2-Amino-5-bromo-3-methylpyridine Chemical Properties

Melting point:

88-95 °C(lit.)

Boiling point:

250.0±35.0 °C(Predicted)

Density 

1.5672 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

4.96±0.49(Predicted)

color 

Yellow

Sensitive 

Hygroscopic

BRN 

386426

InChI

InChI=1S/C6H7BrN2/c1-4-2-5(7)3-9-6(4)8/h2-3H,1H3,(H2,8,9)

InChIKey

KBLGGRWUEVCNPY-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1C

CAS DataBase Reference

3430-21-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-5-bromo-3-methylpyridine Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

2-Amino-5-bromo-3-methylpyridine may be used to synthesize:

• 5-bromo-2-chloro-3-methylpyridine
• 2-azidopyridine 1-oxide
• 2-amino-5-bromo-3-methylpyridine 1-oxide
• 2,5-dibromo-3-methyl pyridine
• ethyl-3,6-dibromo-8-methylimidazo[1,2-a]pyridine-2-carboxylate

General Description

2-Amino-5-bromo-3-methylpyridine can be prepared from 2-amino-3-methylpyridine, via bromination.

Synthesis

General procedure for the synthesis of 2-amino-3-methyl-5-bromopyridine from 2-amino-3-methylpyridine: Bromine (15.4 mL, 0.30 mol) was slowly added dropwise to an anhydrous dichloromethane (1000 mL) solution of 2-amino-3-methylpyridine (32.44 g, 0.30 mol) under stirring at 0-2 °C for 1 hour. The cooling bath was then removed and the yellow suspension was allowed to continue stirring at room temperature for 3 hours and 40 minutes. Upon completion of the reaction, the mixture was alkalized to pH 9 with 2N sodium hydroxide solution (145 mL) and subsequently treated with a mixture of saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium thiosulfate (10 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated to give the brown solid product 2-amino-3-methyl-5-bromopyridine (56.83 g, 102% yield), which could be used in the next reaction without further purification.

References

[1] Patent: WO2004/13139, 2004, A2. Location in patent: Page 25-26
[2] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1129 - 1131
[4] Patent: CN105348177, 2016, A. Location in patent: Paragraph 0012; 0016
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697

2-Amino-5-bromo-3-methylpyridine(3430-21-5)Related Product Information

• 2-Amino-5-bromo-3-(hydroxymethyl)pyridine
• 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one
• Methyl 2-amino-5-bromonicotinate
• 5-BROMO-2,3-DIHYDRO-1H-PYRROLO[2,3-B]PYRIDINE
• 2-Amino-5-bromonicotinic acid
• 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE
• (2-AMINO-5-BROMOPYRIDIN-3-YL)METHANOL HYDROBROMIDE
• 2-AMINO-5-BROMO-3,4-DIMETHYLPYRIDINE
• 2-Amino-5-bromo-3-methylpyridine
• 2-Acetylamino-5-bromo-3-methylpyridine
• 5-AMINO-2-BROMO-3-METHYLPYRIDINE,5-AMINO-2-BROMO-3-PICOLINE (5-AMINO-2-BROMO-3-METHYLPYRIDINE)
• 2-Amino-3-bromo-5-methylpyridine
• 4-Bromo-2-methyl-3-pyridinamine
• 4-AMINO-5-BROMO-3-METHYLPYRIDINE
• 3-Amino-2-bromo-4-methylpyridine
• 5-Amino-2-bromo-4-methylpyridine
• 2-AMINO-3-BROMO-4-METHYLPYRIDINE
• 3-Amino-5-bromo-2-methylpyridine