2-chloro-6-methylaniline
Conditions | Yield |
---|---|
Stage #1: 3-chloro-5-methyl-4-nitroaniline With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hypophosphorous acid In water at 0℃; for 3h; Stage #3: With iron In water at 90℃; for 4h; Reagent/catalyst; | 82.5% |
2-bromo-1-chloro-3-methylbenzene
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h; | 82% |
Conditions | Yield |
---|---|
With N-chloro-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(mesitylselanyl)-2,3-dihydro-1H-inden-1-yl)thiourea In chloroform-d1 at 0℃; for 12h; regioselective reaction; | 65% |
N-(2-chloro-6-methylphenyl)acetamide
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With hydrogenchloride In water at 50 - 55℃; for 7h; Time; | 61.7% |
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With hydrogenchloride In sulfolane; water at 120℃; for 26h; | 60% |
1-azido-2-methyl-benzene
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With sulfuric acid at 165℃; | |
With sulfuric acid at 150 - 160℃; |
Conditions | Yield |
---|---|
With hydrogenchloride |
N-(2-chloro-6-methylphenyl)pivalamide
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With hydrogen bromide for 4.5h; Heating; Yield given; |
N-(o-tolyl)hydroxylamine
A
4-amino-3-methylphenol
B
o-toluidine
C
2-chloro-6-methylaniline
D
4-chloro-2-methylbenzeneamine
Conditions | Yield |
---|---|
With perchloric acid; sodium perchlorate; sodium chloride In water; acetonitrile at 25℃; Rate constant; |
hydrogenchloride
N-(o-tolyl)hydroxylamine
A
N,N'-Di-o-tolyl-diazene N-oxide
B
2-chloro-6-methylaniline
C
5-chloro-2-methyl-benzenamine
D
4-chloro-2-methylbenzeneamine
hydrogenchloride
1-azido-2-methyl-benzene
A
2-chloro-6-methylaniline
B
4-chloro-2-methylbenzeneamine
Conditions | Yield |
---|---|
Aufbewahren an einem kuehlen dunklen Ort; |
hydrogenchloride
ethanol
1-methyl-2-nitrobenzene
A
o-toluidine
B
2-chloro-6-methylaniline
C
4-chloro-2-methylbenzeneamine
hydrogenchloride
ethanol
1-methyl-2-nitrobenzene
A
o-toluidine
B
2-chloro-6-methylaniline
C
4-chloro-2-methylbenzeneamine
sulfuric acid
6-amino-5-chloro-toluene-3-sulfonic acid
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
at 150 - 160℃; |
N-(2-chlorophenyl)-2,2,2-trimethylacetamide
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72.1 percent / TMEDA, n-BuLi / various solvent(s); hexane / 1.) -12 to -20 deg C, 50min, 2.) -20 deg C, 2 h 2: conc. aq. HBr / 4.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: TMEDA, BuLi / various solvent(s); hexane / 1.) 65min, 2.) 1 h 2: conc. aq. HBr / 4.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 25 percent aq. NaOH / various solvent(s) 2: 72.1 percent / TMEDA, n-BuLi / various solvent(s); hexane / 1.) -12 to -20 deg C, 50min, 2.) -20 deg C, 2 h 3: conc. aq. HBr / 4.5 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 25 percent aq. NaOH / various solvent(s) 2: TMEDA, BuLi / various solvent(s); hexane / 1.) 65min, 2.) 1 h 3: conc. aq. HBr / 4.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 2 h / 50 °C 2: acetic acid; hydrogenchloride; dihydrogen peroxide / water / 40 - 50 °C 3: hydrogenchloride / water; sulfolane / 26 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 2.5h; Catalytic behavior; chemoselective reaction; |
Conditions | Yield |
---|---|
With N-chloro-succinimide In chloroform-d1 at 0℃; for 12h; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: chloroform / 12 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 40 °C / 1800.18 - 3000.3 Torr / Inert atmosphere; Autoclave 3.1: sodium nitrite; hydrogenchloride / water / 0.5 h / -3 - 3 °C 3.2: 5.5 h / -3 - 3 °C 4.1: hydrogenchloride / water / 7 h / 50 - 55 °C View Scheme |
N-(2-methyl-6-nitrophenyl)acetamide
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 40 °C / 1800.18 - 3000.3 Torr / Inert atmosphere; Autoclave 2.1: sodium nitrite; hydrogenchloride / water / 0.5 h / -3 - 3 °C 2.2: 5.5 h / -3 - 3 °C 3.1: hydrogenchloride / water / 7 h / 50 - 55 °C View Scheme |
2-chloro-6-methylaniline
4-bromo-2-chloro-6-methylphenylamine hydrobromide salt
Conditions | Yield |
---|---|
With bromine; acetic acid In methanol at 0℃; | 99% |
Conditions | Yield |
---|---|
With hafnium tetrakis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.5h; Friedel Crafts alkylation; | 99% |
In dichloromethane for 72h; Inert atmosphere; Reflux; | 51% |
(E)-1,3-diphenyl-2-propen-1-ol
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With 1,3-bis(carboxymethyl)imidazolium iodide In neat (no solvent) at 80℃; for 6h; regioselective reaction; | 99% |
chloroacetyl chloride
2-chloro-6-methylaniline
2-chloro-N-(2-chloro-6-methylphenyl)acetamide
Conditions | Yield |
---|---|
Stage #1: 2-chloro-6-methylaniline With pyridine In dichloromethane at -10℃; for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at -10 - 20℃; for 2h; | 98% |
at 0 - 25℃; for 2.5h; | 87.6% |
With sodium acetate In water; acetone at 20 - 50℃; for 16h; | 71% |
2-chloro-6-methylaniline
2,6-dichloroimidazo[1,5-a]pyrido[3,2-e]pyrazine
2-Chloro-N-(2-chloro-6-methylphenyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine
Conditions | Yield |
---|---|
Stage #1: 2-chloro-6-methylaniline With sodium hexamethyldisilazane In tetrahydrofuran for 0.5h; Heating; Stage #2: 2,6-dichloroimidazo[1,5-a]pyrido[3,2-e]pyrazine In tetrahydrofuran for 0.5h; Heating; | 98% |
3-oxo-propionic acid ethyl ester
2-chloro-6-methylaniline
C10H10ClNO2
Conditions | Yield |
---|---|
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 10h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Solvent; Reflux; | 97.3% |
acetylacetone
2-chloro-6-methylaniline
(Z)-4-(2-chloro-6-methylphenylamino)pent-3-en-2-one
Conditions | Yield |
---|---|
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.1h; Green chemistry; | 97% |
With zinc trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.2h; stereoselective reaction; | 96% |
2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxylic acid
2-chloro-6-methylaniline
N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl- 4-pyrimidinyl]amino]-5-thiazolecarboxamide
Conditions | Yield |
---|---|
Stage #1: 2-[[6-[4-(2-acetoxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxylic acid With thionyl chloride; sodium hydroxide In water; 1,2-dichloro-ethane at 55 - 60℃; for 4h; Stage #2: 2-chloro-6-methylaniline With triethylamine In 1,2-dichloro-ethane at 40 - 45℃; for 1h; Solvent; Reagent/catalyst; Temperature; | 95.6% |
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 71.7% |
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 71.7% |
2-methyl-4,6-dichloroaniline
o-toluidine
2-chloro-6-methylaniline
4-chloro-2-methylbenzeneamine
Conditions | Yield |
---|---|
With carbon disulfide In acetone | 95.5% |
2-chloro-6-methylaniline
2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid
[5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With Dichlorophenylphosphine; N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 20℃; for 14h; | 95% |
Stage #1: 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Stage #2: 2-chloro-6-methylaniline With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24h; | 48% |
ethyl acetoacetate
2-chloro-6-methylaniline
(Z)-ethyl 3-(2-chloro-6-methylphenylamino)but-2-enoate
Conditions | Yield |
---|---|
With zinc trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.25h; stereoselective reaction; | 94% |
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.133333h; Green chemistry; | 93% |
2-chloro-6-methylaniline
2-chloro-6-methylbenzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; | 94% |
3-oxo-propionic acid ethyl ester
thiourea
2-chloro-6-methylaniline
2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide
Conditions | Yield |
---|---|
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 0.75h; Reflux; Stage #3: thiourea Solvent; Further stages; | 92.31% |
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 0.75h; Reflux; Stage #2: With copper(ll) bromide In tetrahydrofuran for 1h; Reflux; Stage #3: thiourea In tetrahydrofuran at 20 - 25℃; for 0.25h; Reagent/catalyst; | 90.94% |
Conditions | Yield |
---|---|
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Reflux; Stage #3: With copper(ll) bromide In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Reflux; | 91.6% |
Stage #1: 3-oxo-propionic acid ethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-chloro-6-methylaniline In tetrahydrofuran for 1h; Reflux; Stage #3: With copper(I) bromide In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Reflux; | 91.6% |
Stage #1: 3-oxo-propionic acid ethyl ester; 2-chloro-6-methylaniline With sodium methylate In tetrahydrofuran for 1h; Reflux; Stage #2: With copper(I) bromide In tetrahydrofuran for 2h; Solvent; Reflux; | 91.6% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 160℃; for 3h; microwave irradiation; | 91.5% |
4-oxo-5-{[(trifluoromethyl)sulfonyl]oxy}-4H-pyran-2-carboxylic acid
2-chloro-6-methylaniline
6-(2-chloro-6-methylphenylcarbamoyl)-4oxo-4H-pyran-3-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With O-phenyl phosphorodichloridate; triethylamine In dichloromethane at 0℃; Inert atmosphere; | 90% |
(Z)-but-2-ene-1,4-diyl dimethanesulfonate
2-chloro-6-methylaniline
1-(2-Chloro-6-methyl-phenyl)-2,5-dihydro-1H-pyrrole
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; | 89% |
para-bromotoluene
2-chloro-6-methylaniline
N-(2'-chloro-6'-methylphenyl)-4-methylaniline
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 60 - 90℃; Buchwald-Hartwig coupling; | 89% |
carbon disulfide
allyl bromide
2-chloro-6-methylaniline
S-allyl-N-(2-chloro-6-methylphenyl)dithiocarbamate
Conditions | Yield |
---|---|
With tin(II) chloride dihdyrate at 20℃; neat (no solvent); | 89% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 160℃; for 3h; microwave irradiation; | 88% |
2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carboxylic acid
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 80℃; for 0.5h; | 86.8% |
2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde
2-chloro-6-methylaniline
Conditions | Yield |
---|---|
With acetic acid In ethanol at 80℃; for 3h; | 86.5% |
benzoyl chloride
2-chloro-6-methylaniline
N-(2-chloro-6-methylphenyl)benzamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 86% |
With triethylamine In toluene Heating; | 70% |
With triethylamine In dichloromethane at 20℃; | 52% |
Schotten-Baumann reaction; | |
With triethylamine |
Benzoyl isothiocyanate
2-chloro-6-methylaniline
1-Benzoyl-3-(2-chloro-6-methyl-phenyl)-thiourea
Conditions | Yield |
---|---|
In benzene | 86% |
In acetone at 20℃; for 2h; |
Molecular Structure of 2-Amino-3-chlorotoluene (CAS NO.87-63-8):
IUPAC Name: 2-chloro-6-methylaniline
CAS Number: 87-63-8
Molecular Formula: C7H8ClN
Molecular Weight: 141.61
EINECS: 201-759-2
Melting Point: 2°C
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 3.24 Å2
Index of Refraction: 1.585
Molar Refractivity: 40.2 cm3
Molar Volume: 119.9 cm3
Surface Tension: 42.7 dyne/cm
Density: 1.18 g/cm3
Flash Point: 98.9 °C
Enthalpy of Vaporization: 45.13 kJ/mol
Boiling Point: 215 °C at 760 mmHg
Vapour Pressure: 0.151 mmHg at 25°C
Water Solubility: Immiscible
BRN: 774624
Solubility: Immiscible
InChI
InChI=1/C7H8ClN/c1-5-3-2-4-6(8)7(5)9/h2-4H,9H2,1H3
Smiles
c1(c(cccc1Cl)C)N
Product Categories: benzene derivative; Anilines, Aromatic Amines and Nitro Compounds
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | subcutaneous | 200mg/kg (200mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Archiv fuer Hygiene und Bakteriologie. Vol. 110, Pg. 12, 1933. |
Reported in EPA TSCA Inventory.
Poison by subcutaneous route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and Cl−.
Safety Information of 2-Amino-3-chlorotoluene (CAS NO.87-63-8):
Hazard Symbols:Xn
Risk Codes: 36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 3429 6.1/PG 3
WGK Germany: 3
RTECS: XU5100000
HazardClass: 6.1
PackingGroup: III
DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD
2-Amino-3-chlorotoluene , with CAS number of 87-63-8, can be called 2-Chloro-6-methylaniline ; 2-Methyl-6-chloroaniline ; 6-Chloro-2-methylaniline ; 6-Chloro-2-toluidine ; 6-Chloro-o-toluidine . It is a clear yellow to red-brown liquid. 2-Amino-3-chlorotoluene (CAS NO.87-63-8) can be used as a medicine, pesticide, dye intermediate.
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