29241-65-4

Basic information

• Product Name: 5-Bromo-2-chloronicotinic acid
• Synonyms: 5-BROMO-2-CHLORONICOTINIC ACID;5-BROMO-2-CHLOROPYRIDINE-3-CARBOXYLIC ACID;5-BROMO-2-CHLORO-3-PYRIDINECARBOXYLIC ACID;5-Bromo-2-chloronicotinicacid5-Bromo-2-chloronicotinicacid;5-Bromo-2-Chloronicotinic;5-Bromo-2-chloronicotinic acid 97%;5-Bromo-2-chloronicotinic acid ,97%;5-Bromo-2-chloropyridine-3-carboxylic acid, 5-Bromo-3-carboxy-2-chloropyridine
• CAS NO: 29241-65-4
• Molecular Formula: C₆H₃BrClNO₂
• Molecular Weight: 236.45
• Product Categories: blocks;Bromides;Carboxes;Pyridines;Acids and Derivatives;Heterocycles;pharmacetical;Carboxylic Acids;Pyridine;Carboxylic Acids
• Mol File: 29241-65-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 173-176°C
• Boiling Point: 345.1 °C at 760 mmHg
• Flash Point: 162.5 °C
• Appearance: /Solid
• Density: 1.917 g/cm³
• Vapor Pressure: 2.39E-05mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• PKA: 1.61±0.25(Predicted)
• CAS DataBase Reference: 5-Bromo-2-chloronicotinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chloronicotinic acid(29241-65-4)
• EPA Substance Registry System: 5-Bromo-2-chloronicotinic acid(29241-65-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 29241-65-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C6H3BrClNO2/c7-3-1-4(6(10)11)5(8)9-2-3/h1-2H,(H,10,11)

Synthetic route

5-bromo-2-hydroxynicotinic acid (104612-36-4) → 5-bromo-2-chloronicotinic acid (29241-65-4)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 70℃; for 4h;	99%
Stage #1: 5-bromo-2-hydroxynicotinic acid With thionyl chloride In N,N-dimethyl-formamide at 70℃; for 4h; Stage #2: With water In N,N-dimethyl-formamide for 1h;	99%
With thionyl chloride; N,N-dimethyl-formamide	85%

2-hydroxy-3-carboxypyridine (609-71-2) → 5-bromo-2-chloronicotinic acid (29241-65-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / Br2; aq. NaOH / 18 h / 0 - 50 °C 2: 99 percent / thionyl chloride / dimethylformamide / 4 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 63.5 percent / aq. conc. NaOH, aq. NaOBr / 48 h / Ambient temperature 2: 37 percent / SOCl2 / dimethylformamide / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 71 percent / Br2, NaOH / H2O / 90 h / 50 °C 2: 82 percent / SO2Cl2 / dimethylformamide / 2 h / Heating View Scheme

2-chloronicotinic acid (2942-59-8) → 5-bromo-2-chloronicotinic acid (29241-65-4)

Conditions	Yield
With bromine In acetic acid

methanol (67-56-1) + 5-bromo-2-chloronicotinic acid (29241-65-4) → methyl 2-chloro-5-bromonicotinate (78686-79-0)

Conditions	Yield
Stage #1: methanol; 5-bromo-2-chloronicotinic acid With sulfuric acid at 60℃; for 36h; Stage #2: With sodium hydrogencarbonate In water	100%
Stage #1: 5-bromo-2-chloronicotinic acid With thionyl chloride at 70℃; Stage #2: methanol In benzene at 65℃;	95%
With sulfuric acid for 15h; Reflux;	89%

5-bromo-2-chloronicotinic acid (29241-65-4) + tert-butyl alcohol (75-65-0) → tert-butyl 5-bromo-2-chloronicotinate

Conditions	Yield
With sulfuric acid; magnesium sulfate In dichloromethane at 25℃; for 16h;	94%

(S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanamine (46049-49-4) + 5-bromo-2-chloronicotinic acid (29241-65-4) → (S)-5-bromo-2-chloro-N-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)nicotinamide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	93%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

5-bromo-2-chloronicotinic acid (29241-65-4) + N,0-dimethylhydroxylamine (1117-97-1) → 5-bromo-2-chloro-N-methoxy-N-methylnicotinamide (885223-63-2)

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: N,0-dimethylhydroxylamine In dichloromethane at 20℃;	90%
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 30℃; for 0.5h;	82%

d(4)-methanol (811-98-3) + 5-bromo-2-chloronicotinic acid (29241-65-4) → (2H3)methyl 5-bromo-2-chloropyridine-3-carboxylate

Conditions	Yield
With sulfuric acid In water at 60℃; for 48h;	90%

5-bromo-2-chloronicotinic acid (29241-65-4) + 4-methoxy-phenol (150-76-5) → 5-bromo-2-(4-methoxyphenoxy)nicotinic acid (1215864-79-1)

Conditions	Yield
Stage #1: 4-methoxy-phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.233333h; Inert atmosphere; Stage #2: 5-bromo-2-chloronicotinic acid In N,N-dimethyl-formamide; mineral oil at 140℃; for 1h; Inert atmosphere;	83%
Stage #1: 4-methoxy-phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.1h; Stage #2: 5-bromo-2-chloronicotinic acid In N,N-dimethyl-formamide; mineral oil at 20 - 140℃; for 1.16667h;

ammonia (7664-41-7) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-bromo-2-chloronicotinamide (75291-85-9)

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; Stage #2: ammonia In methanol at -10 - 20℃; for 18h;	82%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-bromo-2-chloro-N-methoxy-N-methylnicotinamide (885223-63-2)

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With thionyl chloride at 80℃; for 2h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 1h;	81%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	79%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	79%
Stage #1: 5-bromo-2-chloronicotinic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.166667h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In N,N-dimethyl-formamide for 1h;

5-bromo-2-chloronicotinic acid (29241-65-4) + benzylamine (100-46-9) → 2-(benzylamino)-5-bromonicotinic acid (1258846-87-5)

Conditions	Yield
at 120℃; for 2h;	79%

5-bromo-2-chloronicotinic acid (29241-65-4) + aniline (62-53-3) → 5-Bromo-2-phenylamino-nicotinic acid (115891-15-1)

Conditions	Yield
	76%

4-Iodophenol (540-38-5) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-bromo-2-(4-iodophenoxy)nicotinic acid (1335218-37-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Heating;	76%
Stage #1: p-Iodophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 30℃; for 1h; Inert atmosphere; Stage #2: 5-bromo-2-chloronicotinic acid In N,N-dimethyl-formamide; mineral oil at 115℃; Stage #3: With acetic acid In water; N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; pH=5;
Stage #1: p-Iodophenol With sodium hydride In N,N-dimethyl-formamide at 0 - 30℃; for 1h; Inert atmosphere; Stage #2: 5-bromo-2-chloronicotinic acid In N,N-dimethyl-formamide at 115℃; Inert atmosphere;	765 g
With sodium hydride In N,N-dimethyl-formamide at 115℃;

5-bromo-2-chloronicotinic acid (29241-65-4) → (5-bromo-2-chloro-pyridin-3-yl)-methanol (742100-75-0)

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0 - 23℃; for 18h; Further stages.;	70%
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1.25 h / 0 °C 2: sodium tetrahydroborate / water / 3 h / 0 - 20 °C View Scheme
Stage #1: 5-bromo-2-chloronicotinic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; for 1.5h; Cooling with ice; Stage #2: With sodium tetrahydroborate In water at 20℃; for 20h;

5-bromo-2-chloronicotinic acid (29241-65-4) + isobutyl chloroformate (543-27-1) → (5-bromo-2-chloro-pyridin-3-yl)-methanol (742100-75-0)

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid; isobutyl chloroformate With triethylamine In tetrahydrofuran at 0℃; for 1.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; for 20h;	70%

5-bromo-2-chloronicotinic acid (29241-65-4) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-chloro-5-bromonicotinate (78686-79-0)

Conditions	Yield
In methanol; benzene at 0℃; for 1h;	69%

5-bromo-2-chloronicotinic acid (29241-65-4) + N-butylamine (109-73-9) → 5-bromo-2-(butylamino)nicotinic acid (1247704-98-8)

Conditions	Yield
for 12h; Reflux;	69%

2-(4-bromo-2,6-difluorophenylamino)nicotinic acid (1035689-99-6) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-bromo-2-(3'-ethoxy-3,5-difluorobiphenyl-4-ylamino)nicotinic acid (1035690-18-6)

Conditions	Yield
With toluene-4-sulfonic acid In water at 110℃;	63%

{2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine + 5-bromo-2-chloronicotinic acid (29241-65-4) → N‐({2‐benzyl‐2‐azabicyclo[2.1.1]hexan‐1‐yl}methyl)‐5‐bromo‐2‐chloropyridine‐3‐carboxamide

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Stage #2: {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine In dichloromethane at 20℃; for 1h;	63%

2-aminopyridine N-oxide (14150-95-9) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-Bromo-2-(1-oxy-pyridin-2-ylamino)-nicotinic acid

Conditions	Yield
With Ullmann copper; potassium carbonate In N,N-dimethyl-formamide for 3h; Heating;	60%

5-bromo-2-chloronicotinic acid (29241-65-4) + phenylacetylene (536-74-3) → 1-(5-bromo-2-chloropyridin-3-yl)-3-phenylpropynone

Conditions	Yield
Stage #1: 5-bromo-2-chloronicotinic acid With thionyl chloride for 3h; Reflux; Stage #2: phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube;	60%

2-amino-5-methylpyridine 1-oxide (66362-95-6) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-Bromo-2-(5-methyl-1-oxy-pyridin-2-ylamino)-nicotinic acid

Conditions	Yield
With Ullmann copper; potassium carbonate In N,N-dimethyl-formamide for 3h; Heating;	52%

diazomethane (186581-53-3, 908094-01-9) + 5-bromo-2-chloronicotinic acid (29241-65-4) → methyl 2-chloro-5-bromonicotinate (78686-79-0)

Conditions	Yield
In diethyl ether Ambient temperature;	49%

2-amino-6-methylpyridine 1-oxide (25063-84-7) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-Bromo-2-(6-methyl-1-oxy-pyridin-2-ylamino)-nicotinic acid

Conditions	Yield
With Ullmann copper; potassium carbonate In N,N-dimethyl-formamide for 3h; Heating;	41%

2-amino-4-methylpyridine-1-oxide (83700-78-1) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-Bromo-2-(4-methyl-1-oxy-pyridin-2-ylamino)-nicotinic acid

Conditions	Yield
With Ullmann copper; potassium carbonate In N,N-dimethyl-formamide for 3h; Heating;	41%

4-(aminomethyl)pyridine (3731-53-1) + 5-bromo-2-chloronicotinic acid (29241-65-4) → C12H10BrN3O2

Conditions	Yield
at 130℃;	38%

5-formylfurane-2-boronic acid (27329-70-0) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 2-chloro-5-(5-formylfuran-2-yl)nicotinic acid (1190223-48-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 28h; Suzuki-Miyaura coupling; Inert atmosphere;	28%

5-bromo-2-chloronicotinic acid (29241-65-4) + aniline (62-53-3) → 5-bromo-2-chloro-N-phenylnicotinamide (143094-44-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	26%

4-Trifluoromethoxyphenol (828-27-3) + 5-bromo-2-chloronicotinic acid (29241-65-4) → 5-Bromo-2-[4-(trifluoromethoxy)phenoxy]nicotinic acid (473256-18-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; pentane	24%

1-methyl-3-pyrrolidinol (13220-33-2) + 5-bromo-2-chloronicotinic acid (29241-65-4) → Sodium; 5-bromo-2-(1-methyl-pyrrolidin-3-yloxy)-nicotinate

Conditions	Yield
With sodium hydride In tetrahydrofuran for 1.5h; Heating;	190 g

5-bromo-2-chloronicotinic acid (29241-65-4) + 4-chloro-aniline (106-47-8) → 5-Bromo-2-(4-chloro-phenylamino)-nicotinic acid

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In water Heating;

Upstream product

• 2942-59-8 2-chloronicotinic acid 
• 609-71-2 2-hydroxy-3-carboxypyridine 
• 104612-36-4 5-bromo-2-hydroxynicotinic acid 

Downstream Products

• 885223-63-2 5-bromo-2-chloro-N-methoxy-N-methylnicotinamide 

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