100-39-0

Basic information

• Product Name: Benzyl bromide
• Synonyms: (bromomethyl)-benzen;1-Bromotoluene;ai3-15300;alpha-bromo-toluen;Bromophenylmethane;-Bromotoluene;Bromotoluene, alpha;bromotoluene,alpha
• CAS NO: 100-39-0
• Molecular Formula: C₇H₇Br
• Molecular Weight: 171.03
• EINECS: 202-847-3
• Product Categories: Pharmaceutical Intermediates;Aromatic Halides (substituted);Organics;Benzyl;Biochemistry;Reagents for Oligosaccharide Synthesis;Aryl;Building Blocks;C7;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 100-39-0.mol
• Article Data: 503

Chemical Properties

• Melting Point: -3 °C
• Boiling Point: 198-199 °C(lit.)
• Flash Point: 188 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.44 g/mL at 20 °C
• Vapor Density: 5.8 (vs air)
• Vapor Pressure: 0.506mmHg at 25°C
• Refractive Index: n20/D 1.575(lit.)
• Storage Temp.: Store at RT.
• Solubility: Miscible with benzene, carbon tetrachloride, ethanol and ether.
• Sensitive: Moisture Sensitive/Light Sensi
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,1128
• BRN: 385801
• CAS DataBase Reference: Benzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl bromide(100-39-0)
• EPA Substance Registry System: Benzyl bromide(100-39-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 39-2
• RIDADR: UN 1737 6.1/PG 2
• WGK Germany: 2
• RTECS: XS7965000
• F: 9-19-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 100-39-0(Hazardous Substances Data)

Usage

Chemical Properties

Benzyl bromide is an aromatic compound in which the benzene ring substituted with a bromomethyl group, and is produced by the reaction of toluene with bromine in the presence of an oxidizing agent. It is a combustible, colorless to yellow liquid with a pleasant odor. insoluble in water and easily soluble in most organic solvents. Has a strong tearing effect and unpleasant pungent odor, minimum irritant concentration of 4 mg/m3, intolerable concentration of 50-60 mg/m3.

Uses

Making foaming and frothing agents, organic synthesis.

Uses

Benzyl bromide is widely useful in organic synthesis as a benzyl protecting group for alcohols and carboxylic acids. It is used in the preparation of foaming and frothing agents, quaternary ammonium compounds, peniclins, photographic chemicals, synthetic resins, dyes and plasticizers and esters. It is also involved in the synthesis of (E)-(2-Iodovinyl)benzene by reacting it with diiodomethane.

Application

Benzyl bromide is an aromatic halide that is mainly used as a protecting agent for protecting hydroxy group of alcohols via O-benzylation reaction. It has been used as an initiator in the synthesis of poly(styrene-b-methylmethacrylate) copolymers by atom transfer radical polymerization. It can undergo Menschutkin reaction with 1, 2-dimethylimidazole to form 3-benzyl-1, 2-dimethylimidazolium bromide.

Preparation

Benzyl bromide is synthesized by toluene bromination. Toluene heated to 50°C, add bromine reaction, the reaction temperature of 75-80°C, reaction 6h, fractional distillation at atmospheric pressure to remove the fraction before 140°C, and then distillation under reduced pressure, collect 112-114°C(2.0kPa) fraction, to get benzyl bromide.

Definition

ChEBI: Benzyl bromide is a member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine. It has a role as a lachrymator.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 3412, 1973 DOI: 10.1021/ja00791a072Tetrahedron Letters, 29, p. 707, 1988 DOI: 10.1016/S0040-4039(00)80190-2The Journal of Organic Chemistry, 51, p. 929, 1986 DOI: 10.1021/jo00356a032

General Description

Benzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.

Air & Water Reactions

Sensitive to exposure to light and moisture. Slightly soluble in water.

Reactivity Profile

Benzyl bromide reacts with water, alcohols, common metals (except nickel and lead), bases, amines and oxidizing agents. . Benzyl bromide stored over activated 4A molecular sieve burst a bottle due to condensation-polymerization reaction with generation of HBr gas, [Chem. Eng. News, 1979, 57(12), 74].

Hazard

Highly toxic. Corrosive to skin and tissue. A lachrymator.

Health Hazard

Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach.

Chemical Reactivity

Reactivity with Water Reacts slowly generating hydrogen bromide (hydrobromic acid); Reactivity with Common Materials: Decomposes rapidly in the presence of all common metals except nickel and lead, liberating heat and hydrogen bromide; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Rinse with sodium bicarbonate or lime solution; Polymerization: Polymerizes with evolution of heat and hydrogen bromide when in presence with all common metals except nickel and lead; Inhibitor of Polymerization: None.

Safety Profile

Intensely irritating and corrosiveto skin, eyes, and mucous membranes. Large doses causecentral nervous system depression. Mutation datareported. Reaction with molecular sieve produces toxichydrogen bromide gas.

Potential Exposure

It is used as a chemical intermediate; in organic syntheses; as a foaming and frothing agent.

Shipping

UN1737 Benzyl Bromide, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material.

Purification Methods

Wash benzyl chloride with conc H2SO4 (CARE), water, 10% Na2CO3 or NaHCO3 solution, and again with water. Dry it with CaCl2, Na2CO3 or MgSO4 and fractionally distil it in the dark, under reduced pressure. It has also been thoroughly degassed at 10-6 mm and redistilled in the dark. This gives material with max (MeCN): 226nm ( 8200) [Mohammed & Kosower J Am Chem Soc 93 2709 1971]. [Beilstein 5 IV 829.] Handle in a fume cupboard, extremely LACHRYMATORY.

Incompatibilities

May form explosive mixture with air. Contact with water forms hydrogen bromide and benzyl alcohol. Incompatible with strong oxidizers, bases, magnesium. Attacks metals, except nickel and lead, in the presence of moisture.

Waste Disposal

Pour into vermiculite, sodium bicarbonate, or a sand-soda ash mixture and transfer to paper boxes, then to an open incinerator. Alternatively, mix Benzyl Bromide 417 with flammable solvent and spray into incinerator equipped with after burner and alkali scrubber.

InChI:InChI=1/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

Synthetic route

toluene (108-88-3) → benzyl bromide (100-39-0)

Conditions	Yield
With bromine In tetrachloromethane for 1.5h; Ambient temperature;	100%
With manganese(IV) oxide; bromine In dichloromethane at 0℃; for 1h; Product distribution; Further Variations:; Solvents; Temperatures; reaction time;	100%
With bromine; sodium t-butanolate In cyclohexane Heating;	100%

benzyl alcohol (100-51-6) → benzyl bromide (100-39-0)

Conditions	Yield
With 1,1,1,2,2,2-hexamethyldisilane; pyridinium hydrobromide perbromide In chloroform at 25℃; for 0.5h;	100%
With phosphorus tribromide In benzene at 20℃;	100%
Stage #1: benzyl alcohol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane for 0.0833333h; Stage #2: With potassium bromide In dichloromethane; N,N-dimethyl-formamide for 0.5h;	99%

cis-{(PhCH2)2Co(III)(2,2'-bipyridine)2}ClO4 → benzyl bromide (100-39-0)

Conditions	Yield
With bromine In acetonitrile one-electron oxidn. of cis-Co complex by Br2 at 298 K; monitored by (1)H-NMR;	100%

C13H25N3PS(1+) (103514-63-2) → benzyl bromide (100-39-0)

Conditions	Yield
With bromide In N,N-dimethyl-formamide	98%

benzaldehyde (100-52-7) → benzyl bromide (100-39-0)

Conditions	Yield
With Dichloromethylsilane; phosphorus tribromide; iron(III) chloride In acetonitrile for 4h; Heating;	97%
With polymethylhydrosiloxane; dimethylbromosulphonium bromide In chloroform at 20℃; for 5h;	96%
With chloro-trimethyl-silane; 1,1,3,3-Tetramethyldisiloxane; lithium bromide In acetonitrile at 80℃; for 30h;	94%

iodomethylbenzene (620-05-3) → benzyl bromide (100-39-0)

Conditions	Yield
With bismuth(III) bromide In 1,2-dichloro-ethane at 25℃; for 2.25h;	97%
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Equilibrium constant; other temperatures, Δ G;	26 % Spectr.

2-phenyl-1,3-dioxolane (936-51-6) → benzyl bromide (100-39-0)

Conditions	Yield
With triethylsilane; Acetyl bromide; tin(II) bromide In dichloromethane for 3h; Ambient temperature;	96%

tetrahydro-2-(benzyloxy)-2H-pyran (1927-62-4) → benzyl bromide (100-39-0)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	95%
With boron trifluoride diethyl etherate; lithium bromide In acetonitrile for 24h; Ambient temperature;	89%
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; bromine at 80℃; for 2h;	89%

benzyl fluoride (350-50-5) → benzyl bromide (100-39-0)

Conditions	Yield
With hydrogen bromide at 130℃; for 1h;	95%
Multi-step reaction with 2 steps 1: 12 N HCl / 105 °C 2: 93 percent / 47percent aq. HBr / 1 h / 130 °C View Scheme

benzyloxy-trimethylsilane (14642-79-6) → benzyl bromide (100-39-0)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃;	95%
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; bromine at 80℃; for 1h;	87%
With Tri-n-butylfluorphosphoniumbromid In benzene at 20℃; for 24h;	81%

benzyl mesylate (55791-06-5) → benzyl bromide (100-39-0)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 50℃; for 1h; Inert atmosphere; Green chemistry;	95%
With lithium bromide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	89%
With calcium bromide In dimethyl sulfoxide for 3h; Ambient temperature;	79%

3,5-dimethoxy-4-methylphenylmethyl alcohol (35052-27-8) → 5-(bromomethyl)-1,3-dimethoxy-2-methylbenzene (35047-51-9) + benzyl bromide (100-39-0)

Conditions	Yield
With phosphorus tribromide	A n/a B 95%

(benzyloxy)benzene (946-80-5) → benzyl bromide (100-39-0) + phenol (108-95-2)

Conditions	Yield
With water; boron tribromide In chloroform-d1 at 20℃; Solvent;	A 95% B 88%

benzyl chloride (100-44-7) → benzyl bromide (100-39-0)

Conditions	Yield
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h;	94%
With hydrogen bromide at 130℃; for 1h;	93%
With 1-bromo-butane; Mg6Al2(OH)16Cl2*4H2O In N,N-dimethyl-formamide at 69.9℃; for 20h;	90%

phenylmethanethiol (100-53-8) → benzyl bromide (100-39-0)

Conditions	Yield
With Silphos; bromine In acetonitrile for 0.166667h; Heating;	92%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 5h;	72%

(diethoxymethyl)benzene (774-48-1) → benzyl bromide (100-39-0)

Conditions	Yield
With triethylsilane; Acetyl bromide; tin(II) bromide In dichloromethane for 3h; Ambient temperature;	91%

(benzyloxy)(tert-butyl)dimethylsilane (53172-91-1) → benzyl bromide (100-39-0)

Conditions	Yield
With boron tribromide In dichloromethane for 0.166667h; Ambient temperature;	90%

toluene (108-88-3) → benzyl bromide (100-39-0) + benzyl chloride (100-44-7)

Conditions	Yield
With tetrabutylammomium bromide; hydrogen bromide; potassium bromide In water at 20℃; Irradiation; Green chemistry;	A 90% B n/a
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; cobalt(II) diacetate tetrahydrate In dichloromethane at 25℃; for 20h;

phenylacetic acid (103-82-2) → benzyl bromide (100-39-0)

Conditions	Yield
With tetra-N-butylammonium tribromide; dibromoisocyanuric acid In dichloromethane at 20℃; for 2h; UV-irradiation;	90%

benzaldehyde dimethyl acetal (1125-88-8) → benzyl bromide (100-39-0)

Conditions	Yield
With triethylsilane; Acetyl bromide; tin(II) bromide In dichloromethane for 3h; Ambient temperature;	89%

ammonium acetate (631-61-8) + benzyl alcohol (100-51-6) → Benzyl acetate (140-11-4) + benzyl bromide (100-39-0)

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In acetonitrile at 20℃; for 2h; Cooling with ice;	A 87% B 3%
With bromine; triphenylphosphine In acetonitrile at 20℃; for 0.7h;	A 40% B 53%

toluene (108-88-3) → benzylidene dibromide (618-31-5) + benzyl bromide (100-39-0)

Conditions	Yield
With bromine In dichloromethane for 2h; Ambient temperature; Irradiation;	A 11% B 86%
With hydrogen bromide; dihydrogen peroxide In water at 20℃; for 10h; Irradiation;	A 4% B 81%
With hydrogen bromide; dihydrogen peroxide In water at 27℃; for 24h; Irradiation;	A 7% B 81%

4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-ethyl-piperidine-1-carboxylic acid tert-butyl ester → benzyl bromide (100-39-0)

Conditions	Yield
Stage #1: 4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-ethyl-piperidine-1-carboxylic acid tert-butyl ester With hydrogenchloride In ethyl acetate for 4.08333h; Stage #2: With water; sodium hydrogencarbonate In ethyl acetate	84%

dibenzylmercury(II) (780-24-5) → benzyl bromide (100-39-0) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; benzene Irradiation (UV/VIS); nitrogen atmosphere; mercurial and NBS (2.5 equiv)/CH2Cl2 in deoxygenated solvent irradiated (250-W sunlamp, 40 °C, 6h);; filtration; solvent removed (vacuum); PhCH2CH2Ph and PhCH2Br analysed by (1)H NMR, GLC and GCMS;;	A 84% B 4%
With N-Bromosuccinimide In dichloromethane; benzene Irradiation (UV/VIS); nitrogen atmosphere; mercurial and NBS (2.5 equiv)/CH2Cl2 in deoxygenated solvent irradiated (250-W sunlamp, 40 °C, 4h) in the presence of 20 mol% (t-Bu)2NO (radical);; filtration; solvent removed (vacuum); PhCH2CH2Ph and PhCH2Br analysed by (1)H NMR, GLC and GCMS;;	A 46% B 2%

acetic acid (64-19-7) + toluene (108-88-3) → benzyl bromide (100-39-0) + acetophenone (98-86-2) + benzoic acid (65-85-0)

Conditions	Yield
With hydrogen bromide; oxygen; bromide; cobalt(II) acetate; manganese(II) acetate at 75℃; Kinetics; Product distribution; atmospheric pressure;	A n/a B n/a C 83%

{(η5-C5Me5)Os(CO)(PMe2Ph)CH2Ph} (116670-02-1) + bromine (7726-95-6) → {(η5-C5Me5)Os(CO)(PMe2Ph)Br} (107087-80-9) + benzyl bromide (100-39-0)

Conditions	Yield
In dichloromethane-d2 (N2); electrophilic cleavage reaction by addn. of bromine to a soln. of Cp*Os(CO)(PMe2Ph)CH2Ph in CD2Cl2;; not isolated, detected by NMR;;	A 77% B 83%

[(ethoxymethoxy)methyl]benzene (54673-14-2) → benzyl bromide (100-39-0)

Conditions	Yield
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.075h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	83%

diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate (1539-57-7) → benzyl bromide (100-39-0)

Conditions	Yield
With dipotassium peroxodisulfate; tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate; sodium bromide In water; acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;	83%

pyridine (110-86-1) + benzyl bromide (100-39-0) → N-benzylpyridinium bromide (2589-31-3)

Conditions	Yield
	100%
In acetone; benzene at 20℃; for 24h;	100%
In dichloromethane at 20℃; for 12h;	100%

1-methyl-1H-imidazole (616-47-7) + benzyl bromide (100-39-0) → 3-benzyl-1-methylimidazolium bromide (65039-11-4)

Conditions	Yield
at 100℃; for 2h;	100%
In 1,4-dioxane at 100℃; for 12h;	98%
In ethanol; acetonitrile at 80℃; for 12h;	98%

isoquinoline (119-65-3) + benzyl bromide (100-39-0) → 2-benzylisoquinolin-2-ium bromide (23277-04-5)

Conditions	Yield
In methanol for 336000h; Heating;	100%
In acetone; benzene at 20℃; for 24h;	100%
In methanol for 336h; Heating;	100%

nicotinamide (98-92-0) + benzyl bromide (100-39-0) → 3-(aminocarbonyl)-1-benzylpyridinium bromide (13076-43-2)

Conditions	Yield
In acetone for 12h; Reflux;	100%
In acetonitrile	93%
In acetonitrile at 140℃; for 1.5h; Sealed tube; Microwave irradiation;	89%

2-Hydroxybenzophenone (117-99-7) + benzyl bromide (100-39-0) → o-(benzyloxy)benzophenone (93254-81-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Heating;	100%
With caesium carbonate In acetonitrile at 50℃;	98%
With caesium carbonate In acetonitrile at 50℃; Inert atmosphere;	98%

4-bromo-phenol (106-41-2) + benzyl bromide (100-39-0) → p-benzyloxyphenylbromide (6793-92-6)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h;	100%
Stage #1: 4-bromo-phenol With sodium hydride In N,N-dimethyl-formamide at 5℃; for 0.333333h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	99%
With potassium phosphate; tetrabutylammomium bromide In water at 20℃; for 2h; Sealed tube; Green chemistry;	99%

triallyl phosphite (102-84-1) + benzyl bromide (100-39-0) → diallyl benzylphosphonate (74038-34-9)

Conditions	Yield
In toluene at 95℃; for 4h;	100%

3-nitro-o-cresol (5460-31-1) + benzyl bromide (100-39-0) → 2-benzyloxy-6-nitrotoluene (20876-37-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	87%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;	48.6%

3-methyl-2-nitrophenol (4920-77-8) + benzyl bromide (100-39-0) → 1-(benzyloxy)-3-methyl-2-nitrobenzene (61535-21-5)

Conditions	Yield
With potassium carbonate In acetonitrile Heating / reflux;	100%
With potassium carbonate In acetonitrile at 40 - 75℃; for 7.75h;	99%
With potassium carbonate; acetone

methyl 4-hydroxycinnamate (3943-97-3) + benzyl bromide (100-39-0) → (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate (84184-51-0)

Conditions	Yield
With potassium carbonate In acetone at 23℃; for 4h; Reflux; Inert atmosphere;	100%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 14h; Etherification;	87%
With sodium hydroxide In ethanol	82%

benzyl bromide (100-39-0) + 4-hydroxy-benzaldehyde (123-08-0) → p-benzyloxybenzaldehyde (4397-53-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.16667h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	100%
With potassium carbonate In acetonitrile for 3h;	100%

benzyl bromide (100-39-0) + triphenylphosphine (603-35-0) → benzyltriphenylphosphonium bromide (1449-46-3)

Conditions	Yield
In xylene for 0.00833333h; Heating; microwave irradiation;	100%
In toluene for 12h; Reflux;	100%
at 100℃; for 0.0333333h; Irradiation;	99%

benzyl bromide (100-39-0) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 2,4-dibenzyloxybenzaldehyde (13246-46-3)

Conditions	Yield
With potassium carbonate In acetone Heating;	100%
With caesium carbonate In acetone at 20℃;	100%
With potassium carbonate In acetonitrile at 20℃; Reflux;	98%

benzyl bromide (100-39-0) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 4-benzoxy-salicylaldehyde (52085-14-0)

Conditions	Yield
Stage #1: 2,4-Dihydroxybenzaldehyde With sodium hydrogencarbonate In acetonitrile at 20℃; for 0.75h; Inert atmosphere; Stage #2: benzyl bromide In acetonitrile Inert atmosphere; Reflux;	100%
With potassium hydrogencarbonate In acetonitrile for 15h; Reflux;	85%
With sodium hydrogencarbonate In acetonitrile for 15h; Reflux;	85%

benzyl bromide (100-39-0) → 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
With TiCl2*2THF In tetrahydrofuran for 24h; Heating;	100%
With Wilkinson's catalyst; dimethyl zinc(II) In tetrahydrofuran; hexane at 20℃; for 1h;	100%
With hafnium(II) chloride In tetrahydrofuran for 12h; Heating;	99%

benzyl bromide (100-39-0) → iodomethylbenzene (620-05-3)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 24h;	100%
With sodium iodide In acetone at 20℃; for 24h; Inert atmosphere; Darkness;	100%
With hydrogen iodide; cetyltributylphosphonium bromide at 60℃; for 0.0833333h;	99%

1,3-Benzothiazole (95-16-9) + benzyl bromide (100-39-0) → 3-benzylbenzothiazolium bromide (4614-22-6)

Conditions	Yield
In neat (no solvent) at 75℃;	100%
Inert atmosphere; Neat (no solvent);	99%
for 5h; Reflux;	93%

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) + benzyl bromide (100-39-0) → 4-(benzyloxy)-3-bromo-5-methoxybenzaldehyde (2556-04-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;	97%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	94%

benzyl bromide (100-39-0) + 2,2'-iminobis[ethanol] (111-42-2) → N-benzyl-diethanolamine (101-32-6)

Conditions	Yield
With potassium carbonate In acetone Reflux;	100%
With potassium carbonate In acetone for 8h; Heating;	97%
With potassium carbonate In acetone for 8h; Heating / reflux;	97%

benzyl bromide (100-39-0) + isopropyl alcohol (67-63-0) → benzyl isopropyl ether (937-54-2)

Conditions	Yield
Stage #1: isopropyl alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 5h; Inert atmosphere;	100%
With iron(II) sulfate at 75℃; for 12h;	92%
With silver(II) oxide Heating;	90%
With potassium hydroxide; tetrafluoroboric acid; mercury(II) oxide In dichloromethane 1.) room temp., 1 h;	60%
(i) Ag2O, (ii) Py, PhCOCl; Multistep reaction;

benzyl bromide (100-39-0) + malononitrile (109-77-3) → 2,2-dibenzylmalononitrile (3779-31-5)

Conditions	Yield
With potassium carbonate; tetrabutylammomium bromide for 96h; Ambient temperature;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h;	91%
With 1-butyl-3-methylimidazolium hydroxide at 100℃; under 51.7148 Torr; for 0.0833333h; microwave irradiation;	82%

benzyl bromide (100-39-0) + 1-butyn-4-ol (927-74-2) → ((but-3-yn-1-yloxy)methyl)benzene (22273-77-4)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In trichlorophosphate Heating;	100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 23℃; for 5.5h;	100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; mineral oil at 0 - 23℃; for 18h; Inert atmosphere; Sealed tube;	100%

benzyl bromide (100-39-0) → benzyl nitrate (15285-42-4)

Conditions	Yield
With silver nitrate In acetonitrile at 70℃; for 5h; Darkness;	100%
With silver nitrate In acetonitrile at 20℃; Nitration;	97%
With silver nitrate In acetonitrile at 20℃; for 24h;	82%

1H-imidazole (288-32-4) + benzyl bromide (100-39-0) → 1-benzylimidazole (4238-71-5)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;	100%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 25℃; for 3h;	97%
With caesium carbonate at 100℃; for 0.416667h; Microwave irradiation;	90%

α-picoline (109-06-8) + benzyl bromide (100-39-0) → 1-Benzyl-6-methylpyridinium bromide (2654-66-2)

Conditions	Yield
	100%
In acetone Reflux;	100%
In toluene for 14h; Inert atmosphere; Reflux;	72%

picoline (108-89-4) + benzyl bromide (100-39-0) → 1-benzyl-1-bromo-4-methylpyridinium bromide (57042-58-7)

Conditions	Yield
	100%
In acetonitrile at 45℃; for 3h;	99%
In acetonitrile at 100℃; for 12h;	98.71%

3-ethylpyridine (536-78-7) + benzyl bromide (100-39-0) → 1-benzyl-3-ethylpyridinium bromide (55077-15-1)

Conditions	Yield
	100%
at 0 - 20℃;	99.6%
at 0 - 20℃;	99.6%

caprolactam (105-60-2) + benzyl bromide (100-39-0) → 1-Benzyl-hexahydro-azepin-2-on (33241-96-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 4h; 0 deg C to 25 deg C;	100%
Stage #1: caprolactam With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	98%
With sodium hydride In tetrahydrofuran; paraffin 1.) 0 deg C to room temperature, 2 h, 2.) room temperature, 2 h;	96%

Upstream product

• 10038-98-9 Germanium chloride 
• 100-38-9 2-Diethylaminoethanethiol 
• 100388-99-6 4-(cyclohexyloxy)benzene-1-sulfonyl chloride 
• 1003888-36-5 benzyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate 
• 1003887-72-6 (1S)-2-METHYL-1-[4-(TRIFLUOROMETHYL)PHENYL]PROPYLAMINE 
• 1003887-67-9 (1S)-1-[4-(TRIFLUOROMETHYL)PHENYL]PROPYLAMINE 
• 1003887-64-6 (S,E)-1-phenyl-N-(4-(trifluoromethyl)benzylidene)-2-(trimethylsilyloxy)ethanamine 
• 1003887-62-4 (S)-8-fluorochroman-4-amine 
• 1003886-05-2 (4S,4'S)-2,2'-(Cyclopentane-1,1-diyl)-bis(4-benzyl-4,5-dihydrooxazole) 
• 100388-37-2 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-1-yl)urea 
• 10038-82-1 POTASSIUM TELLURATE 
• 100388-17-8 (2-BROMO-4,5-DIETHOXYPHENYL)ACETIC ACID 
• 100388-15-6 pentyl 5-bromo-2-hydroxy-benzoate 
• 10038-81-0 methyl 2-[(phenylsulfonyl)amino]benzoate 

Downstream Products

• 24131-31-5 3,5-Dibenzyloxybenzyl alcohol 
• 70627-52-0 N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline 
• 14618-80-5 (R)-(-)-Benzyl glycidyl ether 
• 24131-32-6 3,5-BIS(BENZYLOXY)BENZYL BROMIDE 
• 7779-78-4 4-METHYL-1-PHENYL-2-PENTANOL 
• 93093-02-9 O-(2-MethoxyEthoxy)BenzeneSulfonamide 
• 63935-38-6 CYCLOPROTHRIN 
• 73404-00-9 alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol 
• 23680-31-1 N-BOC-O-Benzyl-L-serine 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 607-81-8 Diethyl benzylmalonate 
• 3163-76-6 1,3,5-Benzenetricarboxaldehyde 
• 38194-50-2 Sulindac 
• 1953-54-4 5-Hydroxyindole 
• 68475-42-3 Anagrelide 
• 63610-08-2 Indobufen 
• 122-18-9 Benzyldimethylhexadecylammonium chloride 
• 55052-27-2 6-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE 
• 125942-79-2 BOC-3-IODO-D-ALANINE BENZYL ESTER 
• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 50541-93-0 4-Amino-1-benzylpiperidine 
• 17480-69-2 (S)-(-)-N-Benzyl-1-phenylethylamine 
• 146631-00-7 4-Benzyloxybenzeneboronic acid 
• 2426-87-1 4-BENZYLOXY-3-METHOXYBENZALDEHYDE 
• 139481-59-7 Candesartan 
• 16042-26-5 1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID 
• 5142-23-4 3-METHYLADENINE 
• 77175-51-0 CROCONAZOLE 
• 61439-59-6 2-(4-BENZYLOXYPHENYL)ETHANOL 
• 2815-34-1 trans-2,5-Dimethylpiperazine 
• 101827-46-7 Butenafine hydrochloride 
• 23031-32-5 TERBUTALINE SULFATE 
• 94593-91-6 Cinosulfuron 
• 135632-53-0 4-(Boc-Aminomethyl)piperidine 
• 6373-46-2 4-BENZYLOXYANILINE 
• 28994-41-4 2-Hydroxydiphenylmethane 
• 141774-61-0 2-(Boc-aminomethyl)-piperidine 
• 4410-12-2 1-BENZYL-1,4-DIAZEPANE 
• 7281-04-1 Benzyldodecyldimethylammonium bromide 
• 2380-84-9 7-Hydroxyindole 

Recommend Products

• 146796-40-9  19-benzyl-2,3-dimethoxy-10-oxo-strychnidinium; bromide 
• 357-57-3  brucine 
• 100-74-3  N-ethylmorpholine; 
• 6096-36-2  1-benzyl-2-methyl-4,5-dihydro-1H-imidazole 
• 534-26-9  lysidine 
• 4356-66-5  3-Benzyl-4-methylthiazolium bromide 
• 693-95-8  4-Methylthiazole 
• 4362-23-6  2-methylene-1,3-dioxolane 
• 4057-44-7  1-benzyloxy-pyridinium; bromide 
• 694-59-7  pyridine N-oxide 
• 51290-78-9  benzyl 4-pyridyl sulfide 
• 19829-29-9  4-pyridinethione 
• 62214-78-2  1-benzyl-3-hydroxypyridin-1-ium bromide 
• 109-00-2  3-HYDROXYPYRIDINE