5-Bromo-2-methylpyridine

Base Information

• Chemical Name: 5-Bromo-2-methylpyridine
• CAS No.: 3430-13-5
• Molecular Formula: C6H6BrN
• Molecular Weight: 172.024
• Hs Code.: 29333990
• European Community (EC) Number: 625-656-0
• DSSTox Substance ID: DTXSID80360871
• Nikkaji Number: J1.687.683F
• Wikidata: Q72511479
• Mol file: 3430-13-5.mol

Synonyms:5-Bromo-2-methylpyridine;3430-13-5;5-Bromo-2-picoline;2-Methyl-5-bromopyridine;5-Bromo-2-methyl-pyridine;Pyridine, 5-bromo-2-methyl-;3-bromo-6-methylpyridine;MFCD00661170;5-bromo-2-methyl pyridine;5-Bromo-alpha-picoline;6-methyl-3-bromopyridine;3-BROMO-6-PICOLINE;SCHEMBL303874;5 -Bromo-2 -methyl-pyridine;OFKWIQJLYCKDNY-UHFFFAOYSA-;DTXSID80360871;BCP13752;AKOS000352334;AB06624;AC-2557;CS-W019938;PS-5860;SY002011;A1415;AM20051092;B2572;BB 0262967;FT-0601313;FT-0646053;EN300-68681;5-Bromo-2-methylpyridine, >=99.0% (HPLC);AC-907/30003023;Q-101492

Chemical Property of 5-Bromo-2-methylpyridine

Chemical Property:

• Appearance/Colour: Light yellow cryst.
• Vapor Pressure: 1.09mmHg at 25°C
• Melting Point: 32-36 °C
• Refractive Index: 1.553
• Boiling Point: 182.7 °C at 760 mmHg
• PKA: 3.59±0.10(Predicted)
• Flash Point: 64.3 °C
• PSA: 12.89000
• Density: 1.494 g/cm³
• LogP: 2.15250
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.96836
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-2-picoline ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC=C(C=C1)Br
• Description: It is an important intermediate in the organic synthesis, which has many applications, such as pharmaceutical intermediate, organic synthesis, organic solvent, production of dyes, pesticide, and spice. Specifically, this chemical can act as the raw material to prepare 2:2’-dipyridyl and its derivatives.1 Moreover, this compound may be involved in the synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle.2 In addition, 5-bromo-2-methylpyridine has been demonstrated to function as the substrate in a general palladium-catalyzed coupling of aryl bromides/triflates and thiols.3 Besides, this substance can facilitate the synthesis of 5-arylamino-2-picolines via displacement of bromide by anthranilic acid and decarboxylation.4
• Uses: 5-Bromo-2-picoline is a halogenated pyridine derivative used is a building block in the preparation of nitrogen containing heterocyclic compounds.

Technology Process of 5-Bromo-2-methylpyridine

There total 14 articles about 5-Bromo-2-methylpyridine 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%

5-Amino-2-methylpyridine (80287-53-2,3430-14-6) → 5-bromo-2-methylpyridine (3430-13-5)

Guidance literature:

5-Amino-2-methylpyridine; With hydrogen bromide; bromine; at -20 - -15 ℃; for 1.66667h;

With sodium nitrite; In water; at 20 ℃; for 1h;

With sodium hydroxide; In water; at -15 - 20 ℃; for 1h;

Reference yield: 61.0%

5-bromo-2-pyridylacetic acid hydrochloride → 5-bromo-2-methylpyridine (3430-13-5)

Guidance literature:

at 180 ℃; under 33 Torr;

DOI:10.1016/S0040-4020(97)00491-2

Reference yield: 11.0%

α-picoline (109-06-8) → 5-bromo-2-methylpyridine (3430-13-5)

Guidance literature:

With aluminium trichloride; bromine; at 100 ℃; for 2.5h;

DOI:10.1016/j.bmc.2007.10.094

upstream raw materials:

5-Amino-2-methylpyridine

picoline hydrochloride

α-picoline

6-methylnicotinamide

Downstream raw materials:

ethyl 4-<<4-(6-methyl-pyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl>ethynyl>-benzoate

N-benzhydrylidene-N'-(6-methyl-pyridin-3-yl)-hydrazine

2-methyl-5-(phenethylsulfanyl)pyridine

2-methyl-5-(p-tolyl)pyridine

Refernces

• 1、 -. "Preparation method of 2-4- dibromopyridine-pyridine-formaldehyde (by machine translation)". Paragraph 0013; 0016-0017; 0019-0020; 0023-0024. . Retrieved 2020/01/25.
• 2、 -. "PROTEASE ACTIVATED RECEPTOR 2 (PAR2) ANTAGONISTS". Page/Page column 47. . Retrieved 2012/08/08.