3,5-Dibromo-2-pyridylamine Chemical Properties

Melting point:

104-105 °C (lit.)

Boiling point:

253.9±35.0 °C(Predicted)

Density 

2.147±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.89±0.49(Predicted)

Appearance

Light yellow to yellow Solid

BRN 

119390

InChI

InChI=1S/C5H4Br2N2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9)

InChIKey

WJMJWMSWJSACSN-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1Br

CAS DataBase Reference

35486-42-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:3,5-Dibromo-2-pyridylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dibromo-2-pyridylamine Usage And Synthesis

Chemical Properties

yellow to brown fine crystalline powder

General Description

The synthesis of 2-amino-3,5-dibromopyridine complexes and their analysis by single crystal X-ray diffraction has been studied.

Synthesis

General procedure for the synthesis of 2-amino-5-bromopyridine and 2-amino-3,5-dibromopyridine from 2-aminopyridine: 28.2 g (0.3 mol) of 2-aminopyridine was dissolved in 50 ml of acetic acid. The solution is cooled to below 20°C by means of an ice bath and 48 g (15.4 ml, 0.3 mol) of bromine dissolved in 30 ml of acetic acid is added slowly and dropwise over a period of 1 h under vigorous stirring. The temperature was maintained below 20°C at the beginning of the reaction. Upon addition of half of the bromine solution, the reaction temperature was raised to 50°C to promote precipitation of 2-amino-5-bromopyridine hydrobromide. At 50°C, the hydrobromide typically begins to crystallize when about three-quarters of the bromine is added. After completion of the bromine addition, stirring of the reaction mixture was continued for 1 hour, followed by dilution with 75 mL of water to dissolve the hydrobromide. The reaction solution is transferred to a 500 ml beaker and neutralized by the slow addition of 120 ml of 40% sodium hydroxide solution under stirring and cooling conditions. Filtration and drying gave a crude product of 2-amino-5-bromopyridine containing a small amount of 2-amino-3,5-dibromopyridine. The 2-amino-3,5-dibromopyridine was removed from the crude product by washing with 500 ml of hot petroleum ether in three passes. The final yield of 2-amino-5-bromopyridine was 32-34.7 g (62-67% yield) with a melting point of 134°C (literature value: 132-135°C).

Purification Methods

Steam distil it and recrystallise it from aqueous EtOH or pet ether. [Beilstein 22 H 431, 22 II 333, 22 III/IV 4041.]

References

[1] Synthetic Communications, 1986, vol. 16, # 13, p. 1641 - 1646
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 2, p. 146 - 149
[3] Synthesis (Germany), 2015, vol. 47, # 20, p. 3169 - 3178
[4] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2455 - 2478

3,5-Dibromo-2-pyridylamine(35486-42-1)Related Product Information

• 2-AMINO-3,5-DIBROMO-6-METHYLPYRIDINE
• 2-Amino-3,5-dibromo-4-methylpyridine
• 3,5-DIBROMO-2-NITROPYRIDINE
• 3,5-Dibromopyridine
• 2,4-DIBROMO-3-AMINOPYRIDINE
• 2,6-Dibromopyridin-3-amine
• 4-AMINO-2,6-DIBROMOPYRIDINE
• 3,5-Dibromo-2-pyridylamine
• 2-Amino-3,5-dibromo-4,6-dimethylpyridine
• 2,6-DIAMINE-3,5-DIBROMOPYRIDINE
• 4-(3,5-DIBROMO-2-PYRIDYLAZO)-1,3-PHENYLENEDIAMINE
• 3,5-DIBROMO-6-CHLORO-N-METHYLPYRIDIN-2-AMINE
• 6-AMINO-3,5-DIBROMOPYRIDINE-2-CARBOXAMIDE
• AURORA KA-375
• 3,5-DIBROMO-2-HYDRAZINO-4-METHYLPYRIDINE
• 6-AMINO-3,5-DIBROMOPYRIDINE-2-CARBONITRILE
• 1-(3,5-dibromopyridin-2-yl)-1-methylhydrazine
• 3,5-DIBROMO-N-(PHENYLMETHYL)-2-PYRIDINAMINE