ChemicalBook--->CAS DataBase List--->22282-99-1

22282-99-1

22282-99-1 Structure

22282-99-1 Structure
IdentificationMore
[Name]

4-Bromo-2-methylpyridine
[CAS]

22282-99-1
[Synonyms]

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
CHEMBRDG-BB 4014101
2-Methyl-4-Bromopyridine HCl
4-BROMO-2-METHYLPYRIDINE 98%
4-BROMO-2-PICOLINE 4-BROMO-2-METHYLPYRIDINE
4-BROMO-2-METHYLPYRIDINE (4-BROMO-2-PICOLINE)
[EINECS(EC#)]

624-896-3
[Molecular Formula]

C6H6BrN
[MDL Number]

MFCD03788196
[Molecular Weight]

172.02
[MOL File]

22282-99-1.mol
Chemical PropertiesBack Directory
[Appearance]

Light yellow liquid
[Melting point ]

26-27°
[Boiling point ]

76 °C / 14mmHg
[density ]

1.450 g/mL at 25 °C
[refractive index ]

n 20/D 1.556
[Fp ]

174 °F
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

Dichloromethane
[form ]

Pale Yellow Liquid
[pka]

4.38±0.10(Predicted)
[color ]

Colorless to Light yellow to Light orange
[Water Solubility ]

Miscible with dichloromethane. Immiscible with water.
[InChI]

InChI=1S/C6H6BrN/c1-5-4-6(7)2-3-8-5/h2-4H,1H3
[InChIKey]

JFBMFWHEXBLFCR-UHFFFAOYSA-N
[SMILES]

C1(C)=NC=CC(Br)=C1
[CAS DataBase Reference]

22282-99-1(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)Exclamation Mark (GHS07)
GHS05,GHS07
[Signal word ]

Danger
[Hazard statements ]

H302-H315-H318-H335
[Precautionary statements ]

P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/39:Wear suitable protective clothing and eye/face protection .
S36:Wear suitable protective clothing .
[RIDADR ]

NA 1993 / PGIII
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29333990
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Diethyl ether-->Sodium carbonate-->Chloroform-->Ammonium hydroxide-->Phosphorus trichloride-->4-Nitro-2-picoline N-oxide-->Acetyl bromide-->4-BROMOPYRIDINE-2-CARBALDEHYDE-->2-Picoline-N-oxide-->2-Chloro-4-nitropyridine-->2-Methyl-4-nitropyridine-->Methylmagnesium Bromide-->2,4-Dibromopyridine
[Preparation Products]

(4-METHOXY-PYRIDIN-2-YL)-METHANOL-->4-METHOXYPICOLINALDEHYDE-->4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER-->TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE-->2-METHYLPYRIDINE-4-BORONIC ACID PINACOL ESTER-->4-Bromo-2-pyridinemethanol
Hazard InformationBack Directory
[Chemical Properties]

Light yellow liquid
[Uses]

4-Bromo-2-methylpyridine is a starting material used in a synthesis of crown-ester-bipyridines and viologens via sodium or nickel reductive coupling, side chain oxidation and esterification.
[Uses]

4-Bromo-2-methylpyridine is used as a starting material in the preparation of crown-ester-bipyridines and viologens through sodium or nickel reductive coupling, side chain oxidation and esterification. Further, it serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, agrochemicals and in dyes.
[Uses]

Used in the preparation of phenyloxadiazolyl pyridines as immunomodulating agents.
[Synthesis]

4-Amino-2-picoline

18437-58-6

4-Bromo-2-methylpyridine

22282-99-1

2-Methyl-4-aminopyridine (152) (10.1 g, 93.4 mmol) was used as a raw material, which was dissolved in 48% aqueous hydrobromic acid (165 mL) at -10°C and stirred to form a solution. An aqueous solution of sodium nitrite (7.04 g, 0.102 mol) pre-cooled to 0°C (165 mL) was added dropwise to this solution over a period of 0.5 hours. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction mixture was diluted with 4 M sodium hydroxide solution (400 mL) and subsequently extracted with tert-butyl methyl ether (TBME). All TBME phases were combined, dried with anhydrous magnesium sulfate and finally concentrated under vacuum to give the target product 4-bromo-2-methylpyridine (153). Yield: 14.8 g (92% yield).LC/MS analysis: retention time 0.57 min, mass spectrum (ES+) m/z 172, 174 ([M+H]+).

[References]

[1] Patent: WO2008/57497, 2008, A2. Location in patent: Page/Page column 292
[2] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 203-204
[3] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 292
[4] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 292
[5] Patent: WO2004/14913, 2004, A2. Location in patent: Page 81-82
Spectrum DetailBack Directory
[Spectrum Detail]

4-Bromo-2-methylpyridine(22282-99-1)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

4-Bromo-2-methylpyridine, 97%(22282-99-1)
[Sigma Aldrich]

22282-99-1(sigmaaldrich)
[TCI AMERICA]

4-Bromo-2-picoline,>98.0%(GC)(T)(22282-99-1)
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