2-Bromopyridine

Base Information

• Chemical Name: 2-Bromopyridine
• CAS No.: 109-04-6
• Molecular Formula: C5H4BrN
• Molecular Weight: 157.997
• Hs Code.: 29333999
• European Community (EC) Number: 203-641-6
• NSC Number: 8031
• UNII: 7Z7MLC4VD8
• DSSTox Substance ID: DTXSID6051564
• Nikkaji Number: J32.655K
• Wikipedia: 2-Bromopyridine
• Wikidata: Q209317
• Metabolomics Workbench ID: 57787
• ChEMBL ID: CHEMBL331374
• Mol file: 109-04-6.mol

Synonyms:2-BROMOPYRIDINE;109-04-6;o-Bromopyridine;2-Pyridyl bromide;Pyridine, 2-bromo-;2-bromo-pyridine;2-bromopyridin;beta-Bromopyridine;Pyridine, bromo-;alpha-Bromopyridine;MFCD00006219;.beta.-Bromopyridine;.alpha.-Bromopyridine;Pyridin-2-yl bromide;NSC 8031;EINECS 203-641-6;UNII-7Z7MLC4VD8;BRN 0105789;7Z7MLC4VD8;AI3-17852;DTXSID6051564;CHEBI:51574;NSC-8031;5-20-05-00422 (Beilstein Handbook Reference);bromopyridine;2-bromo pyridine;bromo pyridine;a-Bromopyridine;2-bromopridine;2-pyridylbromide;2-bromo-pyridin;2 -bromopyridine;2-bromanylpyridine;NSC8031;Pyridine, 2-bromo-,;2-Bromopyridine, 99%;PYRIDINE,2-BROMO;WLN: T6NJ BE;SCHEMBL6536;CHEMBL331374;DTXCID0030116;CS-D1419;STR00629;Tox21_303772;BBL027568;STK802248;AKOS000119182;AB00627;PS-4254;NCGC00357064-01;CAS-109-04-6;LS-130297;AM20050660;B0650;FT-0611611;FT-0663861;EN300-18089;S12408;A801959;Q209317;W-108708;Z57160165;F0001-0191

Chemical Property of 2-Bromopyridine

Chemical Property:

• Appearance/Colour: clear slight brown liquid
• Vapor Pressure: 0.784mmHg at 25°C
• Melting Point: 193 °C
• Refractive Index: n20/D 1.572(lit.)
• Boiling Point: 189.5 °C at 760 mmHg
• PKA: pK1: 0.71(+1) (25°C)
• Flash Point: 54.4 °C
• PSA: 12.89000
• Density: 1.598 g/cm³
• LogP: 1.84410
• Storage Temp.: Refrigerator
• Solubility.: 20g/l
• Water Solubility.: Slightly miscible with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 156.95271
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

99% ^*data from raw suppliers

2-Bromopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn,F
• Hazard Codes: T,Xn,F
• Statements: 10-24/25-36/37/38-23/24/25-20/21/22
• Safety Statements: 16-36/37-45-38-36/37/39-28A-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)Br
• Uses: 2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.

Technology Process of 2-Bromopyridine

There total 49 articles about 2-Bromopyridine 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: 100.0%

2,6-Dibromopyridine (626-05-1) → 2-bromo-pyridine (109-04-6)

Guidance literature:

With n-butyllithium; butyl magnesium bromide; In toluene; at -10 ℃;

DOI:10.1021/jo0157425

Reference yield: 97.0%

2-bromopyridine-N-oxide hydrochloride (80866-91-7) → 2-bromo-pyridine (109-04-6)

Guidance literature:

With titanium; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1055/s-1987-28152

Reference yield: 96.0%

2-bromopyridine-N-oxide (14305-17-0) → 2-bromo-pyridine (109-04-6)

Guidance literature:

With Dimethylphenylsilane; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c5ra08845c

upstream raw materials:

pyridine

2-aminopyridine

acetyl hypofluorite

2-bromopyridine-N-oxide

Downstream raw materials:

1-(2-pyridyl)piperazine

1,4-bis-(2-pyridyl)-1,4-diazacyclohexane

1-methyl-4-(pyridin-2-yl)piperazine

N-(2-pyridinyl)-1,3-propandiamine

Refernces

• 1、 Sanz, Roberto,Escribano, Jaime,Fernández, Yolanda,Aguado, Rafael,Pedrosa, María R.,Arnáiz, Francisco J.. "Deoxygenation of N-oxides with triphenylphosphine, catalyzed by dichlorodioxomolybdenum(VI)". . p. 1389 - 1392. Retrieved 2005.
• 2、 Newkome, George R.,Roper, Jerry M.. "POLYORGANOMETALLIC HETEROCYCLES. 2,6-DILITHIOPYRIDINE". . p. 147 - 153. Retrieved 1980.
• 3、 Sugimoto, Osamu,Mori, Miho,Tanji, Ken-ichi. "A facile halogenation of some hydroxyheterocycles using triphenylphosphine and N-halosuccinimide". . p. 7477 - 7478. Retrieved 1999.
• 4、 Malinowski, Marek,Kaczmarek, Lukasz. "Titanium(0) Reagents; 2. A Selective and Efficient Deoxygenation of Halogen Containing Heteroaromatic N-Oxides". . p. 1013 - 1015. Retrieved 1987.
• 5、 Fiorio, Jhonatan L.,Rossi, Liane M.. "Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold". . p. 312 - 318. Retrieved 2021/01/29.
• 6、 Wang, Fangying,Jiang, Hongxia,Deng, Yufang,Yu, Jiang,Zhan, Miao,Zhao, Lifeng,Chen, Yuanwei. "Design, synthesis and biological evaluation of deuterated Vismodegib for improving pharmacokinetic properties". supporting information. p. 2399 - 2402. Retrieved 2018/06/25.