4-Bromopyridine-2-carboxylic acid supplier

Name
4-Bromopyridine-2-carboxylic acid
EINECS -0
CAS No. 30766-03-1
Article Data11
CAS DataBase
Density 1.813 g/cm³
Solubility Sparingly soluble in dimethyl sulfoxide , methanol and water.
Melting Point 172-174 °C
Formula C₆H₄BrNO₂
Boiling Point 347.8 °C at 760 mmHg
Molecular Weight 202.007
Flash Point 164.2 °C
Transport Information
Appearance Fine needles
Safety 24/25-36/37
Risk Codes Xi:;
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Bromopicolinic acid;
PSA 50.19000
LogP 1.54230

Synthetic route

: 22282-99-1
4-bromo-2-methylpyridine

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
With potassium permanganate In water at 80℃;	33%
Stage #1: 4-bromo-2-methylpyridine With potassium permanganate; water at 20℃; for 6.5h; Heating / reflux; Stage #2: With hydrogenchloride; water pH=4;	22%
Stage #1: 4-bromo-2-methylpyridine With potassium permanganate; water for 6.5h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=4;	22%

: 62150-45-2
4-bromo-2-cyanopyridine

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-cyanopyridine With sodium hydroxide In water Reflux; Stage #2: With hydrogenchloride In water at 130℃; for 0.333333h; pH=1 - 2;	20%

: 931-19-1
2-methylpyridine N-oxide

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / H2SO4, fuming HNO3 / 2 h / 100 - 105 °C 2: 85 percent / PCl3 / CHCl3 / 3 h / Ambient temperature 3: 61 percent / AcBr / 6 h / Heating 4: KMnO4 / H2O / Heating View Scheme

: 13508-96-8
2-methyl-4-nitro-pyridine

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / AcBr / 6 h / Heating 2: KMnO4 / H2O / Heating View Scheme

: 5470-66-6
2-methyl-4-nitropyridine N-oxide

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / PCl3 / CHCl3 / 3 h / Ambient temperature 2: 61 percent / AcBr / 6 h / Heating 3: KMnO4 / H2O / Heating View Scheme
Multi-step reaction with 3 steps 1: iron; acetic acid / 2 h / 20 - 100 °C 2: hydrogen bromide; sodium nitrite / water / 16.5 h / -10 - 20 °C 3: potassium permanganate / water / 6.5 h / 20 °C / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1.1: iron; acetic acid / 2 h / 20 - 100 °C 2.1: hydrogen bromide; sodium nitrite / water / 16.5 h / 0 - 20 °C 3.1: potassium permanganate / water / 6.5 h / 20 °C / Heating / reflux 3.2: pH 4 View Scheme

: 18437-58-6
3-methyl-4-pyridinamine

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen bromide; sodium nitrite / water / 16.5 h / -10 - 20 °C 2: potassium permanganate / water / 6.5 h / 20 °C / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen bromide; sodium nitrite / water / 16.5 h / 0 - 20 °C 2.1: potassium permanganate / water / 6.5 h / 20 °C / Heating / reflux 2.2: pH 4 View Scheme

: 1120-87-2
4-bromopyridin

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 17 h / 20 °C 2.1: triethylamine / acetonitrile / 3.5 h / Schlenk technique; Inert atmosphere; Reflux 3.1: sodium hydroxide / water / Reflux 3.2: 0.33 h / 130 °C / pH 1 - 2 View Scheme

: 14248-50-1
4-bromopyridine-1-oxide

: 30766-03-1
4-bromo-2-picolinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetonitrile / 3.5 h / Schlenk technique; Inert atmosphere; Reflux 2.1: sodium hydroxide / water / Reflux 2.2: 0.33 h / 130 °C / pH 1 - 2 View Scheme

: 30766-03-1
4-bromo-2-picolinic acid

: 1117-97-1
N,0-dimethylhydroxylamine

: 1005342-94-8
4-bromo-pyridine-2-carboxylic acid N-methoxy-N-methyl-amide

Conditions

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;	100%

: 89488-25-5
(5‐chloro‐2‐hydroxyphenyl)boronic acid

: 30766-03-1
4-bromo-2-picolinic acid

: 4-(5-chloro-2-hydroxyphenyl)picolinic acid

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 87 - 88℃; for 29h; Inert atmosphere;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 30766-03-1
4-bromo-2-picolinic acid

: 1289210-83-8
tert-butyl 4-bromopyridine-2-carboxylate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 16h;	97.25%

: 30766-03-1
4-bromo-2-picolinic acid

: 207799-10-8
(4-bromopyridin-2-yl)-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
	93%
	93%
	93%

: 89694-48-4
5-chloro-2-methoxyphenyl boronic acid

: 30766-03-1
4-bromo-2-picolinic acid

: 4-(5-chloro-2-methoxyphenyl)picolinic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 16h; Inert atmosphere; Reflux;	92%

: 89499-43-4
methyl 4-aminothiophene-2-carboxylate

: 30766-03-1
4-bromo-2-picolinic acid

: 1354412-71-7
methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate

Conditions

Conditions	Yield
With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃; for 6h;	90%

: 30766-03-1
4-bromo-2-picolinic acid

: 75-65-0
tert-butyl alcohol

: 1289210-83-8
tert-butyl 4-bromopyridine-2-carboxylate

Conditions

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride at 0 - 20℃;	89%
With pyridine; p-toluenesulfonyl chloride at 0℃; for 16h;

: [{Ir(ppy)2(μ-Cl)}2]

: 30766-03-1
4-bromo-2-picolinic acid

: Ir(2-phenylpyridine)2(pyridine-2-carboxylate-Br)

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	87%

: 64-17-5
ethanol

: 30766-03-1
4-bromo-2-picolinic acid

: 62150-47-4
ethyl 4-bromopyridine-2-carboxylate

Conditions

Conditions	Yield
With sulfuric acid at 20 - 70℃; for 12h;	86%
With sulfuric acid at 60℃; for 6h;	73.6%
With sulfuric acid for 3.5h; Schlenk technique; Inert atmosphere; Reflux;	40%

: 30766-03-1
4-bromo-2-picolinic acid

: 2688-84-8
2-phenoxyaniline

: C18H13BrN2O2

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; for 6h; Reagent/catalyst; Solvent; Temperature;	86%

: 1765-93-1
4-fluoroboronic acid

: 30766-03-1
4-bromo-2-picolinic acid

: C12H8FNO2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 98℃; for 24h; Inert atmosphere;	85.8%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;

: 107-10-8
propylamine

: 30766-03-1
4-bromo-2-picolinic acid

: 1289051-27-9
4-bromo-N-propylpyridine-2-carboxamide

Conditions

Conditions	Yield
With 1-hydroxy-1H-benzotriazol hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;	84%

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

: 30766-03-1
4-bromo-2-picolinic acid

: 1005342-94-8
4-bromo-pyridine-2-carboxylic acid N-methoxy-N-methyl-amide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-picolinic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 10℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	83%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	44%
With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0 - 20℃;
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 16h;	5 g

: 30766-03-1
4-bromo-2-picolinic acid

: 94839-07-3
3,4-(methylenedioxy)-benzeneboronic acid

: C13H9NO4

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 98℃; for 24h; Inert atmosphere;	82.1%

: 30766-03-1
4-bromo-2-picolinic acid

: 100-36-7
N,N-diethylethylenediamine

: 1420844-63-8
4-bromo-N-(2-(diethylamino)ethyl)picolinamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-picolinic 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;	82%

: 30766-03-1
4-bromo-2-picolinic acid

: 5378-35-8
3-(1,3,4-oxadiazol-2-yl)aniline

: 1262044-02-9
N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h;	81%

: 5680-79-5
glycine ethyl ester hydrochloride

: 30766-03-1
4-bromo-2-picolinic acid

: 1289199-67-2
methyl 2-(4-bromopicolinamido)acetate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	79.8%

: 30766-03-1
4-bromo-2-picolinic acid

: 98-80-6
phenylboronic acid

: 52565-56-7
4-phenylpyridine-2-carboxylic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 90℃; for 8h; Inert atmosphere;	78.9%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;

: 30766-03-1
4-bromo-2-picolinic acid

: 139301-27-2
4-trifluoromethoxyphenylboronic acid

: C13H8F3NO3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 98℃; for 24h; Inert atmosphere;	77.7%

: 98-16-8
3-trifluoromethylaniline

: 30766-03-1
4-bromo-2-picolinic acid

: 1454657-40-9
4-bromo-N-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-picolinic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.166667h; Stage #2: 3-trifluoromethylaniline In N,N-dimethyl-formamide at 20℃; for 21h; Time;	76%
Stage #1: 4-bromo-2-picolinic acid With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 3-trifluoromethylaniline In N,N-dimethyl-formamide at 20℃; for 21h; Reagent/catalyst; Time;	76%

: 30766-03-1
4-bromo-2-picolinic acid

: 74-88-4
methyl iodide

: 29681-42-3
methyl 4-bromopyridine-2-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	75.3%

: 30766-03-1
4-bromo-2-picolinic acid

: 75-65-0
tert-butyl alcohol

: 207799-10-8
(4-bromopyridin-2-yl)-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine for 26h; Heating;	74%

: 39684-28-1
O-(tert-butyl)hydroxylamine hydrochloride

: 30766-03-1
4-bromo-2-picolinic acid

: 1431470-36-8
4-bromopyridine-2-carboxylic acid tert-butoxyamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h;	74%
Stage #1: 4-bromo-2-picolinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane Stage #2: O-(tert-butyl)hydroxylamine hydrochloride In dichloromethane at 20℃; for 18h;	74%

: 193269-78-2
3-aminoazetidine-1-carboxylic acid tert-butyl ester

: 30766-03-1
4-bromo-2-picolinic acid

: tert-butyl 3-(4-bromopicolinamido)azetidine-1-carboxylate

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 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℃;	74%

: 30766-03-1
4-bromo-2-picolinic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 29681-42-3
methyl 4-bromopyridine-2-carboxylate

Conditions

Conditions	Yield
In methanol; diethyl ether; ethyl acetate at 0 - 20℃; for 1.5h;	73%
In tetrahydrofuran; ethyl acetate at 0 - 20℃; for 5.08h; Product distribution / selectivity;	62%
Stage #1: 4-bromo-2-picolinic acid; diazomethyl-trimethyl-silane With methanol In tetrahydrofuran at 0 - 20℃; Stage #2: With acetic acid In tetrahydrofuran; methanol; water	60%

: 89598-96-9
(3-bromophenyl)boronic acid

: 30766-03-1
4-bromo-2-picolinic acid

: C12H8BrNO2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 98℃; for 24h; Inert atmosphere;	71.9%

: 30766-03-1
4-bromo-2-picolinic acid

: 62-53-3
aniline

: 1454657-45-4
4-bromo-pyridine-2-carboxylic acid phenylamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-picolinic acid With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide for 0.166667h; Stage #2: aniline In N,N-dimethyl-formamide at 20℃; for 66h;	71%
Stage #1: 4-bromo-2-picolinic acid With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.166667h; Stage #2: aniline In N,N-dimethyl-formamide at 20℃; for 66h;	71%

: 292638-84-7
styrene

: 30766-03-1
4-bromo-2-picolinic acid

: 2-chloro-1-phenylethyl 4-bromopicolinate

Conditions

Conditions	Yield
With tert-butylhypochlorite In N,N-dimethyl-formamide at 40℃; for 1h; Schlenk technique;	70%

: 30766-03-1
4-bromo-2-picolinic acid

: 62150-46-3
4-bromopyridine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-picolinic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.25h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 2h;	68%

: [Ir(F2PPy)2Cl]2

: 30766-03-1
4-bromo-2-picolinic acid

: Ir(2-(2,4-difluorophenyl)pyridine)2(pyridine-2-carboxylate-4-Br)

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	68%

4-Bromopyridine-2-carboxylic acid Chemical Properties

Empirical Formula: C₆H₄BrNO₂
Molecular Weight: 202.0055
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: 164.2 °C
Enthalpy of Vaporization: 62.49 kJ/mol
Boiling Point: 347.8 °C at 760 mmHg
Vapour Pressure: 1.97E-05 mmHg at 25 °C
Melting point: 172-174 °C
Appearance: Fine needles
Structure of 4-Bromopyridine-2-carboxylic acid (CAS NO.30766-03-1):

IUPAC Name: 4-Bromopyridine-2-carboxylic acid
Canonical SMILES: C1=CN=C(C=C1Br)C(=O)O
InChI: InChI=1S/C6H4BrNO2/c7-4-1-2-8-5(3-4)6(9)10/h1-3H,(H,9,10)
InChIKey: RPHHYRNGCJYQSP-UHFFFAOYSA-N
Product Category of 4-Bromopyridine-2-carboxylic acid (CAS NO.30766-03-1): Bromides;Carboxes;Acids and Derivatives;Heterocycles;pharmacetical;Pyridine series;Organohalides;Aromatics Compounds;Aromatics

4-Bromopyridine-2-carboxylic acid Uses

4-Bromopyridine-2-carboxylic acid (CAS NO.30766-03-1) is a useful synthetic intermediate.

4-Bromopyridine-2-carboxylic acid Safety Profile

Hazard Codes: Xi
Hazard Note: Irritant

4-Bromopyridine-2-carboxylic acid Specification

4-Bromopyridine-2-carboxylic acid , its cas register number is 30766-03-1. It also can be called 4-Bromopicolinic acid ; and 4-Bromo-2-pyridinecarboxylic acid .

Product Name

4-Bromopyridine-2-carboxylic acid

Synthetic route

4-Bromopyridine-2-carboxylic acid Chemical Properties

4-Bromopyridine-2-carboxylic acid Uses

4-Bromopyridine-2-carboxylic acid Safety Profile

4-Bromopyridine-2-carboxylic acid Specification

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