Conditions | Yield |
---|---|
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.5h; Inert atmosphere; | 100% |
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction; | 100% |
With sodium tetrahydroborate In ethanol; water at 39.84℃; for 2h; Reagent/catalyst; | 100% |
Conditions | Yield |
---|---|
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.5h; Inert atmosphere; | 100% |
With hydrogen In ethanol at 80℃; under 2250.23 Torr; for 5h; Catalytic behavior; Inert atmosphere; | 95% |
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube; | 51% |
Conditions | Yield |
---|---|
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.75h; Inert atmosphere; | 100% |
With palladium 10% on activated carbon; ammonium formate In ethanol at 100℃; for 24h; Reagent/catalyst; | 90% |
Stage #1: 4-nitrobenzaldehdye With hydrazine hydrate at 135℃; for 3h; Stage #2: With potassium hydroxide at 135℃; for 24h; | 63% |
With hydrogen In ethanol; water at 25℃; under 750.075 Torr; for 4h; Schlenk technique; |
N-(tert-butoxycarbonyl)-4-methylaniline
p-toluidine
Conditions | Yield |
---|---|
With water at 100℃; for 10h; Inert atmosphere; | 99% |
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 1h; | 98% |
With Montmorillonite K10 In dichloromethane for 2h; deacylation; Heating; | 97% |
With water at 150℃; for 4h; Subcritical conditions; | 88% |
With zinc(II) iodide In toluene at 120℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Glovebox; |
p-toluidine
Conditions | Yield |
---|---|
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 3h; Sealed tube; Irradiation; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With butyltriphenylphosphonium tetrahydroborate In dichloromethane at 20℃; for 0.266667h; | 98% |
With iron(III) chloride; sodium iodide In acetonitrile at 20℃; for 0.166667h; | 97% |
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0833333h; Ambient temperature; | 97% |
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h; | 98% |
Stage #1: para-bromotoluene With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 9h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 93% |
With ammonium hydroxide In neat (no solvent) at 60℃; for 8h; | 93% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 65 - 70℃; for 1h; | 98% |
With sodium hydroxide; water In 1,4-dioxane at 70℃; Kinetics; Thermodynamic data; isotope effect (D2O); ΔH(excit.), ΔS(excit.); | |
With sodium hydroxide In ethanol; water at 40℃; Kinetics; |
Conditions | Yield |
---|---|
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); | 98% |
With sodium hydroxide In methanol at 80℃; | 92% |
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2; | 83% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen rearrangement; | 98% |
With palladium diacetate; triethylamine In acetonitrile at 90℃; for 24h; Solvent; Lossen Rearrangement; Sealed tube; | 98% |
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Reagent/catalyst; Solvent; Lossen Rearrangement; | 98% |
3-azidohomoadamantane
toluene
A
1-(adamantan-1-ylmethyl)-4-methylbenzene
B
p-toluidine
Conditions | Yield |
---|---|
With aluminium trichloride at 80℃; for 1.5h; Yields of byproduct given; | A 97% B n/a |
p-tolyl triflate
p-toluidine
Conditions | Yield |
---|---|
Stage #1: p-tolyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 6h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 97% |
Multi-step reaction with 2 steps 1: Trimethyl borate; water; trifluoroacetic acid; acetone / 15 °C / UV-irradiation; Inert atmosphere 2: sodium hydroxide / methanol / 80 °C View Scheme |
N-(p-Tolyl)carbamidsaeure-β-chlorethylester
p-toluidine
Conditions | Yield |
---|---|
With ammonium chloride; zinc; hydroxycobalamine In ethanol; water at 20℃; for 15h; | 96% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature; | 96% |
1,1,1-Trimethyl-N-(4-methylphenyl)-N-(trimethylsilyl)silanamine
p-toluidine
Conditions | Yield |
---|---|
With hydrogenchloride; water In methanol at 20℃; for 1h; | 96% |
With hydrogenchloride In diethyl ether | |
With hydrogenchloride In chloroform; water for 1h; | 23.6 mg |
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 96% |
With ammonia; triethylamine In water at 20℃; for 3.5h; | 96% |
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; Kinetics; liquid NH3; | 95% |
1,2,3,4-tetrahydroisoquinoline
1-methyl-4-nitrobenzene
A
quinoline
B
p-toluidine
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 94% B 96% |
Conditions | Yield |
---|---|
at 230℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent; | A 95% B n/a |
trifluoroacetic acid
A
2,2,2-trifluoro-N-(4-methylphenyl)acetamide
B
p-toluidine
C
dimethyl sulfoxide
Conditions | Yield |
---|---|
at 50℃; for 5h; Elimination; acylation; retro-Pummerer reaction; | A 3% B 95% C 67% |
Conditions | Yield |
---|---|
With ammonium formate; zinc In ethylene glycol for 0.05h; microwave irradiation; | 95% |
3-oxo-N-(p-tolyl)butanamide
1,2-diamino-benzene
A
2-Methyl-1H-benzimidazole
B
p-toluidine
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide In neat (no solvent) at 120℃; for 2h; | A 95% B 90% |
4'-methylbenzenesulphenanilide
A
2,7-dimethylphenazine
B
p-toluidine
C
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene at 25℃; | A 35% B 55% C 94% |
7-methyl-1,2,3,4-tetrahydroquinoline
1-methyl-4-nitrobenzene
A
7-methylquinoline
B
p-toluidine
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 92% B 94% |
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In chlorobenzene 1) 15 min, r.t. 2) 5 h, reflux; | 93% |
1,2-di(p-tolyl)diazene
p-toluidine
Conditions | Yield |
---|---|
With potassium hydroxide; nickel-incorporated hexagonal mesoporous aluminophosphate In isopropyl alcohol at 82.84℃; for 1.5h; | 93% |
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.75h; pH=2; Inert atmosphere; Irradiation; | 92% |
With ethanol; iron; calcium chloride at 60℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 12h; | 93% |
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 90% |
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction; | 90% |
N-{(Z)-1,3-Diphenyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide
A
3,5-Diphenyl-2H-1,2-thiazin-1,1-dioxid
B
p-toluidine
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78 - 25℃; for 12h; | A 92% B n/a |
N-{(Z)-3-Phenyl-1-p-tolyl-3-[(Z)-p-tolylimino]-propenyl}-methanesulfonamide
A
5-Phenyl-3-p-tolyl-2H-[1,2]thiazine 1,1-dioxide
B
p-toluidine
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78 - 25℃; for 12h; | A 92% B n/a |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 8h; | 92% |
Stage #1: para-chlorotoluene With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 90℃; for 12h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 90% |
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 110℃; for 12h; Microwave irradiation; | 89% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
In methanol at 20℃; for 24h; | 100% |
In methanol at 20℃; | 85% |
Conditions | Yield |
---|---|
for 1h; Solid phase reaction; condensation; | 100% |
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 8h; | 97% |
In decaethylene glycol at 120℃; for 3h; | 97% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Inert atmosphere; | 100% |
With Methylenediphosphonic acid at 20℃; for 1h; neat (no solvent); | 99% |
With pyridine; aluminum oxide at 125 - 127℃; for 2h; microwave irradiation; | 98% |
cinnamoyl chloride
p-toluidine
N-(4-methylphenyl)-3-phenyl-2-propenamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 100% |
With triethylamine In ethyl acetate at 0 - 20℃; | 88% |
With potassium hydroxide |
3-nitro-benzaldehyde
p-toluidine
N-(3-nitrobenzylidene)-4-methylbenzenamine
Conditions | Yield |
---|---|
100% | |
With chitosan In ethanol; water at 20℃; for 0.333333h; | 85% |
With ethanol |
4-nitrobenzaldehdye
p-toluidine
N-(4-nitrobenzylidene)-4-methylaniline
Conditions | Yield |
---|---|
for 24h; Ambient temperature; | 100% |
100% | |
With montmorillonite at 20℃; for 0.0666667h; Neat (no solvent); | 98% |
2-Hydroxy-1,4-naphthoquinone
p-toluidine
2-(p-toluidino)-1,4-naphthoquinone
Conditions | Yield |
---|---|
In neat (no solvent) at 100℃; under 750.075 Torr; for 0.05h; Microwave irradiation; | 100% |
With acetic acid | |
With ethanol |
Conditions | Yield |
---|---|
for 6h; Ambient temperature; | 100% |
100% | |
In ethyl 2-hydroxypropionate at 20℃; for 0.0333333h; | 90% |
Conditions | Yield |
---|---|
at 20℃; for 0.5h; Solid phase reaction; condensation; | 100% |
With fibrous nano silica sulfuric acid In neat (no solvent) at 80℃; for 0.0333333h; Green chemistry; | 97% |
With silica sulfuric acid In acetonitrile for 0.0194444h; Microwave irradiation; | 96% |
p-toluidine
3,4-dimethoxy-benzaldehyde
1,2-dimethoxy-4-<<(4-methylphenyl)imino>methyl>benzene
Conditions | Yield |
---|---|
In toluene Heating; | 100% |
p-toluidine
p-toluenesulfonyl chloride
4-methyl-N-(4-methylphenyl)benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 16h; | 100% |
With pyridine at 0 - 25℃; | 100% |
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction; | 98% |
p-toluidine
2-chloropropionyl chloride
3-chloro-N-(4-methylphenyl)propionamide
Conditions | Yield |
---|---|
In acetone for 1h; Acylation; Heating; | 100% |
In water; acetone for 6h; Reflux; | 100% |
With potassium carbonate In acetone at 0℃; for 1h; Condensation; | 95% |
Conditions | Yield |
---|---|
100% | |
In ethanol for 3h; Reflux; | 77.2% |
In ethanol for 3h; Reflux; | 77.2% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 24h; Ambient temperature; | 100% |
With toluene |
p-toluidine
dimethyl acetylenedicarboxylate
dimethyl (Z)-N-(4-methylphenyl)aminofumarate
Conditions | Yield |
---|---|
at 20℃; for 0.133333h; Michael addition; | 100% |
In benzene at 5 - 10℃; | 70% |
In diethyl ether |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; for 5h; | 100% |
In diethyl ether at 20℃; for 2h; | 98% |
In chloroform for 7h; | 97% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Heating; 3 equivalents of BzBr; | 100% |
With montmorillonite-KSF clay supported CuO nanoparticles In neat (no solvent) at 20℃; for 0.75h; Sonication; Green chemistry; chemoselective reaction; | 78% |
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h; Inert atmosphere; | 71% |
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h; | 70% |
Conditions | Yield |
---|---|
for 6h; Ambient temperature; | 100% |
In ethyl 2-hydroxypropionate at 20℃; for 0.0333333h; | 96% |
With montmorillonite at 20℃; for 0.1h; Neat (no solvent); | 96% |
glyoxylic acid ethyl ester
p-toluidine
ethyl 2-(4-methylphenylimino)acetate
Conditions | Yield |
---|---|
With sodium sulfate In dichloromethane for 0.5h; | 100% |
With magnesium sulfate In toluene at 25℃; for 0.5h; | 100% |
for 1h; Green chemistry; | 75% |
1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one
p-toluidine
(E)-4-Ethoxy-1,1,1-trifluoro-4-p-tolylamino-but-3-en-2-one
Conditions | Yield |
---|---|
In acetonitrile for 18h; Ambient temperature; | 100% |
(2-formylphenyl)butyl tellurium dibromide
p-toluidine
2-(4'-methylphenyliminomethinyl)phenyltellurenyl bromide
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene | 100% |
2-<(3-Chloropropyl)amino>-4H-3,1-benzoxazin-4-one
p-toluidine
N-(4-Methylphenyl)-2-<3-(3-chloropropyl)ureido>benzamide
Conditions | Yield |
---|---|
for 0.05h; Heating; | 100% |
4-[4a-Methoxy-7-(4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl)-5,8-dioxo-4-phenyl-4a,5,8,8a-tetrahydro-4H-quinolin-1-yl]-benzoic acid
p-toluidine
4-(9-Hydroxy-4a,8-dimethoxy-5,11-dioxo-4-phenyl-6-p-tolyl-4,4a,5,6,11,11a-hexahydro-pyrido[3,2-b]carbazol-1-yl)-benzoic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water for 4h; Heating; | 100% |
Conditions | Yield |
---|---|
for 2h; Ambient temperature; | 100% |
In ethanol for 0.333333h; Reflux; | 95.51% |
sodium hydrogen sulfate; silica gel at 54 - 56℃; for 0.0236111h; microwave irradiation; | 91% |
p-toluidine
3-Bromopropionyl chloride
3-bomo-N-(4-methylphenyl)propanamide
Conditions | Yield |
---|---|
With potassium carbonate In 1,2-dichloro-ethane at 20℃; for 1h; Time; Inert atmosphere; | 100% |
With dmap In tetrahydrofuran at 0 - 20℃; for 1h; | 75% |
With triethylamine In benzene | 70% |
Conditions | Yield |
---|---|
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr; Rate constant; Thermodynamic data; E(a); | 100% |
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr; | 100% |
With Pd/Al2O3; hydrogen In ethanol at 80℃; under 750.075 Torr; for 12h; | 94% |
p-toluidine
Cinnamoyl chloride
(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone at 0℃; for 2h; | 100% |
Stage #1: Cinnamoyl chloride With pyridine; dmap In dichloromethane at 0℃; for 0.416667h; Inert atmosphere; Stage #2: p-toluidine In dichloromethane at 0 - 20℃; | 86% |
With dmap; sodium hydrogencarbonate In dichloromethane at 20℃; | 84% |
Conditions | Yield |
---|---|
With zirconium(IV) chloride at 20℃; for 0.25h; | 100% |
With [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN In neat (no solvent) at 20℃; for 0.166667h; diastereospecific reaction; | 99% |
With zinc(II) perchlorate hexahydrate at 20℃; for 0.5h; | 98% |
Conditions | Yield |
---|---|
With trimethylamine Ambient temperature; | 100% |
In diethyl ether; tetrahydrofyran at 0℃; for 4h; | 95% |
With triethylamine In diethyl ether at 0℃; | 83% |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
1.Introduction of p-Toluidine
The p-Toluidine, with its CAS NO.106-49-0, is a kind of white lustrous plates or leaflets with an amine odour. Its Synonyms are 4-Aminotoluene ; 4-Toluidine ; 1-Amino-4-methylbenzene ; 4-Amino-1-methylbenzene ; 4-Methylaniline ; 4-Methylbenzenamine ; Aniline, p-methyl- ; Benzenamine, 4-methyl- and p-Methylbenzenamine. p-Toluidine should be stored in shady and cool warehouse and mainly used in dyes, and in organic chemical manufacturing.
2.Properties of p-Toluidine
(1) Density: 0.992 g/cm3 (2) Flash Point: 84.5 °C (3) Enthalpy of Vaporization: 43.36 kJ/mol
(4) Boiling Point: 197.4 °C at 760 mmHg (5) Melting Point: 43 °C(6) Water Solubility: 1.1 g/100 mL
(7) Storage temperature: 2-8 °C (8) Vapour Pressure of p-Toluidine (CAS NO.106-49-0): 0.379 mmHg at 25 °C
3.Structure descriptors of p-Toluidine
IUPAC Name: 4-methylaniline
InChI: InChI=1S/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3
InChIKey: RZXMPPFPUUCRFN-UHFFFAOYSA-N
Canonical SMILES : CC1=CC=C(C=C1)N
4. Safety information of p-Toluidine
Hazard Codes: ,
Risk Statements: 23/24/25-36-40-43-50
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
R36: Irritating to eyes.
R40: Limited evidence of a carcinogenic effect.
R43: May cause sensitization by skin contact.
R50: Very toxic to aquatic organisms.
Safety Statements: 28-36/37-45-61
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3451 6.1/PG 2
WGK Germany: 2
RTECS: XU3150000
HazardClass: 6.1
PackingGroup of p-Toluidine (CAS NO.106-49-0): II
5.Toxicity data of p-Toluidine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 42mg/kg (42mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
mouse | LD50 | intraperitoneal | 50mg/kg (50mg/kg) | National Technical Information Service. Vol. AD691-490, | |
mouse | LD50 | oral | 330mg/kg (330mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981. | |
quail | LD50 | oral | 237mg/kg (237mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
rabbit | LD50 | oral | 270mg/kg (270mg/kg) | Vsesoyuznyi Institut Nauchnoi i Tekhnicheskoi Informatsii Vol. #4035-77, | |
rabbit | LD50 | skin | 890mg/kg (890mg/kg) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 31-4/1973, | |
rat | LC50 | inhalation | > 640mg/m3/1H (640mg/m3) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 31-4/1973, | |
rat | LD50 | oral | 336mg/kg (336mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Bromatologia i Chemia Toksykologiczna. Vol. 17, Pg. 51, 1984. |
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