5925-93-9

Basic information

• Product Name: 2-Amino-5-Methyl-Benzonitrile
• Synonyms: 4-Amino-3-cyanotoluene;2-Amino-5-methylbenzonitrile;2-azanyl-5-methyl-benzenecarbonitrile;2-Amino-5-methylbenzonitrile 97%;Benzonitrile, 2-amino-5-methyl-
• CAS NO: 5925-93-9
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16
• EINECS: 1806241-263-5
• Product Categories: Aromatic;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 5925-93-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 59-63 °C
• Boiling Point: 152°C/15mmHg(lit.)
• Flash Point: 132 °C
• Appearance: /Solid
• Density: 1.1 g/cm³
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 2.25±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-Methyl-Benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-Methyl-Benzonitrile(5925-93-9)
• EPA Substance Registry System: 2-Amino-5-Methyl-Benzonitrile(5925-93-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5925-93-9(Hazardous Substances Data)

Usage

Uses

2-Amino-5-methylbenzonitrile can be used in combination therapy to treat Mucopolysaccharidosis I.

InChI:InChI=1/C8H8N2/c1-6-2-3-8(10)7(4-6)5-9/h2-4H,10H2,1H3

Synthetic route

2-nitro-5-methylbenzonitrile (64113-86-6) → 2-amino-5-methylbenzonitrile (5925-93-9)

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%

2-iodo-4-methylaniline (29289-13-2) + copper(l) cyanide → 2-amino-5-methylbenzonitrile (5925-93-9)

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 → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2-iodo-4-methylaniline (29289-13-2) + copper(I) cyanide (544-92-3) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2-bromo-p-toluidine (583-68-6) + copper(I) cyanide (544-92-3) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

methylmagnesium bromide (75-16-1) + 2-azido-5-methylbenzonitrile (156149-46-1) → 2-amino-5-methylbenzonitrile (5925-93-9) + 3,4-dihydro-4-imino-3,6-dimethyl-1,2,3-benzotriazine (1262111-18-1)

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

5-methylisatin-3-oxime (13208-98-5) → 2-amino-5-methylbenzonitrile (5925-93-9)

5-chloromethyl-2-nitro-benzonitrile → 2-amino-5-methylbenzonitrile (5925-93-9)

Conditions	Yield
With hydrogenchloride; tin

N-(2-cyano-4-methyl-phenyl)-2,2,2-trifluoro-acetamide (150893-79-1) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2-iodo-4-methylaniline (29289-13-2) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2,2,2-trifluoro-N-(2-iodo-4-methylphenyl)acetamide (784183-53-5) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

5-methyl-2-nitrobenzoic acid (3113-72-2) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

5-methyl-2-nitrobenzamide (4315-12-2) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2-chloro-4-methyl-1-nitrobenzene (38939-88-7) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

3-(chloromethyl)benzonitrile (64407-07-4) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

3-Methylbenzonitrile (620-22-4) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

p-toluidine (106-49-0) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

5-methyl-indole-2,3-dione (608-05-9) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

5-methyl-2-nitrobenzoyl chloride (38818-49-4) → 2-amino-5-methylbenzonitrile (5925-93-9)

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

2-amino-5-methylbenzonitrile (5925-93-9) + phenylmagnesium bromide (100-58-3) → 2-amino-5-methylbenzophenone (17852-28-7)

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℃;

2-amino-5-methylbenzonitrile (5925-93-9) + carbon dioxide (124-38-9) → 6-methyl-1H-quinazoline-2,4-dione (62484-16-6)

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 + 2-amino-5-methylbenzonitrile (5925-93-9) → 1H-indazole-5-sulfonic acid (2-cyano-4-methylphenyl)amide

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

2-amino-5-methylbenzonitrile (5925-93-9) + 2-(2-bromophenyl)malononitrile → C17H12N4

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

2-amino-5-methylbenzonitrile (5925-93-9) + cyclohexanone (108-94-1) → 7-methyl-1,2,3,4-tetrahydroacridin-9-amine hydrochloride

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%

bis(trichloromethyl) carbonate (32315-10-9) + 2-amino-5-methylbenzonitrile (5925-93-9) → 6-methyl-2,4-dichloroquinazoline (39576-82-4)

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%

2-amino-5-methylbenzonitrile (5925-93-9) + benzyl chloride (100-44-7) → 1-(2-amino-5-methylphenyl)-2-phenylethan-1-one (61871-81-6)

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%

2-amino-5-methylbenzonitrile (5925-93-9) + methyl 4,4-difluoro-2-butynoate (120802-00-8) → methyl 4-amino-2-(difluoromethyl)-6-methylquinoline-3-carboxylate

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%

formic acid (64-18-6) + 2-amino-5-methylbenzonitrile (5925-93-9) → 5-methyl-2-(6-methylquinazolin-4-one-3(4H)-yl)benzonitrile

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;

2-amino-5-methylbenzonitrile (5925-93-9) → 2-(aminomethyl)-4-methylaniline (263713-35-5)

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%

2-amino-5-methylbenzonitrile (5925-93-9) → 2-azido-5-methylbenzonitrile (156149-46-1)

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;

2-amino-5-methylbenzonitrile (5925-93-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-methyl-1H-quinazoline-2,4-dione (62484-16-6)

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

2-amino-5-methylbenzonitrile (5925-93-9) → 2-amino-5-methylbenzamide (40545-33-3)

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%

2-amino-5-methylbenzonitrile (5925-93-9) + (S)-tert-leucinol (112245-13-3) → 2-(4-tert-butyl-4,5-dihydro-oxazol-2-yl)4-methylphenylamine

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

2-amino-5-methylbenzonitrile (5925-93-9) + 3-methoxy-benzaldehyde (591-31-1) → 2-(3-methoxyphenyl)-6-methylquinazolin-4(3H)-one

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

2-amino-5-methylbenzonitrile (5925-93-9) + benzaldehyde (100-52-7) → 6-methyl-2-phenylquinazolin-4(3H)-one (21419-51-2)

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%

2-amino-5-methylbenzonitrile (5925-93-9) + benzyl alcohol (100-51-6) → 6-methyl-2-phenylquinazolin-4(3H)-one (21419-51-2)

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%

nitrostyrene (5153-67-3) + 2-amino-5-methylbenzonitrile (5925-93-9) → 6-methyl-3-nitro-2-phenylquinolin-4-amine

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

2-amino-5-methylbenzonitrile (5925-93-9) + chloroformic acid ethyl ester (541-41-3) → (2-cyano-4-methyl-phenyl)-carbamic acid ethyl ester (1012369-77-5)

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

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 2-amino-5-methylbenzonitrile (5925-93-9) → C26H18N4O2 (1106822-12-1)

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

2-amino-5-methylbenzonitrile (5925-93-9) + anthranilic acid nitrile (1885-29-6) → 6-methyl-2-phenylquinazolin-4(3H)-one (21419-51-2)

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%

2-amino-5-methylbenzonitrile (5925-93-9) + cyclopentanone (120-92-3) → 7-methyl-1H,2H,3H-cyclopenta[b]quinolin-9-amine hydrochloride

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%

2-amino-5-methylbenzonitrile (5925-93-9) + 4-methylphenylboronic acid (5720-05-8) + Triethyl orthoacetate (78-39-7) → 2,6-dimethyl-4-(p-tolyl)quinazoline

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

2-amino-5-methylbenzonitrile (5925-93-9) + cycloheptanone (502-42-1) → 2-methyl-6H,7H,8H,9H,10H-cyclohepta[b]quinolin-11-amine hydrochloride

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%

2-amino-5-methylbenzonitrile (5925-93-9) + trichloromethyl chloroformate (503-38-8) → 6-methyl-2,4-dichloroquinazoline (39576-82-4)

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

methanol (67-56-1) + 2-amino-5-methylbenzonitrile (5925-93-9) → 6-methyl-3H-quinazolin-4-one (19181-53-4)

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

Upstream product

• 583-68-6 2-bromo-p-toluidine 
• 544-92-3 copper(I) cyanide 
• 38818-49-4 5-methyl-2-nitrobenzoyl chloride 
• 608-05-9 5-methyl-indole-2,3-dione 
• 106-49-0 p-toluidine 
• 75-16-1 methylmagnesium bromide 
• 156149-46-1 2-azido-5-methylbenzonitrile 
• 29289-13-2 2-iodo-4-methylaniline 
• 620-22-4 3-Methylbenzonitrile 
• 64407-07-4 3-(chloromethyl)benzonitrile 
• 38939-88-7 2-chloro-4-methyl-1-nitrobenzene 
• 4315-12-2 5-methyl-2-nitrobenzamide 
• 3113-72-2 5-methyl-2-nitrobenzoic acid 
• 784183-53-5 2,2,2-trifluoro-N-(2-iodo-4-methylphenyl)acetamide 

Downstream Products

• 55706-57-5 6-methylquinoline-8-carboxylic acid 
• 64113-84-4 2-fluoro-5-methylbenzonitrile 
• 156149-46-1 2-azido-5-methylbenzonitrile 
• 42872-86-6 2-iodo-5-methylbenzonitrile 
• 612506-07-7 5-methyl-2-(2-nitrophenylamino)benzonitrile 
• 1106822-12-1 C₂₆H₁₈N₄O₂ 
• 1093657-15-8 C₁₆H₁₆N₂O₄S 
• 62484-16-6 6-methyl-1H-quinazoline-2,4-dione 
• 1147856-80-1 1-(2-amino-4-methylphenyl)-2,2-dimethyl-1-propanone 
• 1221292-82-5 C₁₄H₁₈N₂O 
• 5778-79-0 9-amino-7-methyl-1,2,3,4-tetrahydroacridine 
• 1369931-97-4 (2,4-diaminoquinazolin-6-yl)methyl 4-cyclohexylpiperazine-1-carbodithioate 
• 1369931-98-5 (2,4-diaminoquinazolin-6-yl)methyl 4-benzylpiperazine-1-carbodithioate 
• 1369932-02-4 (2,4-diaminoquinazolin-6-yl)methyl 4-phenylpiperazine-1-carbodithioate 

Relevant articles and documents

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