ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine 4-Bromo-2-methylpyridine

4-Bromo-2-methylpyridine

Product Name4-Bromo-2-methylpyridine
CAS22282-99-1
MFC6H6BrN
MW172.02
EINECS624-896-3
MOL File22282-99-1.mol

Chemical Properties

Melting point	26-27°
Boiling point	76 °C/14 mmHg
Density	1.50
refractive index	1.56
Flash point	79 °C
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	Dichloromethane
pka	4.38±0.10(Predicted)
form	clear liquid
color	Colorless to Light yellow to Light orange
Water Solubility	Miscible with dichloromethane. Immiscible with water.
InChI	InChI=1S/C6H6BrN/c1-5-4-6(7)2-3-8-5/h2-4H,1H3
InChIKey	JFBMFWHEXBLFCR-UHFFFAOYSA-N
SMILES	C1(C)=NC=CC(Br)=C1
CAS DataBase Reference	22282-99-1(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-37/38-41-36/37/38-20/21/22
Safety Statements	26-36/39-36
RIDADR	NA 1993 / PGIII
WGK Germany	3
HazardClass	IRRITANT
HS Code	2933399090
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

4-Bromo-2-methylpyridine is a starting material used in a synthesis of crown-ester-bipyridines and viologens via sodium or nickel reductive coupling, side chain oxidation and esterification.

Uses

Used in the preparation of phenyloxadiazolyl pyridines as immunomodulating agents.

Uses

4-Bromo-2-methylpyridine is used as a starting material in the preparation of crown-ester-bipyridines and viologens through sodium or nickel reductive coupling, side chain oxidation and esterification. Further, it serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, agrochemicals and in dyes.

Synthesis

18437-58-6

22282-99-1

2-Methyl-4-aminopyridine (152) (10.1 g, 93.4 mmol) was used as a raw material, which was dissolved in 48% aqueous hydrobromic acid (165 mL) at -10°C and stirred to form a solution. An aqueous solution of sodium nitrite (7.04 g, 0.102 mol) pre-cooled to 0°C (165 mL) was added dropwise to this solution over a period of 0.5 hours. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction mixture was diluted with 4 M sodium hydroxide solution (400 mL) and subsequently extracted with tert-butyl methyl ether (TBME). All TBME phases were combined, dried with anhydrous magnesium sulfate and finally concentrated under vacuum to give the target product 4-bromo-2-methylpyridine (153). Yield: 14.8 g (92% yield).LC/MS analysis: retention time 0.57 min, mass spectrum (ES+) m/z 172, 174 ([M+H]+).

References

[1] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 292
[2] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 203-204
[3] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 292
[4] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 292
[5] Patent: WO2004/14913, 2004, A2. Location in patent: Page 81-82

4-Bromo-2-methylpyridine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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