100-11-8

Basic information

• Product Name: 4-Nitrobenzyl bromide
• Synonyms: 1-(bromomethyl)-4-nitro-benzen;4-(bromomethyl)nitrobenzene;alpha-Bromoparanitrotoluene;alpha-bromo-p-nitro-toluen;-Bromo-4-nitro-toluene;Nitrobenzyl bromide;p-(Bromomethyl)nitrobenzene;p-Nitobenzylbromide
• CAS NO: 100-11-8
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• EINECS: 202-820-6
• Product Categories: Aromatic Halides (substituted);Methyl Halides;Phenyls & Phenyl-Het;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Methyl Halides;Phenyls & Phenyl-Het;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Pyridines;4-Nitrobenzyl Bromide ada@tuskwei.com sky;18031153937@189.cn
• Mol File: 100-11-8.mol
• Article Data: 156

Chemical Properties

• Melting Point: 98 °C
• Boiling Point: 265.51°C (rough estimate)
• Flash Point: 137.8 °C
• Appearance: Light yellow to beige/Crystalline Powder
• Density: 1.6841 (rough estimate)
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: Store at RT.
• Water Solubility: It hydrolyzes in water. Soluble in alcohol and ether.
• Stability: Stable. Incomaptible with bases, amines, oxidizing agents, alcohols. May be moisture sensitive. Corrodes steel.
• BRN: 742796
• CAS DataBase Reference: 4-Nitrobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzyl bromide(100-11-8)
• EPA Substance Registry System: 4-Nitrobenzyl bromide(100-11-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: XS7967000
• F: 10-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 100-11-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

4-Nitrobenzyl bromide is used in the synthesis of di and tri-substituted azoles. It is also used in the preparation of N6-Benzyladenosine-5?-uronamides as selective A3 adenosine agonists.

Definition

ChEBI: A C-nitro compound that consists of nitrobenzene bearing a bromomethyl substituent at the para-position.

Purification Methods

Recrystallise the bromide four times from absolute EtOH, then twice from cyclohexane/hexane/*benzene (1:1:1), followed by sublimation at 0.1mm and final recrystallisation from the same solvent mixture. [Lichtin & Rao J Am Chem Soc 83 2417 1961.] It has also been crystallised from pet ether (b 80-100o, 10mL/g, charcoal). It slowly decomposes even when stored in a desiccator in the dark. IRRITANT. [Beilstein 5 IV 861.]

InChI:InChI=1/C7H6BrNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2

Synthetic route

4-nitrobenzyl chloride (619-73-8) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
Stage #1: 4-nitrobenzyl chloride With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: With tetrabutylammomium bromide at 20℃; Sealed tube; Inert atmosphere;	100%
With N-Bromosuccinimide; triphenylphosphine for 0.00555556h; microwave irradiation;	98%
Stage #1: 4-nitrobenzyl chloride With diisopropyl-carbodiimide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 100℃; for 0.0833333h; microwave irradiation; Stage #2: With Acetyl bromide In tetrahydrofuran at 150℃; for 0.0833333h; microwave irradiation; Further stages.;	98%

1-methyl-4-nitrobenzene (99-99-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reagent/catalyst; Reflux;	100%
With 2,2'-azobis(isobutyronitrile); hydrogen bromide; dihydrogen peroxide at 70 - 120℃; Reagent/catalyst; Temperature;	99.3%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3h; Reflux;	95%

benzyl bromide (100-39-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With sulfuric acid; silica gel; tetramethylammonium nitrate for 0.0333333h;	97%
With sulfuric acid; nitric acid at 0 - 5℃;

2-(4-nitrobenzyloxy)tetrahydro-2H-pyran (18483-99-3) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; for 1.25h;	95%

4-nitrobenzyl trimethylsilyl ether (14856-73-6) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; for 0.833333h;	95%

4-nitro-1-[(ethoxymethoxy)methyl]benzene (1058649-42-5) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With phosphotungstic acid; tetrabutylammomium bromide at 130 - 142℃; for 0.00833333h; Microwave irradiation; Ionic liquid; chemoselective reaction;	94%
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0333333h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	85%

4-nitrobenzaldehdye (555-16-8) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With polymethylhydrosiloxane; dimethylbromosulphonium bromide In chloroform at 20℃; for 8h;	92%
With Dichloromethylsilane; phosphorus tribromide; iron(III) chloride In acetonitrile for 6h; Heating;	92%
With isopinocampheyl-boron dibromide dimethylsulfide complex In hexane at 20℃; for 10h; Reduction; bromination;	65%

1-methyl-4-nitrobenzene (99-99-0) → 1-dibromomethyl-4-nitro-benzene (619-75-0) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 60℃; for 0.833333h; Time; Temperature; Flow reactor; Irradiation;	A n/a B 86%
With N-Bromosuccinimide for 0.15h; microwave irradiation;	A 20% B 70%
With hydrogen bromide; sodium bromide In chloroform; water at 5 - 15℃; Electrolysis;	A 50% B 50%
With N-Bromosuccinimide In Methyl formate Product distribution; with other ten solvents; ylied (max) and selektivity was determined;
With N-Bromosuccinimide at 36℃; for 16h; Irradiation; neat (no solvent);

1-((methoxymethoxy)methyl)-4-nitrobenzene (139884-17-6) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0333333h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	86%

4-nitrobenzyl chloride (619-73-8) + carbon tetrabromide (558-13-4) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With triphenylphosphine In n-heptane; dichloromethane; ethyl acetate	85%
With triphenylphosphine In n-heptane; dichloromethane; ethyl acetate	85%

4-nitrobenzyl chloride (619-73-8) + ammonium acetate (631-61-8) → 4-nitrobenzyl acetate (619-90-9) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In acetonitrile at 20℃; for 12h; Cooling with ice;	A 80% B 10%

N-bromo-S-(p-nitrobenzyl)-S-phenylsulfoximide (85313-81-1) → S-(p-nitrobenzyl)-S-phenylsulfoximide (85313-79-7) + S-(α-bromo-p-nitrobenzyl)-S-phenylsulfoximide (85313-84-4) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
In ethanol; chloroform for 5h; Product distribution; Ambient temperature; further solvents, reaction times;	A 72.9% B 16% C n/a

1-Amino-3-p-nitrobenzylthiopropanephosphonic acid (81979-40-0) → (1RS,8RS)-diamino-4,5-dithiaoctane-1,8-diphosphonic acid (77275-39-9) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With hydrogen bromide Heating; overnight;	A 65% B n/a

1-methyl-4-nitrobenzene (99-99-0) + acetic anhydride (108-24-7) → 4-nitrobenzyl chloride (619-73-8) + 4-nitrobenzyl acetate (619-90-9) + 4-nitrobenzaldehdye (555-16-8) + 4-nitrobenzylidene diacetate (2929-91-1) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With sulfuric acid; ozone; potassium bromide; manganese(II) In acetic acid at 10℃; for 2h; Rate constant; Product distribution; other catalysts (Co(II), Cr(III) or mixture), other times;;	A n/a B n/a C n/a D 42% E n/a

1-methyl-4-nitrobenzene (99-99-0) + sodium acetate (127-09-3) → p-nitrobenzylidyne tribromide (14505-17-0) + 1-dibromomethyl-4-nitro-benzene (619-75-0) + 4-nitrobenzyl acetate (619-90-9) + 1-bromomethyl-4-nitro-benzene (100-11-8) + 4-nitro-benzoic acid (62-23-7)

Conditions	Yield
With dipotassium peroxodisulfate; lithium bromide In acetic acid at 115℃; for 6h; Product distribution; Mechanism; benzylic oxidation, benzylic bromination-acetoxylation, other reactions conditions and other alkylbenzenes;	A n/a B 2% C 38% D 1% E n/a

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + 2,2'-azobis(isobutyronitrile) (78-67-1) + 1-methyl-4-nitrobenzene (99-99-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
at 80℃; Kinetics; Irradiation;

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + 1-methyl-4-nitrobenzene (99-99-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

1-methyl-4-nitrobenzene (99-99-0) + hexabromobenzene (87-82-1) → 4-nitrobenzyl chloride (100-14-1) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
at 200℃; Einleiten von Chlor;

1-methyl-4-nitrobenzene (99-99-0) + α,α,α-tribromoacetophenone (7402-45-1) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
at 160℃;

4-nitrobenzyl chloride (100-14-1) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Equilibrium constant; Δ G;
With ethanol; potassium iodide; potassium bromide
Multi-step reaction with 2 steps 1: 66 percent / HCl / 15 h / Heating 2: conc. HBr / Heating; overnight View Scheme

1-methyl-4-nitrobenzene (99-99-0) → 2-bromo-4-nitrotoluene (7745-93-9) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With ammonium cerium(IV) nitrate; sodium bromide In water; trifluoroacetic acid for 168h; Ambient temperature; Yield given. Yields of byproduct given;

4-nitrobenzyl iodide (3145-86-6) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With tributyltin bromide In pyridine at 50℃; Thermodynamic data; Δ G;	38 % Spectr.

silver-salt of/the/ <4-nitro-phenyl>-acetic acid → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With tetrachloromethane; bromine

4-nitrobenzyl chloride (619-73-8) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Bromotrichloromethane (75-62-7) + <4-NO2C6H4CH2Co(dmgH)2Py> → 1,1,1-trichloro-2-(4-nitrophenyl)-ethane (2201-11-8) + 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
With 1H-imidazole In chloroform at 70℃; for 5h; Title compound not separated from byproducts;

4-nitrobenzyl nitrate (15539-77-2) + N-benzylpyridinium bromide (2589-31-3) + acetone (67-64-1) → 1-bromomethyl-4-nitro-benzene (100-11-8) + 1-benzyl-pyridinium nitrate

Conditions	Yield
at 20℃; Kinetics; sowie bei 40grad;
at 20℃; sowie bei 40grad; Gleichgewicht der Reaktion;

1-methyl-4-nitrobenzene (99-99-0) + bromine (7726-95-6) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
at 150℃; UV-Licht.Irradiation;
at 125 - 130℃;

tetrachloromethane (56-23-5) + 2,2'-azobis(isobutyronitrile) (78-67-1) + 1-methyl-4-nitrobenzene (99-99-0) + bromine (7726-95-6) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Conditions	Yield
at 80℃; Kinetics; Irradiation;

4'-(nitrobenzyl) 4-nitrobenzoate (3481-11-6) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-bromomethyl-4-nitro-benzene (100-11-8) + 4-nitro-benzoic acid (62-23-7)

picoline (108-89-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-methyl-N-(4-nitrobenzyl)pyridinium bromide (57042-61-2)

Conditions	Yield
In acetone; benzene at 20℃; for 24h;	100%
In dichloromethane at 20℃; for 2h;	46%

3-methyl-phenol (108-39-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → (4-nitro-benzyl)-m-tolyl ether

Conditions	Yield
With sodium hydroxide In water for 0.00416667h; microwave irradiation;	100%
With alkaline solution

p-cresol (106-44-5) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-methylphenyl 4-nitrobenzyl ether (67565-47-3)

Conditions	Yield
With sodium hydroxide In water for 0.00277778h; microwave irradiation;	100%
With sodium hydroxide; Aliquat 360 In dichloromethane; water at 25℃; for 24h;	89%
With potassium carbonate; acetone
With alkaline solution

potassium acetate (127-08-2) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-nitrobenzyl acetate (619-90-9)

Conditions	Yield
5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis-(3,6,9-trioxadecyloxy)calix<6>arene In dichloromethane at 40℃; for 24h;	100%
5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis-(3,6,9-trioxadecyloxy)calix<6>arene In dichloromethane; water at 40℃; for 24h;	100%
"octopus-type" calixarene 1 In dichloromethane; water at 40℃; for 24h; Product distribution; other catalysts, content of water, other carboxylates;	100%
With ethanol
5,11,17,23,29,35-hexa-....-calix<6>arene In dichloromethane at 40℃; for 24h; influence of other catalysts;

potassium phtalimide (1074-82-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione (62133-07-7)

Conditions	Yield
In dichloromethane at 20℃; for 2h;	100%
In N,N-dimethyl-formamide	99%
In N,N-dimethyl-formamide	99%

1-bromomethyl-4-nitro-benzene (100-11-8) → 4-nitrobenzaldehdye (555-16-8)

Conditions	Yield
With dipotassium hydrogenphosphate; dimethyl selenoxide In acetonitrile for 5h; Heating;	100%
With 2-dimethylamino-N,N-dimethylaniline N-oxide In acetonitrile at 25℃; for 24h; Oxidation;	97%
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0333333h; Microwave irradiation;	97%

triphenylphosphine (603-35-0) + 1-bromomethyl-4-nitro-benzene (100-11-8) → (p-nitrobenzyl)triphenylphosphonium bromide (2767-70-6)

Conditions	Yield
With sodium hydride; m-Chlorobenzaldehyde In toluene for 12h; Reflux;	100%
In toluene Reflux;	99%
In toluene Heating;	98.6%

1-bromomethyl-4-nitro-benzene (100-11-8) → p-nitrobenzyl azide (17271-88-4)

Conditions	Yield
With sodium azide In dimethyl sulfoxide	100%
With sodium azide In dimethyl sulfoxide at 20℃;	100%
With sodium azide In water; acetone at 20℃; for 6h;	99%

morpholine (110-91-8) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-(4-nitrobenzyl)morpholine (6425-46-3)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h;	100%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 0.25h;	97%
Stage #1: 1-bromomethyl-4-nitro-benzene With potassium carbonate In dichloromethane for 0.333333h; Cooling with ice; Inert atmosphere; Stage #2: morpholine In 1,2-dichloro-ethane at 20℃; Cooling with ice; Inert atmosphere;	97.16%

pyridine (110-86-1) + 1-bromomethyl-4-nitro-benzene (100-11-8) → N-(4-nitrobenzyl)pyridinium bromide (4329-73-1)

Conditions	Yield
In acetone; benzene at 20℃; for 24h;	100%
at 20℃; for 12h;	88%
In nitrobenzene at 40℃; Rate constant; Mechanism;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-aza-1-p-nitrobenzylazoniabicyclo<2.2.2>octane bromide (136497-64-8)

Conditions	Yield
In diethyl ether for 20h;	100%
In diethyl ether	97%

1,1,3,3-tetramethyl-2-thiourea (2782-91-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 1,1,3,3-tetramethyl-2-(4-nitrobenzyl)thiouronium bromide

Conditions	Yield
at 20℃; for 12h;	100%
In ethanol for 0.5h; Heating;	95%

Penicillin G potassium (113-98-4) + 1-bromomethyl-4-nitro-benzene (100-11-8) → p-nitrobenzyl benzylpenicillinate (27487-21-4)

Conditions	Yield
18-crown-6 ether In acetonitrile for 24h; Ambient temperature;	100%
Stage #1: Penicillin G potassium; 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 42 - 45℃; for 2h; Large scale; Stage #2: With acetonyl hydroperoxide at 0 - 5℃; for 2h; Large scale;
Stage #1: Penicillin G potassium; 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 20 - 45℃; for 2h; Large scale; Stage #2: With sulfuric acid In dichloromethane; water at -5 - 0℃; pH=< 5; Large scale;

1-bromomethyl-4-nitro-benzene (100-11-8) → sodium 4-nitrobenzylsulfanesulfonate (94039-56-2)

Conditions	Yield
With sodium thiosulfate In water; toluene	100%
With Sodium thiosulfate pentahydrate In methanol; water at 65℃; for 3 - 24h;

isonicotinic acid ethylester (1570-45-2) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-ethoxycarbonyl-N-(4-nitrobenzyl)pyridinium bromide

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

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8, 87494-13-1) + 1-bromomethyl-4-nitro-benzene (100-11-8) → Boc-Cys(Trt)-PNB (566916-29-8)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonyl-S-trityl-L-cysteine With caesium carbonate In ethanol pH=10; Stage #2: 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 20℃; for 12h; Further stages.;	100%

SEC-BUTYLAMINE (33966-50-6) + 1-bromomethyl-4-nitro-benzene (100-11-8) → N-(sec-butyl)-(4-nitrobenzyl)amine (838824-14-9)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃;	100%

bis-(3-hydroxypropyl)amine (14002-33-6) + 1-bromomethyl-4-nitro-benzene (100-11-8) → N-(p-nitrobenzyl)-dipropropanolamine (881169-78-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 55 - 60℃; for 2h;	100%

1-bromomethyl-4-nitro-benzene (100-11-8) → 1-methyl-3-(4-nitrobenzyl)-2,4-imidazolidinedione (873537-31-6)

Conditions	Yield
Stage #1: 1-methyldiazolidine-2,4-dione With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	100%

decahydro-1H,6H-3a,5a,8a,10a-tetraazapyrene (72738-47-7) + 1-bromomethyl-4-nitro-benzene (100-11-8) → perhydro-3a-(4-nitrobenzyl)-3a,5a,8a,10a-tetraazapyrenium bromide (1021925-74-5)

Conditions	Yield
In acetonitrile for 48h;	100%

(1R,2R,4S)-1-((S)-1-(tert-butyldiphenylsilyloxy)ethyl)-5-hydroxy-4-((2-methoxyethoxy)methoxy)-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione (1192030-70-8) + 1-bromomethyl-4-nitro-benzene (100-11-8) → (1R,2R,4S)-1-((S)-1-(tert-butyldiphenylsilyloxy)ethyl)-4-((2-methoxyethoxy)methoxy)-2-methyl-5-(4-nitrobenzyloxy)-1,2,3,4-tetrahydroanthracene-9,10-dione (1192030-84-4)

Conditions	Yield
With silver(l) oxide In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;	100%

Cyclopentamine (1003-03-8) + 1-bromomethyl-4-nitro-benzene (100-11-8) → N,N-bis(4-nitrobenzyl)cyclopentanamine (1252601-24-3)

Conditions	Yield
Stage #1: Cyclopentamine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 20℃; for 2h;	100%
With potassium carbonate In N,N-dimethyl-formamide

C19H20N2 (946415-03-8) + 1-bromomethyl-4-nitro-benzene (100-11-8) → C26H26N3O2(1+)*I(1-) (1255528-55-2)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 18h;	100%

1-bromomethyl-4-nitro-benzene (100-11-8) + (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one (884492-66-4) → (S)-3-benzyl-1-(4-nitrobenzyl)-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one (1289116-75-1)

Conditions	Yield
Stage #1: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one With sodium hydride In N,N-dimethyl-formamide for 1.5h; Inert atmosphere; Stage #2: 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%

1-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one (1314917-55-9) + 1-bromomethyl-4-nitro-benzene (100-11-8) → C26H25NO11 (1314917-90-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	100%

1-bromomethyl-4-nitro-benzene (100-11-8) + (3,5-dimethyl-1H-pyrazol-4-yl)acetic acid methyl ester (56699-23-1) → [3,5-dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester (1322081-35-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 1h;	100%
With potassium carbonate In acetonitrile at 20℃; for 1h;	100%
With potassium carbonate In acetonitrile at 20℃; for 1h;
With potassium carbonate In acetonitrile at 20℃; for 1h;	7.5 g

1-bromomethyl-4-nitro-benzene (100-11-8) + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis(2,6-diisopropylphenyl)-2-(4-nitrobenzylidene)-2,3-dihydro-1H-imidazole (1357448-32-8)

Conditions	Yield
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran at 20℃; for 38h; Inert atmosphere;	100%
Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium tert-butylate; sodium hydride In tetrahydrofuran at 25℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran at 48℃; for 72h; Schlenk technique; Inert atmosphere;	61%

ethyl p-methoxyphenylacetate (14062-18-1) + 1-bromomethyl-4-nitro-benzene (100-11-8) → ethyl 2-(4-methoxyphenyl)-3-(4-nitrophenyl)propanoate (1428333-35-0)

Conditions	Yield
Stage #1: ethyl p-methoxyphenylacetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 1-bromomethyl-4-nitro-benzene In tetrahydrofuran at 25℃; for 12h;	100%

Upstream product

• 99-99-0 4-Nitrotoluene 

Downstream Products

• 94050-52-9 FLUCYCLOXURON 
• 2609-49-6 DIETHYL(4-NITROBENZYL)PHOSPHONATE 
• 51013-67-3 4-(Morpholinomethyl)aniline 

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