2-Amino-5-methylbenzonitrile supplier

Name
2-Amino-5-Methyl-Benzonitrile
EINECS 625-328-7
CAS No. 5925-93-9
Article Data20
CAS DataBase
Density 1.1 g/cm³
Solubility
Melting Point 59-63 °C
Formula C₈H₈N₂
Boiling Point 294.6 °C at 760 mmHg
Molecular Weight 132.165
Flash Point 132 °C
Transport Information
Appearance
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms m-Tolunitrile,6-amino- (7CI,8CI);2-Amino-5-methylbenzonitrile;5-Methylanthranilonitrile;6-Amino-m-tolunitrile;NSC 51672;
PSA 49.81000
LogP 2.03008

Synthetic route

: 64113-86-6
2-nitro-5-methylbenzonitrile

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Stage #1: 2-nitro-5-methylbenzonitrile With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 30℃; for 1h; Stage #2: With sodium hydroxide In ethanol; water pH=7;	99%
With titanium(III) chloride In water; acetone for 0.5h;	92%
With sodium dithionite In water; acetonitrile at 0 - 25℃; for 0.5h;	78.4%

: 29289-13-2
2-iodo-4-methylaniline

: copper(l) cyanide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one for 24h; Reflux; Inert atmosphere;	91%
With 1-methyl-pyrrolidin-2-one for 24h; Reflux;	91%
Stage #1: 2-iodo-4-methylaniline; copper(l) cyanide In N,N-dimethyl-formamide at 130℃; for 3h; Stage #2: With sodium cyanide In water; N,N-dimethyl-formamide for 1h;	78%

: 3-(hydroxyimino)-5-methylindolin-2-one

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 125 - 135℃; for 2.5h;	85%

: 29289-13-2
2-iodo-4-methylaniline

: 544-92-3
copper(I) cyanide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 130℃; for 3h;	80%

: 583-68-6
2-bromo-p-toluidine

: 544-92-3
copper(I) cyanide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one for 1.25h; Heating / reflux;	60%

: 75-16-1
methylmagnesium bromide

: 156149-46-1
2-azido-5-methylbenzonitrile

A: 5925-93-9
2-amino-5-methylbenzonitrile

B: 1262111-18-1
3,4-dihydro-4-imino-3,6-dimethyl-1,2,3-benzotriazine

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	A 34% B 49%

...Expand

: 13208-98-5
5-methylisatin-3-oxime

: 5925-93-9
2-amino-5-methylbenzonitrile

: 5-chloromethyl-2-nitro-benzonitrile

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 150893-79-1
N-(2-cyano-4-methyl-phenyl)-2,2,2-trifluoro-acetamide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 12h;

: 29289-13-2
2-iodo-4-methylaniline

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethylformamide / 0.5 h / 20 °C 2: dimethylformamide / 0.5 h / 100 °C 3: aq. K2CO3 / methanol / 12 h / 20 °C View Scheme

: 784183-53-5
2,2,2-trifluoro-N-(2-iodo-4-methylphenyl)acetamide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 0.5 h / 100 °C 2: aq. K2CO3 / methanol / 12 h / 20 °C View Scheme

: 3113-72-2
5-methyl-2-nitrobenzoic acid

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) SOCl2; 2.) NH4OH / 1.) PhMe, reflux 2: SOCl2 / Heating 3: 92 percent / 15 percent TiCl3 / acetone; H2O / 0.5 h View Scheme
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; thionyl chloride / chloroform / Reflux 2: ammonium hydroxide / chloroform / 2 h / 20 °C / Cooling with ice 3: trichlorophosphate / chloroform / Reflux 4: tin(ll) chloride / ethanol / 1 h / Reflux View Scheme

: 4315-12-2
5-methyl-2-nitrobenzamide

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: 92 percent / 15 percent TiCl3 / acetone; H2O / 0.5 h View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / chloroform / Reflux 2: tin(ll) chloride / ethanol / 1 h / Reflux View Scheme

: 38939-88-7
2-chloro-4-methyl-1-nitrobenzene

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: various solvent(s) / 5 h / 160 °C 2: 51 percent / SnCl2*2H2O, conc. HCl / 0.25 h / below 40 deg C View Scheme

: 64407-07-4
3-(chloromethyl)benzonitrile

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; potassium nitrate 2: tin; fuming hydrochloric acid View Scheme

: 620-22-4
3-Methylbenzonitrile

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Nitrieren 2: tin; hydrochloric acid / <30 View Scheme
Multi-step reaction with 2 steps 1: (nitration) 2: Fe, AcOH View Scheme

: 106-49-0
p-toluidine

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine; sodium hydrogencarbonate / dichloromethane; water / 20 °C 2: 1-methyl-pyrrolidin-2-one / 24 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; iodine / water; dichloromethane / 14 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 130 °C 2.2: 1 h View Scheme

: 608-05-9
5-methyl-indole-2,3-dione

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / water / 0.67 h / Reflux 2: sodium carbonate / N,N-dimethyl-formamide / 2.5 h / 125 - 135 °C View Scheme

: 38818-49-4
5-methyl-2-nitrobenzoyl chloride

: 5925-93-9
2-amino-5-methylbenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide / chloroform / 2 h / 20 °C / Cooling with ice 2: trichlorophosphate / chloroform / Reflux 3: tin(ll) chloride / ethanol / 1 h / Reflux View Scheme

: 5925-93-9
2-amino-5-methylbenzonitrile

: 100-58-3
phenylmagnesium bromide

: 17852-28-7
2-amino-5-methylbenzophenone

Conditions

Conditions	Yield
With water In tetrahydrofuran; diethyl ether at 20℃; for 17.5h; Solvent; Temperature; Cooling with ice;	100%
With water In tetrahydrofuran at 0 - 20℃;

: 5925-93-9
2-amino-5-methylbenzonitrile

: 124-38-9
carbon dioxide

: 62484-16-6
6-methyl-1H-quinazoline-2,4-dione

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 110℃; under 15001.5 Torr; for 24h; Autoclave;	99%
With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 24h; Schlenk technique;	97%
With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24h;	97%

: 1H-indazole-5-sulfonyl chloride

: 5925-93-9
2-amino-5-methylbenzonitrile

: 1H-indazole-5-sulfonic acid (2-cyano-4-methylphenyl)amide

Conditions

Conditions	Yield
In acetonitrile at 100℃; Microwave irradiation;	99%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 2-(2-bromophenyl)malononitrile

: C17H12N4

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tert-butyl XPhos In toluene at 80℃; for 12h; Inert atmosphere;	98%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 108-94-1
cyclohexanone

: 7-methyl-1,2,3,4-tetrahydroacridin-9-amine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-amino-5-methylbenzonitrile; cyclohexanone With zinc(II) chloride at 150℃; for 0.166667h; Microwave irradiation; Stage #2: With hydrogenchloride In methanol; water at 20℃;	98%

: 32315-10-9
bis(trichloromethyl) carbonate

: 5925-93-9
2-amino-5-methylbenzonitrile

: 39576-82-4
6-methyl-2,4-dichloroquinazoline

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate With triethylamine; Triphenylphosphine oxide In chlorobenzene at 20℃; for 0.5h; Cooling with ice; Stage #2: 2-amino-5-methylbenzonitrile In chlorobenzene at 120℃; for 6h;	95.1%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 100-44-7
benzyl chloride

: 61871-81-6
1-(2-amino-5-methylphenyl)-2-phenylethan-1-one

Conditions

Conditions	Yield
Stage #1: benzyl chloride With iodine; magnesium In tetrahydrofuran at 60℃; for 1.5h; Sealed tube; Stage #2: 2-amino-5-methylbenzonitrile In tetrahydrofuran at 20℃; Sealed tube; Stage #3: With hydrogenchloride; water pH=1;	95%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 120802-00-8
methyl 4,4-difluoro-2-butynoate

: methyl 4-amino-2-(difluoromethyl)-6-methylquinoline-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-amino-5-methylbenzonitrile; methyl 4,4-difluoro-2-butynoate In methanol at 80℃; for 12h; Michael Addition; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 80℃; for 1h; Schlenk technique; regioselective reaction;	94%

: 64-18-6
formic acid

: 5925-93-9
2-amino-5-methylbenzonitrile

: 5-methyl-2-(6-methylquinazolin-4-one-3(4H)-yl)benzonitrile

Conditions

Conditions	Yield
at 70℃; for 16h; Temperature;	93.6%
Stage #1: formic acid; 2-amino-5-methylbenzonitrile at 80℃; for 12h; Stage #2: With water at 20℃; for 3h;

: 5925-93-9
2-amino-5-methylbenzonitrile

: 263713-35-5
2-(aminomethyl)-4-methylaniline

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere;	93%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 48.17h; Inert atmosphere;	61%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24.1667h; Inert atmosphere;	59%
With borane-THF In tetrahydrofuran Inert atmosphere; Reflux;	57%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 156149-46-1
2-azido-5-methylbenzonitrile

Conditions

Conditions	Yield
Stage #1: 2-amino-5-methylbenzonitrile With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With sodium azide; sodium acetate In water at 0 - 5℃; for 0.5h;	91%
With hydrogenchloride; sodium azide; sodium acetate; sodium nitrite 1.) water, 0-5 deg C, 10 min; 2.) water, 0-5 deg C, 0.5 h; Yield given. Multistep reaction;

: 5925-93-9
2-amino-5-methylbenzonitrile

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 62484-16-6
6-methyl-1H-quinazoline-2,4-dione

Conditions

Conditions	Yield
With zinc(II) chloride at 200℃; for 5h; sealed tube;	91%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 40545-33-3
2-amino-5-methylbenzamide

Conditions

Conditions	Yield
With water; potassium carbonate In water at 150℃; for 0.5h; Microwave irradiation;	90%
With water extract of pomelo, peel at 150℃; for 0.5h; Sealed tube; Green chemistry;	90%
With sulfuric acid at 20℃;	88%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 112245-13-3
(S)-tert-leucinol

: 2-(4-tert-butyl-4,5-dihydro-oxazol-2-yl)4-methylphenylamine

Conditions

Conditions	Yield
With zinc(II) chloride In chlorobenzene at 130℃; for 36h;	88%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 591-31-1
3-methoxy-benzaldehyde

: 2-(3-methoxyphenyl)-6-methylquinazolin-4(3H)-one

Conditions

Conditions	Yield
With water; iodine; sodium hydroxide at 20℃; for 12h; Electrochemical reaction;	87%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 100-52-7
benzaldehyde

: 21419-51-2
6-methyl-2-phenylquinazolin-4(3H)-one

Conditions

Conditions	Yield
With water; iodine; sodium hydroxide at 20℃; for 12h; Electrochemical reaction;	86%
With 1,10-Phenanthroline; caesium carbonate; copper dichloride In water at 80℃; for 12h;	84%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 100-51-6
benzyl alcohol

: 21419-51-2
6-methyl-2-phenylquinazolin-4(3H)-one

Conditions

Conditions	Yield
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate In toluene for 12h; Sealed tube; Reflux;	84%

: 5153-67-3
nitrostyrene

: 5925-93-9
2-amino-5-methylbenzonitrile

: 6-methyl-3-nitro-2-phenylquinolin-4-amine

Conditions

Conditions	Yield
With copper(I) bromide In dimethyl sulfoxide at 120℃; for 8h; Sealed tube;	84%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 541-41-3
chloroformic acid ethyl ester

: 1012369-77-5
(2-cyano-4-methyl-phenyl)-carbamic acid ethyl ester

Conditions

Conditions	Yield
for 6h; Reflux;	83%
for 6h; Heating;

: 117-80-6
2,3-Dichloro-1,4-naphthoquinone

: 5925-93-9
2-amino-5-methylbenzonitrile

: 1106822-12-1
C26H18N4O2

Conditions

Conditions	Yield
With potassium carbonate In ethanol at 80 - 90℃; for 15h;	83%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 1885-29-6
anthranilic acid nitrile

: 21419-51-2
6-methyl-2-phenylquinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: anthranilic acid nitrile With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; butyraldehyde oxime In para-xylene at 70℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: 2-amino-5-methylbenzonitrile In para-xylene at 110℃; for 4h; Inert atmosphere; Schlenk technique;	83%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 120-92-3
cyclopentanone

: 7-methyl-1H,2H,3H-cyclopenta[b]quinolin-9-amine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-amino-5-methylbenzonitrile; cyclopentanone With aluminum (III) chloride at 150℃; for 0.166667h; Microwave irradiation; Stage #2: With hydrogenchloride In methanol; water at 20℃;	83%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 5720-05-8
4-methylphenylboronic acid

: 78-39-7
Triethyl orthoacetate

: 2,6-dimethyl-4-(p-tolyl)quinazoline

Conditions

Conditions	Yield
With [2,2]bipyridinyl; palladium diacetate; acetic acid In N,N-dimethyl-formamide at 100℃; for 12h;	82%

...Expand

: 5925-93-9
2-amino-5-methylbenzonitrile

: 502-42-1
cycloheptanone

: 2-methyl-6H,7H,8H,9H,10H-cyclohepta[b]quinolin-11-amine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-amino-5-methylbenzonitrile; cycloheptanone With aluminum (III) chloride at 150℃; for 0.166667h; Microwave irradiation; Stage #2: With hydrogenchloride In methanol; water at 20℃;	81%

: 5925-93-9
2-amino-5-methylbenzonitrile

: 503-38-8
trichloromethyl chloroformate

: 39576-82-4
6-methyl-2,4-dichloroquinazoline

Conditions

Conditions	Yield
In acetonitrile at 130℃; for 12h;	80%

: 67-56-1
methanol

: 5925-93-9
2-amino-5-methylbenzonitrile

: 19181-53-4
6-methyl-3H-quinazolin-4-one

Conditions

Conditions	Yield
With cobalt(II) nitrate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; water; caesium carbonate at 150℃; for 24h; Inert atmosphere; Sealed tube;	80%

2-Amino-5-methylbenzonitrile Specification

The Benzonitrile,2-amino-5-methyl- with the CAS number 5925-93-9 is also called 5-Methylanthranilonitrile. Both the systematic name and IUPAC name are 2-amino-5-methylbenzonitrile. Its molecular formula is C₈H₈N₂. This chemical belongs to the following product categories: (1)C8 to C9; (2)Cyanides/Nitriles; (3)Nitrogen Compounds; (4)Aromatic.

The properties of the Benzonitrile,2-amino-5-methyl- are: (1)ACD/LogP: 1.86; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 27.03Å²; (7)Index of Refraction: 1.575; (8)Molar Refractivity: 39.56 cm³; (9)Molar Volume: 119.5 cm³; (10)Polarizability: 15.68×10^-24cm³; (11)Surface Tension: 50.7 dyne/cm; (12)Enthalpy of Vaporization: 53.43 kJ/mol; (13)Vapour Pressure: 0.0016 mmHg at 25°C.

While using this chemical, you should be very cautious. This chemical is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1cc(ccc1N)C
(2)InChI: InChI=1/C8H8N2/c1-6-2-3-8(10)7(4-6)5-9/h2-4H,10H2,1H3
(3)InChIKey: OZLMBXPYRDASTP-UHFFFAOYAK

Product Name

2-Amino-5-Methyl-Benzonitrile

Synthetic route

2-Amino-5-methylbenzonitrile Specification

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