53207-00-4

Basic information

• Product Name: 2-Bromo-4,5-Dimethoxybenzyl Bromide
• Synonyms: 2-Bromo-4,5-Dimethoxybenzyl Bromide;1-(Bromomethyl)-2-bromo-4,5-dimethoxybenzene;PinaveriuM IMpurity I (1-BroMo-2-(broMoMethyl)-4,5-diMethoxybenzene);2-Bromo-4,5-dimethoxybenzyl bromide OR 2-Bromo Veratryl Bromide
• CAS NO: 53207-00-4
• Molecular Formula: C₉H₁₀Br₂O₂
• Molecular Weight: 309.9825
• Mol File: 53207-00-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 84.0-85.5 °C
• Boiling Point: 320.637 °C at 760 mmHg
• Flash Point: 129.614 °C
• Appearance: /
• Density: 1.693g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Bromo-4,5-Dimethoxybenzyl Bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4,5-Dimethoxybenzyl Bromide(53207-00-4)
• EPA Substance Registry System: 2-Bromo-4,5-Dimethoxybenzyl Bromide(53207-00-4)

Safety Data

• Hazardous Substances Data: 53207-00-4(Hazardous Substances Data)

Usage

General Description

2-Bromo-4,5-dimethoxybenzyl bromide is a chemical compound with the molecular formula C9H10Br2O2. It is a white to off-white crystalline solid that is primarily used as an intermediate in the synthesis of pharmaceuticals and organic compounds. 2-Bromo-4,5-dimethoxybenzyl bromide is a brominated derivative of 4,5-dimethoxybenzyl bromide, and its distinctive structure makes it useful for a variety of chemical reactions, including nucleophilic substitution and carbon-carbon coupling reactions. It is important to handle this compound with care, as it is toxic and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation.

InChI:InChI=1/C9H10Br2O2/c1-12-8-3-6(5-10)7(11)4-9(8)13-2/h3-4H,5H2,1-2H3

Synthetic route

(3,4-dimethoxyphenyl)methanol (93-03-8) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
With bromine In acetic acid at 20℃; for 1h;	100%
With bromine; acetic acid at 25℃;	95%
With bromine; acetic acid at 0 - 20℃;	95%

1,2-dimethoxy-4-methylbenzene (494-99-5) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
Stage #1: 1,2-dimethoxy-4-methylbenzene With sodium bromate; sodium bromide In tetrachloromethane Reflux; Stage #2: With sulfuric acid In tetrachloromethane; water for 2.5h; Stage #3: With 2,2'-azobis-(2,4-dimethylvaleronitrile); sulfuric acid In tetrachloromethane; water for 6h; Reflux;	85%

2-bromo-4,5-dimethoxybenzyl alcohol (54370-00-2) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
With pyridine; phosphorus tribromide In chloroform at 0 - 20℃;	81%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 20h;	39%
With phosphorus tribromide

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 2: NBS; Ph3P View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / dichloromethane / 0.5 h / 20 °C 2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 2.5 h / 0 °C 2: phosphorus tribromide / dichloromethane / 0.75 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: pyridine; phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / methanol 2: NaBH4 3: NBS; Ph3P View Scheme
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / 0.33 h / 0 °C 2.1: acetic acid / 0.5 h / 0 °C 2.2: 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 8 h / 20 °C 2: acetic acid; bromine / 0.83 h / 20 °C View Scheme

1-bromo-4,5-dimethoxy-2-methylbenzene (52806-46-9) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 6h; Wohl-Ziegler Bromination; Irradiation;

2-bromo-4,5-dimethoxybenzoic acid (6286-46-0) → 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 31 h / 0 - 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 h / 0 - 20 °C View Scheme

indole (120-72-9) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxybenzyl)-1H-indole (1314797-89-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	100%
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	75%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + N-methyl-N-(4-methoxyphenyl)amine (5961-59-1) → N-(2-bromo-4,5-dimethoxybenzyl)-4-methoxy-N-methylaniline (1394134-51-0)

Conditions	Yield
Stage #1: N-methyl-N-(4-methoxyphenyl)amine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	99%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + ethyl 2-cyanoacetate (105-56-6) → 2,2-bis(2-bromo-4,5-dimethoxybenzyl)-3-hydroxypropanenitrile

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate With potassium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In acetonitrile at 20℃; Stage #3: With sodium tetrahydroborate In ethanol at 0 - 20℃; for 12h;	97%

2-pyrrole aldehyde (1003-29-8) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxybenzyl)-1H-pyrrole-2-carbaldehyde

Conditions	Yield
Stage #1: 2-pyrrole aldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere;	97%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + triphenylphosphine (603-35-0) → (2-bromo-4,5-dimethoxybenzyl)triphenylphosphonium bromide

Conditions	Yield
In toluene for 0.5h; Reflux;	96%
In toluene	95%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2-amino-4-hydroxyphenylacetic acid methyl ester → methyl 2-amino-4-(2-bromo-4,5-dimethoxybenzyloxy)phenylacetate

Conditions	Yield
With palladium / hydroxyapatite In acetone at 80℃; for 4h;	95%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine (38284-47-8) → Pinaverium bromide (53251-94-8)

Conditions	Yield
In butanone Solvent; Reflux;	92.1%

1,2,3-Benzotriazole (95-14-7) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxybenzyl)-1H-benzotriazole

Conditions	Yield
In N,N-dimethyl-formamide microwave irradiation;	92%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + N-phenyl methyl carbamate (2603-10-3) → methyl 2-bromo-4,5-dimethoxybenzyl(phenyl)carbamate (1449388-47-9)

Conditions	Yield
Stage #1: N-phenyl methyl carbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	92%

1-indoline (496-15-1) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxybenzyl)-2,3-dihydroindole (636608-03-2)

Conditions	Yield
With tetraethylammonium iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 70℃; for 0.5h;	91%

N-phenyl benzoyl amide (93-98-1) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → N-(2-bromo-4,5-dimethoxybenzyl)-N-phenylbenzamide (1449388-49-1)

Conditions	Yield
Stage #1: N-phenyl benzoyl amide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	91%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2,4-dihydroxyphenylacetic acid methyl ester → methyl 2-hydroxy-4-(2-bromo-4,5-dimethoxybenzyloxy)phenylacetate

Conditions	Yield
With palladium on activated charcoal at 80℃; for 4h; Reagent/catalyst;	91%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	90%

N-(3-methoxyphenyl)benzamide (13031-49-7) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → N-(2-bromo-4,5-dimethoxybenzyl)-N-(3-methoxyphenyl)benzamide (1449388-54-8)

Conditions	Yield
Stage #1: N-(3-methoxyphenyl)benzamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	90%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 5-bromo-3-methoxysalicylaldehyde (5034-74-2) → -4-bromo-2-(2-bromo-4,5-dimethoxystyryl)-6-methoxyphenol

Conditions	Yield
Stage #1: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene With triphenylphosphine In toluene for 5h; Reflux; Stage #2: 5-bromo-3-methoxysalicylaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; toluene for 12h; Reagent/catalyst;	90%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + N-methyl-6,7-(methylenedioxy)-1-naphthylamine (219781-97-2) → N-(2-bromo-4,5-dimethoxybenzyl)-N-methylnaphtho[2,3-d][1,3]dioxol-5-amine (1449388-29-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	89%

2-pyrrolidinon (616-45-5) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxybenzyl)pyrrolidin-2-one

Conditions	Yield
With sodium hydride In tetrahydrofuran; hexane for 24.5h; Cooling;	89%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + salicylaldehyde (90-02-8) → 2-(2-bromo-4,5-dimethoxybenzyloxy)benzaldehyde (1015221-50-7)

Conditions	Yield
With potassium carbonate In acetone for 3h; Heating;	88%

N-(2-chlorophenyl)acetamide (533-17-5) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → N-(2-bromo-4,5-dimethoxybenzyl)-N-(2-chlorophenyl)acetamide

Conditions	Yield
Stage #1: N-(2-chlorophenyl)acetamide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;	88%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + sodium thiomethoxide (5188-07-8) → (2-bromo-4,5-dimethoxybenzyl)(methyl)sulfane

Conditions	Yield
In ethanol at 25℃; for 24h;	88%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride → C20H27BrN2O3 (960004-51-7)

Conditions	Yield
In N,N-dimethyl-formamide for 0.0180556h; microwave irradiation;	87%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + Acetanilid (103-84-4) → N-(2-bromo-4,5-dimethoxybenzyl)-N-phenylacetamide (1449388-48-0)

Conditions	Yield
Stage #1: Acetanilid With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	87%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + m-methoxyacetanilide (588-16-9) → N-(2-bromo-4,5-dimethoxybenzyl)-N-(3-methoxyphenyl)acetamide (1449388-53-7)

Conditions	Yield
Stage #1: m-methoxyacetanilide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	87%

α-naphthol (90-15-3) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-((2-bromo-4,5-dimethoxybenzyl)oxy)naphthalene (1532552-81-0)

Conditions	Yield
Stage #1: α-naphthol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	86%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol (96013-75-1) → 2-[4-(2-bromo-4,5-dimethoxybenzyloxy)phenyl]ethan-1-ol (1008355-80-3) + 2-[4-(2-bromo-4,5-dimethoxybenzyloxy)phenyl]-1-t-butyldimethylsilyloxyethane (1008355-79-0)

Conditions	Yield
Stage #1: 2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol With sodium hydride In N,N-dimethyl-formamide Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide at 60℃; for 4h;	A 84% B 14%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + N-methylaniline (100-61-8) → N-(2-bromo-4,5-dimethoxybenzyl)-N-methylaniline (1394134-47-4)

Conditions	Yield
Stage #1: N-methylaniline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	84%

indole-2-carboxylic acid methyl ester (1202-04-6) + 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) → 1-(2-bromo-4,5-dimethoxy-benzyl)-1H-indole-2-carboxylic acid methyl ester (238750-16-8)

Conditions	Yield
With potassium carbonate In acetonitrile Alkylation; Heating;	83%

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + indole-2,3-dione (91-56-5) → N-(6-bromo-3,4-dimethoxy)benzyl isatin (1394134-40-7)

Conditions	Yield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene In N,N-dimethyl-formamide at 0 - 23℃; Inert atmosphere;	82%

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 164228-22-2 3-(2-Bromo-3,4-dimethoxy-benzyloxy)-2-methyl-phenol 
• 1314797-89-1 1-(2-bromo-4,5-dimethoxybenzyl)-1H-indole 
• 109305-98-8 2-bromo-4,5-dimethoxybenzonitrile 
• 272766-46-8 1-allyl-2-bromo-4,5-dimethoxybenzene 
• 417702-93-3 5,6-dideoxy-1,2-O-isopropylidene-3-O-(2-bromo-4,5-dimethoxybenzyl)-α-D-xylo-hex-5-enofuranoside 
• 417703-07-2 5,6-dideoxy-1,2-O-isopropylidene-3-O-(2-bromo-4,5-dimethoxybenzyl)-α-D-ribo-hex-5-enofuranoside 
• 866890-76-8 (3aR,5S,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 866890-79-1 (3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole 

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