|
| | 1-Bromonaphthalene Basic information |
| | 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 | | 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 | Naphthalene, 1-bromo- (90-11-9) |
| 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 | | F | 8 | | TSCA | Yes | | HazardClass | 6.1(b) | | PackingGroup | III | | HS Code | 29036990 | | Toxicity | LD50 orally in Rabbit: 810 mg/kg |
| | 1-Bromonaphthalene Usage And Synthesis |
| 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 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: 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 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.] |
| | 1-Bromonaphthalene Preparation Products And Raw materials |
| 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 |
|
