Product Name

  • Name

    3-Aminobenzonitrile

  • EINECS 218-800-5
  • CAS No. 2237-30-1
  • Article Data141
  • CAS DataBase
  • Density 1.14 g/cm3
  • Solubility
  • Melting Point 48-53 °C(lit.)
  • Formula C7H6N2
  • Boiling Point 290 °C at 760 mmHg
  • Molecular Weight 118.138
  • Flash Point 129.2 °C
  • Transport Information
  • Appearance brown crystalline solid
  • Safety 36/37-36-26
  • Risk Codes 20/21/22-43-22-36/37/38
  • Molecular Structure Molecular Structure of 2237-30-1 (3-Aminobenzonitrile)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Benzonitrile,m-amino- (6CI,7CI,8CI);Benzonitrile, 3-amino-;3-Cyanoaniline;3-Cyanophenylamine;NSC 7626;m-Aminobenzonitrile;m-Cyanoaniline;
  • PSA 49.81000
  • LogP 1.72168

Synthetic route

3-nitrobenzonitrile
619-24-9

3-nitrobenzonitrile

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry;99%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;99%
With maghemite; methylhydrazine In ethanol at 60℃; for 0.2h; Sealed tube; Inert atmosphere; chemoselective reaction;99%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

3-bromoaniline
591-19-5

3-bromoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere;98%
(3-cyano-phenyl)-carbamic acid 4-trifluoromethyl-benzyl ester

(3-cyano-phenyl)-carbamic acid 4-trifluoromethyl-benzyl ester

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; ethyl acetate at 20℃; for 2.16667h; Hydrogenolysis;97%
m-aminobenzaldehyde
1709-44-0

m-aminobenzaldehyde

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With aluminum oxide; hydroxylamine hydrochloride; methanesulfonyl chloride at 100℃; for 0.333333h;97%
Multi-step reaction with 2 steps
1: NH2OH*HCl; ZnO / Heating
2: 90 percent / CH3COCl; ZnO / 0.33 h / Heating
View Scheme
3-iodobenzonitrile
69113-59-3

3-iodobenzonitrile

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With copper(l) iodide; ammonia; potassium carbonate; L-proline In water; dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere;97%
3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
Stage #1: 3-cyanobromobenzene With 2,2,2-trifluoroacetamide; potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In 1,4-dioxane at 75℃;
Stage #2: With methanol In 1,4-dioxane at 75℃; Further stages.;		95%
With ammonium hydroxide; copper(l) iodide; phosphate potassium salt In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;50%
Stage #1: 3-cyanobromobenzene With polystyrene Rink amine resin; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; tert-butyl alcohol at 80℃; for 20h;
Stage #2: In dichloromethane for 0.75h; Further stages.;
With sodium azide; copper; L-proline In water; dimethyl sulfoxide at 150℃; under 37503.8 Torr; for 0.583333h; Flow reactor; chemoselective reaction;
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-chloro-aniline
108-42-9

3-chloro-aniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; sodium carbonate; triethylamine In water; acetonitrile at 70℃; for 18h;95%
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;91%
potassium ferrocyanide

potassium ferrocyanide

m-aminobenzaldehyde
1709-44-0

m-aminobenzaldehyde

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With Aloe vera mediated silver nanoparticles In water at 50℃; for 0.5h; Green chemistry;95%
3-azidobenzonitrile
31656-78-7

3-azidobenzonitrile

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 2.4h; Heating;94%
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 1h; Reduction;93%
With Ca(BH2S3)2 In tetrahydrofuran for 0.8h; Reduction; Heating;90%
With formic acid; 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 12h; Irradiation;91 %Chromat.
3-Aminobenzamide
3544-24-9

3-Aminobenzamide

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With lead acetate In dichloromethane for 12h; Reflux;93%
With thionyl chloride In toluene at 90 - 100℃; Temperature; Solvent;91.3%
With 3 Angstroem melecular sieves at 180 - 500℃; under 0.005 Torr; for 0.5h; Pyrolysis;79%
Stage #1: 3-Aminobenzamide With C39H45N2 In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;		40%
m-aminobenzylamine
4403-70-7

m-aminobenzylamine

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;92.8%
With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindoline)(PPh3)2 In toluene at 110℃; for 24h; Inert atmosphere; Glovebox; chemoselective reaction;54%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-bromoaniline
591-19-5

3-bromoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; potassium tert-butylate; triethylamine; bis(dibenzylideneacetone)-palladium(0) In dichloromethane; water; acetonitrile at 50℃; for 24h; Inert atmosphere;91%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 15h;87%
3-nitrobenzonitrile
619-24-9

3-nitrobenzonitrile

A

3-Aminobenzamide
3544-24-9

3-Aminobenzamide

B

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With graphitic carbon nitride; hydrazine hydrate In water at 80℃; for 20h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;A 91%
B 9%
m-aminobenzaldehyde oxime
2835-66-7

m-aminobenzaldehyde oxime

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With acetyl chloride; zinc(II) oxide for 0.333333h; Heating;90%
benzonitrile
100-47-0

benzonitrile

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; CH5NO3S*CHF3O3S at 60℃; for 2h;89%
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; KNO3
2: tin dichloride; concentrated hydrochloric acid
View Scheme
potassium (3-cyanophenyl)trifluoroborate

potassium (3-cyanophenyl)trifluoroborate

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With ammonium hydroxide; copper(ll) sulfate pentahydrate; sodium hydroxide In water at 25℃; for 24h;88%
3-nitrobenzylamine hydrochloride
26177-43-5

3-nitrobenzylamine hydrochloride

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;87%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-aminophenyl tosylate
3865-15-4

3-aminophenyl tosylate

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate In water; tert-butyl alcohol at 80℃; for 18h; Inert atmosphere;85%
3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

A

C14H9N3

C14H9N3

B

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere; Schlenk technique;A n/a
B 85%
3-Iodoaniline
626-01-7

3-Iodoaniline

potassium ferrocyanide

potassium ferrocyanide

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 5h;79%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-Iodoaniline
626-01-7

3-Iodoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; copper(II) bis(trifluoromethanesulfonate); potassium carbonate at 130℃; for 24h;78%
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h;77%
potassium cyanide

potassium cyanide

3-bromoaniline
591-19-5

3-bromoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube;
Stage #2: m-Bromoaniline With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;		77%
3-Bromonitrobenzene
585-79-5

3-Bromonitrobenzene

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

A

nitrobenzene
98-95-3

nitrobenzene

B

m-cyanoaniline
2237-30-1

m-cyanoaniline

C

3-nitrobenzonitrile
619-24-9

3-nitrobenzonitrile

Conditions
ConditionsYield
Stage #1: m-nitrobromobenzene With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In N,N-dimethyl-formamide at 110℃; for 6h;
Stage #2: 2-hydroxy-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 60h;		A 10.0 % Chromat.
B 3.5 % Chromat.
C 75%
...Expand
2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

3-chloro-aniline
108-42-9

3-chloro-aniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; XPhos In butan-1-ol at 100℃; for 2h; Inert atmosphere;73%
3-<(trifluoromethanesulfonyl)oxy>benzonitrile
66152-74-7

3-<(trifluoromethanesulfonyl)oxy>benzonitrile

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
Stage #1: 3-<(trifluoromethanesulfonyl)oxy>benzonitrile With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 12h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether		70%
copper(l) cyanide

copper(l) cyanide

3-bromoaniline
591-19-5

3-bromoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With L-proline In N,N-dimethyl-formamide at 120℃; for 45h; Rosenmund-von Braun reaction;69%
formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

3-bromoaniline
591-19-5

3-bromoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; palladium on activated charcoal; potassium carbonate; triphenylphosphine at 25 - 130℃; for 12.1667h;69%
sodium cyanide
773837-37-9

sodium cyanide

3-Iodoaniline
626-01-7

3-Iodoaniline

m-cyanoaniline
2237-30-1

m-cyanoaniline

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;63%
formaldehyd
50-00-0

formaldehyd

m-cyanoaniline
2237-30-1

m-cyanoaniline

3-(dimethylamino)benzonitrile
38803-30-4

3-(dimethylamino)benzonitrile

Conditions
ConditionsYield
With sodium cyanoborohydride In acetonitrile at 20℃; for 2h;100%
With sodium cyanoborohydride; acetic acid In tetrahydrofuran at 23 - 50℃; for 18h; Inert atmosphere;95%
With sodium cyanoborohydride; acetic acid In acetonitrile for 2h;94%
With sodium cyanoborohydride; acetic acid In water; acetonitrile for 2.5h; Ambient temperature;94%
With sodium cyanoborohydride In water; acetonitrile at 0 - 20℃; for 4h;92.9%
m-cyanoaniline
2237-30-1

m-cyanoaniline

3-Aminobenzamide
3544-24-9

3-Aminobenzamide

Conditions
ConditionsYield
With dihydrogen peroxide; hexadecyltrimethylammonium methanesulfonate; sodium hydroxide In water at 25℃; for 1h;100%
With Amberlyst A-26 (OH- form); dihydrogen peroxide In methanol at 20℃; for 1.7h; Hydrolysis;95%
With water at 150℃; under 5171.62 - 6205.94 Torr; for 0.5h; Inert atmosphere; Microwave irradiation;94%
m-cyanoaniline
2237-30-1

m-cyanoaniline

m-aminobenzylamine
4403-70-7

m-aminobenzylamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol100%
With C28H29Cl2CoNP2; hydrogen; sodium triethylborohydride In 1,4-dioxane at 80℃; under 37503.8 Torr; for 6h;75%
In methanol; palladium-carbon0.516 g (~100%)
m-cyanoaniline
2237-30-1

m-cyanoaniline

3-cyano-phenylhydrazine hydrochloride

3-cyano-phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 2h;		100%
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite
Stage #2: With hydrogenchloride; tin(ll) chloride		78%
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0 - 20℃; for 2h;
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite In water for 0.25h; Cooling with ice;
Stage #2: With tin(ll) chloride In water for 1h; Cooling with ice;		118 mg
2-chloro-5-nitro-4(1H)-pyrimidinone
282101-98-8

2-chloro-5-nitro-4(1H)-pyrimidinone

m-cyanoaniline
2237-30-1

m-cyanoaniline

C11H7N5O3

C11H7N5O3

Conditions
ConditionsYield
In 2-methoxy-ethanol at 100 - 110℃; for 3h;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

m-cyanoaniline
2237-30-1

m-cyanoaniline

3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile
1186230-83-0

3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester
1400997-47-8

(+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester

m-cyanoaniline
2237-30-1

m-cyanoaniline

(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester
1415757-41-3

(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; (+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester With sodium carbonate In dichloromethane; water at 20℃; for 2.5h;
Stage #2: m-cyanoaniline In dichloromethane; water at 20℃; for 2h;		100%
Stage #1: bis(trichloromethyl) carbonate; (+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester With sodium carbonate In dichloromethane; water at 20℃; for 2.5h;
Stage #2: m-cyanoaniline In dichloromethane; water at 20℃; for 2h;		100%
...Expand
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate
1400997-62-7

tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate

m-cyanoaniline
2237-30-1

m-cyanoaniline

tert-butyl (RS)-2-(3-chloro-4-(3-(3-cyanophenyl)ureido)phenyl)morpholine-4-carboxylate
1415757-42-4

tert-butyl (RS)-2-(3-chloro-4-(3-(3-cyanophenyl)ureido)phenyl)morpholine-4-carboxylate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate With sodium carbonate In dichloromethane; water at 20℃; for 2.5h;
Stage #2: m-cyanoaniline In dichloromethane; water at 20℃; for 2h;		100%
Stage #1: bis(trichloromethyl) carbonate; tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate With sodium carbonate In dichloromethane; water at 20℃; for 2.5h;
Stage #2: m-cyanoaniline In dichloromethane; water at 20℃; for 2h;		100%
...Expand
4-chloro-7-isothiocyanato-7-de(acetamide)colchicine
1267993-72-5

4-chloro-7-isothiocyanato-7-de(acetamide)colchicine

m-cyanoaniline
2237-30-1

m-cyanoaniline

4-chloro-N-[(3-cyanophenyl)thiocarbamoyl]deacetyl colchicine
1267990-93-1

4-chloro-N-[(3-cyanophenyl)thiocarbamoyl]deacetyl colchicine

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; Inert atmosphere;100%
1-(2,4-dinitrophenyl)-pyridinium chloride
4185-69-7

1-(2,4-dinitrophenyl)-pyridinium chloride

m-cyanoaniline
2237-30-1

m-cyanoaniline

1-(3-cyanophenyl)pyridin-1-ium chloride

1-(3-cyanophenyl)pyridin-1-ium chloride

Conditions
ConditionsYield
In ethanol; water at 150℃; for 1h; Microwave irradiation;100%
m-cyanoaniline
2237-30-1

m-cyanoaniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
214360-46-0

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions
ConditionsYield
With tert.-butylnitrite In acetonitrile at 0 - 80℃; for 2h;99.8%
With tert.-butylnitrite In acetonitrile at 0 - 80℃; for 2h;99.8%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;64%
With tert-butyl nitrite; benzoyl peroxide In acetonitrile MeCN, (CN)C6H4NH2 (1 mmol) and tBuONO (1.5 mmol) added to B2pin2 (1.2 mmol) and benzoyl peroxide (0.01 mmol), mixt. stirred at room temp. for 2 h; soln. concd. (under reduced pressure), residue chromd.;22%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

m-cyanoaniline
2237-30-1

m-cyanoaniline

N-(3-cyanophenyl)methanesulfonamide
50790-30-2

N-(3-cyanophenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 4h;99%
With pyridine In dichloromethane at 0 - 20℃; for 4h;99%
chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

m-cyanoaniline
2237-30-1

m-cyanoaniline

C31H24N2P2

C31H24N2P2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h;99%
cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

m-cyanoaniline
2237-30-1

m-cyanoaniline

3-(cyclohex-2-enylamino)benzonitrile

3-(cyclohex-2-enylamino)benzonitrile

Conditions
ConditionsYield
With [(9,9-Me2-4,5-(PPh2)2-xanthene]Pd(η3-allyl)Cl In tetrahydrofuran at 25℃; for 24h;99%
2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

m-cyanoaniline
2237-30-1

m-cyanoaniline

3-(4,5-dihydrothiazol-2-yl)aniline

3-(4,5-dihydrothiazol-2-yl)aniline

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 80℃; for 0.5h;99%
With tetrakis(μ2-α-methacrylate-O,O')-bis(H2O)-dicopper(II); sodium acetate at 80℃; for 5h; Neat (no solvent);84%
bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione
4314-19-6

bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione

m-cyanoaniline
2237-30-1

m-cyanoaniline

1-[(3-cyanophenyl)thiocarbamoyl]benzotriazole

1-[(3-cyanophenyl)thiocarbamoyl]benzotriazole

Conditions
ConditionsYield
In acetonitrile for 0.166667h; Milling; Green chemistry;99%
m-cyanoaniline
2237-30-1

m-cyanoaniline

N-(3-cyanophenyl)acetamide
58202-84-9

N-(3-cyanophenyl)acetamide

Conditions
ConditionsYield
With acetic anhydride In methanol at 20℃; for 1h;98.52%
m-cyanoaniline
2237-30-1

m-cyanoaniline

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

((3-cyanophenyl)amino)phenoxymethane-1-thione
302577-09-9

((3-cyanophenyl)amino)phenoxymethane-1-thione

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h; Condensation;98%
m-cyanoaniline
2237-30-1

m-cyanoaniline

3-azidobenzonitrile
31656-78-7

3-azidobenzonitrile

Conditions
ConditionsYield
Stage #1: m-cyanoaniline With hydrogenchloride In water at 0 - 5℃;
Stage #2: With sodium nitrite In water
Stage #3: With sodium azide In water at 0 - 5℃; for 1h; Further stages.;		98%
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite In methanol; water at 0℃; for 0.333333h;
Stage #2: With sodium azide In methanol; water at 20℃; for 2h;		90%
Stage #1: m-cyanoaniline With hydrogenchloride; sodium nitrite In water
Stage #2: With sodium azide In water at 0 - 5℃; for 24h;		85%
benzaldehyde
100-52-7

benzaldehyde

m-cyanoaniline
2237-30-1

m-cyanoaniline

N-(3-cyanophenyl)benzylamine

N-(3-cyanophenyl)benzylamine

Conditions
ConditionsYield
With 2-amino-4(3H)-quinazolinone; phenylsilane; acetic acid In neat (no solvent) at 20℃; for 5h; Green chemistry;98%
With copper(I) iodide; phenylsilane In ethanol at 80℃; for 4h;85%
m-cyanoaniline
2237-30-1

m-cyanoaniline

2-amino-6-O-(p-toluenesulfonyl)-9-[2-deoxy-3,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine
177533-37-8

2-amino-6-O-(p-toluenesulfonyl)-9-[2-deoxy-3,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine

N6-(3-cyanophenyl)-2,6-diamino-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine

N6-(3-cyanophenyl)-2,6-diamino-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate; DavePhos In 1,4-dioxane; tert-butyl alcohol at 110℃; for 0.5h;97%
diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

m-cyanoaniline
2237-30-1

m-cyanoaniline

diethyl 2-[((3-cyanophenyl)amino)methylene]malonate
59551-10-9

diethyl 2-[((3-cyanophenyl)amino)methylene]malonate

Conditions
ConditionsYield
at 110℃; for 0.75h;97%
In toluene at 110℃;95%
at 80℃; for 1h;
ethyl bromoacetate
105-36-2

ethyl bromoacetate

m-cyanoaniline
2237-30-1

m-cyanoaniline

ethyl 2-(3-cyanophenylamino)acetate
92316-76-2

ethyl 2-(3-cyanophenylamino)acetate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 6h; Heating / reflux;97%
With sodium carbonate In N,N-dimethyl-formamide at 70℃; for 5h;76%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

m-cyanoaniline
2237-30-1

m-cyanoaniline

3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile
1186230-83-0

3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

Conditions
ConditionsYield
In ethanol at 90℃; for 2h;97%
In ethanol for 2h; Reflux;87%
...Expand
sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

m-cyanoaniline
2237-30-1

m-cyanoaniline

N-(3-cyanophenyl)acetamide
58202-84-9

N-(3-cyanophenyl)acetamide

Conditions
ConditionsYield
With acetic anhydride96.3%

3-Aminobenzonitrile Chemical Properties

Molecule structure of 3-Aminobenzonitrile (CAS NO.2237-30-1):

IUPAC Name: 3-Aminobenzonitrile 
Molecular Weight: 118.13594 g/mol
Molecular Formula: C7H6N2 
Density: 1.14 g/cm3 
Melting Point: 48-53 °C(lit.)
Boiling Point: 288-290 °C
Flash Point: 112 °C
Index of Refraction: 1.59
Molar Refractivity: 34.93 cm3
Molar Volume: 103.4 cm3
Surface Tension: 54.3 dyne/cm 
Enthalpy of Vaporization: 52.93 kJ/mol
Vapour Pressure: 0.00213 mmHg at 25 °C
XLogP3: 1.1
H-Bond Donor: 1
H-Bond Acceptor: 2
Exact Mass: 118.053098
MonoIsotopic Mass: 118.053098
Topological Polar Surface Area: 49.8
Heavy Atom Count: 9
Canonical SMILES: C1=CC(=CC(=C1)N)C#N
InChI: InChI=1S/C7H6N2/c8-5-6-2-1-3-7(9)4-6/h1-4H,9H2
InChIKey: NJXPYZHXZZCTNI-UHFFFAOYSA-N
EINECS: 218-800-5
Product Categories: FINE Chemical & INTERMEDIATES;Amines and Anilines;Boron, Nitrile, Thio,& TM-Cpds;Aromatic Nitriles

3-Aminobenzonitrile Uses

 3-Aminobenzonitrile (CAS NO.2237-30-1) is used as a pharmaceutical intermediate.

3-Aminobenzonitrile Toxicity Data With Reference

1.    

mma-sat 100 mg/L

     ENMUDM    Environmental Mutagenesis. 5 (1983),803.
2.    

orl-qal LD50:562 mg/kg

     AECTCV    Archives of Environmental Contamination and Toxicology. 12 (1983),355.
3.    

orl-bwd LD50:562 mg/kg

     AECTCV    Archives of Environmental Contamination and Toxicology. 12 (1983),355.

3-Aminobenzonitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List.

3-Aminobenzonitrile Safety Profile

Hazard Codes: HarmfulXn, IrritantXi
Risk Statements: 20/21/22-43-22-36/37/38 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-36-26 
S36/37:Wear suitable protective clothing and gloves. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3276
WGK Germany: 3
RTECS: DI2454000
Hazard Note: Harmful
HazardClass: 6.1
PackingGroup: III
Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.

3-Aminobenzonitrile Specification

 3-Aminobenzonitrile (CAS NO.2237-30-1) is also named as 3-Cyanoaniline ; 4-14-00-01095 (Beilstein Handbook Reference) ; BRN 0636498 ; NSC 7626 ; m-Aminobenzonitrile ; m-Anthranilonitrile ; m-Cyanoaniline ; Benzonitrile, 3-amino- (9CI) ; Benzonitrile, m-amino- . 3-Aminobenzonitrile (CAS NO.2237-30-1) is brown crystalline solid. It is toxic. It is flammable by fire. It will produce toxic nitrile and nitrogen oxide gas by heat. So the storage environment should be ventilate, low-temperature and dry. Keep 3-Aminobenzonitrile separate from food, oxidant and acid.

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