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6-Bromo-2(1H)-pyridinone

6-Bromo-2(1H)-pyridinone structure

CAS No:
27992-32-1
Formula:
C5H4BrNO
Chemical Name:
6-Bromo-2(1H)-pyridinone
Synonyms:
2(1H)-Pyridinone,6-bromo-;2(1H)-Pyridone,6-bromo-;6-Bromo-2(1H)-pyridinone;6-Bromo-2-pyridone;6-Bromo-2-pyridinol;2-Hydroxy-6-bromopyridine;6-Bromo-2-hydroxypyridine;6-Bromo-1,2-dihydropyridin-2-one;2-Bromo-6-hydroxypyridine;29981-38-2
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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6-Bromo-2(1H)-pyridinone Basic Attributes

Molecular Weight：

174

Exact Mass：

174.00

EC Number：

1533716-785-6

DSSTox ID：

DTXSID40356210

HScode：

2933399090

Characteristics

PSA：

29.1

XLogP3：

1.1

Density：

1.8±0.1 g/cm3

Melting Point：

123 °C

Boiling Point：

336.6ºC at 760mmHg

Flash Point：

166.8±22.3 °C

Refractive Index：

1.614

Vapor Pressure：

0.000111mmHg at 25°C

Safety Information

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

6-Bromo-2(1H)-pyridinone Use and Manufacturing

A mixture of 2, 6-dibromopyridine (1) (4 g, 17 mmol), potassium t-butoxide (20 g, 0.27 mol), and redistilled t-butyl alcohol (100 mL) was refluxed overnight. After cooling, the solvent was removed in vacuo, ice/water was carefully added, and the aqueous layer was extracted with chloroform (100 mL.x.2), which removed the unreacted staring material. The aqueous layer was acidified with 3 N HCl, extracted with chloroform (100 mL.x.2), washed with brine, dried over anhydrous NaGeneral procedure: In a dry Schlenk tube 2-bromo-6-methylpyridine (5.98 g, 35.0 mmol) was dissolved in 100 mL oft-AmylOH and KOt-Bu (39.3 g , 350.0 mmol) was added. The mixture was stirred at 100 °C for 40 h. The solvent was removed under reduced pressure and the residue was dissolved in 50 mL of HCOPotassium tert-butoxide (4.74 g, 42.2 mmol) was added to a solution of 2, 6- dibromopyridine (1.00 g, 4.22 mmol) in tert-Butyl alcohol (25 mL). The reactionmixture was refluxed for 18 hours, and concentrated in vacuo. A mixture of ice and water (20 mL) was added to the residue. The aqueous layer was washed with ethyl acetate (2 x 25 mL), acidified with concentrated hydrochloric acid until pH 3 and extracted with dichloromethane (2 x 30 mL). The organic layer was washed with brine (30 mL), then dried over sodium sulfate and concentrated in vacuo to provide 6-bromo-1, 2-dihydropyridin-2-one (40a) (125mg, 0.72 mmol, 17percent).General procedure: In a round bottom flask were added (pyridine or quinoline or isoquinoline) of nitrogen oxides (1.0eq.), PyBrOP (2.0eq.), Sodium acetate (3.0 eq.), Water (10 to 20.0 eq.), Adding 1, 2-dichloroethane (substrate concentration 0.25 mol / L), And then heated to 60 ~ 85 degrees reaction, TLC followed the reaction until the end of the reaction (6 to 14 h).After completion of the reaction, petroleum ether: ethyl acetate = 5: 1 ~ 1: 1 as the mobile phase, Column chromatography gave the compounds shown in Table 1, Yield 45-92%.To a solution of 6-bromopyridin-2(1 H)-one (800 mg, 4.59 mmol) and PPh3 (2.39 g, 9.19 mmol) in dry THF (30 mL) under N2 was added DEAD (1.20 g, 6.89 mmol) and methyl 3-hydroxypropanoate (479 mg, 4.59 mmol). The mixture was stirred at rt overnight, quenched with sat. NLLCI (60 mL) and extracted with EA (2 x 30 mL). The combined organic layer was washed with brine (2 x 30 mL), dried over Na2S04, concentrated and purified by prep-TLC (EA:PE = 1 ;4) to give compound P11 as a white solid

Computed Properties

Molecular Weight:174.00
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:172.94763
Monoisotopic Mass:172.94763
Topological Polar Surface Area:29.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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