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100-11-8 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.]

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

100-11-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0181)  4-Nitrobenzyl Bromide  >98.0%(GC)(T)

  • 100-11-8

  • 25g

  • 410.00CNY

  • Detail
  • TCI America

  • (N0181)  4-Nitrobenzyl Bromide  >98.0%(GC)(T)

  • 100-11-8

  • 100g

  • 1,190.00CNY

  • Detail
  • TCI America

  • (N0181)  4-Nitrobenzyl Bromide  >98.0%(GC)(T)

  • 100-11-8

  • 500g

  • 3,790.00CNY

  • Detail
  • Alfa Aesar

  • (A15236)  4-Nitrobenzyl bromide, 97+%   

  • 100-11-8

  • 25g

  • 414.0CNY

  • Detail
  • Alfa Aesar

  • (A15236)  4-Nitrobenzyl bromide, 97+%   

  • 100-11-8

  • 100g

  • 1341.0CNY

  • Detail
  • Alfa Aesar

  • (A15236)  4-Nitrobenzyl bromide, 97+%   

  • 100-11-8

  • 500g

  • 5641.0CNY

  • Detail
  • Aldrich

  • (N13054)  4-Nitrobenzylbromide  99%

  • 100-11-8

  • N13054-25G

  • 441.09CNY

  • Detail
  • Aldrich

  • (N13054)  4-Nitrobenzylbromide  99%

  • 100-11-8

  • N13054-100G

  • 1,670.76CNY

  • Detail

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.

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.

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.

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.

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

Carbon-Halogen Bonding Studies. Halogen Redistribution Reactions between Alkyl or Acetyl Halides and Tri-n-butyltin Halides

Friedrich, Edwin C.,Abma, Charles B.

, p. 1367 - 1371 (1980)

The equilibrium positions have been determined for the halogen redistribution reactions of tri-n-butyltin halides with a variety of structurally different types of alkyl halides and with acetyl halides.These have been related through the reaction ΔGo values to carbon-halogen bond dissociation energy differences.It is suggested that the trends observed in the latter may provide evidence for the existence of a small steric bond weakening effect in the order C-I > C-Br > C-Cl bonds on going from methyl to primary, secondary, and tertiary alkyl halides.On the other hand, with the 2,3-? bond containing allyl, benzyl, and propargyl halides , α-haloacetones, and haloacetonitriles, there may be some type of electronic carbon-halogen bond strengthening effect which lies in order C-I > C-Br > C-Cl.Finally, for the acetyl halides, the data are in agreement with increases in bond strengths resulting from ? contributions being in the order C-Cl > C-Br > C-I.

Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions

Firouzabadi, Habib,Iranpoor, Nasser,Ebrahimzadeh, Farzaneh

, p. 1771 - 1775 (2006)

N-Bromo and N-iodosaccharins in the presence of triphenylphosphine convert alcohols into the corresponding bromides and iodides in good to excellent yields at room temperature under neutral conditions.

N-bromosuccinimide: A facile reagent for the oxidation of benzylic alcohols to aldehydes

Adimurthy, Subbarayappa,Patoliya, Paresh U.

, p. 1571 - 1577 (2007)

The oxidation of benzylic alcohols to aldehydes using N-bromosuccinimide (NBS) under ambient conditions without use of a transition-metal catalyst has been described. Copyright Taylor & Francis Group, LLC.

HOMOLYTIC DISPLACEMENT AT CARBON VI. SYNTHESIS OF TRICHLOROETHYLARENES FROM BENZYLCOBALOXIMES

Bougeard, Peter,Gupta, B. Dass,Johnson, Michael D.

, p. 211 - 219 (1981)

Benzylbis(dimethylglyoximato)pyridinecobalt(III) reacts with bromotrichloromethane at from 50 to 90 deg C in chloroform to give good yields of trichloroethylbenzene, which are higher when imidazole is present in the reaction mixture.Methyl- and polymethyl-substituted benzylbis(dimethylglyximato)pyridinecobalt(III) complexes give higher yields of the corresponding trichloroethylarenes (85-90percent), whereas 4-chlorobenzylbis(dimethylglyoximato)pyridinecobalt(III) only gives the 4-nitro-trichloroethylarene when imidazole is present during the reaciton.Similar reactions were observed with benzylcobaloximes and trichloromethanesulphonyl chloride both thermally and under irradiation by tungsten lamps through all-pyrex apparatus.The reactions are interpreted as a direct attack of the trichloromethyl radical on the α-carbon of the benzyl ligand.

Catalytic Bromination of Alkyl sp3C-H Bonds with KBr/Air under Visible Light

Zhao, Mengdi,Lu, Wenjun

, p. 5264 - 5267 (2018)

Alkyl sp3C-H bonds of cycloalkanes and functional branch/linear alkanes have been successfully brominated with KBr using air or O2 as an oxidant at room temperature to 40 °C. The reactions are carried out in the presence of catalytic NaNO2 in 37% HCl (aq)/solvent under visible light, combining aerobic oxidations and photochemical radical processes. For various alkane substrates, CF3CH2OH, CHCl3, or CH2Cl2 is employed as an organic solvent, respectively, to enhance the efficiency of bromination.

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide

Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej

, p. 4429 - 4439 (2009)

A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.

Efficient organic transformations mediated by ZrOCl28H 2O in Water

Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Heidari, Mahdieh

, p. 1470 - 1482 (2011)

Operationally simple and environmentally benign methods for some organic transformations comprising reductive coupling of sulfonyl chlorides, chemoselective deoxygenation of sulfoxides, and halogenation of alcohols mediated by ZrOCl28H2O/MX in water have been developed.

A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers

Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya

, p. 5531 - 5534 (2006)

A new diphenylphosphinite ionic liquid (IL-OPPh2) is introduced. This ionic liquid is used as both a reagent and a solvent to convert alcohols and trimethylsilyl and tetrahydropyranyl (THP) ethers into their corresponding alkyl bromides, thiocyanates or isothiocyanates in the presence of Br2 and SCN- at 80 °C. In this ionic liquid, bromination and thiocyanation of alcohols occurs highly selectively in the presence of trimethylsilyl and THP-ethers and also between different classes of alcohols. The use of this ionic liquid allows easy separation of the desired products from the phosphinate by-product.

Arylmethyl radicals from arylmethoxybromodiazirines

Moss, Robert A.,Fu, Xiaolin

, p. 3353 - 3356 (2004)

(Chemical Equation Presented) Photolytic decompositions of 3-arylmethoxy-3-bromodiazirines afford arylmethyl radicals by homolyses of the diazirines' excited states.

Benzylic Bromination-Acetoxylation of Toluenes by Bromide Ion Catalyzed Thermal Decomposition of Peroxydisulfate in Acetic Acid in the Presence of Acetate Ions

Citterio, Attilio,Santi, Roberto,Pagani, Anselmo

, p. 4925 - 4927 (1987)

Side-chain bromination and acetoxylation of alkylaromatics by halide ion induced decomposition of potassium peroxydisulfate in acetic acid have been studied by product analysis techniques.Catalytic amounts of lithium bromide in the presence of sodium acetate were found effective in promoting benzylic bromination, followed by conversion to the corresponding benzyl acetates by reaction with acetate.The reaction is interpreted to take place by the redox and free-radical chain mechanism involving bromine atoms (ρ = -1.38 vs. ? + for substituted toluenes).In competiti ve experiments, benzyl and 4-nitrobenzyl acetates were found lees reactive than the corresponding toluenes in acetic acid with the couple S2O82-/Br- but more reactive in carbon tetrachloride with N-bromosuccinimide.

A novel stereoselective one-pot conversion of alcohols into alkyl halides mediated by N,N′-diisopropylcarbodiimide

Crosignani, Stefano,Nadal, Brice,Li, Zhengning,Linclau, Bruno

, p. 260 - 261 (2003)

Alcohols can be converted in high yields to the corresponding alkyl halides in a one-pot procedure via the corresponding O-alkylisourea; very short reaction times are possible when microwave irradiation is used.

Temperature Effects on Rates of Dehalogenation of Aromatic Anion Radicals

Meot-Ner (Mautner), M.,Neta, P.,Norris, Robert K.,Wilson, Karen

, p. 168 - 173 (1986)

The temperature dependence of the unimolecular dehalogenation of radical anions of nitrobenzyl halides and haloacetophenones was measured between -7 and 70 deg C.Activation parameters range from Ea=11.2-16.9 kcal/mol and log A=12.7-17.1.Both Ea and log A increase from p- to o-nitro radicals and from chloro to bromo radicals.Unfavorable steric effects that move the halogen atom out of the aromatic plane result in lowered A factors.In general, the variation of k294 with structure depends in a complex way on the combination of Ea and log A factors, which suggests caution in the evaluation of rate constants at one temperature.The fast unimolecular dissociation of (p-NO2C6H4CH2Br)(1-). (k294=4.6*105 s-1) allows measurement of the slower bimolecular electron transfer (C6H5NO2)(1-).+p-NO2C6H4CH2Br->(p-NO2C6H4CH2Br)(1-).+C6H5NO2 (k294=1.9*106 M-1 s-1).Both the activation energy and probability factor contribute to the slow rate, possibly due to a geometry change upon the reduction of ArNO2.Extending the temperature studies to supercooled solutions shows no discontinuity of the unimolecular rate constants near the phase transition temperatures.

-

Baker,Nathan

, p. 236,237 (1936)

-

NaIO4-mediated C-H activation of alkylbenzenes and alkanes with LiBr

Shaikh, Tanveer M.,Sudalai, Arumugam

, p. 5589 - 5592 (2005)

NaIO4 oxidizes lithium bromide efficiently under acidic conditions to functionalize alkylbenzenes and alkanes and produce the corresponding bromo and acetoxy derivatives in excellent yields. The protocol also demonstrates the direct conversion of cyclohexane into trans-1,2- dibromocyclohexane in moderate yield.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

Houle, Camille,Savoie, Paul R.,Davies, Clotilde,Jardel, Damien,Champagne, Pier Alexandre,Bibal, Brigitte,Paquin, Jean-Fran?ois

, p. 10620 - 10625 (2020)

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

-

Bernstein,Roth,Miller

, p. 2310,2313 (1948)

-

Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent

Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Arkile, Manisha,Khedkar, Vijay M.,Jadhav, Nandadeep,Sarkar, Dhiman,Shingate, Bapurao B.

, p. 561 - 569 (2016)

In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 μg/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents.

Catalyst and solvent-free bromination of toluene derivatives by HBr-H 2O2 with visible-light photocatalysis using a continuous-flow micro reactor

Yu, Wu-Bin,Yu, Dong-Ping,Zheng, Ming-Ming,Shan, Shu-Ting,Li, Yu-Jin,Gao, Jian-Rong

, p. 258 - 260 (2012)

The efficiency of the bromination of toluene derivatives has been improved significantly by utilising a combination of hydrogen peroxide (30%) and hydrogen bromide (40%) in a continuous-flow micro reactor. This catalyst and solvent-free reaction takes place by visible-light photocatalysis.

Bromine/Bentonite Earth System, Promoter of Phenylmethanes from Toluene

Salmon, Manuel,Angeles, Enrique,Miranda, Rene

, p. 1188 - 1190 (1990)

The condensation of toluene to produce o- and p-methylphenylmethanes by use of bromine with a bentonitic earth catalyst has been investigated and a mechanism is proposed based on the isolated intermediates and other related reactions.

An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide

Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Laxminarayana, Keetha,Narender, Ravirala

, p. 6681 - 6683 (2007)

Polymethylhydrosiloxane (PMHS) in combination with (bromodimethyl)sulfonium bromide or NBS has been utilized for the first time for reductive bromination of aromatic aldehydes at room temperature to afford the corresponding benzyl bromides in excellent yields.

Photocatalytic continuous bromination method

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Paragraph 0066-0067, (2021/04/03)

The invention provides a photocatalytic continuous bromination method. The method comprises the following steps: carrying out a first-stage photocatalytic continuous bromination reaction on a materialcontaining an aromatic substrate with a structural general formula I and a bromination reagent in a first continuous illumination reactor to form a first continuous system; overflowing the obtained first continuous system into a second continuous illumination reactor for a second-stage photocatalytic continuous bromination reaction to form a second continuous system; and purifying the second continuous system, wherein the structural general formula I is shown in the specification, R is selected from any one of carboxyl, ester group, NO2, CN, C1 to C8 alkyl and alkoxy, and R1 is C1 to C8 alkyl; n is 1 or 2; X is N or C, and the bromination reagent is Nbromo succinimide or dibromohydantoin. According to the bromination reagent, the selectivity of a product is improved, so the yield of the product is improved; the photocatalytic continuous bromination reaction of the two stages effectively relieves the reaction heat accumulation, and enhances the yield of the target product.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.

, (2021/08/07)

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Preparation method of p-nitrobenzyl bromide

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Paragraph 0029-0051, (2020/06/05)

The invention discloses a preparation method of p-nitrobenzyl bromide, and belongs to the technical field of organic synthesis processes. According to the preparation method, p-nitrotoluene is used asa raw material, hydrobromic acid is used as a bromine s

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