2-Bromonaphthalene

Base Information

• Chemical Name: 2-Bromonaphthalene
• CAS No.: 580-13-2
• Molecular Formula: C10H7Br
• Molecular Weight: 207.07
• Hs Code.: 29039990
• European Community (EC) Number: 209-452-5
• NSC Number: 4011
• UNII: SYU33I753N
• DSSTox Substance ID: DTXSID3060378
• Nikkaji Number: J94.978G
• Wikidata: Q27289466
• Pharos Ligand ID: KU8UXQUFLX5X
• ChEMBL ID: CHEMBL192643
• Mol file: 580-13-2.mol

Synonyms:2-BROMONAPHTHALENE;580-13-2;Naphthalene, 2-bromo-;2-Naphthyl bromide;2-Bromo-naphthalene;2-BROMO NAPHTHALCNE;beta-Bromonaphthalene;.beta.-Bromonaphthalene;180-13-2;beta-Naphthyl bromide;.beta.-Naphthyl bromide;Naphthalene,2-Bromo-;UNII-SYU33I753N;CHEMBL192643;SYU33I753N;NSC 4011;NSC-4011;EINECS 209-452-5;AI3-19928;2-BROMO NAPHTHALENE;2-bromonaphtalene;2-bromonapthalene;6-bromonaphthalene;MFCD00004051;2-bromanylnaphthalene;Naftaleno, 2-bromo-;2-Bromonaphthalene, 97%;SCHEMBL154221;2-BROMONAPHTHALENE [MI];DTXSID3060378;NSC4011;STR03261;BDBM50159272;AKOS000121092;AC-3107;CS-W007537;PS-8067;AM20050153;B0619;FT-0611584;EN300-23847;A831702;Q-200246;Q27289466;Z166622678

Chemical Property of 2-Bromonaphthalene

Chemical Property:

• Appearance/Colour: UN 1230 3/PG 2
• Vapor Pressure: 0.00565mmHg at 25°C
• Melting Point: 52-55 °C(lit.)
• Refractive Index: 1.6382
• Boiling Point: 282.7 °C at 760 mmHg
• Flash Point: 127.8 °C
• PSA: 0.00000
• Density: 1.481 g/cm3
• LogP: 3.60230
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble50mg/mL, clear, colorless to yellow
• Water Solubility.: slightly soluble
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 205.97311
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

2-Bromonaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, T
• Hazard Codes: Xn,Xi,T
• Statements: 22-36-39/23/24/25-23/24/25-36/37/38-20/21/22
• Safety Statements: 26-36-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)Br
• Uses: 2-Bromonaphthalene is used as a raw material in the preparation of biaryls through Suzuki cross coupling reaction. Further, it plays a vital role in the preparation of dyes. It is also used to study potential tumorigenicity.

Technology Process of 2-Bromonaphthalene

There total 51 articles about 2-Bromonaphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

potassium 2-naphthyltrifluoroborate → 2-bromonaphthalene (580-13-2)

Guidance literature:

With tetra-N-butylammonium tribromide; In tetrahydrofuran; water; at 20 ℃; for 0.333333h; chemoselective reaction;

DOI:10.1021/ol9027144

Reference yield: 98.0%

2-naphthyl triflate (3857-83-8) → 2-bromonaphthalene (580-13-2)

Guidance literature:

With tris(2,4-pentanedionato)ruthenium(III); 3,4,7,8-Tetramethyl-o-phenanthrolin; ethylmagnesium bromide; lithium bromide; In 1,4-dioxane; at 120 ℃; for 48h;

DOI:10.1039/b907761h

Reference yield: 96.0%

naphthalene-2-boronic acid (32316-92-0) → 2-bromonaphthalene (580-13-2)

Guidance literature:

With sodium nitrite; In acetonitrile; at 80 ℃; for 1h; Sealed tube;

DOI:10.1016/j.tetlet.2019.151020

upstream raw materials:

naphthalene

1-Bromonaphthalene

sodium 2-naphtholate

naphthalen-2-ylamine

Downstream raw materials:

1-naphthalen-1-yl-piperidine

N-(2-naphthyl)piperidine

naphthalene

1-(6-bromonaphthalen-2-yl)ethanone

Refernces

• 1、 Achaefer,Higgins. "". . p. 1607. Retrieved 1967.
• 2、 Berliner et al.. "". . p. 495. Retrieved 1958.
• 3、 Fu, Fang,Gurung, Laxman,Czaun, Miklos,Mathew, Thomas,Prakash, G.K. Surya. "ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents". supporting information. . Retrieved 2019/08/26.
• 4、 Zarate, Cayetana,Nakajima, Masaki,Martin, Ruben. "A mild and ligand-free Ni-catalyzed silylation via C-OMe cleavage". supporting information. p. 1191 - 1197. Retrieved 2017/05/16.