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4-Nitrobenzyl bromide, also known as para-nitrobenzyl bromide, is a C-nitro compound that consists of nitrobenzene bearing a bromomethyl substituent at the para-position. It is a white to light yellow crystal powder and is widely used in various chemical reactions and pharmaceutical applications.

100-11-8 Suppliers

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  • 100-11-8 Structure
  • Basic information

    1. Product Name: 4-Nitrobenzyl bromide
    2. 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
    3. CAS NO:100-11-8
    4. Molecular Formula: C7H6BrNO2
    5. Molecular Weight: 216.03
    6. EINECS: 202-820-6
    7. 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
    8. Mol File: 100-11-8.mol
    9. Article Data: 130
  • Chemical Properties

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

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

100-11-8 Usage

Uses

Used in Pharmaceutical Industry:

4-Nitrobenzyl bromide is used as a synthetic intermediate for the preparation of di and tri-substituted azoles, which are important compounds in the development of various pharmaceuticals. These azoles have a wide range of applications, including antifungal, antibacterial, and antiviral properties.
Used in Medicinal Chemistry:
4-Nitrobenzyl bromide is used as a key building block in the synthesis of N6-Benzyladenosine-5'-uronamides, which are selective A3 adenosine agonists. These agonists have potential therapeutic applications in various diseases, such as neurodegenerative disorders, inflammation, and cancer.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-11-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 100-11:
(5*1)+(4*0)+(3*0)+(2*1)+(1*1)=8
8 % 10 = 8
So 100-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BrNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2

100-11-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-nitrobenzyl bromide

1.2 Other means of identification

Product number -
Other names 1-(Bromomethyl)-4-nitrobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-11-8 SDS

100-11-8Synthetic route

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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-methyl-4-nitrobenzene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

benzyl bromide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

2-(4-nitrobenzyloxy)tetrahydro-2H-pyran

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; for 1.25h;95%
4-nitrobenzyl trimethylsilyl ether
14856-73-6

4-nitrobenzyl trimethylsilyl ether

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; for 0.833333h;95%
4-nitro-1-[(ethoxymethoxy)methyl]benzene
1058649-42-5

4-nitro-1-[(ethoxymethoxy)methyl]benzene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

4-nitrobenzaldehdye

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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-methyl-4-nitrobenzene

A

1-dibromomethyl-4-nitro-benzene
619-75-0

1-dibromomethyl-4-nitro-benzene

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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-((methoxymethoxy)methyl)-4-nitrobenzene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

4-nitrobenzyl chloride

carbon tetrabromide
558-13-4

carbon tetrabromide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With triphenylphosphine In n-heptane; dichloromethane; ethyl acetate85%
With triphenylphosphine In n-heptane; dichloromethane; ethyl acetate85%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

ammonium acetate
631-61-8

ammonium acetate

A

4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

N-bromo-S-(p-nitrobenzyl)-S-phenylsulfoximide

A

S-(p-nitrobenzyl)-S-phenylsulfoximide
85313-79-7

S-(p-nitrobenzyl)-S-phenylsulfoximide

B

S-(α-bromo-p-nitrobenzyl)-S-phenylsulfoximide
85313-84-4

S-(α-bromo-p-nitrobenzyl)-S-phenylsulfoximide

C

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

1-Amino-3-p-nitrobenzylthiopropanephosphonic acid

A

(1RS,8RS)-diamino-4,5-dithiaoctane-1,8-diphosphonic acid
77275-39-9

(1RS,8RS)-diamino-4,5-dithiaoctane-1,8-diphosphonic acid

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With hydrogen bromide Heating; overnight;A 65%
B n/a
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

acetic anhydride
108-24-7

acetic anhydride

A

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

B

4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

C

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

D

4-nitrobenzylidene diacetate
2929-91-1

4-nitrobenzylidene diacetate

E

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

1-methyl-4-nitrobenzene

sodium acetate
127-09-3

sodium acetate

A

p-nitrobenzylidyne tribromide
14505-17-0

p-nitrobenzylidyne tribromide

B

1-dibromomethyl-4-nitro-benzene
619-75-0

1-dibromomethyl-4-nitro-benzene

C

4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

D

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

E

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
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

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2,2'-azobis(isobutyronitrile)
78-67-1

2,2'-azobis(isobutyronitrile)

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
at 80℃; Kinetics; Irradiation;
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

hexabromobenzene
87-82-1

hexabromobenzene

A

4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
at 200℃; Einleiten von Chlor;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

α,α,α-tribromoacetophenone
7402-45-1

α,α,α-tribromoacetophenone

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
at 160℃;
4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

1-methyl-4-nitrobenzene

A

2-bromo-4-nitrotoluene
7745-93-9

2-bromo-4-nitrotoluene

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
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

4-nitrobenzyl iodide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With tributyltin bromide In pyridine at 50℃; Thermodynamic data; Δ G;38 % Spectr.
silver-salt of/the/ <4-nitro-phenyl>-acetic acid

silver-salt of/the/ <4-nitro-phenyl>-acetic acid

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With tetrachloromethane; bromine
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Bromotrichloromethane
75-62-7

Bromotrichloromethane

<4-NO2C6H4CH2Co(dmgH)2Py>

<4-NO2C6H4CH2Co(dmgH)2Py>

A

1,1,1-trichloro-2-(4-nitrophenyl)-ethane
2201-11-8

1,1,1-trichloro-2-(4-nitrophenyl)-ethane

B

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
With 1H-imidazole In chloroform at 70℃; for 5h; Title compound not separated from byproducts;
4-nitrobenzyl nitrate
15539-77-2

4-nitrobenzyl nitrate

N-benzylpyridinium bromide
2589-31-3

N-benzylpyridinium bromide

acetone
67-64-1

acetone

A

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

B

1-benzyl-pyridinium nitrate

1-benzyl-pyridinium nitrate

Conditions
ConditionsYield
at 20℃; Kinetics; sowie bei 40grad;
at 20℃; sowie bei 40grad; Gleichgewicht der Reaktion;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

bromine
7726-95-6

bromine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
at 150℃; UV-Licht.Irradiation;
at 125 - 130℃;
tetrachloromethane
56-23-5

tetrachloromethane

2,2'-azobis(isobutyronitrile)
78-67-1

2,2'-azobis(isobutyronitrile)

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

bromine
7726-95-6

bromine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Conditions
ConditionsYield
at 80℃; Kinetics; Irradiation;
4'-(nitrobenzyl) 4-nitrobenzoate
3481-11-6

4'-(nitrobenzyl) 4-nitrobenzoate

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

A

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

picoline
108-89-4

picoline

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-methyl-N-(4-nitrobenzyl)pyridinium bromide
57042-61-2

4-methyl-N-(4-nitrobenzyl)pyridinium bromide

Conditions
ConditionsYield
In acetone; benzene at 20℃; for 24h;100%
In dichloromethane at 20℃; for 2h;46%
3-methyl-phenol
108-39-4

3-methyl-phenol

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(4-nitro-benzyl)-m-tolyl ether

(4-nitro-benzyl)-m-tolyl ether

Conditions
ConditionsYield
With sodium hydroxide In water for 0.00416667h; microwave irradiation;100%
With alkaline solution
p-cresol
106-44-5

p-cresol

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-methylphenyl 4-nitrobenzyl ether
67565-47-3

4-methylphenyl 4-nitrobenzyl ether

Conditions
ConditionsYield
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

potassium acetate

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

Conditions
ConditionsYield
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

potassium phtalimide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione
62133-07-7

2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;100%
In N,N-dimethyl-formamide99%
In N,N-dimethyl-formamide99%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
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

triphenylphosphine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(p-nitrobenzyl)triphenylphosphonium bromide
2767-70-6

(p-nitrobenzyl)triphenylphosphonium bromide

Conditions
ConditionsYield
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

1-bromomethyl-4-nitro-benzene

p-nitrobenzyl azide
17271-88-4

p-nitrobenzyl azide

Conditions
ConditionsYield
With sodium azide In dimethyl sulfoxide100%
With sodium azide In dimethyl sulfoxide at 20℃;100%
With sodium azide In water; acetone at 20℃; for 6h;99%
morpholine
110-91-8

morpholine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-(4-nitrobenzyl)morpholine
6425-46-3

4-(4-nitrobenzyl)morpholine

Conditions
ConditionsYield
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

pyridine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N-(4-nitrobenzyl)pyridinium bromide
4329-73-1

N-(4-nitrobenzyl)pyridinium bromide

Conditions
ConditionsYield
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

1,4-diaza-bicyclo[2.2.2]octane

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-aza-1-p-nitrobenzylazoniabicyclo<2.2.2>octane bromide
136497-64-8

4-aza-1-p-nitrobenzylazoniabicyclo<2.2.2>octane bromide

Conditions
ConditionsYield
In diethyl ether for 20h;100%
In diethyl ether97%
1,1,3,3-tetramethyl-2-thiourea
2782-91-4

1,1,3,3-tetramethyl-2-thiourea

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

1,1,3,3-tetramethyl-2-(4-nitrobenzyl)thiouronium bromide

1,1,3,3-tetramethyl-2-(4-nitrobenzyl)thiouronium bromide

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol for 0.5h; Heating;95%
Penicillin G potassium
113-98-4

Penicillin G potassium

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

p-nitrobenzyl benzylpenicillinate
27487-21-4

p-nitrobenzyl benzylpenicillinate

Conditions
ConditionsYield
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

1-bromomethyl-4-nitro-benzene

sodium 4-nitrobenzylsulfanesulfonate
94039-56-2

sodium 4-nitrobenzylsulfanesulfonate

Conditions
ConditionsYield
With sodium thiosulfate In water; toluene100%
With Sodium thiosulfate pentahydrate In methanol; water at 65℃; for 3 - 24h;
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-ethoxycarbonyl-N-(4-nitrobenzyl)pyridinium bromide

4-ethoxycarbonyl-N-(4-nitrobenzyl)pyridinium bromide

Conditions
ConditionsYield
In acetone; benzene at 20℃; for 24h;100%
N-tert-butyloxycarbonyl-S-trityl-L-cysteine
21947-98-8, 87494-13-1

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Boc-Cys(Trt)-PNB
566916-29-8

Boc-Cys(Trt)-PNB

Conditions
ConditionsYield
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

SEC-BUTYLAMINE

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N-(sec-butyl)-(4-nitrobenzyl)amine
838824-14-9

N-(sec-butyl)-(4-nitrobenzyl)amine

Conditions
ConditionsYield
In DMF (N,N-dimethyl-formamide) at 20℃;100%
bis-(3-hydroxypropyl)amine
14002-33-6

bis-(3-hydroxypropyl)amine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N-(p-nitrobenzyl)-dipropropanolamine
881169-78-4

N-(p-nitrobenzyl)-dipropropanolamine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 55 - 60℃; for 2h;100%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

1-methyl-3-(4-nitrobenzyl)-2,4-imidazolidinedione
873537-31-6

1-methyl-3-(4-nitrobenzyl)-2,4-imidazolidinedione

Conditions
ConditionsYield
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

decahydro-1H,6H-3a,5a,8a,10a-tetraazapyrene

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

perhydro-3a-(4-nitrobenzyl)-3a,5a,8a,10a-tetraazapyrenium bromide
1021925-74-5

perhydro-3a-(4-nitrobenzyl)-3a,5a,8a,10a-tetraazapyrenium bromide

Conditions
ConditionsYield
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

(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

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(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

(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

Conditions
ConditionsYield
With silver(l) oxide In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;100%
Cyclopentamine
1003-03-8

Cyclopentamine

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N,N-bis(4-nitrobenzyl)cyclopentanamine
1252601-24-3

N,N-bis(4-nitrobenzyl)cyclopentanamine

Conditions
ConditionsYield
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

C19H20N2

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

C26H26N3O2(1+)*I(1-)
1255528-55-2

C26H26N3O2(1+)*I(1-)

Conditions
ConditionsYield
With sodium iodide In acetone at 20℃; for 18h;100%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
884492-66-4

(S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

(S)-3-benzyl-1-(4-nitrobenzyl)-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one
1289116-75-1

(S)-3-benzyl-1-(4-nitrobenzyl)-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one

Conditions
ConditionsYield
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-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

C26H25NO11
1314917-90-2

C26H25NO11

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;100%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(3,5-dimethyl-1H-pyrazol-4-yl)acetic acid methyl ester
56699-23-1

(3,5-dimethyl-1H-pyrazol-4-yl)acetic acid methyl ester

[3,5-dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester
1322081-35-5

[3,5-dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester

Conditions
ConditionsYield
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-bromomethyl-4-nitro-benzene

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride
250285-32-6

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride

1,3-bis(2,6-diisopropylphenyl)-2-(4-nitrobenzylidene)-2,3-dihydro-1H-imidazole
1357448-32-8

1,3-bis(2,6-diisopropylphenyl)-2-(4-nitrobenzylidene)-2,3-dihydro-1H-imidazole

Conditions
ConditionsYield
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

ethyl p-methoxyphenylacetate

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

ethyl 2-(4-methoxyphenyl)-3-(4-nitrophenyl)propanoate
1428333-35-0

ethyl 2-(4-methoxyphenyl)-3-(4-nitrophenyl)propanoate

Conditions
ConditionsYield
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%

100-11-8Relevant articles and documents

Microreactor-mediated benzylic bromination in concentrated solar radiation

Kim, Young Joon,Jeong, Myung Jin,Kim, Ji Eun,In, Insik,Park, Chan Pil

, p. 1653 - 1656 (2015)

Sunlight-induced bromination of benzylic compounds was conducted in a capillary microreactor, resulting in mono-brominated compounds with yields of up to 94%. These reactions can be considered to be eco-friendly since they were carried out without an artificial light source or additional temperature control. In addition, up to 257.9mmol could be produced daily using cost-effective molecular bromine, which leads to potential improvement of industrial processes.

Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study

Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Nawale, Laxman,Arkile, Manisha,Sarkar, Dhiman,Shingate, Bapurao B.

, p. 413 - 421 (2017)

A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.

An efficient and fast method for the preparation of benzylic bromides

Lee, Jong Chan,Hwang, Eui Yong

, p. 2959 - 2963 (2004)

A mixture of triphenylphosphine and N-bromosuccinimide system is found to promote efficient conversion of benzylic alcohols into benzylic bromides under microwave irradiation conditions.

Difunctional chemosensor for Cu(ii) and Zn(ii) based on Schiff base modified anthryl derivative with aggregation-induced emission enhancement and piezochromic characteristics

Yang, Mingdi,Zhang, Yan,Zhu, Weiju,Wang, Huizhen,Huang, Jing,Cheng, Longhuai,Zhou, Hongping,Wu, Jieying,Tian, Yupeng

, p. 1994 - 2002 (2015)

Three new anthryl Schiff base derivatives containing a similar molecular structure were synthesized through a simple method and their fluorescent properties were investigated in detail. Among these, compound 1 displayed an aggregation-induced emission (AIE) feature, 2 exhibited an aggregation-induced emission enhancement (AIEE) property, while 3 showed aggregation-caused quenching (ACQ) behavior. Single-crystal structure and theoretical calculation analysis show that the larger conjugation and the existence of multiple intra- and intermolecular interactions restricts the intramolecular vibration and rotation, which benefit the emission in the condensed state, while the tight dimer structure and intramolecular torsional motion induce fluorescence quenching. Moreover, compound 2 can be utilized as fluorescence on-off type sensor for Cu2+ in methanol-H2O (4/1, v/v, pH 7.2) HEPES buffer solution, as well as fluorescence off-on type sensor for Zn2+ in pure methanol solution. The 2:1 ligand-to-metal coordination pattern of the 2-Cu2+ and 2-Zn2+ were calculated through a Job's plot, and were further confirmed by X-ray crystal structures of complexes 2-CuBr2 and 2-ZnCl2. In addition, 2 also exhibits a piezofluorochromic characteristic. This journal is

Preparation and properties of a novel solution of hydrogen bromide (HBr) in 1,4-dioxane: An alternative reagent to HBr gas without protic solvents

Nishio, Yuya,Mifune, Ryota,Sato, Taisuke,Ishikawa, Shin-ich,Matsubara, Hiroshi

, p. 1190 - 1193 (2017)

A solution of hydrogen bromide (HBr) in 1,4-dioxane was prepared and investigated for its ability to brominate alcohols, and hydrobrominate alkenes. This study revealed that the brominating ability of this HBr/1,4-dioxane solution is equal or superior to that of hydrobromic acid or HBr in acetic acid. The solution of HBr in 1,4-dioxane is robust, exhibiting no decomposition of the solvent, and retaining 97% of its original concentration, when kept at ?25 °C for 30 days. This solution is a liquid alternative to HBr gas without protic solvents.

Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles

Kamal, Ahmed,Hussaini, Syed Mohammed Ali,Faazil, Shaikh,Poornachandra,Narender Reddy,Kumar, C. Ganesh,Rajput, Vikrant Singh,Rani, Chitra,Sharma, Rashmi,Khan, Inshad Ali,Jagadeesh Babu

, p. 6842 - 6846 (2013)

A series of 5-nitrofuran-triazole conjugates were synthesized and evaluated for their antimicrobial activity against both Gram-positive and Gram-negative bacterial strains. All the compounds exhibited promising inhibition towards Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 8a, 8b, 8e, 8f, 8h are most active among the series exhibiting MIC value of 1.17 μg/ml against different bacterial strains. The bactericidal activity is found to be in accordance with the bacterial growth inhibition data. Compound 8e was found to be equipotent to the standard drug Ciprofloxacin displaying MBC value of 1.17 μg/ml against the bacterial strain Bacillus subtilis. The compounds have also demonstrated promising antibacterial activity against the resistant strain MRSA and were found to be effective inhibitors of biofilm formation. The compound 8b exhibited excellent anti-biofilm activity with IC50 value as low as 0.8 μg/ml. These conjugates were also screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Compound 8e showed promising antitubercular activity with MIC value of 0.25 μg/ml. Most of these compounds are less toxic to normal mammalian cells than the widely used antibacterial drug Ciprofloxacin.

Direct oxidative conversion of methylarenes into aromatic nitriles

Tsuchiya, Daisuke,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo

, p. 4194 - 4197 (2013)

A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.

Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions

Jereb, Marjan,Zupan, Marko,Stavber, Stojan

, p. 555 - 566 (2009)

The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.

Polymeric ionic liquids: A strategy for preparation of novel polymeric materials

Farzin, Manoochehr,Nosratzadegan, Keyvan,Azarnia, Jamshid,Ferdosi, Mohammad

, p. 1211 - 1218 (2015)

A novel polymeric ionic liquid (PIL), bearing high C-N and N-N content, potentially suitable for new safe energetic materials and catalyst supports was introduced. The PIL was prepared by way of radical co-polymerisation of 1-vinyl-3-p-nitrobenzylimidazol

Clay-Supported Cu(II) Catalyst: An Efficient, Heterogeneous, and Recyclable Catalyst for Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Alloxan-Derived Terminal Alkyne and Substituted Azides Using Click Chemistry

Dubey, Nitin,Sharma, Pratibha,Kumar, Ashok

, p. 2608 - 2626 (2015)

A novel series of alloxan-derived 1,4-disubstituted 1,2,3-triazoles was synthesized in excellent yields under catalytic conditions using a click reaction strategy through 1,3-dipolar cycloaddition. Their structures have been ascertained on the basis of spectroanalytical and elemental analysis data. Synthesis of hybrid compounds with varying substitutions in the triazole ring was achieved by reaction between alloxan-derived terminal alkyne and a pertinent azide derivative in the presence of clay-Cu(II) as the catalyst in methanolic medium. Also, comparative evaluation of various catalytic systems [viz., CuI, CuSO4, CuI-zeolite, K10Ti, and clay-Cu(II)] was investigated. Of these catalytic systems, clay-Cu(II) was observed to be the best. The catalyst was recyclable for several runs without showing significant loss in its activity. The good selectivity, cost-efficiency, short reaction time, milder reaction conditions, and simple workup procedure are the added salient features of this synthetic protocol.