Product Name

  • Name

    4-CYANOBENZAMIDE

  • EINECS 221-223-1
  • CAS No. 3034-34-2
  • Article Data97
  • CAS DataBase
  • Density 1.24 g/cm3
  • Solubility
  • Melting Point 227ºC
  • Formula C8H6 N2 O
  • Boiling Point 350.2 ºC at 760 mmHg
  • Molecular Weight 146.148
  • Flash Point 165.6 ºC
  • Transport Information
  • Appearance Beige powder
  • Safety Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic vapors of NOx.
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 3034-34-2 (4-CYANOBENZAMIDE)
  • Hazard Symbols Xn
  • Synonyms Benzamide,p-cyano- (6CI,7CI,8CI); 4-Cyanobenzamide; p-Cyanobenzamide
  • PSA 66.88000
  • LogP 1.35748

Synthetic route

4-cyanobenzaldehyde oxime
52707-54-7, 52707-59-2, 64847-77-4

4-cyanobenzaldehyde oxime

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With Cu(II) on nano silica functionalized triazine dendrimer In water at 20℃; for 0.5h; Beckmann Rearrangement; Green chemistry;98%
With Cu(II)-metformin immobilized ongraphene oxide In water at 100℃; for 0.5h; Beckmann Rearrangement; Green chemistry;96%
With [Ru(κ(3)-tpy)(κ(1)-P-PPh2Py)Cl2] In toluene for 12h; Beckmann rearrangement; Reflux;80%
With Cu(II) complex on SiO2-coated Fe3O4 nanoparticles at 80℃; for 1h; Beckmann Rearrangement; Green chemistry;80%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzaldehyde With hydroxylamine hydrochloride; sodium hydrogencarbonate In water
Stage #2: In water at 100℃; for 10h;		98%
With hydroxylamine hydrochloride; sodium carbonate In water at 80℃; for 48h;96%
With hydroxylamine hydrochloride; sodium carbonate In water at 80℃; for 22h; Green chemistry;95%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-iodobenzamide
3956-07-8

4-iodobenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 10h; Sealed tube; Inert atmosphere;98%
4-Cyanobenzyl alcohol
874-89-5

4-Cyanobenzyl alcohol

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; silver trifluoroacetate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 8℃; for 9h; Reagent/catalyst; Solvent;96.2%
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; hydroxylamine hydrochloride; iodine; potassium carbonate In 1,2-dichloro-ethane at 90℃; for 32h;83%
terephthalonitrile
623-26-7

terephthalonitrile

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
Stage #1: terephthalonitrile With Br(1-)*C24H30N4Rh(1+); water In isopropyl alcohol at 25℃; for 0.5h; Inert atmosphere;
Stage #2: With potassium tert-butylate In isopropyl alcohol at 25℃; for 12h; Inert atmosphere;		96%
With water In dimethyl sulfoxide at 100℃; Green chemistry;96%
With sodium tetrahydroborate In ethanol; water at 80℃; for 4h; regioselective reaction;94%
4-cyano-N-phenyl-N-tosylbenzamide

4-cyano-N-phenyl-N-tosylbenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With ammonium carbonate In dimethyl sulfoxide at 25℃; for 6h;85%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

p-bromobenzamide
698-67-9

p-bromobenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 10h; Schlenk technique; Inert atmosphere;82%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

p-bromobenzamide
698-67-9

p-bromobenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube;82%
para-methylbenzamide
619-55-6

para-methylbenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 2,4,6-triphenylpyrylium tetrafluoroborate; oxygen; ammonium bromide In acetonitrile at 40℃; under 750.075 Torr; for 24h; Molecular sieve; Irradiation;82%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

4-chlorobenzamide
619-56-7

4-chlorobenzamide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube;80%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Inert atmosphere; Sealed tube;80%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

A

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

B

sodium 4-cyanobenzoate
17264-66-3

sodium 4-cyanobenzoate

Conditions
ConditionsYield
Stage #1: 4-cyanobenzaldehyde With ammonia at -33℃; for 1h; Inert atmosphere;
Stage #2: With potassium permanganate at -33℃; for 1h; Inert atmosphere; Reflux;
Stage #3: With sodium sulfite		A 78%
B 20%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

A

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

B

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzaldehyde With ammonia at -33℃; for 1h; Inert atmosphere;
Stage #2: With potassium permanganate for 1h; Inert atmosphere; Reflux;		A n/a
B 78%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With ammonium chloride; N-ethyl-N,N-diisopropylamine; 2-(1-oxypyridin-2-yl)-1,1,3,3-tetramethylisothiouronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.5h;77%
With tris[2-phenylpyridinato-C2,N]iridium(III); dipotassium hydrogenphosphate; borane-ammonia complex; di-tert-butyl dicarbonate; magnesium chloride In acetonitrile at 20℃; for 36h; Schlenk technique; Irradiation; Green chemistry;58%
Multi-step reaction with 2 steps
1: (COCl)2, DMF / CH2Cl2 / Heating
2: conc. NH4OH / ethyl acetate / 0.17 h
View Scheme
4-cyanobenzoyl chlorIde
6068-72-0

4-cyanobenzoyl chlorIde

methylamine
74-89-5

methylamine

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice;76%
4-(2,6-dioxopiperidine-1-carbonyl)benzonitrile

4-(2,6-dioxopiperidine-1-carbonyl)benzonitrile

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With lithium hydroxide monohydrate In water at 20℃; for 2h;76%
terephthalonitrile
623-26-7

terephthalonitrile

A

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

B

terephthalamide
3010-82-0

terephthalamide

Conditions
ConditionsYield
With water; palladium diacetate; acetic acid; scandium tris(trifluoromethanesulfonate) at 30℃; for 24h;A 65%
B 18%
With chitosan-supported ruthenium catalyst (ChRu) In water at 120℃; for 1h; Microwave irradiation; Sealed tube; Overall yield = 7 %;
With nitrile hydratase from Rhodococcus rhodochrous J1 W72Y mutant In aq. phosphate buffer at 35℃; for 4h; pH=7.4; Reagent/catalyst; Enzymatic reaction; regioselective reaction;
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

carbon monoxide
201230-82-2

carbon monoxide

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With (1,3-(dicyclohexylphosphino)propane )Pd(ethylene); ammonia; potassium carbonate In dimethyl sulfoxide at 110℃; under 450 Torr; for 24h; Schlenk technique; Inert atmosphere;60%
With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 130℃; under 3000.3 Torr; for 20h; Autoclave;32 %Chromat.
With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 130℃; under 1500.15 Torr; for 20h;30 %Chromat.
terephthalaldehyde oxime
69386-99-8, 18705-39-0

terephthalaldehyde oxime

A

terephthalonitrile
623-26-7

terephthalonitrile

B

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With nickel(II) chloride dihydrate In acetonitrile at 80℃; Molecular sieve; Inert atmosphere;A 58%
B 42%
formic acid
64-18-6

formic acid

4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With palladium diacetate; ammonium bicarbonate; dicyclohexyl-carbodiimide; triphenylphosphine In acetonitrile at 100℃; Inert atmosphere;55%
4-cyanophenyl methyl ketone
1443-80-7

4-cyanophenyl methyl ketone

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Conditions
ConditionsYield
With sodium azide; iodine; sodium hydrogencarbonate In water at 100℃; for 2h;53%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
96%
With sodium nitrite In sulfuric acid95%
94%
With acetic anhydride; acetic acid; sodium nitrite In water92%
With sulfuric acid; acetic acid; sodium nitrite In water86%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

1-(4-cyanophenyl)urea
86065-51-2

1-(4-cyanophenyl)urea

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; ammonium carbamate In 2,2,2-trifluoroethanol at 0 - 20℃; for 23.5h; Reagent/catalyst; Solvent; Hofmann Rearrangement; Inert atmosphere;95%
4-chloro-2-(trichloromethyl)quinazoline
3137-63-1

4-chloro-2-(trichloromethyl)quinazoline

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-cyano-N-(2-trichloromethylquinazolin-4-yl)benzamide

4-cyano-N-(2-trichloromethylquinazolin-4-yl)benzamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;95%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-(aminomethyl)benzamide
369-53-9

4-(aminomethyl)benzamide

Conditions
ConditionsYield
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;91%
With formic acid; palladium 10% on activated carbon; triethylamine In tetrahydrofuran at 40℃; for 3h;98 %Chromat.
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

diphenyl acetylene
501-65-5

diphenyl acetylene

C36H22N2O
1253388-71-4

C36H22N2O

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 115℃; for 10h; Inert atmosphere;90%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With iron(II) chloride tetrahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In tetrahydrofuran at 70℃; for 2h;90%
With diethyl chlorophosphate at 120℃; for 0.25h; Neat (no solvent);86%
Stage #1: 4-cyanobenzamide With N-methylbenzamide; phenylsilane; C28H18ClMnN2O2; potassium tert-butylate In tetrahydrofuran at 50℃; Inert atmosphere; Glovebox; Sealed tube;
Stage #2: With sodium hydroxide In tetrahydrofuran for 2h; Inert atmosphere; Glovebox; Sealed tube;
Stage #3: Glovebox; Inert atmosphere;		82%
at 315℃; for 1h; Temperature;72%
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; zinc trifluoromethanesulfonate In tetrahydrofuran at 70℃; for 24h; chemoselective reaction;
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-Amidinobenzamide
54050-86-1

4-Amidinobenzamide

Conditions
ConditionsYield
With sodium amide In dimethyl sulfoxide Reagent/catalyst; Solvent; Sealed tube;85%
With hydrogenchloride; ethanol; benzene Behandeln des Reaktionsprodukts mit aethanol. Ammoniak;
ethylthioacetic acid methyl ester
2432-51-1

ethylthioacetic acid methyl ester

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

N-butyryl-4-cyanobenzamide
1181384-68-8

N-butyryl-4-cyanobenzamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzamide With N-Bromosuccinimide; iron(II) chloride In acetonitrile at 20℃; for 0.0166667h;
Stage #2: ethylthioacetic acid methyl ester In acetonitrile at 45℃; for 20h;		85%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

N,N-Boc2-4-cyanobenzamide

N,N-Boc2-4-cyanobenzamide

Conditions
ConditionsYield
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;85%
With dmap In acetonitrile at 20℃; for 15h; Inert atmosphere; Sealed tube;85%
With dmap In dichloromethane at 0 - 23℃; Inert atmosphere;84.5%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

N-(4-cyanobenzoyl)-N'-(4-cyanophenyl)urea

N-(4-cyanobenzoyl)-N'-(4-cyanophenyl)urea

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1h; Ambient temperature;83%
1-iodocyclohexane
626-62-0

1-iodocyclohexane

4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-cyano-N-cyclohexylbenzamide

4-cyano-N-cyclohexylbenzamide

Conditions
ConditionsYield
Stage #1: Cyclohexyl iodide; 4-cyanobenzamide With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;		83%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

terephthalamide
3010-82-0

terephthalamide

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 90℃; for 17h;82%
With potassium tert-butylate In tert-butyl alcohol at 20℃; for 12h; Solvent; Inert atmosphere;78%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

Hexafluoroacetone
684-16-2

Hexafluoroacetone

4-cyano-N-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)benzamide

4-cyano-N-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)benzamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzamide; Hexafluoroacetone With pyridine In benzene at 20℃; for 0.5h;
Stage #2: With thionyl chloride In benzene at 20℃; for 2h;		82%

4-CYANOBENZAMIDE Chemical Properties

IUPAC Name: 4-Cyanobenzamide
Synonyms: 4-Cyanobenamide ; 4-Cyano-benzamid;benzamide, 4-cyano- ; Cyanobenzamide ; P-Cyano-benzamid ; P-Cyano benzamide ; 4-Cyanobenzamide ; Benzamide, 4-cyano- (9ci)
Product Categories: AMIDE;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatic Building Blocks
CAS NO: 3034-34-2
Molecular Formula: C8H6N2O
Molecular Weight: 146.15
Molecular Structure:
EINECS: 221-223-1 Mol
File: 3034-34-2.mol
Index of Refraction: 1.592
Surface Tension: 59.9 dyne/cm
Density: 1.24 g/cm3
Flash Point: 165.6 °C
Melting point: 227 °C
Enthalpy of Vaporization: 59.48 kJ/mol
Boiling Point: 350.2 °C at 760 mmHg
Vapour Pressure: 4.46E-05 mmHg at 25°C
Appearance: 4-Cyanobenzamide (CAS NO.3034-34-2) is beige powder.

4-CYANOBENZAMIDE Toxicity Data With Reference

1.    

ipr-rat LD50:609 mg/kg

     APFRAD    Annales Pharmaceutiques Francaises. 48 (1990),23.
2.    

orl-mus LD :>1620 mg/kg

     APFRAD    Annales Pharmaceutiques Francaises. 41 (1983),391.
3.    

ipr-mus LD50:783 mg/kg

     APFRAD    Annales Pharmaceutiques Francaises. 48 (1990),23.

4-CYANOBENZAMIDE Safety Profile

Risk Statements 20/21/22-36/37/38
R20/21/22: 4-Cyanobenzamide (CAS NO.3034-34-2) is harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: When 4-Cyanobenzamide (CAS NO.3034-34-2) is used ,wear suitable gloves and eye/face protection.
RIDADR 3439
RTECS CV2484500

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