5-Bromonicotinic Acid supplier

Name
5-Bromonicotinic acid
EINECS 244-065-5
CAS No. 20826-04-4
Article Data18
CAS DataBase
Density 1.814 g/cm³
Solubility
Melting Point 178-180 °C(lit.)
Formula C₆H₄BrNO₂
Boiling Point 328.535 °C at 760 mmHg
Molecular Weight 202.007
Flash Point 152.5 °C
Transport Information
Appearance Light yellow cryst.
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3-pyridinecarboxylic acid, 5-bromo-;3-Pyridinecarboxylic acid, 5-bromo- (9CI);5-bromopyridine-3-carboxylate;Nicotinic acid, 5-bromo-;5-Bromo-3-pyridinecarboxylic acid;5-bromopyridine-3-carboxylic acid;5-bromo-3-pyridine carboxlic acid;
PSA 50.19000
LogP 1.54230

Synthetic route

: 28733-43-9
5-bromonicotinamide

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With acetic acid; isopentyl nitrite at 80℃; for 24h; Inert atmosphere;	98%

: 10400-19-8
3-pyridinecarbonyl chloride

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With bromine at 0 - 155℃; for 10h;	94%

: 29681-44-5
5-bromo-3-pyridine carboxylic acid methyl ester

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 12h; Ambient temperature;	91%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h;	33%

: 27848-84-6, 28057-46-7, 58001-19-7, 58001-20-0, 58001-21-1, 140387-88-8
nicergoline

A: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

B: 35155-28-3
1-Methyl-10alpha-methoxy-9,10-dihydrolysergol

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating;	A 12% B 91%

: 625-92-3
3,5-dibromopyridine

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With n-butyllithium; diethyl ether at -30℃; Behandeln der Reaktionsloesung mit festem CO2;

: 59-67-6
nicotinic acid

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With thionyl chloride Erhitzen des Reaktionsprodukts mit Brom auf 150-170grad und Behandeln des Reaktionsgemisches mit H2O bei pH 3;

: 5332-24-1
3-bromoquinoline

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With nitric acid at 150℃;

: 98555-51-2
5-Bromo-pyridine-2,3-dicarboxylic acid

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With acetic acid
beim Schmelzen;

: 99-73-0
para-bromophenacyl bromide

: <5-3H>-sesbanine

A: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

B: 109440-03-1
<5-3H>-nicotinic acid

C: 5-Bromo-nicotinic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester

Conditions

Conditions	Yield
With pyridine; potassium hydroxide; potassium permanganate; thionyl chloride; bromine; benzoyl chloride multistepreaction to study the origin of the carbon skeleton;

...Expand

3.bz.bz-tribromo-6-methoxy-quinoline: 3.bz.bz-tribromo-6-methoxy-quinoline

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With nitric acid

5-bromo-quinolinic acid: 5-bromo-quinolinic acid

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

diazotized 5-amino-nicotinic acid: diazotized 5-amino-nicotinic acid

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With copper(I) bromide

: 3430-16-8
5-bromo-3-picoline

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

Conditions

Conditions	Yield
With potassium permanganate Heating;

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 144222-22-0
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate

: tert-butyl 4-((5-bromonicotinamido)methyl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 80℃; for 2h; Microwave irradiation;	100%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: tert-butyl-4-(5-bromonicotinoyl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 80℃; for 2h; Microwave irradiation;	100%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 64-17-5
ethanol

: 20986-40-7
ethyl 5-bromo-3-pyridinecarboxylate

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-pyridinecarboxylic acid With thionyl chloride Reflux; Stage #2: ethanol for 2h; Reflux; Stage #3: With sodium hydrogencarbonate In dichloromethane; water pH=8;	99%
With sulfuric acid for 18h; Heating;	94%
With sulfuric acid for 18h; Inert atmosphere; Reflux; Cooling with ice;	89%

: 915285-91-5
5-((1S,2S)-2-Hydroxy-1-methyl-5-oxo-cyclopentyl)-pentanoic acid methyl ester

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 5-Bromo-nicotinic acid (1S,2S)-2-(4-methoxycarbonyl-butyl)-2-methyl-3-oxo-cyclopentyl ester

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 20h;	99%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 4534-11-6
3-methyl-4-isopropylaniline hydrochloride

: 5-bromo-N-(4-isopropyl-3-methylphenyl)pyridine-3-carboxamide

Conditions

Conditions	Yield
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℃;	98.2%

: 186581-53-3, 908094-01-9
diazomethane

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 29681-44-5
5-bromo-3-pyridine carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether for 2h; Ambient temperature;	97%
In diethyl ether for 0.25h;

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 872175-75-2
1-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6,7,8-tetrahydro-isoquinoline

: 872175-89-8
5-(1-methoxy-5,6,7,8-tetrahydro-isoquinolin-4-yl)-nicotinic acid

Conditions

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In DMF (N,N-dimethyl-formamide) at 110℃; for 18h; Suzuki Coupling;	97%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: (S)-tert-butyl(dimethyl)[3-(S-phenylsulfonimidoyl)propoxy]silane

: (S)-5-bromo-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl-λ4-sulfanylidene]nicotinamide

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;	97%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 3282-30-2
pivaloyl chloride

: 133343-68-7
tert-butylcarbonyl-5-bromonicotinic acid

Conditions

Conditions	Yield
With triethylamine In benzene for 16h; Ambient temperature; 1.) C6H6, RT, 1 h, 2.) C6H6, 16 h;	96%
With triethylamine In benzene	95%
Stage #1: 5-bromo-3-pyridinecarboxylic acid With triethylamine In toluene at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: pivaloyl chloride In toluene at 0 - 20℃; Inert atmosphere; Schlenk technique;	77%

: 67-56-1
methanol

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 29681-44-5
5-bromo-3-pyridine carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-pyridinecarboxylic acid With boron trichloride Stage #2: methanol	96%
sulfuric acid for 3h; Heating / reflux;	90%
With sulfuric acid at 65℃;	88%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 1765-93-1
4-fluoroboronic acid

: C20H19NO4

: (S)-1-[5-(4-Fluoro-phenyl)-pyridine-3-carbonyl]-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multistep reaction;	96%

...Expand

: 915285-93-7
4-((1S,2S)-2-Hydroxy-1-methyl-5-oxo-cyclopentyl)-butyric acid methyl ester

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 5-Bromo-nicotinic acid (1S,2S)-2-(3-methoxycarbonyl-propyl)-2-methyl-3-oxo-cyclopentyl ester

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 20h;	96%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

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

: 263270-02-6
tert-butyl 5-bromopyridine-3-carboxylate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran Reflux;	96%
With 4-pyrrolidin-1-ylpyridine; triethylamine In tetrahydrofuran at 20℃; for 48h;	91%
With dmap In tetrahydrofuran at 20℃; for 1.5h; Cooling with ice;	82%
With dmap In tetrahydrofuran for 1h; Reflux;	79%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 35944-64-0
3-iodo-4-methylaniline

: C13H10BrIN2O

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-pyridinecarboxylic acid With thionyl chloride In toluene at 82℃; for 2h; Stage #2: 3-iodo-4-methylaniline With triethylamine In toluene at 20℃;	96%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 39620-02-5
5-bromonicotinoyl chloride

Conditions

Conditions	Yield
With thionyl chloride for 12h; Reflux;	95%
With thionyl chloride In dichloromethane for 2h; Reflux;	64%
With thionyl chloride

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 5-bromonicotinic acid chloride hydrochloride

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane Reflux;	95%
With thionyl chloride for 4h;	92%
With oxalyl dichloride
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide 0 deg C, 1 h; RT, 30 min;

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 59-02-9
Tocopherol

: (R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl 5-bromonicotinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran Inert atmosphere;	95%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 29681-44-5
5-bromo-3-pyridine carboxylic acid methyl ester

Conditions

Conditions	Yield
In methanol	94%
Multi-step reaction with 2 steps 1: SOCl2 View Scheme

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 60933-65-5
(R)-S-methyl-S-phenylsulfoximine

: 1027725-42-3
(R)-5-bromo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.66667h;	94%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: [{Mo(O)(5,10,15,20-meso-tetrakis(4-bromophenyl)porphyrin)}2O]

: [Mo(O)(5,10,15,20-meso-tetrakis(4-bromophenyl)porphyrin)(5-bromonicotinate)]

Conditions

Conditions	Yield
In methanol; chloroform for 0.5h;	94%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 24242-19-1
5-aminonicotinic acid

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-pyridinecarboxylic acid With copper(ll) sulfate pentahydrate; ammonia In water at 170 - 180℃; for 19h; Autoclave; Stage #2: In water pH=4 - 5; Acidic aq. solution;	93%
With copper(I) sulfate; ammonia In water at 120℃; for 16h; Acidic aqueous solution;	74%
With ammonia; copper(II) sulfate In water at 180℃; for 15h;	64%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 35661-60-0
Fmoc-Leu-OH

: 1765-93-1
4-fluoroboronic acid

: (S)-2-{[5-(4-Fluoro-phenyl)-pyridine-3-carbonyl]-amino}-4-methyl-pentanoic acid

Conditions

Conditions	Yield
Multistep reaction;	93%

...Expand

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

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

: 183608-47-1
N-methyl-N-methoxy-5-bromopyridine-3-carboxamide

Conditions

Conditions	Yield
With oxalyl dichloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 4h;	93%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	86%
Stage #1: 5-bromo-3-pyridinecarboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 3.5h;	73%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1-methyl-pyrrolidin-2-one; dichloromethane at 0 - 20℃;	51.1%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1-methyl-pyrrolidin-2-one; dichloromethane at 0 - 20℃;	51.1%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 98-80-6
phenylboronic acid

: 10177-12-5
5-phenylnicotinic acid

Conditions

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 70℃; for 1.66667h; Suzuki Coupling;	93%
With meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrinatopalladium(II); potassium carbonate In water at 80℃; for 4.66667h; Suzuki Coupling; Green chemistry;	91%
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 0.333333h; Catalytic behavior; Suzuki-Miyaura Coupling;	82%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 100643-71-8
descarboethoxyloratadine

: (5-Bromo-pyridin-3-yl)-[4-(8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-methanone

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 18h; Ambient temperature;	92%

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 4381-25-3, 33903-50-3, 60933-65-5, 81162-81-4
(S)-S-methyl-S-phenylsulfoximine

: 1027729-52-7
(S)-5-bromo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h;	92%

: 504-24-5
4-aminopyridine

: 20826-04-4
5-bromo-3-pyridinecarboxylic acid

: 634173-90-3
5-bromo-N-(pyridin-4-yl)nicotinamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	92%

5-Bromonicotinic Acid Chemical Properties

Molecular Structure of 5-Bromonicotinic Acid (CAS NO.20826-04-4):

IUPAC Name: 5-bromopyridine-3-carboxylic acid
Empirical Formula: C₆H₄BrNO₂
Molecular Weight: 202.0055
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 39.19Å²
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: 152.5 °C
Enthalpy of Vaporization: 60.27 kJ/mol
Boiling Point: 328.5 °C at 760 mmHg
Vapour Pressure: 7.59E-05 mmHg at 25°C
EINECS: 244-065-5
Melting point : 178-180 °C(lit.)
BRN :115854
Product Categories: blocks; Bromides; Carboxes; Pyridines; Pyridine; pyridine derivative; Acids and Derivatives; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; pharmacetical; Pyridine series; Carboxylic Acids; Organic acids; Pyridines derivates; Protected amino acid & peptides; Bromopyridines; Halopyridines; Carboxylic Acids

5-Bromonicotinic Acid Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LD50	unreported	800mg/kg (800mg/kg)		Pharmaceutical Chemistry Journal Vol. 20, Pg. 29, 1986.
mouse	LD50	intraperitoneal	462mg/kg (462mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Journal of Pharmacobio-Dynamics. Vol. 10, Pg. 35, 1987.

5-Bromonicotinic Acid Safety Profile

Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
Hazard Codes: Xi
RTECS: QT0868000
Hazard Note: Irritant
WGK Germany: 3
HS Code: 29333999

5-Bromonicotinic Acid Specification

5-Bromonicotinic Acid , with CAS number of 20826-04-4, can be called 3-Pyridinecarboxylic acid, 5-bromo- (9CI) ; 3-pyridinecarboxylic acid, 5-bromo- ; 5-bromopyridine-3-carboxylate ; 5-Bromo-Nicotinic Acid ; 5-Bromo-3-pyridinecarboxylic acid ; Nicotinic acid, 5-bromo- ; 5-bromopyridine-3-carboxylic acid ; 5-bromo-3-pyridine carboxlic acid ; LDP15:5-Bromo Nicotinic Acid ; 5-Bromonicotic acid ; 5-Bromonicotinic acid 98% . It is a light yellow cryst.

Product Name

5-Bromonicotinic acid

Synthetic route

5-Bromonicotinic Acid Chemical Properties

5-Bromonicotinic Acid Toxicity Data With Reference

5-Bromonicotinic Acid Safety Profile

5-Bromonicotinic Acid Specification

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