19524-06-2

Basic information

• Product Name: 4-Bromopyridine hydrochloride
• Synonyms: 4-BROMOPYRIDINIUM CHLORIDE FOR SYNTHESIS;4 - broMide pyridine hydrochloride;4-Bromopyridine hydrochloride 4-Bromopyridinium chloride;4-BROMOPYRIDINE HCL;4-BROMOPYRIDINE HYDROCHLORIDE;4-BROMOPYRIDINIUM CHLORIDE;TIMTEC-BB SBB003600;Pyridine, 4-bromo-, hydrochloride
• CAS NO: 19524-06-2
• Molecular Formula: C₅H₅BrN*Cl
• Molecular Weight: 194.46
• EINECS: 243-128-4
• Product Categories: Heterocyclic Building Blocks;alkyl bromide;Pharmaceutical intermediates;Pyridine;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Pyridines derivates;Heterocyclic Compounds;Bromopyridines;Halopyridines;Pyridinium Compounds;Bases & Related Reagents;Nucleotides;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles
• Mol File: 19524-06-2.mol

Chemical Properties

• Melting Point: 270 °C (dec.)(lit.)
• Boiling Point: 185.2 °C at 760 mmHg
• Flash Point: 65.8 °C
• Appearance: White to peach/Powder
• Density: 1.598 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water
• Water Solubility: Soluble in DMSO, Methanol and Water.
• Sensitive: Hygroscopic
• BRN: 3621847
• CAS DataBase Reference: 4-Bromopyridine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromopyridine hydrochloride(19524-06-2)
• EPA Substance Registry System: 4-Bromopyridine hydrochloride(19524-06-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• RIDADR: 2811
• WGK Germany: 3
• F: 3-10
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19524-06-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Bromopyridine hydrochloride is used as a synthetic intermediate for the production of various organic compounds, facilitating the creation of a wide range of chemical entities.
Used in Pharmaceuticals:
4-Bromopyridine hydrochloride is used as a key raw material and intermediate in the pharmaceutical industry, playing a crucial role in the development and synthesis of numerous medicinal compounds.
Used in Agrochemicals:
4-Bromopyridine hydrochloride is utilized as a vital component in the agrochemical sector, contributing to the formulation of effective crop protection products and other agricultural applications.
Used in Dyestuff:
4-Bromopyridine hydrochloride is employed as a significant intermediate in the dyestuff industry, aiding in the production of various dyes and pigments for different applications.

InChI:InChI=1/C15H19NO4/c1-15(2,3)20-14(19)16-8-7-11-10(9-16)5-4-6-12(11)13(17)18/h4-6H,7-9H2,1-3H3,(H,17,18)

Synthetic route

4-formylphenylboronic acid, (87199-17-5) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(pyridin-4-yl)benzaldehyde (99163-12-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 4h; Suzuki Coupling; Reflux; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	84%

4-bromopyridine hydrochloride (19524-06-2) → 4-bromopyridin (1120-87-2)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 6h; Inert atmosphere; Schlenk technique;	100%
With sodium hydroxide In water at 20℃; for 0.166667h;	100%
With sodium hydrogencarbonate In water	84%

4-(cyanomethyl)phenylboronic acid (91983-26-5) + 4-bromopyridine hydrochloride (19524-06-2) → 2-(4-(pyridin-4-yl)phenyl)acetonitrile (112170-33-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	61%
Stage #1: 4-(cyanomethyl)phenylboronic acid; 4-bromopyridine hydrochloride With potassium carbonate In isopropyl alcohol; toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) for 7h; Inert atmosphere; Reflux;

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 4-bromopyridine hydrochloride (19524-06-2) → [RuCl2(p-cymene)(4-BrNC5H4)] (1587730-27-5)

Conditions	Yield
In dichloromethane at 20℃;	100%
In dichloromethane at 20℃;	97%

4-bromopyridine hydrochloride (19524-06-2) + (3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine (147081-44-5) → (S)-3-(pyridin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (1010446-43-1)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 70℃; for 4h;	99%

4-bromopyridine hydrochloride (19524-06-2) + 1-butyn-4-ol (927-74-2) → 4-(pyridin-4-yl)butyl-3-yn-1-ol (192643-83-7)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; lithium chloride In water for 2h; Sonogashira coupling; Reflux; Inert atmosphere;	99%

3,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl diethylcarbamate (1032189-97-1) + 4-bromopyridine hydrochloride (19524-06-2) → 3,5-dimethoxy-2-(pyridin-4-yl)phenyl diethylcarbamate (1032189-92-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 20h; Suzuki-Miyaura coupling;	99%

4-methylphenylboronic acid (5720-05-8) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(p-tolyl)pyridine (4423-10-3)

Conditions	Yield
With Pd(PPh2)(m-C6H4SO3Na)*(H2O)4; sodium carbonate In methanol; water; benzene at 80℃; for 6.5h;	98%
With palladium diacetate; sodium hydrogencarbonate; triphenylphosphine In water; N,N-dimethyl-formamide for 18h; Suzuki reaction; Heating; Inert atmosphere;	80%

2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) + 4-bromopyridine hydrochloride (19524-06-2) → 4-manisylpyridine (338989-70-1)

Conditions	Yield
Stage #1: 2-bromo-5-methoxy-1,3-dimethyl-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: 4-bromopyridine hydrochloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; hexane for 12h; Negishi coupling; Heating;	98%

5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine (1429747-36-3) + 4-bromopyridine hydrochloride (19524-06-2) → 5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)-pyrimidin-4-amine (1429745-32-3)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 105℃; Inert atmosphere;	98%
With tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 72h; Inert atmosphere;	81%

4-bromopyridine hydrochloride (19524-06-2) + methyl 5-ethynylpyridine-2-carboxylate (17880-61-4) → methyl 5-(pyridin-4-ylethynyl)picolinate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 75℃; for 24h; Schlenk technique;	98%

4-(5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribosyl)-2H-1,2,3-triazole + 4-bromopyridine hydrochloride (19524-06-2) → 2-(4-pyridyl)-4-(2,3-isopropylidene-5-tert-butyldiphenylsilyl-β-D-ribosyl)-1,2,3-triazole

Conditions	Yield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 2-(di-1-adamantylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl In toluene at 120℃; for 10h; Sealed tube; Inert atmosphere;	98%

4-bromopyridine hydrochloride (19524-06-2) + phenylacetylene (536-74-3) → 4-(phenylethynyl)pyridine (13295-94-8)

Conditions	Yield
With copper(l) iodide; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 100℃; for 20h;	97%
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine at 20℃; for 5h; Arylation; Heating;	96%
With pyrrolidine; triphenylphosphine; palladium dichloride In water at 120℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	94%

4-methoxyphenylboronic acid (5720-07-0) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(4-methoxylphenyl)pyridine (5938-16-9)

Conditions	Yield
With sodium phosphate; palladium on activated charcoal In isopropyl alcohol at 80℃; for 3h; Suzuki-Miyaura coupling reaction;	97%
With sodium phosphate dodecahydrate; palladium 10% on activated carbon In isopropyl alcohol at 80℃; for 3h; hetero-Suzuki-Miyaura cross-coupling; Inert atmosphere;	97%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In N,N-dimethyl-formamide at 85℃; for 2.25h; Suzuki cross-coupling;	92%
With potassium carbonate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane at 80℃; for 14h; Suzuki coupling;	74%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 130℃; for 0.75h; Sealed tube; Inert atmosphere; Microwave irradiation;	74%

1-methyl-piperazine (109-01-3) + 4-bromopyridine hydrochloride (19524-06-2) → 1-methyl-4-(pyridin-4-yl)piperazine

Conditions	Yield
With palladium diacetate; sodium t-butanolate; XPhos In 1,2-dimethoxyethane Buchwald-Hartwing reaction;	97%

4-bromopyridine hydrochloride (19524-06-2) + 3-pyridylboronic acid (1692-25-7) → 3,4'-bipyridyl (4394-11-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 20 - 100℃; for 18h; Sealed tube; Inert atmosphere;	97%

4-bromopyridine hydrochloride (19524-06-2) + trimethylsilylacetylene (1066-54-2) → 4-(trimethylsilanylethynyl)pyridine hydrochloride

Conditions	Yield
Stage #1: 4-bromopyridine hydrochloride With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In methanol at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: trimethylsilylacetylene In methanol at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In diethyl ether for 0.25h; Inert atmosphere; Schlenk technique;	97%

4-bromopyridine hydrochloride (19524-06-2) + trimethylsilylacetylene (1066-54-2) → 4-(2-(trimethylsilyl)ethynyl)pyridine (133810-35-2)

Conditions	Yield
With triethylamine; triphenylphosphine; palladium dichloride; zinc dibromide In tetrahydrofuran at 0 - 60℃; for 4.5h;	96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 72h; Sonogashira coupling;	89%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 65℃; for 3h;	89%

4-bromopyridine hydrochloride (19524-06-2) + 9,9-diethyl-2,7-diethynylfluorene (349087-20-3) → 9,9-diethyl-2,7-bis(4-pyridylethynyl)fluorene (349086-56-2)

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 70℃; for 24h;	96%

4-bromopyridine hydrochloride (19524-06-2) + 10-hexyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine (405198-29-0) → 10-hexyl-3-(pyridin-4-yl)-10H-phenothiazine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling;	96%

4-bromopyridine hydrochloride (19524-06-2) + 3-formyl-4-methoxyphenylboronic acid → 2-methoxy-5-(pyridin-4-yl)benzaldehyde (385802-40-4)

Conditions	Yield
Stage #1: 4-bromopyridine hydrochloride; 3-formyl-4-methoxyphenylboronic acid With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In ethanol; water at 80℃; for 2h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water; ethyl acetate at 40 - 50℃; for 0.5h; pH=2 - 3; Stage #3: With sodium hydroxide In water for 1h; pH=12 - 13; Product distribution / selectivity;	96%

trans-3-{[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzeneboronic acid + 4-bromopyridine hydrochloride (19524-06-2) → [4-(2-methoxy-5-pyridin-4-ylbenzylamino)cyclohexyl]methylcarbarnic acid t-butyl ester

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 105℃; for 4h; Product distribution / selectivity;	96%

4-bromopyridine hydrochloride (19524-06-2) + 1,3,5,7-tetrakis(4-ethinylphenyl)adamantane (144970-32-1) → 1,3,5,7-tetrakis(4-(pyridyl-4′-yl-ethynyl)phenyl)adamantine (1287733-25-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In toluene for 24h; Sonogashira coupling; Inert atmosphere; Reflux;	96%

cis-tert-butyl 2-(3-(2'-fluoro-5'-hydroxy-[1,1'-biphenyl]-4-yl)cyclobutoxy)acetate + 4-bromopyridine hydrochloride (19524-06-2) → cis-2-(3-(2'-fluoro-5'-(pyridin-4-yloxy)-[1,1'-biphenyl]-4-yl)cyclobutoxy)acetic acid

Conditions	Yield
Stage #1: cis-tert-butyl 2-(3-(2'-fluoro-5'-hydroxy-[1,1'-biphenyl]-4-yl)cyclobutoxy)acetate; 4-bromopyridine hydrochloride With potassium carbonate In N,N-dimethyl-formamide at 150℃; Stage #2: With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃;	96%

4-bromopyridine hydrochloride (19524-06-2) + S-Methylisothiourea sulfate (867-44-7) → 4-methylthiopyridine (22581-72-2)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 4h;	96%

4-bromopyridine hydrochloride (19524-06-2) + phenylboronic acid (98-80-6) → p-phenylpyridine (939-23-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0); Merrifield polymer In ethanol; water; toluene at 80℃; for 24h;	95%
With palladium on activated charcoal; tetrabutylammomium bromide; sodium carbonate In 1,2-dimethoxyethane at 80℃; for 9h; Suzuki-Miyaura coupling;	95%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; for 4h; Suzuki coupling;	93%

1,4-diethynylbenzene (935-14-8) + 4-bromopyridine hydrochloride (19524-06-2) → 1,4-bis(2-(4-pyridyl)ethynyl)benzene (158525-01-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 18h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	95%
With copper(l) iodide; diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 47℃; for 3.75h; Sonogashira-Hagihara coupling;	67%
With bis-triphenylphosphine-palladium(II) chloride; copper (I) iodide; diethylamine for 36h; Ambient temperature;	51%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; for 72h; Arylation;

phenylmagnesium chloride (100-59-4) + 4-bromopyridine hydrochloride (19524-06-2) → p-phenylpyridine (939-23-1)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 5h;	95%

4-ethynyl-N,N-diethylaniline (41876-70-4) + 4-bromopyridine hydrochloride (19524-06-2) → N,N-diethyl-N-[4-(2-(pyridin-4-yl)ethynyl)phenyl]amine (562813-17-6) + bis-(p-diethylaminophenyl)butadiyne

Conditions	Yield
With piperidine; copper(l) iodide; hydrogen; bis-triphenylphosphine-palladium(II) chloride In acetonitrile for 8h; Sonogashira coupling; Heating;	A 95% B 2.5%

4-(dimethylamino)benzene-boronic acid (28611-39-4) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(4-dimethylaminophenyl)pyridine (1137-80-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Suzuki coupling reaction; Heating;	95%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 18h; Suzuki coupling; Inert atmosphere;	79%
With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide Reflux;	30%

Downstream Products

• 143924-51-0 4-(2'-Piperidinyl)pyridine 
• 462-08-8 pyridin-3-ylamine 
• 504-24-5 4-aminopyridine 
• 60776-05-8 γ,γ'-dipyridylmethane 
• 4916-57-8 1,2-bis(4'-pyridyl)ethane 
• 39795-60-3 4-(4-bromophenyl)pyridine 
• 4423-10-3 4-(p-tolyl)pyridine 
• 145364-14-3 3-(4-fluorophenyl)-7-methyl-1-(4-pyridinyl)-1H-indole 
• 141306-67-4 2,5-dimethyl-3-(4-fluorophenyl)-1-(4-pyridinyl)-1H-indole 
• 14548-46-0 4-Benzoylpyridine 
• 5005-38-9 α-phenyl-4-pyridylacetonitrile 
• 112170-33-9 2-(4-(pyridin-4-yl)phenyl)acetonitrile 
• 112177-34-1 2-(4-pyridyl)phenylacetonitrile 
• 98420-86-1 4-Bromo-2-phenyl-2H-pyridine-1-carboxylic acid phenyl ester