2-BROMO-4,6-DIMETHYLPYRIDINE Chemical Properties

Boiling point:

68°C/0.8mmHg(lit.)

Density 

1.415±0.06 g/cm3(Predicted)

refractive index 

1.5510 to 1.5550

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

2.17±0.10(Predicted)

color 

Colorless to Light yellow

λmax

268nm(EtOH)(lit.)

InChI

InChI=1S/C7H8BrN/c1-5-3-6(2)9-7(8)4-5/h3-4H,1-2H3

InChIKey

IRTOCXBLUOPRFT-UHFFFAOYSA-N

SMILES

C1(Br)=NC(C)=CC(C)=C1

CAS DataBase Reference

4926-26-5(CAS DataBase Reference)

Safety Information

HS Code 

2933399990

2-BROMO-4,6-DIMETHYLPYRIDINE Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Bromo-4,6-dimethylpyridine is a reactant in regioselective and diastereoselective syntheses of the natural product CCR5 antagonist anibamine and its three olefin isomers.

Synthesis

General procedure for the synthesis of 2-bromo-4,6-dimethylpyridine from 2-amino-4,6-dimethylpyridine: A 48% aqueous hydrobromic acid solution (Aldrich, 65 mL, 1.2 mol, 10 eq.) was cooled to -5 °C and 4,6-dimethylpyridin-2-amine (Aldrich, 15.0 g, 0.12 mol, 1.0 eq.) was added. Bromine (Aldrich, 19.7 mL, 0.38 mol, 3.1 eq.) was added slowly and dropwise with mechanical stirring to the thick white salt mixture formed. The resulting red mixture was treated with aqueous sodium nitrite (32 mL water, Aldrich, 22.1 g, 0.32 mol, 2.6 eq.) for 1 hr below 5 °C. The temperature was maintained below 5°C during the nitrite addition process, followed by a gradual warming to 20°C over 2 hr. The reaction mixture was adjusted to pH 14 with aqueous sodium hydroxide and extracted with methyl tert-butyl ether (MTBE). The organic phase was washed sequentially with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product (29 g of red oily material) was purified by fast chromatography (silica gel, 350 g) using 2-7% ethyl acetate-cyclohexane as eluent to give an orange oily product (11.0 g, 48% yield). The product was purified by 1H NMR (DMSO-d6, 300 MHz) δ 7.30 (1H, s), 7.13 (1H, s), 2.39 (3H, s), 2.26 (3H, s); 13C NMR (DMSO-d6, 75 MHz) δ 159.4, 151.3, 140.9, 125.7, 123.4, 23.7, 20.3 ; ESI-MS m/z 186/188 ([M+H]+).

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7945 - 7952
[2] Helvetica Chimica Acta, 1992, vol. 75, # 5, p. 1578 - 1592
[3] Patent: WO2004/56806, 2004, A1. Location in patent: Page 50
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 16, p. 7126 - 7135
[5] Patent: EP3124482, 2017, A1. Location in patent: Paragraph 0512; 0513

2-BROMO-4,6-DIMETHYLPYRIDINE(4926-26-5)Related Product Information

• 2-BROMO-6-METHYL-4-TRIFLUOROMETHYLPYRIDINE
• 6-BROMO-2,4-DIMETHYLPYRIDIN-3-YLBORONIC ACID
• 2-BROMO-4,6-DIMETHYLPYRIDINE
• 3-AMINO-2-BROMO-4,6-DIMETHYLPYRIDINE,5-Amino-2-bromo-4,6-dimethylpyridine
• 4-Chlorophenethylamine
• 2-AMINO-5-BROMO-3,4-DIMETHYLPYRIDINE,2-AMINO-5-BROMO-3,4-DIMETHYLPYRIDINE 97%
• 5-Bromo-2-(dimethylamino)pyridine
• 2-AMINO-3-BROMO-5,6-DIMETHYLPYRIDINE
• 4-Bromo-2,6-dimethylpyridine
• 3-Bromo-2,6-dimethylpyridine 98%,3-BROMO-2,6-DIMETHYLPYRIDINE
• 3-Bromo-2,5-dimethylpyridine
• 3-BROMO-2,4-DIMETHYLPYRIDINE
• 6-BROMO-[2,2'-BIPYRIDINE]-4-CARBOXYLIC ACID
• 6-BROMO-4,4'-DIMETHYL-2,2'-BIPYRIDINE
• METHYL 2-BROMO-6-METHYLISONICOTINATE
• 3-BROMO-4,5-DIMETHYLPYRIDINE
• 5-BROMO-2,3-DIMETHYLPYRIDINE
• 6-Bromo-3-iodo-2,4-dimethylpyridine