + HBr.
Reaction: add carbon tetrachloride and naphthalene in the reaction pot, stirring and heating, and slowly add bromine at 45℃. After adding, keep the reaction at 70-80℃ for 3-4h. distillation to recover carbon tetrachloride, wash the reaction product, distill under reduced pressure, wash again, filter, dry and get the finished product.
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 1, p. 121, 1941
Tetrahedron, 64, p. 4999, 2008 DOI: 10.1016/j.tet.2008.03.085
General DescriptionThe vibrational spectra of 1-bromonaphthalene has been studied.
Purification MethodsPurify 1-bromonaphthalene by passage through activated alumina, and three vacuum distillations. [Beilstein 5 H 547, 5 IV 1665.]
1-Hexadecylpyridinium bromide 3-Hydroxy-7-bromonaphthalene-2-carboxylic acid 2-BROMONAPHTHALENE SOLUTION 2000UG/ML IN METHANOL 1ML 4-BROMONAPHTHALENE-1-CARBOXYLIC ACID 5-Bromoacenaphthene 2-BROMONAPHTHALENE SOLUTION 2000UG/ML IN METHANOL 5ML 6-Bromonaphthalene-1,2-dione 2-Methoxymethyl-1-bromonaphthalene 4-Bromonaphthalene-1-amine,1-AMINO-4-BROMONAPHTHALENE Bis(1-bromonaphthalene-2-carboxylic acid)(1S,2S)-1,2-diphenylethane-1,2-diyl ester 2-BROMONAPHTHALENE SOLUTION 2000UG/ML IN METHANOL 5X1ML 4-Bromonaphthalene-1-ol Sulfuric acid 6-bromonaphthalene-2-yl=potassium salt 2-Bromonaphthalene-1-ol 1,1'-Bi(2-bromonaphthalene) 2-BROMONAPHTHALENE-BIS(HEXACHLOROCYCLOPENTADIENE) ADDUCT 2-(BENZYLOXY)-6-BROMONAPHTHALENE 7-BROMONAPHTHALENE-2-CARBALDEHYDE

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