Product Name

  • Name

    6-Bromonicotinic acid

  • EINECS 628-671-0
  • CAS No. 6311-35-9
  • Article Data15
  • CAS DataBase
  • Density 1.814 g/cm3
  • Solubility
  • Melting Point 200-203 °C(lit.)
  • Formula C6H4BrNO2
  • Boiling Point 343.261 °C at 760 mmHg
  • Molecular Weight 202.007
  • Flash Point 161.399 °C
  • Transport Information
  • Appearance Off-white plates
  • Safety 26-36
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 6311-35-9 (6-Bromonicotinic acid)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 6-bromopyridine-3-carboxylic acid;6-bromopyridine-3-carboxylate;2-Bromopyridine-5-carboxylic acid;2-bromo-5-Pyridinecarboxylic acid;3-Pyridinecarboxylic acid, 6-bromo-;2-bromo-5-pyridine carboxylic acid;
  • PSA 50.19000
  • LogP 1.54230

Synthetic route

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

Conditions
ConditionsYield
With potassium permanganate; Aliquat 336 In water for 4.5h; Heating;50%
With potassium permanganate; Alquat-336 In water for 1.5h; Heating;50%
With potassium permanganate; Aliquat 336 In water at 110℃; for 2.5h;44%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / 1.) aq. 48percent HBr, bromine; 2.) aq. sodium nitrite / 1.) -20 deg C, 90 min; 2.) 15 deg C, 1 h 45 min
2: 50 percent / potassium permanganate / aliquat-336 / H2O / 4.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: bromine; aqueous sodium nitrite solution; aqueous hydrobromic acid
2: aqueous KMnO4
View Scheme
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

Conditions
ConditionsYield
With phosphorus pentabromide
With phosphorus(V) oxybromide at 170℃; for 0.166667h; Neat (no solvent);
6-bromonicotinaldehyde
149806-06-4

6-bromonicotinaldehyde

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

Conditions
ConditionsYield
With 1,4-dithio-D,L-threitol; recombinant aldehyde dehydrogenase from Escherichia coli; water‐forming NADH oxidase from Streptococcus mutans; NAD In aq. phosphate buffer at 40℃; for 4h; pH=8.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; chemoselective reaction;
methyl 6-bromonicotinate
26218-78-0

methyl 6-bromonicotinate

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran at 25℃; for 16h;13.0 g
methanol
67-56-1

methanol

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

methyl 6-bromonicotinate
26218-78-0

methyl 6-bromonicotinate

Conditions
ConditionsYield
With sulfuric acid Reflux;100%
With triphenylphosphine; diethylazodicarboxylate In diethyl ether for 1.16667h; Ambient temperature;79%
Stage #1: 6-bromonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h;
Stage #2: methanol		55%
piperidine
110-89-4

piperidine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(6-bromopyridin-3-yl)(piperidin-1-yl)methanone

(6-bromopyridin-3-yl)(piperidin-1-yl)methanone

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 18h;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 23℃; for 15h; Inert atmosphere;75%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;60%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

tert-butyl 4-[6-(dimethoxyboryl)-4H-1,3-benzodioxin-2-yl]piperidine-1-carboxylate
1200575-98-9

tert-butyl 4-[6-(dimethoxyboryl)-4H-1,3-benzodioxin-2-yl]piperidine-1-carboxylate

6-{2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-4H-1,3-benzodioxin-6-yl} nicotinic acid
1200576-01-7

6-{2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-4H-1,3-benzodioxin-6-yl} nicotinic acid

Conditions
ConditionsYield
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; acetonitrile at 160℃; for 0.333333h; Irradiation;100%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

methyl iodide
74-88-4

methyl iodide

methyl 6-bromonicotinate
26218-78-0

methyl 6-bromonicotinate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;94%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 55℃; for 4h;0.909 g
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(3R)-3-methyl-1,4'-bipiperidine dihydrochloride

(3R)-3-methyl-1,4'-bipiperidine dihydrochloride

(6-bromopyridin-3-yl)[(3R)-3-methyl-1,4'-bipiperidin-1'-yl]methanone

(6-bromopyridin-3-yl)[(3R)-3-methyl-1,4'-bipiperidin-1'-yl]methanone

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile at 20℃; for 18h;93%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

methyl (2S)-pyrrolidine carboxylate
2577-48-2

methyl (2S)-pyrrolidine carboxylate

C12H13BrN2O3

C12H13BrN2O3

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;93%
5-bromo-2-pyridylamine
1072-97-5

5-bromo-2-pyridylamine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

6-bromo-N-(5-bromopyridin-2-yl)nicotinamide
1029088-43-4

6-bromo-N-(5-bromopyridin-2-yl)nicotinamide

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 96h;91%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

benzene-1,2-disulfonamide
27291-96-9

benzene-1,2-disulfonamide

6-bromo-N-(2-sulfamoylphenylsulfonyl)nicotinamide
1154060-75-9

6-bromo-N-(2-sulfamoylphenylsulfonyl)nicotinamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;91%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;91%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;91%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

C13H11NO3

C13H11NO3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; Inert atmosphere; Sealed tube;91%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 6-bromonicotinate
26218-78-0

methyl 6-bromonicotinate

Conditions
ConditionsYield
In methanol; diethyl ether; hexane for 5h;90%
In methanol; ethyl acetate at 30℃; for 1h;
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

phenylboronic acid
98-80-6

phenylboronic acid

6-phenylpyridine-3-carboxylic acid
29051-44-3

6-phenylpyridine-3-carboxylic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 100℃; for 24h; Suzuki coupling; Inert atmosphere;90%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; Inert atmosphere; Sealed tube;88%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; for 12h; Sealed tube;88%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

6-bromo-N,N-dimethylnicotinamide
869640-49-3

6-bromo-N,N-dimethylnicotinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;90%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

6-(2-fluorophenyl)pyridine-3-carboxylic acid
505082-91-7

6-(2-fluorophenyl)pyridine-3-carboxylic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; Inert atmosphere; Sealed tube;90%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

6-bromopyridine-3-carboxamide
889676-37-3

6-bromopyridine-3-carboxamide

Conditions
ConditionsYield
With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;88%
Stage #1: 6-bromonicotinic acid With 1,1'-carbonyldiimidazole In dimethyl sulfoxide at 20℃; for 16h;
Stage #2: With ammonia In water; dimethyl sulfoxide at 0℃; for 1h;		81%
Stage #1: 6-bromonicotinic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 3h;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃;		79%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

dimethyl amine
124-40-3

dimethyl amine

6-(dimethylamino)-3-pyridinecarboxylic acid
82846-28-4

6-(dimethylamino)-3-pyridinecarboxylic acid

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 130℃; for 15h; Substitution; under pressure;87%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(o-hydroxyphenyl)diphenylphosphine
60254-10-6

(o-hydroxyphenyl)diphenylphosphine

2-(diphenylphosphano)phenyl 6-bromonicotinate
1312717-17-1

2-(diphenylphosphano)phenyl 6-bromonicotinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 60℃; Steglich reaction;87%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

C10H8BrN3O

C10H8BrN3O

6-bromo-N-(5-(4-bromophenyl)-1H-pyrazol-3-yl)nicotinamide

6-bromo-N-(5-(4-bromophenyl)-1H-pyrazol-3-yl)nicotinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;86%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

6-bromo-N-methoxy-N-methylpyridine-3-carboxamide
149806-05-3

6-bromo-N-methoxy-N-methylpyridine-3-carboxamide

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 23℃;84%
With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In 2-methyltetrahydrofuran at 20℃;67%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 25℃; for 16h; Concentration; Time;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3h;
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

4-(4-(2-methoxyphenyl)-1,4-diazepan-1-yl)butan-1-amine
1435684-52-8

4-(4-(2-methoxyphenyl)-1,4-diazepan-1-yl)butan-1-amine

6-bromo-N-[4-[4-(2-methoxyphenyl)-1,4-diazepan-1-yl]butyl]nicotinamide
1435685-96-3

6-bromo-N-[4-[4-(2-methoxyphenyl)-1,4-diazepan-1-yl]butyl]nicotinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 15h;83%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

C18H19FN4O

C18H19FN4O

(6-bromopyridin-3-yl)(4-(3-(4-fluorophenyl)-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl) methanone

(6-bromopyridin-3-yl)(4-(3-(4-fluorophenyl)-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl) methanone

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;83%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

dimethyl amine
124-40-3

dimethyl amine

6-bromo-N,N-dimethylnicotinamide
869640-49-3

6-bromo-N,N-dimethylnicotinamide

Conditions
ConditionsYield
Stage #1: 6-bromonicotinic acid With thionyl chloride at 80℃; for 2h; Inert atmosphere;
Stage #2: dimethyl amine With triethylamine In dichloromethane at 25℃; for 16h; Inert atmosphere;		83%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

cyclohexylamine
108-91-8

cyclohexylamine

6-bromo-N-cyclohexylnicotinamide
443346-20-1

6-bromo-N-cyclohexylnicotinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;82%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

toluene-3-thiol
108-40-7

toluene-3-thiol

C13H11NO2S
253594-30-8

C13H11NO2S

Conditions
ConditionsYield
Stage #1: toluene-3-thiol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 1h;
Stage #2: 6-bromonicotinic acid In DMF (N,N-dimethyl-formamide) for 6h; Heating / reflux;		80%
morpholine
110-91-8

morpholine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(6-bromo-pyridin-3-yl)-morpholin-4-yl-methanone
1180131-60-5

(6-bromo-pyridin-3-yl)-morpholin-4-yl-methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 14h;79%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

6-bromo-N-(2-(diethylamino)ethyl)nicotinamide
1420844-65-0

6-bromo-N-(2-(diethylamino)ethyl)nicotinamide

Conditions
ConditionsYield
Stage #1: 6-bromonicotinic acid With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 3h;
Stage #2: N,N-diethylethylenediamine In N,N-dimethyl-formamide at 20℃; for 2h;		78%
pyrrolidine
123-75-1

pyrrolidine

6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(6-bromopyridin-3-yl)pyrrolidin-1-ylmethanone
1209460-17-2

(6-bromopyridin-3-yl)pyrrolidin-1-ylmethanone

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 18h;78%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

benzene
71-43-2

benzene

(6-bromopyridin-3-yl)(phenyl)methanone
80100-16-9

(6-bromopyridin-3-yl)(phenyl)methanone

Conditions
ConditionsYield
Stage #1: 6-bromonicotinic acid With thionyl chloride for 3h; Reflux;
Stage #2: benzene With aluminum (III) chloride at 5℃; Reflux;		77%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(3-ethoxy-4-methoxyphenyl)boronic acid
915201-13-7

(3-ethoxy-4-methoxyphenyl)boronic acid

3'-ethoxy-4'-methoxybiphenyl-3-carboxylic acid

3'-ethoxy-4'-methoxybiphenyl-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 6-bromonicotinic acid; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.25h;
Stage #2: (3-ethoxy-4-methoxyphenyl)boronic acid With sodium carbonate In 1,2-dimethoxyethane; water for 24h; Heating / reflux;		76%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

C12H19BrClNOSi

C12H19BrClNOSi

5-(4-bromo-2-chlorophenyl)-2-(6-bromopyridin-3-yl)-4,5-dihydrooxazole

5-(4-bromo-2-chlorophenyl)-2-(6-bromopyridin-3-yl)-4,5-dihydrooxazole

Conditions
ConditionsYield
With pyridine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In dichloromethane at -78 - 20℃; for 2h;76%
6-bromonicotinic acid
6311-35-9

6-bromonicotinic acid

(4-acetylaminophenyl)boronic acid
101251-09-6

(4-acetylaminophenyl)boronic acid

6-(4-acetamidophenyl)nicotinic acid

6-(4-acetamidophenyl)nicotinic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 100℃; Inert atmosphere; Sealed tube;76%

6-Bromonicotinic acid Chemical Properties

The Molecular Structure of 6-Bromonicotinic acid (CAS NO.6311-35-9):

Empirical Formula: C6H4BrNO2
Molecular Weight: 202.0055 
IUPAC Name: 6-bromopyridine-3-carboxylic acid  
Appearance: Off-white Plates 
Nominal Mass: 201 Da
Average Mass: 202.0055 Da
Monoisotopic Mass: 200.942533 Da 
Index of Refraction: 1.616
Molar Refractivity: 38.96 cm3
Molar Volume: 111.3 cm3
Surface Tension: 63.2 dyne/cm
Density: 1.813 g/cm3
Flash Point: 161.4 °C
Enthalpy of Vaporization: 61.96 kJ/mol
Boiling Point: 343.3 °C at 760 mmHg
Vapour Pressure: 2.73E-05 mmHg at 25°C 
Synonyms: Ilab-bb f1921-0015 ; Iflab-bb f1926-0006 ; Aurora 23320 ; Akos bbs-00001340 ; 6-Bromonicotinc acid ; 6-Bromonicotinic acid ; 6-Bromopyridine-3-carboxylic acid ; 6-Bromo-3-pyridinecarboxylic acid
Product Categories: blocks;Bromides;Carboxes;Pyridines;Pyridine;pyridine derivative;Acids and Derivatives;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Carboxylic Acids;Bromopyridines;Halopyridines;Carboxylic Acids;Picolinic acid series

6-Bromonicotinic acid Safety Profile

Hazard Codes: HarmfulXnIrritantXi
Risk Statements: 22-36/37/38 
R22: Harmful if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safe Statements:
S26: In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice 
S36: Wear suitable protective clothing
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT

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