73870-24-3

Basic information

• Product Name: 4-(Bromomethyl)pyridine hydrobromide
• Synonyms: 4-(BROMOMETHYL)PYRIDINE, HYDROBROMIDE;4-(BROMOMETHYL)PYRIDINE HYDROBROMIDE, 97;Fs000895;4-(BroMoMethyl)pyridine hydrobroMide 97%;4-(BROMOMETHYL)PYRIDINE HBR
• CAS NO: 73870-24-3
• Molecular Formula: BrH*C₆H₆BrN
• Molecular Weight: 252.93
• EINECS: 1592732-453-0
• Product Categories: C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Heterocycle-Pyridine series
• Mol File: 73870-24-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 189-192 °C(lit.)
• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: Soluble in water
• CAS DataBase Reference: 4-(Bromomethyl)pyridine hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Bromomethyl)pyridine hydrobromide(73870-24-3)
• EPA Substance Registry System: 4-(Bromomethyl)pyridine hydrobromide(73870-24-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 73870-24-3(Hazardous Substances Data)

Usage

Uses

4-(Bromomethyl)pyridine hydrobromide may be used in the preparation of: 3-(4-pyridylmethyl)-2′,3′-di-O-oleyl-5′-O-(4,4′-dimethoxytriphenylmethyl)uridine3-(4-pyridylmethyl)-3′-O-oleyl-5′-O-(4,4-dimethoxytriphenylmethyl)-thymidine1,4-bis(N-hexyl-4-pyridinium)butadiene diperchlorateIt may also be used in the preparation of the following benzoxazine derivatives:2-morpholin-4-yl-7-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one8-methyl-2-morpholin-4-yl-7-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one2-morpholin-4-yl-8-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one

General Description

4-(Bromomethyl)pyridine hydrobromide is a substituted pyridine. It reacts with 1,2-ethanediamine and 1,3-propanediamine to form the corresponding diamines.

InChI:InChI=1/C6H6BrN.BrH/c7-5-6-1-3-8-4-2-6;/h1-4H,5H2;1H

Synthetic route

4-(hydroxymethyl)pyridine hydrobromide (65737-59-9) → 4-bromomethyl pyridine hydrobromide (73870-24-3)

Conditions	Yield
With phosphorus tribromide In chloroform at 45℃;	93%
With phosphorus tribromide In chloroform for 3h; Heating;	91%
With phosphorus tribromide In chloroform for 4.5h; Reflux;	78%

pyridine-4-methanol (586-95-8) → 4-bromomethyl pyridine hydrobromide (73870-24-3)

Conditions	Yield
With phosphorus pentabromide In chloroform	58.1%
With hydrogen bromide In water at 150℃;	50%
With hydrogen bromide In water for 8h; Product distribution / selectivity; Reflux;
Multi-step reaction with 2 steps 1: hydrogen bromide / water / 4 h / Reflux 2: phosphorus tribromide / chloroform / 4.5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: hydrogen bromide / 4 h / 100 °C 2: phosphorus tribromide / chloroform / 45 °C View Scheme

pyridine-4-carbaldehyde (872-85-5) → 4-bromomethyl pyridine hydrobromide (73870-24-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 2 h / 0 - 25 °C 2: hydrogen bromide / 4 h / 100 °C 3: phosphorus tribromide / chloroform / 45 °C View Scheme

4-bromomethyl pyridine hydrobromide (73870-24-3) → 4-(2-azidomethyl)pyridine (864528-34-7)

Conditions	Yield
Stage #1: 4-bromomethyl pyridine hydrobromide With potassium carbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 20℃; for 3h;	100%
Stage #1: 4-bromomethyl pyridine hydrobromide With potassium carbonate at 20℃; for 0.25h; Inert atmosphere; Stage #2: With sodium azide at 20℃; for 72h; Inert atmosphere;	49%
Stage #1: 4-bromomethyl pyridine hydrobromide With potassium carbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 20℃; for 4h;

4-bromomethyl pyridine hydrobromide (73870-24-3) + 2-fiuoro-5-nitrophenol (22510-08-3) → C12H9FN2O3

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	100%

4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 4-pyridylmethyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	99%

N-{3-[(4-fluorobenzyl)oxy]phenyl}piperidine-4-carboxamide hydrochloride (1124219-46-0) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → N-{3-[(4-fluorobenzyl)oxy]phenyl}-1-(pyridin-4-ylmethyl)piperidine-4-carboxamide (1472647-67-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	97%

tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate + 4-bromomethyl pyridine hydrobromide (73870-24-3) → rac-tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(pyridin-4-yl)propanoate

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h;	96.53%
Stage #1: tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 4-bromomethyl pyridine hydrobromide In tetrahydrofuran at -78 - 20℃; for 2h;
Stage #1: tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 4-bromomethyl pyridine hydrobromide In tetrahydrofuran at -78 - 20℃; for 2h;
Stage #1: tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 4-bromomethyl pyridine hydrobromide at -78 - 20℃; for 2h;

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → (S)-3-(pyridin-4-yl-methoxy)-1,2-O-isopropyliden-propane-1,2-diol

Conditions	Yield
Stage #1: (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: 4-bromomethyl pyridine hydrobromide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	95%

4-bromomethyl pyridine hydrobromide (73870-24-3) + 3,6-bis(5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)thiophen-2-yl)-9H-carbazole → 9-(pyridin-4-ylmethyl)-3,6-bis(5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)thiophen-2-yl)-9H-carbazole

Conditions	Yield
Stage #1: 3,6-bis(5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)thiophen-2-yl)-9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Schlenk technique; Stage #2: 4-bromomethyl pyridine hydrobromide With potassium carbonate In tetrahydrofuran; diethyl ether; water; mineral oil at 20℃; Inert atmosphere; Schlenk technique;	91%

C62H108N2O17 (1148015-61-5) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → DOPU (1148015-62-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 59.84℃; for 2h;	90%

7-Hydroxy-8-methyl-2-(morpholin-4-yl)-4H-1,3-benzoxazin-4-one (952106-37-5) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 8-methyl-2-morpholin-4-yl-7-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one (1257411-71-4)

Conditions	Yield
Stage #1: 7-Hydroxy-8-methyl-2-(morpholin-4-yl)-4H-1,3-benzoxazin-4-one With caesium carbonate In acetonitrile for 2h; Reflux; Stage #2: 4-bromomethyl pyridine hydrobromide In acetonitrile for 0.5h; Reflux;	90%

4-bromomethyl pyridine hydrobromide (73870-24-3) + (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-96-8) → 7-benzyl 8-(tert-butyl) (5S,8S)-2,4-dioxo-3-(pyridin-4-ylmethyl)-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	90%

diphenyl diselenide (1666-13-3) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 4-(phenylselenomethyl)pyridine (1268397-89-2)

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In ethanol at 20℃; Inert atmosphere;	89%

(9H-carbazol-3-yl)(piperidin-1-yl)methanone (1358040-39-7) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → piperidin-1-yl(9-(pyridin-4-ylmethyl)-9H-carbazol-3-yl)methanone (1358039-43-6)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 48h;	89%

4-bromomethyl pyridine hydrobromide (73870-24-3) + 5'-O-tritylthymidine (7791-71-1) → 3'-O-(4-picolyl)thymidine

Conditions	Yield
Stage #1: 5'-O-tritylthymidine With sodium hydride In tetrahydrofuran for 0.333333h; Inert atmosphere; Sonication; Stage #2: 4-bromomethyl pyridine hydrobromide In tetrahydrofuran; water for 0.75h; Inert atmosphere; Sonication; Stage #3: With hydrogenchloride In ethanol; water at 80℃; for 1h;	88%

Octanal (124-13-0) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → (R)-2-(pyridin-4-ylmethyl)octanal (1245640-45-2)

Conditions	Yield
With 2,6-dimethylpyridine; (2R,5S)-5-benzyl-2,3-dimethylimidazolidin-4-one; tris-(2-phenylpyridinato-C(2),N)iridinium(III) In dimethyl sulfoxide at 20℃; for 3h; Inert atmosphere; Fluorescent light; optical yield given as %ee; enantioselective reaction;	87%

carbon disulfide (75-15-0) + 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-2-phenylethanone (39604-80-3) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 3-phenyl-7-(phenylmethoxy)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one (746640-15-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	86%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran	86%

carbon disulfide (75-15-0) + 4-bromomethyl pyridine hydrobromide (73870-24-3) + 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methylphenyl)ethanone (474391-07-6) → 7-methoxy-3-(4-methylphenyl)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	86%

C15H22O4 + 4-bromomethyl pyridine hydrobromide (73870-24-3) → C21H27NO4

Conditions	Yield
Stage #1: C15H22O4 With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromomethyl pyridine hydrobromide In tetrahydrofuran at 0 - 23℃; Inert atmosphere;	86%

carbon disulfide (75-15-0) + 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-2-(4-methoxyphenyl)ethanone (95307-71-4) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 3-(4-methoxyphenyl)-7-(phenylmethoxy)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one (746640-16-4)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	84%

carbon disulfide (75-15-0) + 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (39604-64-3) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 7-methoxy-3-(4-methoxyphenyl)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	82%

carbon disulfide (75-15-0) + 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone (18439-96-8) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → 7-methoxy-3-phenyl-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one (746640-10-8)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃;	81%

Betulinic acid (472-15-1) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → pyridin-4-ylmethyl 3-hydroxylup-20(29)-en-28-oate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	80%

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 586-95-8 pyridine-4-methanol 
• 65737-59-9 4-(hydroxymethyl)pyridine hydrobromide 

Downstream Products

• 746640-15-3 3-phenyl-7-(phenylmethoxy)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one 
• 746640-10-8 7-methoxy-3-phenyl-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one 
• 746640-16-4 3-(4-methoxyphenyl)-7-(phenylmethoxy)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one 
• 54751-01-8 4-(bromomethyl)pyridine 
• 1160786-60-6 N-(1-(pyridin-4-ylmethyl)piperidin-4-yl)-2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide 
• 1166185-25-6 methyl 2-{2-[4-(pyridin-4-ylmethoxy)phenyl]ethyl}-5-phenylpentanoate 
• 1241801-28-4 4-((tris-2,2,2-(3-phenylpyrazol-1-yl)ethoxy)methyl)pyridine 
• 1359980-19-0 3-(6-chloro-2-methyl-1-pyridin-4-ylmethyl-1H-indol-3-ylsulfanyl)-benzoic acid 
• 102547-80-8 4-((allyloxy)methyl)pyridine 
• 1416265-04-7 4-((1-(1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)ethoxy)methyl)pyridine 
• 1415672-29-5 C₂₅H₁₈N₄O₂ 
• 1361208-88-9 C₃₆H₃₅N₃O₈ 

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