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128-08-5

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128-08-5 Usage

Chemical Description

Different sources of media describe the Chemical Description of 128-08-5 differently. You can refer to the following data:
1. N-bromosuccinimide is a brominating agent that is commonly used in organic synthesis.
2. N-bromosuccinimide is a brominating agent.
3. N-bromosuccinimide is a brominating agent used in organic synthesis.

Chemical Properties

white to light yellow crystalline powder

Uses

N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.

Application

In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.

Definition

ChEBI: N-bromosuccinimide is a five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom. It has a role as a reagent. It is a dicarboximide, a pyrrolidinone and an organobromine compound. It is functionally related to a succinimide.

Preparation

N-Bromosuccinimide is prepared by addition of bromine to a cold aqueous solution of succinimide or by reaction of succinimide with NaBrO2 in the presence of HBr.1.62mol (160g) succinimide is dissolved in a mixture of 1.60mol (64g) NaOH, 300g crushed ice and 400ml water. Cool the mixture in an ice bath, and add 85ml (1.65 mol, 264g) Br2 at once while stirring violently. Stir for two more minutes, then filter the precipitated product and wash with ice water. Dry in a desiccator. Yield 75-81%.Don't clean up NBS too much, the stinky yellow stuff still containing a bit of Br2 works best. N-Bromosuccinimide is a brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route. An irritating poison to skin, eyes, and mucous membranes. Reacts explosively with adme, dtallyl sulfide, and hydrazine hydrate. Explosive reaction with propiononitrile after heating to 105℃ for 24 hours. Violent reaction with dtbenzoyl peroxide + 4-tok acid. When heated to decomposition it emits toxic fumes of Brand NOx. See also BROMIDES and NITROGEN MONOXIDE.

Purification Methods

N-Bromosuccinimide (30g) is purified by dissolving rapidly in 300mL of boiling water and filtering through a fluted filter paper into a flask immersed in an ice bath, and left for 2hours. The crystals are filtered off, washed thoroughly with ca 100mL of ice-cold water and drained on a Büchner funnel before drying under vacuun over P2O5 or CaCl2 [Dauben & McCoy J Am Chem Soc 81 4863 1959]. This brominating agent has also been crystallised from acetic acid or water (10 parts), washed in water and dried in vacuo [Wilcox et al. J Am Chem Soc 108 7693 1986, Shell et al. J Am Chem Soc 108 121 1986, Phillips & Cohen J Am Chem Soc 108 2013 1986, Beilstein 21/9 V 543.]

Check Digit Verification of cas no

The CAS Registry Mumber 128-08-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 128-08:
(5*1)+(4*2)+(3*8)+(2*0)+(1*8)=45
45 % 10 = 5
So 128-08-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

128-08-5 Well-known Company Product Price

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

  • (B0656)  N-Bromosuccinimide  >98.0%(T)

  • 128-08-5

  • 25g

  • 80.00CNY

  • Detail
  • TCI America

  • (B0656)  N-Bromosuccinimide  >98.0%(T)

  • 128-08-5

  • 100g

  • 250.00CNY

  • Detail
  • TCI America

  • (B0656)  N-Bromosuccinimide  >98.0%(T)

  • 128-08-5

  • 500g

  • 580.00CNY

  • Detail
  • Alfa Aesar

  • (A15922)  N-Bromosuccinimide, 99%   

  • 128-08-5

  • 250g

  • 433.0CNY

  • Detail
  • Alfa Aesar

  • (A15922)  N-Bromosuccinimide, 99%   

  • 128-08-5

  • 1000g

  • 1243.0CNY

  • Detail
  • Alfa Aesar

  • (A15922)  N-Bromosuccinimide, 99%   

  • 128-08-5

  • 5000g

  • 5406.0CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-5G

  • 269.10CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-100G

  • 356.85CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-250G

  • 466.83CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-500G

  • 939.51CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-1KG

  • 1,341.99CNY

  • Detail
  • Aldrich

  • (B81255)  N-Bromosuccinimide  ReagentPlus®, 99%

  • 128-08-5

  • B81255-5KG

  • 5,235.75CNY

  • Detail

128-08-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N-bromosuccinimide

1.2 Other means of identification

Product number -
Other names 1-bromopyrrolidine-2,5-dione

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:128-08-5 SDS

128-08-5Synthetic route

Succinimide
123-56-8

Succinimide

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorite; sodium bromide In water at 0 - 25℃; for 1.5h; Temperature;96%
With sodium bromate; sulfuric acid; hydrogen bromide In water for 0.166667h; Ambient temperature;95%
With [bis(acetoxy)iodo]benzene In tetrachloromethane at 20℃; Solvent;94%
Succinimide
123-56-8

Succinimide

N-bromoacetamide
79-15-2

N-bromoacetamide

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N-chloro-succinimide
128-09-6

N-chloro-succinimide

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Conditions
ConditionsYield
With tetraethylammonium bromide halogen exchange durin complex formation between an N-halogensuccinimide and quaternary ammonium halide;
With water; sodium bromide
benzotelluracyclopentane bromide succinimide
82815-39-2

benzotelluracyclopentane bromide succinimide

A

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

B

1,1-dibromo-3,4-benzo-1-telluracyclopentane

1,1-dibromo-3,4-benzo-1-telluracyclopentane

Conditions
ConditionsYield
With bromine Te-N cleavage;
Succinimide
123-56-8

Succinimide

bromine
7726-95-6

bromine

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Succinimide
123-56-8

Succinimide

hypobromous acid

hypobromous acid

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

Succinimide
123-56-8

Succinimide

A

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

B

H2O

H2O

Conditions
ConditionsYield
Equilibrium constant;
Succinimide
123-56-8

Succinimide

A

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

B

HBr

HBr

Conditions
ConditionsYield
With bromine Equilibrium constant;
2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane

2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane

Succinimide
123-56-8

Succinimide

A

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

B

2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane

2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane

Conditions
ConditionsYield
In dichloromethane-d2
C21H16BrS(1+)*C4H4NO2(1-)

C21H16BrS(1+)*C4H4NO2(1-)

A

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

B

1-methylthiotriptycene
74067-58-6

1-methylthiotriptycene

Conditions
ConditionsYield
In dichloromethane-d2 at 22℃; Equilibrium constant; Inert atmosphere; Schlenk technique;
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dioxa-3,5 exo p-nitrophenyl-4 syn tricyclo<5.2.1.02,6>decane
31199-21-0

dioxa-3,5 exo p-nitrophenyl-4 syn tricyclo<5.2.1.02,6>decane

1-[(1S,2R,6S,7R)-4-(4-Nitro-phenyl)-3,5-dioxa-tricyclo[5.2.1.02,6]dec-4-yl]-pyrrolidine-2,5-dione
77085-46-2

1-[(1S,2R,6S,7R)-4-(4-Nitro-phenyl)-3,5-dioxa-tricyclo[5.2.1.02,6]dec-4-yl]-pyrrolidine-2,5-dione

Conditions
ConditionsYield
In tetrachloromethane for 1h; Heating;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

5-tert-butyl-2-methoxy-3H-azepine
443694-36-8

5-tert-butyl-2-methoxy-3H-azepine

5-bromo-4-t-butyl-5,6-dihydro-7-methoxy-2-succinimidyl-2H-azepine

5-bromo-4-t-butyl-5,6-dihydro-7-methoxy-2-succinimidyl-2H-azepine

Conditions
ConditionsYield
In dichloromethane at -98℃;100%
2,4,5-trimethyloxazole
20662-84-4

2,4,5-trimethyloxazole

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

5-(bromomethyl)-2,4-dimethyloxazole
141567-40-0

5-(bromomethyl)-2,4-dimethyloxazole

Conditions
ConditionsYield
With dibenzoyl peroxide In tetrachloromethane for 1h; Heating / reflux;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

3-benzyloxy-4-ethyl-1-methoxybenzene
511277-65-9

3-benzyloxy-4-ethyl-1-methoxybenzene

5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene
511277-67-1

5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene

Conditions
ConditionsYield
In tetrachloromethane for 16h; silica gel 60 (EM Science);100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N-bromosuccinamide

N-bromosuccinamide

2-Bromo-5-(trifluoromethyl)-6-methoxy-1-naphthalene-carboxylic acid
122670-62-6

2-Bromo-5-(trifluoromethyl)-6-methoxy-1-naphthalene-carboxylic acid

2-chloro-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene
122670-68-2

2-chloro-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene
122670-63-7

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene

Conditions
ConditionsYield
In tetrachloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2-bromo-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene
122670-67-1

2-bromo-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene

2-Bromo-1-(bromomethyl)-5-(trifluoromethyl)-6-methoxynaphthalene
122670-66-0

2-Bromo-1-(bromomethyl)-5-(trifluoromethyl)-6-methoxynaphthalene

Conditions
ConditionsYield
With dibenzoyl peroxide In tetrachloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N-bromosuccinamide

N-bromosuccinamide

2-chloro-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene
122670-68-2

2-chloro-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene
122670-63-7

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene

Conditions
ConditionsYield
In tetrachloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2-bromo-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene
122670-67-1

2-bromo-6-methoxy-1-methyl-5-(trifluoromethyl)naphthalene

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene
122670-63-7

1-bromomethyl-2-chloro-6-methoxy-5-trifluoromethylnaphthalene

2-Bromo-1-(bromomethyl)-5-(trifluoromethyl)-6-methoxynaphthalene
122670-66-0

2-Bromo-1-(bromomethyl)-5-(trifluoromethyl)-6-methoxynaphthalene

Conditions
ConditionsYield
With dibenzoyl peroxide In tetrachloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

3-ethoxy-4-methyl-5-(thien-2-yl)isoxazole

3-ethoxy-4-methyl-5-(thien-2-yl)isoxazole

4-bromomethyl-3-ethoxy-5-(thien-2-yl)isoxazole

4-bromomethyl-3-ethoxy-5-(thien-2-yl)isoxazole

Conditions
ConditionsYield
In tetrachloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

tris(2,4-pentanedionato)ruthenium(III)
31378-26-4, 31378-27-5, 14284-93-6

tris(2,4-pentanedionato)ruthenium(III)

tris(3-bromo-2,4-pentanedionato)ruthenium(III)

tris(3-bromo-2,4-pentanedionato)ruthenium(III)

Conditions
ConditionsYield
In chloroform column (aluminumoxid), evapn., recrystn. (EtOH), elem. anal.;100%
In chloroform ratio of succinimide to (Ru(OCCH3CHCCH3O)3) is 3.0;; column chromatographic separation (Al2O3 90), eluent was evaporated to dryness, residue recrystd. from ethanol, crystals dried under vacuum, elem. anal., UV, NMR;
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

((C2H5)2C2B4H4)Nb(Cl)2(C5H5)
167033-03-6

((C2H5)2C2B4H4)Nb(Cl)2(C5H5)

C5H5Cl2Nb((C2H5)2C2B4H3Br)
266323-95-9

C5H5Cl2Nb((C2H5)2C2B4H3Br)

Conditions
ConditionsYield
In tetrahydrofuran Nb-complex was dissolved in THF, ligand was added, shaken for 5 min under inert atm.; after 10 min solvent was removed by rotary evaporator, residue was redissolved in CH2Cl2, flash-chromd. on silica, solvent was removed; elem. anal.;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

((Me3Si)2CH)3C6H2(H)SnC5H6
1254037-04-1

((Me3Si)2CH)3C6H2(H)SnC5H6

((Me3Si)2CH)3C6H2(Br)SnC5H6
1254037-01-8

((Me3Si)2CH)3C6H2(Br)SnC5H6

Conditions
ConditionsYield
In benzene addn. of NBS in C6H6 to Sn compd. at room temp., stirring for 1 h;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C18H17N5O2

C18H17N5O2

C18H16BrN5O2

C18H16BrN5O2

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h; Cooling with acetone-dry ice;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C19H16N2O2

C19H16N2O2

C19H15BrN2O2

C19H15BrN2O2

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h; Cooling with acetone-dry ice;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C16H13N5O

C16H13N5O

C16H12BrN5O

C16H12BrN5O

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h; Cooling with acetone-dry ice;100%
1-formyl-5-(4-(2-(triisopropylsilyl)ethynyl)phenyl)dipyrromethane

1-formyl-5-(4-(2-(triisopropylsilyl)ethynyl)phenyl)dipyrromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C27H33BrN2OSi

C27H33BrN2OSi

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h; Cooling with acetone-dry ice;100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

(2-aminophenyl)(phenyl)methanone
2835-77-0

(2-aminophenyl)(phenyl)methanone

2-amino-5-bromobenzophenone
39859-36-4

2-amino-5-bromobenzophenone

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;100%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C150H106Ir3N18Ru(5+)*5F6P(1-)

C150H106Ir3N18Ru(5+)*5F6P(1-)

C150H102Br4Ir3N18Ru(5+)*5F6P(1-)

C150H102Br4Ir3N18Ru(5+)*5F6P(1-)

Conditions
ConditionsYield
Stage #1: N-Bromosuccinimide; C150H106Ir3N18Ru(5+)*5F6P(1-) In acetonitrile at 20℃; for 38h;
Stage #2: potassium hexafluorophosphate In water
100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

5,15-bis(mesityl)norcorrolatonickel(II)

5,15-bis(mesityl)norcorrolatonickel(II)

C38H30Br2N4Ni

C38H30Br2N4Ni

Conditions
ConditionsYield
With pyridine In chloroform-d1 at 0℃;100%
In methanol; dichloromethane at 20℃; for 0.333333h;96%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

silver thiocyanate
1701-93-5

silver thiocyanate

1-thiocyanatopyrrolidine-2,5-dione
163276-49-1

1-thiocyanatopyrrolidine-2,5-dione

Conditions
ConditionsYield
In dichloromethane100%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N,N-dibutyl-(3,3,3-trifluoro-1-propynyl)amine
211803-10-0

N,N-dibutyl-(3,3,3-trifluoro-1-propynyl)amine

N-[2-Bromo-1-(N',N'-dibutylamino)-3,3,3-trifluoro-1-propenyl]succinimide
353301-02-7

N-[2-Bromo-1-(N',N'-dibutylamino)-3,3,3-trifluoro-1-propenyl]succinimide

Conditions
ConditionsYield
With 4 A molecular sieve In acetonitrile at 20℃; for 1h;99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

9-(naphthyl-2-yl)anthracene
7424-72-8

9-(naphthyl-2-yl)anthracene

9-bromo-10-(2-naphtyl)-anthracene
474688-73-8

9-bromo-10-(2-naphtyl)-anthracene

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

(C5(CH3)5)Co((CH3CH2)2C2B3H4Br)

(C5(CH3)5)Co((CH3CH2)2C2B3H4Br)

(C5(CH3)5)Co((CH3CH2)2C2B3H3Br2)

(C5(CH3)5)Co((CH3CH2)2C2B3H3Br2)

Conditions
ConditionsYield
In tetrahydrofuran dissoln. of Co-complex in THF, addn. of 1.5 equiv. of succinimide-compd., stirring for < 5 min (color change from orange to dark orange-brown);99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

[(1-pyrrolylimido)F(dpe)2tungsten](BF4)

[(1-pyrrolylimido)F(dpe)2tungsten](BF4)

W(((C6H5)2PCH2)2)2FNN(CH)3CBr(1+)*BF4(1-)*ClCH2CH2Cl=[W(((C6H5)2PCH2)2)2FNN(CH)3CBr]BF4*ClCH2CH2Cl

W(((C6H5)2PCH2)2)2FNN(CH)3CBr(1+)*BF4(1-)*ClCH2CH2Cl=[W(((C6H5)2PCH2)2)2FNN(CH)3CBr]BF4*ClCH2CH2Cl

Conditions
ConditionsYield
In tetrahydrofuran (N2); stirring (-50°C, 9 h), addn. (5% aq. Na2S2O3); washing (5% aq. Na2S2O3, 5% NH4BF4), drying (MgSO4), evapn.; elem. anal.;99%
In tetrahydrofuran (N2); stirring (-78°C, 26 h), addn. (5% aq. Na2S2O3); washing (5% aq. Na2S2O3, 5% NH4BF4), drying (MgSO4), evapn.; elem. anal.;43%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2-[2,4,6-tris(bis(trimethylsilyl)methyl)phenyl]-1,2-dihydro-2-germanaphthalene
392335-71-6

2-[2,4,6-tris(bis(trimethylsilyl)methyl)phenyl]-1,2-dihydro-2-germanaphthalene

2-bromo-2-[2,4,6-tris(bis(trimethylsilyl)methyl)phenyl]-1,2-dihydro-2-germanaphthalene
392335-72-7

2-bromo-2-[2,4,6-tris(bis(trimethylsilyl)methyl)phenyl]-1,2-dihydro-2-germanaphthalene

Conditions
ConditionsYield
With BPO In benzene bromination with NBS (BPO cat.) in refluxing benzene;99%
With catalyst: benzoyl peroxide In benzene under Ar, soln. was refluxed for 2 h; solvent was evapd., hexane added, mixt. was filtered, solvent was evapd.; elem. anal.;99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N-[5-(10,20-diphenylporphirinato) zinc(II)]-N'-(octyl)pyromellitic diimide
403830-45-5

N-[5-(10,20-diphenylporphirinato) zinc(II)]-N'-(octyl)pyromellitic diimide

N-[5-(15-bromo-10,20-diphenylporphinato)zinc(II)]-N'-(octyl)pyromellitic diimide
403830-46-6

N-[5-(15-bromo-10,20-diphenylporphinato)zinc(II)]-N'-(octyl)pyromellitic diimide

Conditions
ConditionsYield
In dichloromethane ligand in CH2Cl2 was added to soln. of Zn-complex in CH2Cl2 under N2, stirred at room temp. for 5 min, quenched with acetone; washed with water, dried over Na2SO4, volatiles were removed, chromd. onsilica gel with CHCl3;99%
3-(dimesitylboryl)-2,2'-bithiophene

3-(dimesitylboryl)-2,2'-bithiophene

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

5,5'-dibromo-3-(dimesitylboryl)-2,2'-bithiophene
942612-25-1

5,5'-dibromo-3-(dimesitylboryl)-2,2'-bithiophene

Conditions
ConditionsYield
In dichloromethane thiophene-compd. and N-bromosuccinimide in CH2Cl2;99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

5,15-bis-(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phenyl)porphyrin zinc
1051971-71-1

5,15-bis-(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phenyl)porphyrin zinc

C46H46Br2N4O8Zn
1051971-72-2

C46H46Br2N4O8Zn

Conditions
ConditionsYield
With pyridine In chloroform for 0.75h;99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

C57H61N5O10Zn
1062503-73-4

C57H61N5O10Zn

C57H60BrN5O10Zn
1062503-75-6

C57H60BrN5O10Zn

Conditions
ConditionsYield
With pyridine In chloroform at 0℃;99%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

[Ir(1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C2,N)(6-phenyl-2,2'-bipyridine(-H))](hexafluorophosphate)
1008133-49-0

[Ir(1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C2,N)(6-phenyl-2,2'-bipyridine(-H))](hexafluorophosphate)

[Ir(1-bromo-3,5-di(2-pyridyl)-2,6-dimethylbenzene-N,C4,N)(6-(p-bromophenyl)-2,2'-bipyridine(-H))](hexafluorophosphate)
1008133-64-9

[Ir(1-bromo-3,5-di(2-pyridyl)-2,6-dimethylbenzene-N,C4,N)(6-(p-bromophenyl)-2,2'-bipyridine(-H))](hexafluorophosphate)

Conditions
ConditionsYield
In acetonitrile treatment of iridium compd. with 2 equiv. of NBS in CH3CN at 20°Cfor several hs; NMR;99%

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A N-bromosuccinimide (NBS) mediated decarboxylative sulfonylation of β-keto acids with sodium sulfinates is developed. The transformation exhibits a broad substrate scope and good functional group tolerance. Preliminary mechanistic studies showed that this reaction is likely to proceed through ...detailed

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A highly stereoselective dibromination of diphenylphosphorylallenes using N-bromosuccinimide (NBS) as bromine reagent is developed, wherein a variety of 2-bromo-substituted allyl bromides were obtained in good to excellent yields under mild reaction conditions. Moreover, the dibromination reacti...detailed

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A highly efficient method for the synthesis of α-halocarbonyl compounds has been achieved via selective monobromination of aromatic and aliphatic carbonyl compounds with N-bromosuccinimide catalyzed by p-toluenesulfonic acid under microwave irradiation within 30 min.detailed

N-Bromosuccinimide (cas 128-08-5) mediated synthesis of triazatruxenes from indoles☆09/24/2019

A new synthetic method for triazatruxenes from indoles is developed using N-bromosuccinimide (NBS) as a user-friendly reagent. Major reaction parameters including the amount of NBS, substrate concentration, temperature, addition rate and addition method are investigated. Additional experiments a...detailed

128-08-5Relevant articles and documents

TIN(IV) MEDIATED SYNTHESIS OF N-HALO COMPOUNDS

Soundararajan, R.,Krishnamurthy, S.,Srinivasan, Vilanoor S.,Balasubramanian, T.R.

, p. 295 - 298 (1983)

Some representative N-halo compounds like N-bromosuccinimide, N-iodosuccinimide, N-bromophthalimide, N-iodophthalimide, N-iodobenzimidazole and N-iodobenzotriazole have been synthesised in good yields under neutral and mild conditions via an intermediate formed from the parent NH species and bis(tri-n-butyltin) oxide.The tin oxide is recovered as recyclable tri-n-butyltin halide.

Organic Synthesis Using Sodium Bromate. II. A Facile Synthesis of N-Bromo Imides and Amides Using Sodium Bromate and Hydrobromic Acid (or Sodium Bromide) in the Presence of Sulfuric Acid

Fujisaki, Shizuo,Hamura, Satoshi,Eguchi, Hisao,Nishida, Akiko

, p. 2426 - 2428 (1993)

The reaction of imides and amides in water (or aqueous acetic acid) with sodium bromate and hydrobromic acid (or sodium bromide) in the presence of sulfuric acid under mild conditions gave the corresponding N-bromides in high yields.

A Practical Synthesis of N-Bromo Imides by Use of Sodium Bromite

Kajigaeshi, Shoji,Nakagawa, Takashi,Fujisaki, Shizuo,Nishida, Akiko

, p. 769 - 770 (1985)

N-Bromo imides can be readily prepared under mild conditions by a reaction of imides with sodium bromite in the presence of hydrobromic acid in fairly good yields.The scope and limitation are also presented.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro

supporting information, p. 1621 - 1629 (2020/02/04)

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Preparation method of 2-amino-5-bromopyridine

-

Paragraph 0018; 0020; 0022, (2018/04/01)

The invention discloses a preparation method of 2-amino-5-bromopyridine. The preparation method is characterized in that 2-aminopyridine is used as the raw material, and two different bromination agents, namely bromine and N-bromo-succinimide (NBS), are sequentially added; the reaction temperature is strictly controlled, and thus 2-amino-5-bromopyridine can be quickly prepared with high yield andhigh purity; and the preparation method is applicable to industrial production. Additionally, a high-purity by-product, namely succinimide, is separated out in the preparation process and is brominated into high-purity NBS through potassium bromide, potassium bromate and sulfuric acid; and the NBS is applied to the synthesizing of 2-amino-5-bromopyridine in the method and has the same effect as the commercial NBS. According to the method, the quantity of used NBS is decreased, the raw material conversion rate is increased, and the bromination agents are recycled, so that the cost is greatly decreased; the main byproduct is only inorganic salt potassium sulfate; and the synthesizing method is green and environmentally friendly.

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