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4-Bromo-2-methylpyridine

4-Bromo-2-methylpyridine structure

CAS No:
22282-99-1
Formula:
C6H6BrN
Chemical Name:
4-Bromo-2-methylpyridine
Synonyms:
CHEMBRDG-BB 4014101;2-METHYL-4-BROMOPYRIDINE;4-BROMO-2-METHYLPYRIDINE;4-BROMO-2-METHYL-PYRIDINE HYDROCHLORIDE;4-BROMO-2-METHYL-PYRIDINIUM, CHLORIDE;4-BROMO-2-PICOLINE;4-BROMO-2-PICOLINE HCL;4-BROMO-METHYL-PYRIDINE
Categories:
Organic Chemistry > Free Radicals

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Description

Light yellow liquid

4-Bromo-2-methylpyridine Basic Attributes

Molecular Weight：

172.02

Exact Mass：

170.968353

EC Number：

-0

DSSTox ID：

DTXSID20376496

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

1.8

Appearance：

Light yellow liquid

Density：

1.5±0.1 g/cm3

Boiling Point：

76 °C / 14mmHg

Flash Point：

174 °F

Refractive Index：

1.553

Water Solubility：

Miscible with dichloromethane. Immiscible with water.

Vapor Pressure：

0.581mmHg at 25°C

Safety Information

Hazard category：

IRRITANT

Transport codes：

NA 1993 / PGIII

wgk germany：

hazard class code：

22-37/38-41-36/37/38-20/21/22

safety instructions：

26-36/39-36

Marks：

Xn,Xi

Hazard note：

Irritant

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H302-H315-H318-H335

GHS Classification：

|Danger|H302 (95.83%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

4-Bromo-2-methylpyridine Use and Manufacturing

Methods of Manufacturing

4-Bromo-2-methylpyridine (153)A stirred solution of amino-pyridine 152 (10.1 g, 93.4 mmol) in 48percent aqueous HBr (165 mL) at -10'C is treated with a pre-cooled (0°C) solution of sodium nitrite (7.04 g, 0.102 mol) in water (165 mL) dropwise over 0.5 h. The solution is then warmed to RT and stirred 16 h. It is then diluted with 4 M NaOH (400 mL) and extracted into TBME (4 x 150 mL). The TBME phases are combined, dried (MgSO4-Bromo-2-methylpyridine (153)A stirred solution of amino-pyridine 152 (10.1 g, 93.4 mmol) in 48percent aqueous HBr (165 mL) at -10°C was treated with a pre-cooled (0°C) solution of sodium nitrite 4-Bromo-2-methylpyridine (153); A stirred solution of amino-pyridine 152 (10.1 g, 93.4 mmol) in 48percent aqueous HBr (165 mL) at -104-Bromo-2-methylpyridine (153); A stirred solution of amino-pyridine 152 (10.1 g, 93.4 mmol) in 48percent aqueous HBr(165 mL) at -10°C is treated with a pre-cooled (0°C) solution of sodium nitrite (7.04 g, 0.102 mol) in water (165 mL) dropwise over 0.5 h. The solution is then warmed toRT and stirred 16 h. It is then diluted with 4 M NaOH (400 mL) and extracted into TBME (4 x 150 mL). The TBME phases are combined, dried (MgSO-Methyl-4-aminopyridine (3. 86 g, 35.69 mmol) in [48percent] aqueous HBr (24 [ML)] was cooled to -15°C and [NAN02] (4.9 g, 71.4 mmol) in water (34 mL) was added slowly. (Note: The temperature was maintained between-10 to [15 °C] during the addition. ) CuBr [(510 MG, ] 3.6 mmol) was added to the above reaction mixture at-15° C and slowly allowed to warm to room temperature over 12 hours. The pH of the reaction mixture was adjusted to [PH =10, ] by addition [OF NAOH (11 G] in 21 mL water). The reaction mixture was filtered through celite and washed with ether/water. The layers were separated and the aqueous layer was extracted twice with ether. The combined organic extracts were dried [(NA2SO4), ] concentrated under vacuum, and purified by silica gel chromatography (50percent ether in hexanes) to afford [4-BROMO-2-METHYLPYRIDINE] [(5.] 48 g, 89percent yield).

Uses

Used in the preparation of phenyloxadiazolyl pyridines as immunomodulating agents.

Computed Properties

Molecular Weight:172.02
XLogP3:1.8
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

Material

Ammonium hydroxide

Sodium carbonate

Phosphorus trichloride

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