877-88-3

Basic information

• Product Name: 3,5-DIMETHOXYBENZYL BROMIDE
• Synonyms: 3,5-DIMETHOXYBENZYL BROMIDE;ALPHA-BROMO-3,5-DIMETHOXYTOLUENE;1-(Bromomethyl)-3,5-dimethoxybenzene;3,5-DIMETHOXYBENZYLBROMID;Benzene, 1-(bromomethyl)-3,5-dimethoxy-;3,5-Dimethoxybenzylamine Bromide;5-(BroMoMethyl)-1,3-diMethoxybenzene;α-BroMo-3,5-diMethoxytoluene
• CAS NO: 877-88-3
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.08644
• Product Categories: Miscellaneous;Building Blocks for Dendrimers;Functional Materials;Ethers;Organic Building Blocks;Oxygen Compounds;Aromatics;Miscellaneous Reagents;Building Blocks;C9;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 877-88-3.mol
• Article Data: 48

Chemical Properties

• Melting Point: 69-70 °C(lit.)
• Boiling Point: 292.1 °C at 760 mmHg
• Flash Point: 129.9 °C
• Appearance: White to brown/Crystalline Powder
• Density: 1.384 g/cm³
• Vapor Pressure: 0.00327mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3,5-DIMETHOXYBENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHOXYBENZYL BROMIDE(877-88-3)
• EPA Substance Registry System: 3,5-DIMETHOXYBENZYL BROMIDE(877-88-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 877-88-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 877-88-3 differently. You can refer to the following data:
1. 3,5-Dimethoxybenzyl bromide may be used in various organic?synthesis such as?3,4,3′,5′-tetramethoxystilbene; 3,5-dimethoxyphenylacetic acid; 1-(3,5-dimethoxyphenyl)-4-pentene etc., and 3,5-Dimethoxybenzyl bromide may be used as starting material in the multi-step synthesis of resveratroland 3,5-dimethoxyhomophthalic acid.
2. 3,5-Dimethoxybenzyl bromide may be used in the synthesis of:3,4,3′,5′-tetramethoxystilbene3,5-dimethoxyphenylacetic acid1-(3,5-dimethoxyphenyl)-4-penteneIt may be used as starting material in the multi-step synthesis of resveratrol and 3,5-dimethoxyhomophthalic acid.
3. 3,5-DIMETHOXYBENZYL BROMIDE is used in dimethoxybenzene alkyl addition.

Chemical Properties

3,5-DIMETHOXYBENZYL BROMIDE is White Solid

General Description

3,5-Dimethoxybenzyl bromide is an aromatic bromide.

InChI:InChI=1/C9H11BrO2/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-5H,6H2,1-2H3

Synthetic route

3,5-dimethoxybenzyl alcohol (705-76-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With phosphorus tribromide In benzene at 20℃;	100%
With phosphorus tribromide In 1,4-dioxane at 40℃; for 1h; Inert atmosphere;	99%
Stage #1: 3,5-dimethoxybenzyl alcohol With triphenylphosphine In dichloromethane at 20℃; for 0.166667h; Appel reaction; Stage #2: With carbon tetrabromide In dichloromethane at -78 - -50℃; Appel reaction;	98%

1,3-Dimethoxy-5-(4-methoxy-benzyloxymethyl)-benzene → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 1.5h;	48%

ethyl 3,5-dimethoxybenzoate (17275-82-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
(i) LiAlH4, (ii) PBr3; Multistep reaction;

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With phosphorus tribromide In dichloromethane for 1h; Ambient temperature; Yield given;
Multi-step reaction with 2 steps 1: 93 percent / NaBH4 / methanol / 0 °C 2: 89 percent / PBr3 / CH2Cl2 / 12 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 98 percent / NaBH4 / ethanol 2: 88 percent / PBr3, pyridine / diethyl ether / 1 h View Scheme

(3,5-dimethoxyphenyl)methyl methanesulfonate (192997-46-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With lithium bromide In tetrahydrofuran for 15h; Ambient temperature; Yield given;

methyl 3,5-dimethoxybenzoate (2150-37-0) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
(i) LiAlH4, (ii) PBr3; Multistep reaction;
Multi-step reaction with 2 steps 1: 92 percent / LiAlH4 / diethyl ether 2: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: HBr / benzene View Scheme

3,5-dimethoxybenzoic acid (1132-21-4) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LiAlH4 / tetrahydrofuran / 3 h / 20 °C 1.2: 97 percent / Na/K tartrate / tetrahydrofuran / 1 h / 20 °C 2.1: 86 percent / PBr3 / CH2Cl2 / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: SOCl2 2: 92 percent / LiAlH4 / diethyl ether 3: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: BH3 / tetrahydrofuran / 2 h / Heating 2: CBr4; tri-n-octylphosphine / diethyl ether / 2 h / 20 °C View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: NaOH 2: SOCl2 3: 92 percent / LiAlH4 / diethyl ether 4: 94 percent / PBr3 / CH2Cl2 View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.17 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.17 h / 20 °C 3.2: -78 - -50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 4.5 h / 60 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2.5 h / 70 °C 3: phosphorus tribromide / dichloromethane / 2 h / 20 °C View Scheme

3,5-dimethoxybenzoyl chloride (17213-57-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / LiAlH4 / diethyl ether 2: 94 percent / PBr3 / CH2Cl2 View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) + dimethyl sulfate (77-78-1) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Stage #1: 3,5-Dihydroxybenzoic acid; dimethyl sulfate With potassium carbonate In acetone for 4h; Reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Stage #3: With phosphorus tribromide In dichloromethane at 0 - 20℃;

1,3-dimethoxy-5-methylbenzene (4179-19-5) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 25℃; for 1h; Inert atmosphere;	1.05 g

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 3,5-dimethoxybenzyl bromide (877-88-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 48 h / 50 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C 3: phosphorus tribromide / tetrahydrofuran / -10 °C View Scheme

3,5-dimethoxybenzyl bromide (877-88-3) + triphenylphosphine (603-35-0) → (3,5-dimethoxybenzyl)triphenylphosphonium bromide (24131-30-4)

Conditions	Yield
In acetonitrile for 4.5h; Reflux;	100%
In benzene for 2h; reflux;	99%
In toluene for 24h; Inert atmosphere; Reflux;	99%

3,5-dimethoxybenzyl bromide (877-88-3) + triethyl phosphite (122-52-1) → diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1)

Conditions	Yield
Esterification; Arbusov reaction;	100%
at 100℃;	98%
In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Michaelis-Arbuzov reaction; Reflux; Inert atmosphere;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + sodium cyanide (143-33-9) → 3,5-dimethoxyphenylacetonitrile (13388-75-5)

Conditions	Yield
In dimethyl sulfoxide at 35 - 40℃; for 1.5h;	100%
In N,N-dimethyl-formamide for 1h;	83%

3,5-dimethoxybenzyl bromide (877-88-3) + vinyl magnesium bromide (1826-67-1) → Methoxyeugenol (64118-89-4)

Conditions	Yield
Stage #1: vinyl magnesium bromide With copper(l) iodide In tetrahydrofuran at -50℃; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran at -30 - 20℃;	100%

3,5-dimethoxybenzyl bromide (877-88-3) + methyl 2-cyanoacetate (105-34-0) → cyano-di(3,5-dimethoxy-benzyl)acetic acid methyl ester (1202779-02-9)

Conditions	Yield
Stage #1: methyl 2-cyanoacetate With sodium methylate In methanol at 20℃; Stage #2: 3,5-dimethoxybenzyl bromide In methanol Reflux;	100%

1-(3-methoxyphenethyl)-3,5-bis(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1006606-32-1) + 3,5-dimethoxybenzyl bromide (877-88-3) → Br(1-)*C37H42NO5(1+) (1187632-62-7)

Conditions	Yield
In acetone at 60℃; Inert atmosphere;	100%

3,5-dimethoxybenzyl bromide (877-88-3) + trimethylsilylacetylene (1066-54-2) → (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane (1394837-78-5)

Conditions	Yield
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.5h; Stage #2: With copper(I) bromide In tetrahydrofuran; diethyl ether at 20℃; for 0.25h; Stage #3: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; diethyl ether at 66℃;	100%

5-hydroxy-6-methoxy-2-methylisoquinolin-1(2H)-one (1043429-55-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 5-(3,5-dimethoxybenzyloxy)-6-methoxy-2-methylisoquinolin-1(2H)-one (1043429-21-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%

3,5-dimethoxybenzyl bromide (877-88-3) + dimethyl (prop-2-yn-1-yl)malonate (95124-07-5) → dimethyl 2-(3,5-dimethoxybenzyl)-2-(prop-2-yn-1-yl)malonate

Conditions	Yield
Stage #1: dimethyl (prop-2-yn-1-yl)malonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h; Inert atmosphere;	100%

5-(hydroxymethyl)benzene-1,3-diol (29654-55-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 3,5-bis(3,5-dimethoxybenzyloxy)benzyl alcohol (176650-92-3)

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetone for 36h; Inert atmosphere; Reflux;	99%

3,5-dihydroxybenzaldehyde (26153-38-8) + 3,5-dimethoxybenzyl bromide (877-88-3) → 3,5-bis-(3,5-dimethoxy-benzyloxy)-benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1.5h;	99%
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;	77%

triethyl phosphate (78-40-0) + 3,5-dimethoxybenzyl bromide (877-88-3) → diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1)

Conditions	Yield
at 160℃; for 4h;	99%
at 120℃; for 10h;	95%
at 160℃; for 4h;	95%

3,5-dimethoxybenzyl bromide (877-88-3) + quinindine (56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2) → C29H35N2O4(1+)*Br(1-)

Conditions	Yield
In toluene at 80℃; for 2h;	99%

3,5-dimethoxybenzyl bromide (877-88-3) + diothiothreitol (3483-12-3, 6892-68-8, 7634-42-6, 16096-97-2, 27565-41-9, 35454-97-8) → 1,4-bis-(3,5-dimethoxy-benzylsulfanyl)-butane-2,3-diol

Conditions	Yield
Stage #1: diothiothreitol With sodium hydroxide In ethanol Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; ethanol at 20℃; for 5h;	98%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 3,5-dimethoxybenzyl bromide (877-88-3) → N,N'-ethane-1,2-diyl N,N'-bis(3,5-dimethoxybenzyloxy) N,N,N',N'-tetramethylammonium dibromide

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	98%
In N,N-dimethyl-formamide at 70℃; for 15h; Inert atmosphere;	98%

3,5-dimethoxybenzyl bromide (877-88-3) + phenylacetylene (536-74-3) → 1-(3,5-dimethoxybenzyl)-4-phenyl-1H-1,2,3-triazole

Conditions	Yield
With sodium azide; CuNPs/C In water at 70℃; for 4h;	98%
With sodium azide; copper nanoparticles on activated carbon In water at 70℃; for 4h; regioselective reaction;	98%
With sodium azide at 50℃; for 48h;	89%
With sodium azide In water at 80℃; for 6h;	86%

2,2,4,4-tetramethylpentane-1,3-diol (33950-45-7) + 3,5-dimethoxybenzyl bromide (877-88-3) → 1-(3,5-dimethoxybenzyloxy)-2,2,4,4-tetramethylpentan-3-ol (1313999-66-4)

Conditions	Yield
Stage #1: 2,2,4,4-tetramethylpentane-1,3-diol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 0.75h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; for 5h;	97%

3,5-dimethoxybenzyl bromide (877-88-3) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → (S)-tert-butyl N-(diphenylmethylene)-(3,5-dimethoxyphenyl)alaninate

Conditions	Yield
With C37H37N2O(1+)*Br(1-); potassium hydroxide In chloroform; water; toluene at -40℃; for 72h; enantioselective reaction;	97%

3,5-dimethoxybenzyl bromide (877-88-3) + C11H13F3O3SZn → 1-(4-tert-butylbenzyl)-3,5-dimethoxybenzene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere; Schlenk technique;	97%

3,5-dimethoxybenzyl bromide (877-88-3) → (E)-3,3',5,5'-tetramethoxystilbene (80715-09-9, 125910-10-3, 125910-07-8)

Conditions	Yield
With Benzyl phenyl selenoxide; potassium hexamethylsilazane In toluene at 25℃; for 4h; Inert atmosphere;	96%
With lithium diisopropyl amide In tetrahydrofuran; hexane a.) -50 deg C, 30 min, b.) RT, 1.5 h;	69%
Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C View Scheme

3,5-dimethoxybenzyl bromide (877-88-3) + phenyltriisopropoxytitanium(IV) (16635-23-7) → (3,5-dimethoxyphenyl)phenylmethane (52692-17-8)

Conditions	Yield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 60℃; for 2h; Inert atmosphere;	96%

4,4'-bipyridine (553-26-4) + 3,5-dimethoxybenzyl bromide (877-88-3) → C28H30N2O4(2+)*2Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 55℃; for 96h;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + C54H68N2O11 → C72H88N2O15

Conditions	Yield
With potassium carbonate In chloroform for 24h; Reflux;	96%

3,5-dimethoxybenzyl bromide (877-88-3) + malononitrile (109-77-3) → C21H22N2O4

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h; Green chemistry;	96%

silver(I) trifluoromethoxide (1006904-72-8) + 3,5-dimethoxybenzyl bromide (877-88-3) → 1,3-dimethoxy-5-((trifluoromethoxy)methyl)benzene

Conditions	Yield
Stage #1: 3,5-dimethoxybenzyl bromide In acetonitrile at -30℃; for 0.0833333h; Glovebox; Stage #2: silver(I) trifluoromethoxide In acetonitrile at 20℃; for 12h; Glovebox;	95.8%

3,5-dimethoxybenzyl bromide (877-88-3) → 3,5,3',5'-tetramethoxy-bibenzyl (22976-41-6)

Conditions	Yield
With iodine; magnesium In diethyl ether for 2.5h; Heating;	95%
With (Cp2TiCl)2; water In tetrahydrofuran for 3h; Inert atmosphere;	90%
With sodium In diethyl ether for 20h; Heating;	68%

3,5-dimethoxybenzyl bromide (877-88-3) → 2-bromo-1-(bromomethyl)-3,5-dimethoxybenzene (34132-25-7)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h;	95%
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h;	95%
With N-Bromosuccinimide In dichloromethane at 20℃; for 1h;	87%
With N-Bromosuccinimide In dichloromethane at 20℃; for 4h;	86%
With N-Bromosuccinimide In dichloromethane at 0℃; for 1h; Inert atmosphere;

2-Methylcyclopentanone (1120-72-5) + 3,5-dimethoxybenzyl bromide (877-88-3) → 2-(3,5-dimethoxybenzyl)-2-methylcyclopentanone

Conditions	Yield
Stage #1: 2-Methylcyclopentanone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 6.5h; Stage #2: 3,5-dimethoxybenzyl bromide In tetrahydrofuran; hexane for 96h; Heating; Further stages.;	95%

3,5-dimethoxybenzyl bromide (877-88-3) + sodium benzenesulfonate (873-55-2) → 3,5-dimethoxybenzyl phenyl sulfone

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 2h;	95%

Upstream product

• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 192997-46-9 (3,5-dimethoxyphenyl)methyl methanesulfonate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 

Downstream Products

• 41497-39-6 1-(3,5-Dimethoxyphenyl)-2-methylsulfonyl-pentan-3-on 
• 41497-40-9 2-(3,5-Dimethoxybenzyl)-1-(3,5-dimethoxyphenyl)-2-methylsulfonyl-pentan-3-on 
• 41497-41-0 1-(3,5-Dimethoxyphenyl)-2-methylsulfonyl-hexan-3-on 
• 41497-42-1 1-(3,5-Dimethoxyphenyl)-2-methylsulfonyl-octan-3-on 
• 41497-43-2 1-(3,5-Dimethoxyphenyl)-2-methylsulfonyl-undecan-3-on 
• 41497-50-1 1,14-Bis-(3,5-dimethoxy-phenyl)-2,13-bis-methanesulfonyl-tetradecane-3,12-dione 
• 22976-41-6 3,5,3',5'-tetramethoxy-bibenzyl 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 73569-69-4 1-methylmethoxy-3,5-dimethoxybenzene 
• 141045-28-5 1,3-bis<1-(3,5-dimethoxybenzyl)benzimidazolo-2-yl>benzene 
• 141045-27-4 2,6-bis<1-(3,5-dimethoxybenzyl)benzimidazol-2-yl>pyridine 
• 125846-91-5 trans-2-<(3,5-dimethoxyphenyl)methyl>-3--cyclohexan-1-one 
• 74149-58-9 2-(3,5-dimethoxyphenylmethyl)-2-s-butyl-1,3-dithian 

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