| Identification | More | [Name]
1-Bromonaphthalene | [CAS]
90-11-9 | [Synonyms]
A-BROMONAPHTHALENE
ALPHA-BROMONAPHTHALENE
ALPHA-MONOBROMONAPHTHALENE
ALPHA-NAPHTHYL BROMIDE
1-bromo-naphthalen
1-Naphthyl bromide
1-naphthylbromide
α-bromonaphthalene
1-BROMO NAPTHALENE
1-Bromonaphtalene
1-Bromonaphthalene solution
| [EINECS(EC#)]
201-965-2 | [Molecular Formula]
C10H7Br | [MDL Number]
MFCD00003868 | [Molecular Weight]
207.07 | [MOL File]
90-11-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to yellow-brown liquid | [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 | [Detection Methods]
GC | [Merck ]
14,1425 | [BRN ]
1906414 | [Dielectric constant]
5.1（19℃） | [InChIKey]
DLKQHBOKULLWDQ-UHFFFAOYSA-N | [LogP]
4.06 | [CAS DataBase Reference]
90-11-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Naphthalene, 1-bromo-(90-11-9) | [EPA Substance Registry System]
90-11-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
2810 | [WGK Germany ]
3
| [RTECS ]
QJ1545000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29036990 | [Toxicity]
LD50 orally in Rabbit: 810 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Government regulation-->Carbon tetrachloride-->1-Chloronaphthalene | [Preparation Products]
N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine-->1-Naphthoic acid-->1-NAPHTHALENETHIOL-->1-Naphthylboronic acid-->1-Cyanonaphthalene-->1'-Acetonaphthone-->4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione-->1-(4-Bromophenyl)-naphthlene-->(4R,5R)-(-)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRA(1-NAPHTHYL)-1,3-DIOXOLANE-4,5-DIMETHANOL-->1-Bromo-4-chloronaphthalene-->1-(2-CHLOROETHYL)NAPHTHALENE-->Benzenamine, 4-(1-naphthalenyl)--->1-NAPHTHYLMAGNESIUM BROMIDE |
| Hazard Information | Back Directory | [Chemical Properties]
Thick 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.
| [Uses]
1-Bromonaphthalene(90-11-9) 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.
| [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. | [Preparation]
1-Bromonaphthalene is synthesized by the reaction of naphthalene with bromine. 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 Description]
The vibrational spectra of 1-bromonaphthalene has been studied. | [Purification Methods]
Purify 1-bromonaphthalene by passage through activated alumina, and three vacuum distillations. [Beilstein 5 H 547, 5 IV 1665.] |
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