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2042-37-7

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2042-37-7 Usage

Chemical Properties

white to light yellow crystal powder

Uses

2-Bromobenzonitrile belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 2042-37-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,4 and 2 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2042-37:
(6*2)+(5*0)+(4*4)+(3*2)+(2*3)+(1*7)=47
47 % 10 = 7
So 2042-37-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H4BrN/c8-7-4-2-1-3-6(7)5-9/h1-4H

2042-37-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A10679)  2-Bromobenzonitrile, 99%   

  • 2042-37-7

  • 5g

  • 535.0CNY

  • Detail
  • Alfa Aesar

  • (A10679)  2-Bromobenzonitrile, 99%   

  • 2042-37-7

  • 25g

  • 1274.0CNY

  • Detail
  • Alfa Aesar

  • (A10679)  2-Bromobenzonitrile, 99%   

  • 2042-37-7

  • 100g

  • 4368.0CNY

  • Detail

2042-37-7Synthetic route

2-bromobenzaldehyde oxime
34158-72-0, 52707-51-4, 52707-56-9

2-bromobenzaldehyde oxime

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester; triethylamine In acetonitrile at 20℃; for 0.583333h;98%
With oxalyl dichloride; Tropone; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 0.25h; Schlenk technique; Inert atmosphere;98%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 1h; Swern Oxidation;93%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
Stage #1: 2-methylphenyl bromide With hydrogen bromide; dihydrogen peroxide In tetrachloromethane; water at 20℃; for 1h; Irradiation;
Stage #2: With ammonia; iodine In tetrachloromethane; water; acetonitrile at 20 - 60℃; for 24h;
97%
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 70℃; for 24h; Inert atmosphere; Sealed tube;80%
Stage #1: 2-methylphenyl bromide With sodium azide; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; zinc trifluoromethanesulfonate In acetonitrile at 25℃; Irradiation;
Stage #2: With trifluorormethanesulfonic acid In acetonitrile for 1h;
51%
2-bromo-6-iodobenzonitrile

2-bromo-6-iodobenzonitrile

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With formic acid; tributyl-amine; 1,1′-(10-(4-acetylphenyl)-10H-phenothiazine-3,7-diyl)bis(ethan-1-one) In acetonitrile at 23℃; for 24h; UV-irradiation; chemoselective reaction;97%
2-Bromobenzamide
4001-73-4

2-Bromobenzamide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h;95%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.666667h; Swern Oxidation;95%
With C36H38Cl6N6Pd3S2 In water; acetonitrile at 80℃; for 6h; Reagent/catalyst;78%
ortho-bromophenylacetic acid
18698-97-0

ortho-bromophenylacetic acid

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 26h; Green chemistry;95%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With ammonium acetate; phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 15h;94%
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;93%
With ammonium iodide In dimethyl sulfoxide at 20℃; for 4h; Electrolysis;91%
o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Phenylglycine; sodium hydroxide In methanol at 100℃; for 18h; Cooling with ice;90%
With ammonia; oxygen In tert-Amyl alcohol; water at 130℃; under 3750.38 Torr; for 24h;90%
Stage #1: o-bromobenzyl alcohol With sodium azide; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; zinc trifluoromethanesulfonate In acetonitrile at 25℃; Irradiation;
Stage #2: With trifluorormethanesulfonic acid In acetonitrile for 1h;
73%
Multi-step reaction with 3 steps
1: potassium carbonate; fluorosulfonyl fluoride; dimethyl sulfoxide / 12 h / 20 °C
2: hydroxylamine hydrochloride; potassium carbonate / 20 °C
3: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C
View Scheme
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
Stage #1: anthranilic acid nitrile With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h;
Stage #2: With acetic acid In dichloromethane; water at 23℃; for 1h;
89%
With tetrabutylammomium bromide; 10-camphorsulfonic acid; sodium nitrite In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;75%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide68%
2-(2-bromo-phenyl)[1,3,4]oxadiazole
928722-52-5

2-(2-bromo-phenyl)[1,3,4]oxadiazole

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 4h;88%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

potassium ferrocyanide

potassium ferrocyanide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;88%
With 3% Au/CeO2; sodium carbonate In dimethyl sulfoxide; isopropyl alcohol at 65℃; for 12h; Irradiation;83%
benzonitrile
100-47-0

benzonitrile

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; palladium diacetate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 70℃; for 12h; Sealed tube;87%
2-bromobenzylamine
3959-05-5

2-bromobenzylamine

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;85.4%
With potassium hydroxide; dipotassium peroxodisulfate; ruthenium trichloride In water for 1.5h;83%
With isoquinoline; oxygen; copper; ammonium bromide In toluene at 100℃; under 760.051 Torr; for 24h; Green chemistry;64.9 %Chromat.
With ammonia; oxygen; silica gel; 11-pyridino[3,2-h]quinoxalino[2,3-f]quinolin-11-ylpyridino[3,2-h]quinoxalino[2,3-f]quinoline In tert-Amyl alcohol; N,N-dimethyl-formamide at 110 - 800℃; under 1500.15 Torr; for 16h; Sonication; Inert atmosphere; Calcination;73.27 %Chromat.
2-bromobenzaldehyde oxime
34158-72-0, 52707-51-4, 52707-56-9

2-bromobenzaldehyde oxime

1,3-diphenyl-2-propynone
7338-94-5

1,3-diphenyl-2-propynone

A

3-hydroxy-1,3-diphenyl-2-propen-1-one
1704-15-0, 62961-62-0

3-hydroxy-1,3-diphenyl-2-propen-1-one

B

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 25℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube;A 88 %Spectr.
B 85%
2-cyano-benzenediazonium tetrafluoroborate
55165-45-2

2-cyano-benzenediazonium tetrafluoroborate

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;84%
2-<(trifluoromethanesulfonyl)oxy>benzonitrile
138313-23-2

2-<(trifluoromethanesulfonyl)oxy>benzonitrile

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere;83%
2-bromobenzylamine hydrochloride
5465-63-4

2-bromobenzylamine hydrochloride

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With cis-[Os(VIII)O4(OH)2](2-); [Fe(CN)6](3-); acetonitrile at 20℃; for 1.5h;82%
2,2-dimethylmalononitrile
7321-55-3

2,2-dimethylmalononitrile

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
Stage #1: 1-Bromo-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 23℃; for 3h;
82%
benzonitrile
100-47-0

benzonitrile

A

3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

B

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With bromine fluoride In ethanol; chloroform at -40℃; for 0.25h;A 81%
B 10%
With bromine trifluoride; bromine at 0 - 10℃;A 45%
B 12%
2-bromostyrene
2039-88-5

2-bromostyrene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With formic acid; sodium nitrite In acetonitrile at 70℃; for 4h; Schlenk technique;78%
With formic acid; 5,10,15,20‐tetrakis‐(4‐sulfonatophenyl)‐porphyrin‐iron(III) chloride; sodium nitrite In acetonitrile at 70℃; for 4.5h;78.49%
With [bis(acetoxy)iodo]benzene; ammonium bicarbonate In methanol; water at 36℃; for 12h; Sealed tube;65%
2-bromo-N-(isopropyl)benzamide
64141-90-8

2-bromo-N-(isopropyl)benzamide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 30℃; for 12h; chemoselective reaction;77%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

A

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

B

2-Bromobenzamide
4001-73-4

2-Bromobenzamide

Conditions
ConditionsYield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Inert atmosphere; Sealed tube; Green chemistry;A n/a
B 76%
2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With aluminum oxide; aminosulfonic acid; urea for 0.216667h; Irradiation;75%
Multi-step reaction with 3 steps
1: thionyl chloride
2: aqueous ammonia
3: thionyl chloride
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / 21 h / Inert atmosphere; Reflux
2.1: sodium diisobutyl-tert-butoxyaluminium hydride / tetrahydrofuran / 4 h / -40 - 0 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
View Scheme
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; ammonium carbonate; tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide at 120℃; for 5h; Schlenk technique;70%
2-bromobenzylamine
3959-05-5

2-bromobenzylamine

A

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 1.5h;A 68%
B 6 %Chromat.
2-bromobenzylamine
3959-05-5

2-bromobenzylamine

A

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

B

2-Bromobenzamide
4001-73-4

2-Bromobenzamide

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 16h;A 64.1%
B 28.1%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 20h;64%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

2-bromoaniline
615-36-1

2-bromoaniline

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With acetic acid; sodium nitrite In neat (no solvent) at 50℃; for 1h;55%
2-bromo-1-ethynylbenzene
766-46-1

2-bromo-1-ethynylbenzene

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With tert.-butylnitrite; benzyl-methyl-amine In dimethyl sulfoxide at 110℃; for 12h;54%
ethyl 2-azido-2-(2-bromophenyl)acetate
1221966-47-7

ethyl 2-azido-2-(2-bromophenyl)acetate

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 60℃; under 760.051 Torr;47%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

3',5'-Di-tert-butyl-2'-hydroxy-biphenyl-2-carbonitrile

3',5'-Di-tert-butyl-2'-hydroxy-biphenyl-2-carbonitrile

2,4-di-tert-butyldibenzopyran-6-one

2,4-di-tert-butyldibenzopyran-6-one

Conditions
ConditionsYield
With silica gel In dichloromethane Ambient temperature;100%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-2-carbonitrile
24973-49-7

biphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With potassium phosphate; (dppf)Ni(o-tol)Cl In 1,4-dioxane at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Sealed tube;100%
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.1h; Suzuki cross-coupling reaction;99%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-Cyano-4'-methylbiphenyl
114772-53-1

2-Cyano-4'-methylbiphenyl

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 50℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With potassium carbonate; [1-cyclohexyl-3-(di-pyridin-2-yl-methyl)-urea][PdCl2] In water at 100℃; for 1h; Suzuki-Miyaura coupling;99%
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Suzuki cross-coupling reaction;99%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

2-(2-(4-methoxyphenyl)ethynyl)benzonitrile
351862-56-1

2-(2-(4-methoxyphenyl)ethynyl)benzonitrile

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere;83%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 2h; Inert atmosphere;
2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
425378-68-3

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2'-fluoro-5'-nitrobiphenyl-2-carbonitrile
425378-69-4

2'-fluoro-5'-nitrobiphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; 1,4-dioxane at 20 - 50℃; for 1.5h;100%
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20 - 50℃;
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

2'-fluoro-[1,1'-biphenyl]-2-carbonitrile
400820-15-7

2'-fluoro-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; 1,4-dioxane at 20 - 50℃; for 0.75h;100%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 150℃; for 0.5h; Suzuki cross-coupling; microwave irradiation;88%
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate In N,N-dimethyl-formamide at 150℃; for 0.5h; Suzuki coupling; Inert atmosphere; Microwave irradiation;81%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

A

biphenyl-2,2'-dicarbonitrile
4341-02-0

biphenyl-2,2'-dicarbonitrile

B

benzonitrile
100-47-0

benzonitrile

C

2-cyanophenylzinc bromide
131379-17-4

2-cyanophenylzinc bromide

Conditions
ConditionsYield
With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide In acetonitrile the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;A 0%
B 0%
C 100%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4'-(tert-butyl)-[1,1'-biphenyl]-2-carbonitrile

4'-(tert-butyl)-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0833333h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;100%
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling;67%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0333333h; Catalytic behavior; Suzuki-Miyaura Coupling;100 %Chromat.
With potassium carbonate In water; isopropyl alcohol at 80℃; for 0.5h; Suzuki-Miyaura Coupling;45 %Chromat.
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-(o-Tolyl)benzonitrile
157366-46-6

2-(o-Tolyl)benzonitrile

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 5-[3-(4-carboxy-2,6-dimethylphenyl)-2-thioxoimidazolidin-1-yl]benzene-1,2,3-tricarboxylic acid; tetrabutylammomium bromide; potassium hydroxide In water at 20℃; for 48h; Suzuki-Miyaura Coupling; Sealed tube;99%
With Pd/C; diisopropylamine In water at 100℃; for 3h; Suzuki Coupling; Green chemistry;98%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene at 80℃; Suzuki-Miyaura cross coupling reaction; Inert atmosphere;94%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4'-methoxybiphenyl-2-carbonitrile
125610-78-8

4'-methoxybiphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium phosphate; [5-(3-butylbenzimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxy calix[4]arene] (pyridine) palladium(II) dibromide In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;99%
With potassium carbonate In water at 80℃; for 10h; Suzuki-Miyaura Coupling; Green chemistry;95%
Stage #1: 4-methoxyphenylboronic acid With potassium phosphate; 2C2F6NO4S2(1-)*C44H66Cl2N2P2Pd(2+); 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide In water at 65℃; Suzuki-Miyaura reaction; Inert atmosphere;
Stage #2: o-cyanobromobenzene In water at 65℃; for 2h; Suzuki-Miyaura reaction; Inert atmosphere;
92%
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100℃; Suzuki-Miyaura coupling; Inert atmosphere;91%
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling;68%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-bromobenzylamine hydrochloride
5465-63-4

2-bromobenzylamine hydrochloride

Conditions
ConditionsYield
Stage #1: o-cyanobromobenzene With [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; diethylphenylsilane at 20℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;
99%
Stage #1: o-cyanobromobenzene With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃;
98%
Stage #1: o-cyanobromobenzene With 1,1,3,3-Tetramethyldisiloxane; titanium(IV)isopropoxide In methyl cyclohexane at 60℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In methyl cyclohexane at 20℃; Inert atmosphere;
98%
benzophenone hydrazone
5350-57-2

benzophenone hydrazone

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-(2-(diphenylmethylene)hydrazinyl)benzonitrile
1219024-53-9

2-(2-(diphenylmethylene)hydrazinyl)benzonitrile

Conditions
ConditionsYield
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.05h; Inert atmosphere;
Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 20 - 100℃; for 7h; Inert atmosphere;
99%
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.25h; Inert atmosphere;
Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 100℃; for 43h; Inert atmosphere;
74%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 12h; Inert atmosphere;
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

isopropyl zinc bromide
77047-87-1

isopropyl zinc bromide

2-Isopropyl-1-benzonitrile
40751-52-8

2-Isopropyl-1-benzonitrile

Conditions
ConditionsYield
With [1,3-bis(2,6-diisoheptylphenyl)-4,5-dichloroimidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride In tetrahydrofuran; toluene at 0 - 23℃; Reagent/catalyst; Negishi Coupling; Inert atmosphere; Schlenk technique;99%
Stage #1: o-cyanobromobenzene With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice;
Stage #2: isopropyl zinc bromide In tetrahydrofuran; toluene at 23℃; for 0.5h; Inert atmosphere;
76%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

phenol
108-95-2

phenol

o-phenoxybenzonitrile
6476-32-0

o-phenoxybenzonitrile

Conditions
ConditionsYield
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique;99%
With copper(II) oxide; potassium hydroxide In N,N-dimethyl acetamide at 27℃; for 24h; Ullmann Condensation; Inert atmosphere; Sealed tube;61%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

cyclopentylzinc bromide lithium chloride

cyclopentylzinc bromide lithium chloride

2-cyclo-pentylbenzonitrile
221626-03-5

2-cyclo-pentylbenzonitrile

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 20℃; for 0.5h; Negishi Coupling; Schlenk technique; Inert atmosphere;99%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

3-formyl-4-methoxyphenylboronic acid

3-formyl-4-methoxyphenylboronic acid

3'-formyl-4'-methoxybiphenyl-2-carbonitrile

3'-formyl-4'-methoxybiphenyl-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0166667h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;99%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.05h; Catalytic behavior; Suzuki-Miyaura Coupling;94 %Chromat.
With potassium carbonate In water; isopropyl alcohol at 80℃; for 0.5h; Suzuki-Miyaura Coupling;65 %Chromat.
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

phenylmanganese(II) chloride
71478-47-2

phenylmanganese(II) chloride

biphenyl-2-carbonitrile
24973-49-7

biphenyl-2-carbonitrile

Conditions
ConditionsYield
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 3h;98%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-methoxyphenylmagnesium chloride
699-19-4

4-methoxyphenylmagnesium chloride

4'-methoxybiphenyl-2-carbonitrile
125610-78-8

4'-methoxybiphenyl-2-carbonitrile

Conditions
ConditionsYield
Stage #1: 4-methoxyphenylmagnesium chloride With 2-iodo-propane In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere;
Stage #2: o-cyanobromobenzene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In tetrahydrofuran at 25℃; for 0.0833333h; Kumada coupling reaction; Inert atmosphere;
98%
Stage #1: 4-methoxyphenylmagnesium chloride With N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In tetrahydrofuran at 80℃; for 0.25h; microwave irradiation;
Stage #2: o-cyanobromobenzene; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 120℃; for 0.0333333h; Negishi cross-coupling; microwave irradiation;
92%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

3-Aminophenylboronic acid
30418-59-8

3-Aminophenylboronic acid

3'-aminobiphenyl-2-carbonitrile
342613-84-7

3'-aminobiphenyl-2-carbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 80℃; for 20h; Suzuki coupling;98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 80℃; for 20h;98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 20h;98%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

3-aminobenzeneboronic acid monohydrate

3-aminobenzeneboronic acid monohydrate

A

3'-aminobiphenyl-2-carbonitrile
342613-84-7

3'-aminobiphenyl-2-carbonitrile

B

3'-(7-Formylimidazo[1,2-α]pyridin-3-yl)bilphenyl-2-carbonitrile

3'-(7-Formylimidazo[1,2-α]pyridin-3-yl)bilphenyl-2-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetateA n/a
B 98%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-Bromobenzamide
4001-73-4

2-Bromobenzamide

Conditions
ConditionsYield
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 50℃; for 48h;98%
With Wilkinson's catalyst; Acetaldehyde oxime In toluene at 110℃;90%
With Wilkinson's catalyst; Acetaldehyde oxime In toluene at 110℃; for 4h;90%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-fluoro-3-(trimethylsilanyl)phenylboronic Acid
1410703-15-9

2-fluoro-3-(trimethylsilanyl)phenylboronic Acid

2′-fluoro-3′-(trimethylsilanyl)biphenyl-2-carbonitrile
1410703-17-1

2′-fluoro-3′-(trimethylsilanyl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 90℃; for 14h; Inert atmosphere;98%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

(2-cyanophenyl)acetic acid tert-butyl ester

(2-cyanophenyl)acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: bromoacetic acid tert-butyl ester With zinc In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;
Stage #2: o-cyanobromobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Sealed tube;
98%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

2-(2-bromophenyl)-4,5-dihydrothiazole

2-(2-bromophenyl)-4,5-dihydrothiazole

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 80℃; for 1.5h;98%
NH-pyrazole
288-13-1

NH-pyrazole

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-(1H-pyrazol-1-yl)-benzonitrile
25775-03-5

2-(1H-pyrazol-1-yl)-benzonitrile

Conditions
ConditionsYield
With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere;98%
With quebrachitol; copper; caesium carbonate In water; dimethyl sulfoxide at 110℃; for 24h; Ullmann Condensation; Inert atmosphere; Green chemistry;89%
With D-galacturonic acid; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 80 - 100℃; Inert atmosphere; Green chemistry;87%
With copper(I) oxide; caesium carbonate; N-phenyl-2-pyridincarboxamide-1-oxide In dimethyl sulfoxide at 120℃; for 20h; Catalytic behavior; Solvent; Temperature; Inert atmosphere;70%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

3-aminobenzeneboronic acid monohydrate

3-aminobenzeneboronic acid monohydrate

A

3'-aminobiphenyl-2-carbonitrile
342613-84-7

3'-aminobiphenyl-2-carbonitrile

B

3'-(7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile

3'-(7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; ethyl acetateA n/a
B 98%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan
402503-13-3

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan

2-(2-benzofuranyl)-benzonitrile
121668-44-8

2-(2-benzofuranyl)-benzonitrile

Conditions
ConditionsYield
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 12h; Suzuki-Miyaura Coupling;98%
benzaldehyde p-toluenesulfonylhydrazone
1666-17-7

benzaldehyde p-toluenesulfonylhydrazone

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

4-(2-bromophenyl)-5-phenyl-2H-1,2,3-triazole
120106-68-5

4-(2-bromophenyl)-5-phenyl-2H-1,2,3-triazole

Conditions
ConditionsYield
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 4h; Inert atmosphere;98%
1-[(4-methoxyphenyl)sulfanyl]pyrrolidine-2,5-dione
80172-73-2

1-[(4-methoxyphenyl)sulfanyl]pyrrolidine-2,5-dione

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-((4-methoxyphenyl)thio)benzonitrile
128958-95-2

2-((4-methoxyphenyl)thio)benzonitrile

Conditions
ConditionsYield
With N,N,N'N'-tetramethyl-1,3-propanediamine; trimethoxonium tetrafluoroborate; copper(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In acetonitrile at 80℃; for 3h; Reagent/catalyst;97.7%

2042-37-7Relevant articles and documents

-

Herbst,Wilson

, p. 1142,1145 (1957)

-

-

Varma,Sen-Gupta

, p. 593 (1933)

-

Method for catalyzing oxidation of amines to generate nitrile by using nonmetal mesoporous nitrogen-doped carbon material

-

Paragraph 0019; 0039, (2021/05/08)

The invention discloses a method for preparing nitrile by catalyzing amine oxidation with a non-metal mesoporous nitrogen-doped carbon material catalyst, which is applied to the field of synthesis, the material is prepared by using a nitrogen-containing organic ligand as a precursor and silica sol as a template agent, calcining in the atmosphere of inert gases such as N2 or Ar and then removing the template agent; oxygen or air is used as an oxygen source, the reaction is performed at 80-130 DEG C under the action of ammonia water in the presence of a solvent, the effect is good, and the product still keeps higher activity after being recycled for more than 8 times, and has a wide industrial application prospect. The invention provides a heterogeneous non-metal catalytic system for catalyzing amine oxidation to prepare nitrile for the first time, and compared with a reported metal catalyst, the heterogeneous non-metal catalytic system does not bring metal pollution to a product to influence the effect of cyano drugs.

Efficient nitriding reagent and application thereof

-

Paragraph 0230-0232, (2021/03/31)

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

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