Product Name

  • Name

    4-Bromobenzonitrile

  • EINECS 210-764-9
  • CAS No. 623-00-7
  • Article Data334
  • CAS DataBase
  • Density 1.609 g/cm3
  • Solubility Very slightly soluble in water(0.2g/L). Soluble in alcohol and ether.
  • Melting Point 110-115 °C(lit.)
  • Formula C7H4BrN
  • Boiling Point 236.796 °C at 760 mmHg
  • Molecular Weight 182.019
  • Flash Point 97.011 °C
  • Transport Information UN 3439 6.1/PG 3
  • Appearance white to light yellow powder or flakes
  • Safety 61-36/37/39-26
  • Risk Codes 22-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 623-00-7 (4-Bromobenzonitrile)
  • Hazard Symbols HarmfulXn, ToxicT, IrritantXi
  • Synonyms Benzonitrile, p-bromo-;Benzonitrile, p-bromo- (8CI);Benzonitrile, 4-bromo-;1-Bromo-4-cyanobenzene;p-Bromobenzonitrile;4-Bromo Benzonitrile;4-bromophenylcarbonitrile;
  • PSA 23.79000
  • LogP 2.32078

Synthetic route

zinc(II) cyanide
557-21-1

zinc(II) cyanide

4-bromophenyl trifluoromethanesulfonate
66107-30-0

4-bromophenyl trifluoromethanesulfonate

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride100%
4-(3,3-diethyltriaz-1-en-1-yl)benzonitrile
79664-67-8

4-(3,3-diethyltriaz-1-en-1-yl)benzonitrile

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With cation exchange resin BioRad AG 50W-X12 (H+); lithium bromide In acetonitrile at 75℃; Product distribution; further solvent: THF, DMSO;99%
With chloro-trimethyl-silane; lithium bromide In acetonitrile at 60℃; for 0.333333h;95 % Chromat.
With sulfonic acid resin (H+ form); lithium bromide In acetonitrile for 0.5h; Mechanism; Heating;99 % Chromat.
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenemethanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;		99%
With ammonium hydroxide; oxygen In tert-Amyl alcohol under 7500.75 Torr; for 16h; Green chemistry;99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure;99%
4-bromobenzaldehyde Oxime
25062-46-8, 34158-73-1, 40979-16-6

4-bromobenzaldehyde Oxime

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 20℃; for 1h; Beckmann rearrangement; Inert atmosphere;99%
With iron(III) trifluoromethanesulfonate In toluene at 125℃; for 48h; Inert atmosphere; Green chemistry;71%
With 2,4,6-triphenylpyrylium tetrafluoroborate In acetonitrile at 40℃; under 750.075 Torr; for 24h; Molecular sieve; Irradiation; Inert atmosphere;65%
4-hydrazinobenzonitrile hydrochloride
2863-98-1

4-hydrazinobenzonitrile hydrochloride

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h; Reagent/catalyst; Temperature;99%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;98%
With ammonium hydroxide; cerium(III) chloride heptahydrate; urea hydrogen peroxide adduct; potassium iodide at 60℃; for 4h; Reagent/catalyst; Time;98%
With sodium azide; sodium carbonate In acetonitrile at 0 - 25℃; for 0.5h;97%
4-bromobenzaldehyde N,N-dimethylhydrazone
32787-75-0

4-bromobenzaldehyde N,N-dimethylhydrazone

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; acetonitrile at 55℃; for 60h;98%
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 20℃; for 3h;92%
With dihydrogen peroxide In methanol; water at 20℃; for 0.166667h;89%
4-bromobenzaldehyde oxime
25062-46-8, 40979-16-6, 34158-73-1

4-bromobenzaldehyde oxime

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With pyridine hydrochloride; dimethyl sulfoxide at 90℃; for 4h;98%
With acetonitrile for 1h; Reflux; Green chemistry;98%
With phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester; triethylamine In acetonitrile at 20℃; for 0.416667h;95%
p-bromobenzamide
698-67-9

p-bromobenzamide

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide for 2h; Product distribution; Ambient temperature; also in (C2H5O)3PO, other temperature, other time;97%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide for 2h; Ambient temperature;97%
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;95%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

potassium ferrocyanide

potassium ferrocyanide

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; Inert atmosphere;97%
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique;91%
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;90%
4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;97%
With sodium nitrite In acetonitrile at 80℃; for 14h; Sealed tube;84%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;84%
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;74%
4-Bromobenzylamine
3959-07-7

4-Bromobenzylamine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 15h; Reagent/catalyst;95%
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;90.7%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;88%
p-bromothiobanzamide
26197-93-3

p-bromothiobanzamide

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With triphenyl bismuth (2+); dichloride; triethylamine In dichloromethane at 20℃; for 0.25h;95%
With iodine; triethylamine In dichloromethane at 20℃; for 0.5h;94%
With oxygen; sodium hydroxide In tetrahydrofuran; water at 20℃; for 10h;85%
C14H10BrNO2

C14H10BrNO2

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.0833333h; Schlenk technique;95%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 110℃; for 1h; Schlenk technique; Inert atmosphere;93%
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With formic acid; 5,10,15,20‐tetrakis‐(4‐sulfonatophenyl)‐porphyrin‐iron(III) chloride; sodium nitrite In acetonitrile at 70℃; for 4.5h;92.22%
With formic acid; sodium nitrite In acetonitrile at 70℃; for 4h; Schlenk technique;91%
With [bis(acetoxy)iodo]benzene; ammonium bicarbonate In methanol; water at 36℃; for 12h; Sealed tube;88%
With tetrabutylammonium acetate; sodium nitrite at 100℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;95 %Chromat.
4-cyanophenyl trifluoromethanesulfonate
66107-32-2

4-cyanophenyl trifluoromethanesulfonate

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere;92%
With tetrabutylammomium bromide In toluene for 72h; Heating;32%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With sodium azide; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 0.833333h;92%
With aluminum oxide; aminosulfonic acid; urea for 0.05h; Irradiation;80%
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
With ammonia; trichlorophosphate at 60 - 260℃; for 0.916667h; Temperature; Autoclave; Inert atmosphere;
4-bromo-N,N-dichlorobenzylamine

4-bromo-N,N-dichlorobenzylamine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;92%
4-(methylamino)phenyl thiocyanate
33192-08-4

4-(methylamino)phenyl thiocyanate

4-Bromophenylboronic acid

4-Bromophenylboronic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;92%
4-Bromobenzaldehyde dimethylhydrazone

4-Bromobenzaldehyde dimethylhydrazone

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; 2-nitrobenzeneseleninic acid In methanol at 20℃; for 48h;91%
para-bromotoluene
106-38-7

para-bromotoluene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: para-bromotoluene With hydrogen bromide In water at 20 - 60℃; for 0.333333h;
Stage #2: With dihydrogen peroxide In water at 60℃; for 1h;
Stage #3: With ammonia; iodine In water; acetonitrile at 20 - 60℃; for 4h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;		91%
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 70℃; for 24h; Inert atmosphere; Sealed tube;88%
Stage #1: para-bromotoluene 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;		54%
With tert.-butylhydroperoxide; ammonium fluoride; iodine; oxygen In water; dimethyl sulfoxide at 70℃; for 60h; Schlenk technique; Sealed tube;51%
Multi-step reaction with 2 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / acetonitrile / 2 h / 20 °C / Irradiation
2: ammonium hydroxide; iodine / 4 h / 20 - 60 °C
View Scheme
para-chlorotoluene
106-43-4

para-chlorotoluene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: para-chlorotoluene With hydrogen bromide In water at 20 - 60℃; for 0.333333h;
Stage #2: With dihydrogen peroxide In water at 60℃; for 1h;
Stage #3: With ammonia; iodine In water; acetonitrile at 20 - 60℃; for 4h;		91%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: 1-methyl-4-nitrobenzene With hydrogen bromide In water at 20 - 60℃; for 0.333333h;
Stage #2: With dihydrogen peroxide In water at 60℃; for 1h;
Stage #3: With ammonia; iodine In water; acetonitrile at 20 - 60℃; for 4h;		91%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

K4[Fe(CN)6]

K4[Fe(CN)6]

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium fluoride; palladium diacetate In water at 150℃; for 0.333333h;90%
With triethylamine; nanostructured pyridine-functionalized silica Pd(II) complex In N,N-dimethyl-formamide for 24h; Heating;76%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: 4-Aminobenzonitrile With Bromotrichloromethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h; Inert atmosphere;
Stage #2: With acetic acid In dichloromethane; water at 23℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere;		90%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; hydrogen bromide; sodium nitrite In water at 10 - 55℃; for 2h; Reagent/catalyst;83%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;82%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

p-bromothiobanzamide
26197-93-3

p-bromothiobanzamide

Conditions
ConditionsYield
With pyridine; diammonium sulfide; triethylamine In water at 50℃;100%
Stage #1: 4-bromobenzenecarbonitrile With Lawessons reagent; boron trifluoride diethyl etherate In diethyl ether; toluene at 50℃; for 14h; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In diethyl ether; toluene at 20℃; for 0.333333h; Inert atmosphere;		97%
With O,O-Diethyl hydrogen phosphorodithioate In 2-methyltetrahydrofuran; water at 82℃; for 22h; Inert atmosphere;97%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 3-(4-cyanophenyl)propenoate
67472-79-1

methyl 3-(4-cyanophenyl)propenoate

Conditions
ConditionsYield
With triethylamine; [Pd(Cl)(L-κ-C,N,N)] In N,N-dimethyl acetamide for 24h; Product distribution; Further Variations:; Catalysts; Reaction partners; Reagents; Solvents; temperature, reaction time, catalyst concentrations; Heck arylation; Heating;100%
With sodium acetate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 115 - 120℃; for 1h; Heck reaction; Inert atmosphere;100%
With polystyrene-supported palladacycle catalyst; sodium acetate In N,N-dimethyl acetamide at 100℃; for 10h; Heck reaction;98%
styrene
292638-84-7

styrene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanostilbene
13041-79-7, 14064-68-7, 68331-40-8, 144606-12-2, 1552-58-5, 130059-93-7

4-cyanostilbene

Conditions
ConditionsYield
With cis-(N,N'-bis(2,2-diethoxyethyl)imidazolin-2-ylidene)dichlorotriphenylphosphinepalladium(II); tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 2h; Heck reaction;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Heck Reaction;99%
With bis(2-isopropoxyphenyl)phenylarsine; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 2h; Heck Reaction;99%
1-Heptyne
628-71-7

1-Heptyne

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(1-hept-1-ynyl)benzonitrile
64146-59-4

4-(1-hept-1-ynyl)benzonitrile

Conditions
ConditionsYield
With copper(I) bromide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 90℃; for 0.166667h;100%
With nickel(II) ferrite; potassium carbonate In water at 100℃; for 2.25h; Sonogashira Cross-Coupling;87%
With copper(I) bromide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20℃; Rate constant;
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

2-(4-cyanophenyl)-N,N-dimethylacetamide
79149-55-6

2-(4-cyanophenyl)-N,N-dimethylacetamide

Conditions
ConditionsYield
With potassium In ammonia100%
Stage #1: N,N-dimethyl acetamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h;
Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h;
Stage #3: 4-bromobenzenecarbonitrile With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 4h;		89%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

phenylacetylene
536-74-3

phenylacetylene

4-(2-phenylethynyl)benzonitrile
29822-79-5

4-(2-phenylethynyl)benzonitrile

Conditions
ConditionsYield
With copper(l) iodide; diethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 30h;100%
With 1,4-diaza-bicyclo[2.2.2]octane; PdCl2[4,4'-bis(n-C10F21CH2OCH2)-2,2'-bipyridine] In N,N-dimethyl-formamide at 140℃; for 0.67h; Catalytic behavior; Sonogashira Cross-Coupling; Microwave irradiation;100%
With pyrrolidine In water at 100℃; for 24h;99%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-[2-(trimethylsilyl)ethynyl]benzonitrile
75867-40-2

4-[2-(trimethylsilyl)ethynyl]benzonitrile

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene at 20℃; Sonogashira coupling; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 45℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In water; ethyl acetate at 50℃;96%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

Conditions
ConditionsYield
With copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane for 24h; Reflux;100%
With iodine; sodium iodide In acetonitrile at 20℃; for 72h; Inert atmosphere; UV-irradiation; Green chemistry;86%
With tributylphosphine; sodium iodide; nickel dibromide In 1-methyl-pyrrolidin-2-one at 180℃; for 3h; Finkelstein reaction; Inert atmosphere; Molecular sieve; Sealed tube;84%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

5-(4-bromophenyl)-1H-tetrazole
50907-23-8

5-(4-bromophenyl)-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; copper(II) sulfate In dimethyl sulfoxide at 140℃; for 1h;100%
With sodium azide; ammonium cerium (IV) nitrate In N,N-dimethyl-formamide at 110℃; for 6h; Inert atmosphere; Green chemistry;98%
With bismuth(III) chloride; sodium azide In water; isopropyl alcohol at 160℃; for 4h; Microwave irradiation;98%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

phenylboronic acid
98-80-6

phenylboronic acid

4-cyano-1,1'-biphenyl
2920-38-9

4-cyano-1,1'-biphenyl

Conditions
ConditionsYield
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 6h; Suzuki cross-coupling;100%
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; for 1h; Kinetics; Product distribution; Further Variations:; Reaction partners; Suzuki cross-coupling;100%
With [(5-tBuC6H3-2-OH)CH2(μ-NC4H8N)CH2(5-tBuC6H3-2-OH)]; palladium diacetate; potassium carbonate In methanol at 20℃; Suzuki-Miyaura cross-coupling; Aerobic conditions;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

sodium 4-methoxyphenolate
1122-95-8

sodium 4-methoxyphenolate

4-(4-methoxyphenoxy)benzonitrile
78338-68-8

4-(4-methoxyphenoxy)benzonitrile

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 115℃; for 18h;100%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 30h;92%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

sodium phenoxide
139-02-6

sodium phenoxide

4-phenoxybenzonitrile
3096-81-9

4-phenoxybenzonitrile

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 115℃; for 18h;100%
With CF3-DPPF; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 20h;79.6%
With CF3-DPPF ligand; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 30h; Product distribution; various DPPF ligands for the Pd-catalyzed formation of diaryl ethers;
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

4-(4-cyanophenyl)-benzaldehyde
50670-55-8

4-(4-cyanophenyl)-benzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; Schlenk technique; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; Schlenk technique; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Suzuki Coupling; Reflux; Inert atmosphere;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

3-formyl-4-methoxyphenylboronic acid

3-formyl-4-methoxyphenylboronic acid

3'-formyl-4'-methoxybiphenyl-4-carbonitrile
408372-36-1

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

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.00833333h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene at 80℃; for 12h; Suzuki coupling;70%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 80℃; for 12h;70%
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0166667h; Catalytic behavior; Suzuki-Miyaura Coupling;100 %Chromat.
With potassium carbonate In water; isopropyl alcohol at 80℃; for 0.0833333h; Suzuki-Miyaura Coupling;84 %Chromat.
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

sodium 4-methylphenoxide
1121-70-6

sodium 4-methylphenoxide

4-(4'-methylphenoxy)benzonitrile
37563-42-1

4-(4'-methylphenoxy)benzonitrile

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 115℃; for 18h;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

sodium 4-chlorophenolate
1193-00-6

sodium 4-chlorophenolate

4-(4'-chlorophenoxy)benzonitrile
74448-92-3

4-(4'-chlorophenoxy)benzonitrile

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 115℃; for 18h;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4-(naphthalen-1-yl)benzonitrile
27331-37-9

4-(naphthalen-1-yl)benzonitrile

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0166667h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;100%
With potassium tert-butylate In ethanol; water at 25℃; for 1h; Suzuki-Miyaura Coupling;95%
With palladium on silica; potassium hydroxide In water for 0.116667h; Suzuki Coupling; Microwave irradiation; Green chemistry;93%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

hexafluoroacetone perfluorobutyrylimine
59857-56-6

hexafluoroacetone perfluorobutyrylimine

2-(4-bromophenyl)-6-(heptafluoropropyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine
491859-18-8

2-(4-bromophenyl)-6-(heptafluoropropyl)-4,4-bis(trifluoromethyl)-4H-1,3,5-oxadiazine

Conditions
ConditionsYield
In diethyl ether100%
trans-3-{[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzeneboronic acid

trans-3-{[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzeneboronic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

trans-tert-butyl {4-[(4'-cyano-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

trans-tert-butyl {4-[(4'-cyano-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Conditions
ConditionsYield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 20 - 120℃; for 1.75h; Suzuki Coupling; Microwave irradiation;100%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 20 - 120℃; for 0.75 - 1.75h; Suzuki Coupling; Microwave irradiation 150 W;
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 80 - 120℃; for 1.5h; Suzuki Coupling; Microwave irradiation;
trans-3-{[4-(Boc-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzeneboronic acid
945996-91-8

trans-3-{[4-(Boc-methyl-amino)-cyclohexylamino]-methyl}-4-methoxy-benzeneboronic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

trans-tert-butyl {4-[(4'-cyano-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate
1025060-99-4

trans-tert-butyl {4-[(4'-cyano-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Conditions
ConditionsYield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 80 - 120℃; for 0.5 - 1.5h; Suzuki Coupling; microwave irradiation;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

1,2-bis(4-bromophenyl)acetylene
2789-89-1

1,2-bis(4-bromophenyl)acetylene

Conditions
ConditionsYield
With hex-3-yne; NW(OC(CF3)2Me)3(DME) In toluene at 95℃; for 15h; Inert atmosphere;100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4'-tert-butyl-biphenyl-4-carbonitrile
192699-51-7

4'-tert-butyl-biphenyl-4-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 0.0166667h; Catalytic behavior; Suzuki-Miyaura Coupling; Green chemistry;100%
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.0833333h; Suzuki cross-coupling;99%
With 4C27H21N9O6*12NO3(1-)*6Pd(2+)*6C12H10; potassium carbonate In ethanol; water at 55℃; for 10h; Suzuki-Miyaura Coupling;95%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(imidazo[1,2-a]pyridin-3-yl)benzonitrile
59182-08-0

4-(imidazo[1,2-a]pyridin-3-yl)benzonitrile

Conditions
ConditionsYield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
With sodium acetate In N,N-dimethyl acetamide at 166℃; for 12h; Inert atmosphere; Sonication; regioselective reaction;95%
With palladium 10% on activated carbon; potassium acetate In N,N-dimethyl acetamide at 150℃; for 16h; Solvent; Inert atmosphere;94%
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;80%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanobenzenethiol
36801-01-1

4-cyanobenzenethiol

Conditions
ConditionsYield
Stage #1: 4-bromobenzenecarbonitrile With caesium carbonate; copper(II) sulfate In dimethyl sulfoxide for 0.166667h; Inert atmosphere;
Stage #2: With ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere;		100%
With copper(ll) sulfate pentahydrate; caesium carbonate; ethane-1,2-dithiol In dimethyl sulfoxide at 110℃; for 20h; Inert atmosphere;87%
Multi-step reaction with 2 steps
1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine / toluene / 14 h / 120 °C / Inert atmosphere
2: sodium methylate / methanol; mineral oil / 14 h / 0 - 20 °C
View Scheme
Stage #1: 4-bromobenzenecarbonitrile With TurboGrignard In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

(2-cyclopropylethynyl)trimethylsilane
81166-84-9

(2-cyclopropylethynyl)trimethylsilane

4‐(2‐cyclopropylethynyl)benzonitrile
1208119-65-6

4‐(2‐cyclopropylethynyl)benzonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenecarbonitrile With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; cesium fluoride In water at 20℃; for 0.25h; Sealed tube; Inert atmosphere;
Stage #2: (2-cyclopropylethynyl)trimethylsilane In water at 80℃; for 16h; Sealed tube; Inert atmosphere;		100%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

potassium 1-benzyl-1H-[1,2,3]-triazole-4-yltrifluoroborate

potassium 1-benzyl-1H-[1,2,3]-triazole-4-yltrifluoroborate

4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzonitrile
1262782-76-2

4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate In ethanol at 85℃; for 18h; Reagent/catalyst; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;99.9%

4-Bromobenzonitrile Chemical Properties

IUPAC Name:  4-Bromobenzonitrile
Synonyms of 4-Bromobenzonitrile (CAS NO.623-00-7): 1-Bromo-4-cyanobenzene ; p-Bromobenzonitrile ; Benzonitrile, 4-bromo- ; Benzonitrile, p-bromo- (8CI)
CAS NO: 623-00-7
Molecular Formula: C7H4BrN
Molecular Weight: 182.02
Molecular Structure:
EINECS: 210-764-9
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 23.79 Å2
Index of Refraction: 1.606
Molar Refractivity: 39.04 cm3
Molar Volume: 113.1 cm3
Surface Tension: 52.1 dyne/cm
Density: 1.6 g/cm3
Flash Point: 97 °C
Enthalpy of Vaporization: 47.36 kJ/mol
Boiling Point: 236.8 °C at 760 mmHg
Vapour Pressure: 0.0464 mmHg at 25°C 
Melting Point: 110-115 °C(lit.)
Appearance: white to light yellow powder or flakes
Product Categories of 4-Bromobenzonitrile (CAS NO.623-00-7): FINE Chemical & INTERMEDIATES;blocks;Bromides;Carboxes;Halides;Phenyls & Phenyl-Het;Nitrile;Nitriles;Miscellaneous;Bromine Compounds;Benzonitriles (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Phenyls & Phenyl-Het;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds

4-Bromobenzonitrile Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   Farmaco, Edizione Scientifica. Vol. 41, Pg. 41, 1986.
mouse LD50 oral 237mg/kg (237mg/kg)   Journal of Medicinal Chemistry. Vol. 21, Pg. 906, 1978.

4-Bromobenzonitrile Safety Profile

Safety Information about 4-Bromobenzonitrile (CAS NO.623-00-7):
Hazard Codes:HarmfulXn,Xi ToxicT
Risk Statements: 36/37/38-20/21/22
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 61-36/37/39-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3439 6.1/PG 3
WGK Germany: 2
RTECS: DI2460000
Hazard Note: Toxic/Irritant
HazardClass: 6.1
PackingGroup: III
HS Code: 29269095

4-Bromobenzonitrile Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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