Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 0.5h; | 98% |
With palladium 10% on activated carbon; hydrogen In methanol; ethanol at 20℃; under 3102.97 Torr; for 16h; Inert atmosphere; | 98% |
With iron; acetic acid at 60℃; for 1h; | 91% |
Conditions | Yield |
---|---|
With C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Inert atmosphere; Sealed tube; | 91% |
1,2-diamino-benzene
carbonic acid dimethyl ester
A
1,3-dihydro-2H-benzimidazol-2-one
B
1,3-dimethyl-1,3-dihydrobenzimidazol-2-one
C
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With lead(II) nitrate at 169.85℃; for 0.5h; | A 88% B n/a C n/a |
1,2-diamino-benzene
carbonic acid dimethyl ester
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
at 110℃; for 12h; Inert atmosphere; Molecular sieve; | 77% |
at 110℃; for 12h; Inert atmosphere; Molecular sieve; | 77% |
With zeolite NaY for 2h; Heating; | 75% |
NaY-faujasite zeolite for 5h; Heating / reflux; | |
With aluminum 1,4-benzenedicarboxylate at 170℃; for 8h; |
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With water | 74% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; | 61% |
With methanol |
Conditions | Yield |
---|---|
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h; | 60% |
1-methyl-4-phenyl-1H-benzo[b][1,4]diazepin-2(3H)-one
A
3-phenyl-4H-isoxazol-5-one
B
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol Ambient temperature; | A 40% B 25% |
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Ambient temperature; | A 40% B 25% |
Conditions | Yield |
---|---|
With sodium amide; naphthalene-1,8-diamine In xylene at 120 - 130℃; for 3h; | 38% |
carbon dioxide
phenylsilane
1,2-diamino-benzene
A
benzoimidazole
C
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate at 50℃; under 750.075 Torr; for 8h; Time; Temperature; Pressure; | A 20% B 35% C n/a |
1,2-diamino-benzene
carbonic acid dimethyl ester
A
1,3-dihydro-2H-benzimidazol-2-one
B
1-methyl-2-benzimidazolone
C
1,3-dimethyl-1,3-dihydrobenzimidazol-2-one
D
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With lead acetate at 159.85℃; for 1h; | A n/a B n/a C n/a D 6% |
With lead(II) nitrate at 159.85℃; for 1h; Product distribution; Further Variations:; Reagents; Reaction partners; Temperatures; |
1-methyl-1H-benzo[d][1,2,3]triazole
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With ammonium bromide; ammonia; sodium |
1-(N-methyl-N-4-toluenesulfonylamino)-2-(N-4-toluenesulfonylamino)benzene
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With sulfuric acid |
1-[bis-(toluene-4-sulfonyl)-amino]-2-[methyl-(toluene-4-sulfonyl)-amino]-benzene
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With sulfuric acid |
methanol
1,2-diamino-benzene
methyl iodide
N-methyl-1,2-phenylenediamine
1,2-dimethyl-1H-benzimidazole
bromobenzene
A
acetophenone
B
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With hydrogenchloride; lithium In diethyl ether; toluene for 4h; Product distribution; 4h 20 grad C, 1h reflux; |
4,5-Dihydro-2-<(2-aminophenyl)methylamino>-4-oxo-3-furancarboxylic acid ethyl ester
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With sodium carbonate Heating; |
Conditions | Yield |
---|---|
at 150℃; |
1-methyl-1H-benzo[d][1,2,3]triazole
ammonia
N-methyl-1,2-phenylenediamine
hydrogenchloride
N-nitroso N-methyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
hydrogenchloride
N-nitroso N-methyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
N-nitroso N-methyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
hydrogenchloride
N-nitroso N-ethyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
hydrogenchloride
N-nitroso N-ethyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
N-nitroso N-ethyl-N-(2-nitroaniline)
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / methanol; H2O / Heating 2: 98 percent / H2 / Pd/C / methanol / 0.5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 82 percent / Et3N / CH2Cl2 / Ambient temperature 2: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 60 - 70 °C 3: 59 percent / cyclohexene / 10percent Pd/C / ethanol / Heating 4: 7percent aq. Na2CO3 / Heating View Scheme |
4,5-Dihydro-2-<(2-nitrophenyl)amino>-4-oxo-3-furancarboxylic acid ethyl ester
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 60 - 70 °C 2: 59 percent / cyclohexene / 10percent Pd/C / ethanol / Heating 3: 7percent aq. Na2CO3 / Heating View Scheme |
4,5-Dihydro-2-<(2-nitrophenyl)methylamino>-4-oxo-3-furancarboxylic acid ethyl ester
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 59 percent / cyclohexene / 10percent Pd/C / ethanol / Heating 2: 7percent aq. Na2CO3 / Heating View Scheme |
4-bromo-benzaldehyde
N-methyl-1,2-phenylenediamine
2-(4-bromophenyl)-1-methyl-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With oxygen; cetylpyridinium bromide In water at 20℃; for 0.75h; | 100% |
With dodecatungstosilic acid In ethyl acetate at 20℃; for 0.5h; | 99% |
3,5-di-tert-butyl-2-hydroxybenzaldehyde
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
In benzene for 2h; Reflux; | 100% |
In methanol for 16h; | 71% |
N-methyl-1,2-phenylenediamine
3-(adamantan-1-yl)-2-hydroxy-5-methylbenzaldehyde
Conditions | Yield |
---|---|
In benzene for 2h; Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; | 100% |
Conditions | Yield |
---|---|
In ethanol for 2h; | 100% |
N-methyl-1,2-phenylenediamine
2-nitro-benzaldehyde
1-methyl-2-(2-nitrophenyl)-2,3-dihydrobenzimidazole
Conditions | Yield |
---|---|
In methanol for 1h; Heating; | 99.5% |
With ethanol |
N-methyl-1,2-phenylenediamine
trifluoroacetic acid
1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
at 70℃; for 16h; | 99% |
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: N-methyl-1,2-phenylenediamine With trimethylaluminum chloride In toluene at 0 - 20℃; Stage #2: hydroxymethyl JandaJelTM resin-bound 4-CF3-Ph ester In toluene for 24h; Heating; Further stages.; | 99% |
N-methyl-1,2-phenylenediamine
2-nitro-benzaldehyde
1-methyl-2-(2-nitrophenyl)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With dodecatungstosilic acid In ethyl acetate at 20℃; for 0.0833333h; | 99% |
With Oxone In water; N,N-dimethyl-formamide at 20℃; | 80% |
4-chlorobenzaldehyde
N-methyl-1,2-phenylenediamine
2-(4-chlorophenyl)-1-methyl-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With dodecatungstosilic acid In ethyl acetate at 20℃; for 0.333333h; | 99% |
N-methyl-1,2-phenylenediamine
benzylamine
1-methyl-2-phenylbenzimidazole
Conditions | Yield |
---|---|
With 4-tert-butyl-5-methoxy-1,2-benzoquinone; oxygen; toluene-4-sulfonic acid In acetonitrile at 60℃; for 24h; Schlenk technique; | 99% |
With sulfur In neat (no solvent) at 140℃; for 16h; Inert atmosphere; | 85% |
With C8H7NO3; copper(ll) bromide In water; isopropyl alcohol at 45℃; for 24h; Green chemistry; | 85% |
benzoic acid anhydride
N-methyl-1,2-phenylenediamine
1-methyl-2-phenylbenzimidazole
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one; water at 445℃; under 187519 Torr; for 0.00277778h; Supercritical conditions; | 99% |
With water In 1-methyl-pyrrolidin-2-one at 400℃; under 187519 Torr; for 0.000491667h; Flow reactor; Green chemistry; | > 99 %Chromat. |
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
N-methyl-1,2-phenylenediamine
4-Hydroxy-6-methyl-3-{1-[(E)-2-methylamino-phenylimino]-ethyl}-pyran-2-one
Conditions | Yield |
---|---|
In methanol | 98% |
N-methyl-1,2-phenylenediamine
3-amino propanoic acid
2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethanamine dihydrochloride
Conditions | Yield |
---|---|
Stage #1: N-methyl-1,2-phenylenediamine; 3-amino propanoic acid With hydrogenchloride In water for 96h; Reflux; Stage #2: In ethanol; water at 8℃; for 24h; | 97% |
With hydrogenchloride for 100h; Heating; | 70% |
benzaldehyde
N-methyl-1,2-phenylenediamine
1-methyl-2-phenylbenzimidazole
Conditions | Yield |
---|---|
With sodium metabisulfite In N,N-dimethyl-formamide Reflux; | 97% |
With Ag2CO3/celite In ethanol at 70℃; for 3h; | 94% |
In water; N,N-dimethyl-formamide at 80℃; | 90% |
N-(Benzyloxycarbonyl)glycine
N-methyl-1,2-phenylenediamine
N-[2-(N-methylamino)phenyl]-2-[(phenylmethoxy)carbonylamino]ethanamide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 6h; | 97% |
3,5-Pyridinedicarboxylic acid
N-methyl-1,2-phenylenediamine
pyridine-3,5-bis(1-methyl-benzimidazole-2-yl)
Conditions | Yield |
---|---|
With polyphosphoric acid at 100 - 200℃; for 26h; | 97% |
tert-butylisonitrile
N-methyl-1,2-phenylenediamine
N-tert-butyl-1-methyl-1H-benzo[d]imidazol-2-amine
Conditions | Yield |
---|---|
With oxygen; palladium diacetate In 2-methyltetrahydrofuran at 75℃; for 2h; Molecular sieve; | 97% |
With dipotassium peroxodisulfate; sodium acetate; cobalt(II) diacetate tetrahydrate In 1,4-dioxane at 100℃; for 18h; | 87% |
With tert.-butylhydroperoxide; sodium carbonate; cobalt acetylacetonate In 1,4-dioxane at 75℃; for 1h; Sonication; | 69% |
With cobalt(II) acetate; potassium carbonate In acetonitrile at 80℃; for 24h; Sealed tube; | 44% |
Conditions | Yield |
---|---|
With dimethylamine borane; potassium carbonate In ethanol; water under 15001.5 Torr; for 18h; Catalytic behavior; Autoclave; | 97% |
With tris(pentafluorophenyl)borate; phenylsilane In tetrahydrofuran at 120℃; under 7500.75 Torr; for 24h; Autoclave; | 95% |
With dimethylamine borane In water at 100℃; under 18751.9 Torr; for 24h; Heating; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 4.5h; | 96% |
glycolic Acid
N-methyl-1,2-phenylenediamine
(1-methyl-1H-benzimidazol-2-yl)methanol
Conditions | Yield |
---|---|
With hydrogenchloride In water at 130℃; Sealed tube; | 96% |
With phosphoric acid at 130℃; for 3h; | 76% |
With hydrogenchloride Heating; | |
Stage #1: glycolic Acid; N-methyl-1,2-phenylenediamine With hydrogenchloride In water at 95℃; for 12h; Phillips cyclocondensation; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In water Saturated solution; | |
With hydrogenchloride In water at 65 - 100℃; for 5h; |
N,N-dimethyl-formamide
N-methyl-1,2-phenylenediamine
1-Methylbenzimidazole
Conditions | Yield |
---|---|
With hydrogenchloride In water at 150℃; for 0.0333333h; Microwave irradiation; | 96% |
With zinc(II) acetate dihydrate In neat (no solvent) at 120℃; under 7600.51 Torr; for 18h; Autoclave; Inert atmosphere; Green chemistry; | 95% |
With phenylsilane at 120℃; for 12h; | 31% |
With Triethoxysilane; carbon dioxide; tris(pentafluorophenyl)borate at 120℃; for 24h; | 94 %Spectr. |
N-methyl-1,2-phenylenediamine
Conditions | Yield |
---|---|
With phosphorus trichloride 1) ether, 0.5 h, room temperature, 2) reflux, 36 h; | 95.7% |
4-nitrobenzaldehdye
N-methyl-1,2-phenylenediamine
1-methyl-2-(4-nitrophenyl)-1H-benzimidazole
Conditions | Yield |
---|---|
With dodecatungstosilic acid In ethyl acetate at 20℃; for 0.0833333h; | 95% |
With oxygen; cetylpyridinium bromide In water at 20℃; for 1.75h; | 95% |
With p-toluenesulfonic acid adsorbed on silica gel at 60 - 70℃; for 0.0833333h; | 77% |
With ethanol |
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 12h; Acylation; | 95% |
4-methyl-benzaldehyde
N-methyl-1,2-phenylenediamine
1-methyl-2-p-tolyl-1H-benzoimidazole
Conditions | Yield |
---|---|
With dodecatungstosilic acid In ethyl acetate at 20℃; for 0.5h; | 95% |
With palladium 10% on activated carbon In dodecane; N,N-dimethyl acetamide at 120℃; for 14h; Inert atmosphere; | 80% |
The Molecular formula of N-METHYL-o-PHENYLENEDIAMINE (4760-34-3):C7H10N2
The Molecular Weight of N-METHYL-o-PHENYLENEDIAMINE (4760-34-3):122.17
The Molecular Structure of N-METHYL-o-PHENYLENEDIAMINE (4760-34-3) is:
Density:1.098 g/cm3
Melting point:22 °C(lit.)
Boiling point:52.4 °C at 760 mmHg
Flash point:122.4 °C
Index of Refraction:1.64
Molar Refractivity:40.09 cm3
Molar Volume:111.1 cm3
Polarizability:15.89 10-24cm3
Surface Tension:47.5 dyne/cm
Enthalpy of Vaporization:48.98 kJ/mol
Vapour Pressure:0.0193 mmHg at 25°C
Appearance:yellow to red to very dark brown liquid
IUPAC Name: 1-N-methylbenzene-1,2-diamine
Synonyms: N-METHYL-2-PHENYLENEDIAMINE ; N-METHYL-1,2-PHENYLENEDIAMINE ; N-METHYL-1,2-BENZENEDIAMINE ; 2-(methylamino)aniline ; 2-amino-n-methylaniline ; n-methyl-2-benzenediamine ; n-methyl-o-phenylenediamin ; N-METHYL-O-PHENYLENEDIAMINE
It's used as a medicine and dye intermediates.
1. | mma-sat 2500 µg/plate | FCTOD7 Food and Chemical Toxicology. 23 (1985),695. |
Reported in EPA TSCA Inventory.
Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.
Hazard Codes:Xn,Xi
Risk Statements
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
WGK Germany:3
RTECS:ST2770000
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