Product Name

  • Name

    3-Bromoisonicotinic acid

  • EINECS -0
  • CAS No. 13959-02-9
  • Article Data16
  • CAS DataBase
  • Density 1.813 g/cm3
  • Solubility
  • Melting Point 237-238 °C
  • Formula C6H4BrNO2
  • Boiling Point 403.1 at 760 mmHg
  • Molecular Weight 202.007
  • Flash Point 197.6 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 13959-02-9 (3-Bromoisonicotinic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Isonicotinicacid, 3-bromo- (7CI,8CI);3-Bromo-4-pyridinecarboxylic acid;
  • PSA 50.19000
  • LogP 1.54230

Synthetic route

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
With bromine In methanol at 30 - 45℃; for 5h; Temperature;96.3%
3-Bromo-4-methylpyridin
3430-22-6

3-Bromo-4-methylpyridin

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
Stage #1: 3-Bromo-4-methylpyridin With Co0.27CuO3; water
Stage #2: With oxygen at 90℃;		90%
With potassium permanganate In water Heating / reflux;32%
With hydrogenchloride; potassium permanganate In water
3-Bromopyridine
626-55-1

3-Bromopyridine

carbon dioxide
124-38-9

carbon dioxide

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; Inert atmosphere;		10%
Stage #1: 3-Bromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.5h; Cooling with acetone-dry ice;
Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #1: 3-Bromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.5h;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at 20℃;
Stage #3: With hydrogenchloride In tert-butyl methyl ether; water pH=3;
3-bromo-N-phenylpyridine-4-carboxamide
71541-34-9

3-bromo-N-phenylpyridine-4-carboxamide

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
With hydrogenchloride for 15h; Heating;
N-phenylisonicotinamide
3034-31-9

N-phenylisonicotinamide

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi, 2.) 1,2-dibromoethane / 1.) THF, -78 deg C - 0.5 h, room temperature - 1 h, 2.) THF, -78 deg C - 1 h, room temperature - 2 h
2: aq. HCl / 15 h / Heating
View Scheme
3-Bromopyridine
626-55-1

3-Bromopyridine

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Conditions
ConditionsYield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -40℃; for 0.5h; Cooling with acetone-dry ice;
Stage #2: 3-Bromopyridine In tetrahydrofuran; hexane at -60℃; for 0.5h;
Stage #3: With hydrogenchloride In water for 1h; pH=3; Cooling with ice;
2-aminopyridine-5-boronic acid pinacol ester
827614-64-2

2-aminopyridine-5-boronic acid pinacol ester

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

6'-amino-[3,3'-bipyridine]-4-carboxylic acid

6'-amino-[3,3'-bipyridine]-4-carboxylic acid

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 120℃; for 16h; Inert atmosphere;100%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

3-vinyl-4-picolinic acid

3-vinyl-4-picolinic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3-Aminopyridine-4-carboxylic acid
7579-20-6

3-Aminopyridine-4-carboxylic acid

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide at 100 - 105℃; for 8h; Time; Autoclave;95.2%
ethanol
64-17-5

ethanol

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

ethyl 3-bromopyridine-4-carboxylate
13959-01-8

ethyl 3-bromopyridine-4-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 12h; Reflux;95%
With sulfuric acid for 12h; Reflux;88%
With sulfuric acid Reflux; Inert atmosphere;78%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 3-bromoisonicotinate
59786-31-1

methyl 3-bromoisonicotinate

Conditions
ConditionsYield
In methanol; diethyl ether; toluene for 2h; Inert atmosphere; Schlenk technique;94%
In methanol; diethyl ether; toluene at 20℃; for 2h;
4-amino-5-(2,3,5-trichlorophenyl)-4H-[1,2,4]triazole-3-thiol
1029491-80-2

4-amino-5-(2,3,5-trichlorophenyl)-4H-[1,2,4]triazole-3-thiol

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

6-(3-bromopyridin-4-yl)-3-(2,3,5-trichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

6-(3-bromopyridin-4-yl)-3-(2,3,5-trichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Conditions
ConditionsYield
With trichlorophosphate Heating;84%
2-isopropyliodobenzene
19099-54-8

2-isopropyliodobenzene

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

diphenyl acetylene
501-65-5

diphenyl acetylene

7-isopropyl-5,6-diphenylbenzo[h]isoquinoline

7-isopropyl-5,6-diphenylbenzo[h]isoquinoline

Conditions
ConditionsYield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;80%
...Expand
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

aniline
62-53-3

aniline

3-bromo-N-phenylpyridine-4-carboxamide
71541-34-9

3-bromo-N-phenylpyridine-4-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;79%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

A

ethyl 3-bromopyridine-4-carboxylate
13959-01-8

ethyl 3-bromopyridine-4-carboxylate

B

3-bromopyridine-4-carboxamide
13958-99-1

3-bromopyridine-4-carboxamide

Conditions
ConditionsYield
Stage #1: chloroformic acid ethyl ester; 3-bromoisonicotinic acid With triethylamine In tetrahydrofuran at 0℃; for 1h;
Stage #2: With ammonia In tetrahydrofuran for 0.25h;		A 5%
B 78%
...Expand
6-amino-4-methylquinolin-2-ol
90914-95-7

6-amino-4-methylquinolin-2-ol

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3-bromo-N-(2-hydroxy-4-methyl-6-quinolyl)pyridine-4-carboxamide

3-bromo-N-(2-hydroxy-4-methyl-6-quinolyl)pyridine-4-carboxamide

Conditions
ConditionsYield
With dmap; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 1h;78%
4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1,2,3-triazol-1-yl]piperidine

4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1,2,3-triazol-1-yl]piperidine

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

(3-bromopyridin-4-yl)-{4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1H-1,2,3-triazol-1-yl]piperidin-1-yl}methanone

(3-bromopyridin-4-yl)-{4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1H-1,2,3-triazol-1-yl]piperidin-1-yl}methanone

Conditions
ConditionsYield
Stage #1: 3-bromoisonicotinic acid With 1,1'-carbonyldiimidazole In 1,4-dioxane at 80℃; for 0.5h;
Stage #2: 4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1,2,3-triazol-1-yl]piperidine In 1,4-dioxane at 100℃; for 3h;		75%
2-isopropyliodobenzene
19099-54-8

2-isopropyliodobenzene

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

7-isopropylbenzo[h]isoquinoline

7-isopropylbenzo[h]isoquinoline

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;72%
...Expand
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

N-[(diphenylphosphinoyl)methyl]-N-methylamine
122365-23-5

N-[(diphenylphosphinoyl)methyl]-N-methylamine

3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide
380227-43-0

3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;69%
pyrrolidine
123-75-1

pyrrolidine

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

(3-bromopyridin-4-yl)(pyrrolidin-1-yl)methanone
1357094-61-1

(3-bromopyridin-4-yl)(pyrrolidin-1-yl)methanone

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;68.7%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3-bromo-N-methyl-N-(methyloxy)-4-pyridinecarboxamide
909532-61-2

3-bromo-N-methyl-N-(methyloxy)-4-pyridinecarboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; water at 20℃; for 16h;67%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h;67%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

diethyl malonate
105-53-3

diethyl malonate

3-[2-ethoxy-1-(ethoxycarbonyl)-2-oxoethyI]isonicotinic acid
929301-89-3

3-[2-ethoxy-1-(ethoxycarbonyl)-2-oxoethyI]isonicotinic acid

Conditions
ConditionsYield
Stage #1: 3-bromoisonicotinic acid; diethyl malonate With sodium hydride; copper(I) bromide at 80℃; for 2h;
Stage #2: With hydrogenchloride In water pH=4;		66%
diazomethane
186581-53-3, 908094-01-9

diazomethane

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

methyl 3-bromoisonicotinate
59786-31-1

methyl 3-bromoisonicotinate

Conditions
ConditionsYield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h; Inert atmosphere;66%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3-bromo-N-(4-methoxyphenyl)pyridine-4-carboxamide

3-bromo-N-(4-methoxyphenyl)pyridine-4-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;64%
methanol
67-56-1

methanol

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

methyl 3-bromoisonicotinate
59786-31-1

methyl 3-bromoisonicotinate

Conditions
ConditionsYield
With sulfuric acid Heating / reflux;62%
Stage #1: methanol; 3-bromoisonicotinic acid With sulfuric acid Reflux;
Stage #2: With sodium hydrogencarbonate; sodium hydroxide In water at 0℃; pH=7 - 8;
With sulfuric acid for 14h; Reflux;
With sulfuric acid Cooling with ice; Reflux;335.3 mg
5-iodoquinoline
1006-50-4

5-iodoquinoline

4,4'-dimethoxydiphenylacetylene
2132-62-9

4,4'-dimethoxydiphenylacetylene

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

5,6-bis(4-methoxyphenyl)isoquinolino[7,8-f]quinoline

5,6-bis(4-methoxyphenyl)isoquinolino[7,8-f]quinoline

Conditions
ConditionsYield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;55%
...Expand
3,3-difluoroazetidine hydrochloride
288315-03-7

3,3-difluoroazetidine hydrochloride

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

(3-bromopyridin-4-yl)(3,3-difluoroazetidin-1-yl)methanone

(3-bromopyridin-4-yl)(3,3-difluoroazetidin-1-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 dichloromethane at 20℃; for 48h;55%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3-bromo-4-(hydroxymethyl)pyridine
146679-66-5

3-bromo-4-(hydroxymethyl)pyridine

Conditions
ConditionsYield
Stage #1: 3-bromoisonicotinic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate In water at 0℃; for 1h;		52%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

methyl chloroformate
79-22-1

methyl chloroformate

3-bromo-4-(hydroxymethyl)pyridine
146679-66-5

3-bromo-4-(hydroxymethyl)pyridine

Conditions
ConditionsYield
Stage #1: 3-bromoisonicotinic acid; methyl chloroformate With triethylamine In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1h;		52%
azetidine
503-29-7

azetidine

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

Azetidin-1-yl(3-bromopyridin-4-yl)methanone

Azetidin-1-yl(3-bromopyridin-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 dichloromethane at 20℃; for 48h;52%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

beta-Naltrexamine dihydrochloride
63463-07-0

beta-Naltrexamine dihydrochloride

C26H28BrN3O4*2ClH

C26H28BrN3O4*2ClH

Conditions
ConditionsYield
Stage #1: 3-bromoisonicotinic acid; beta-Naltrexamine dihydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Molecular sieve;
Stage #2: With potassium carbonate In methanol; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride In methanol at 20℃; for 0.5h;		51.4%
3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

3,4,5-trifluoro aniline
163733-96-8

3,4,5-trifluoro aniline

2-bromo-N-(3,4,5-trifluorophenyl)isonicotinamide

2-bromo-N-(3,4,5-trifluorophenyl)isonicotinamide

Conditions
ConditionsYield
With dmap; 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℃; Inert atmosphere;50%
5-iodoquinoline
1006-50-4

5-iodoquinoline

bis(4-chlorophenyl)acetylene
1820-42-4

bis(4-chlorophenyl)acetylene

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

5,6-bis(4-chlorophenyl)isoquinolino[7,8-f]quinoline

5,6-bis(4-chlorophenyl)isoquinolino[7,8-f]quinoline

Conditions
ConditionsYield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;42%
...Expand
2-amino-4-methoxyacetophenone hydrochloride
335104-63-7

2-amino-4-methoxyacetophenone hydrochloride

3-bromoisonicotinic acid
13959-02-9

3-bromoisonicotinic acid

PC-033
1202402-05-8

PC-033

Conditions
ConditionsYield
With 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 22℃; for 18h;41.7%

3-Bromoisonicotinic acid Specification

The 3-Bromoisonicotinic acid is an organic compound with the formula C6H4BrNO2. The systematic name of this chemical is 3-bromopyridine-4-carboxylic acid. With the CAS registry number 13959-02-9, it is also named as 4-Pyridinecarboxylic acid, 3-bromo-. The product's categories are Blocks; Bromides; Carboxes; Pyridines; Pyridines, Pyrimidines, Purines and Pteredines; Picolinic Acid Series.

Physical properties about 3-Bromoisonicotinic acid are: (1)ACD/LogP: 1.05; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 3; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 39.19 Å2; (10)Index of Refraction: 1.616; (11)Molar Refractivity: 38.96 cm3; (12)Molar Volume: 111.3 cm3; (13)Polarizability: 15.44 10-24cm3; (14)Surface Tension: 63.2 dyne/cm; (15)Density: 1.813 g/cm3; (16)Flash Point: 197.6 °C; (17)Enthalpy of Vaporization: 69.01 kJ/mol; (18)Boiling Point: 403.1 °C at 760 mmHg; (19)Vapour Pressure: 3.19E-07 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1ccncc1Br
(2)InChI: InChI=1/C6H4BrNO2/c7-5-3-8-2-1-4(5)6(9)10/h1-3H,(H,9,10)
(3)InChIKey: AVXWWBFBRTXBRM-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C6H4BrNO2/c7-5-3-8-2-1-4(5)6(9)10/h1-3H,(H,9,10)
(5)Std. InChIKey: AVXWWBFBRTXBRM-UHFFFAOYSA-N

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