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3-Bromo-4-methylpyridine

3-Bromo-4-methylpyridine structure

CAS No:
3430-22-6
Formula:
C6H6BrN
Chemical Name:
3-Bromo-4-methylpyridine
Synonyms:
Pyridine,3-bromo-4-methyl-;4-Picoline,3-bromo-;3-Bromo-4-methylpyridine;3-Bromo-4-picoline;4-Methyl-3-bromopyridine
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Clear Liquid

3-Bromo-4-methylpyridine Basic Attributes

Molecular Weight：

172.02

Exact Mass：

172.02

BRN：

878354

EC Number：

1592732-453-0

DSSTox ID：

DTXSID80355828

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

1.9

Appearance：

Clear colorless to yellow Liquid

Density：

1.5±0.1 g/cm3

Boiling Point：

47-48 °C @ Press: 0.6 Torr

Flash Point：

175 °F

Refractive Index：

1.553

Safety Information

Packing level：

III

Hazard category：

IRRITANT

Transport codes：

Cool,dry,tightlyclosed

wgk germany：

hazard class code：

36/37/38-20/21/22

safety instructions：

26-36-2636

Marks：

Xi,Xn

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3-Bromo-4-methylpyridine Use and Manufacturing

Methods of Manufacturing

0.054 mol of 4-methylpyridine was added to a 60 mL constant pressure dropping funnel; under nitrogen protection and stirring at room temperature, slowly added dropwise to a mixture consisting of 0.07 mol of AlCl3 and 0. 01 mol of potassium bromide, and the mixture was stirred and stirred for 1 hour. Using a condensing device, heated to 120 ° C, drop 0.07mol bromine, about 1h drop finished ; Keep heating and stirring for 26h; The reaction solution was cooled to room temperature and the reaction solution was poured into crushed ice with stirring. The sodium hydroxide was added and stirred to dissolve. The aqueous layer was extracted with methylene chloride and the organic layers were combined and the solvent recovered by steam. The resulting oil was purified by column chromatography (V4-Methylpyridine (50 g) was added slowly to aluminum chloride (182 g) with vigorous stirring under nitrogen over 1 hour. The resulting mixture was maintained at 95°C to 105°C and bromine (51 g) was introduced through the condenser over 5 hours. The reaction mixture was stirred at 95°C to 105°C for 15 hours. Additional bromine (32 g) was added to the reaction mixture over 3 hours and the reaction mixture was stirred for20 hours at 95°C to 105°C. The mixture was cooled to 25°C to 30°C and poured over crushed ice (1.3 kg) slowly with vigorous stirring. A saturated aqueous sodium hydroxide solution was added to the aqueous mixture until all the inorganic material was dissolved. The aqueous layer was extracted with dichloromethane (2 x 300 mL), and the combined organic layer was recovered under vacuum. The oil obtained was fractionally distilled under 13 mm pressure to obtain the title compound. Yield= 46 g (49percent)This reagent is described in Bull. Soc. Chim. Fr. 1976, 530. Stirring well, 31 ml of 4-picoline (0.322 mol, 1 eq.) is added drop by drop to 107 g of aluminum chloride (0.805 mol, 2.5 eq.) in a 11 three-necked flask equipped. with a cooling apparatus in nitrogen. 9.9 ml of bromine (0.193 mol, 0.6 eq.) is then introduced progressively, while keeping the temperature at 95-100° C. The mixture is left under stirring at this temperature for 18 hrs, 6.6 ml of bromine (0.129 mol, 0.4 eq.) is added and stirring is continued for 4 hrs. After that, the reaction medium is poured into 1000 ml of ice, soda is added until the inorganic salts have dissolved. The oily phase is retrieved, the aqueous phase is extracted 3 times with ethyl ether and the combined organic phase is washed with a sodium bisulfite solution and then with water. Drying is performed on Na

Uses

An intermediate of pyridinyl pyrrole compounds as proton pump inhibitors with improved gastric acid secretion suppressive activity

Computed Properties

Molecular Weight:172.02
XLogP3:1.9
Hydrogen Bond Acceptor Count:1
Exact Mass:170.96836
Monoisotopic Mass:170.96836
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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