Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h; | 100% |
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere; | 91% |
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h; | 86% |
With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide In water at 100℃; for 6h; | 74% |
Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
With borane-ammonia complex In methanol; water at 49.84℃; for 0.166667h; Catalytic behavior; | 99% |
With sodium tetrahydroborate In water at 60℃; for 0.0166667h; | 96% |
Stage #1: 5-nitro-m-xylene With Cu(OH)x impregnated on Fe3O4 In water for 0.0833333h; Green chemistry; Stage #2: With sodium tetrahydroborate In water at 55 - 60℃; for 0.116667h; Green chemistry; | 95% |
3,5-dimethylphenyl iodide
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h; | 99% |
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; ammonia In water; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction; | 95% |
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation; | 99% |
Multi-step reaction with 2 steps 1.1: sulfuric acid; nitric acid / 30 °C / Cooling with ice 2.1: palladium on activated charcoal / ethanol / 0.5 h / 50 °C / Autoclave 2.2: 0.83 h / 65 °C / 2250.23 Torr / Autoclave View Scheme |
N-hydroxy-3,5-dimethylbenzamide
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 90℃; for 4h; Lossen Rearrangement; | 97% |
Conditions | Yield |
---|---|
With palladium/alumina; ammonia; hydrogen In toluene at 250℃; under 2250.23 Torr; Temperature; Pressure; Solvent; | 95% |
With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere; | 71% |
With ammonia at 350℃; under 117681 - 183877 Torr; | |
With aluminum oxide; nitrogen; ammonia; hydrogen at 450℃; under 147102 Torr; |
3,5-dimethyl-cyclohexanone oxime
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With Pd(OH)x/LDH In N,N-dimethyl acetamide at 130℃; for 11h; Schlenk technique; Inert atmosphere; | 91% |
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 100℃; Sealed tube; | 88% |
1,2,3,4-tetrahydroisoquinoline
5-nitro-m-xylene
A
quinoline
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 73% B 76% |
5-nitro-m-xylene
2-methyl indoline
A
2-methyl-1H-indole
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 74% B 76% |
Conditions | Yield |
---|---|
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Schlenk technique; | 71% |
ethanol
5-nitro-m-xylene
A
2,5,7-trimethylquinoline
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With platinum-loaded TiO2 at 30℃; for 5h; UV-irradiation; | A 68% B 16% |
Conditions | Yield |
---|---|
Stage #1: 2,4-Xylenol With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4; | 67% |
5-methoxyindoline
5-nitro-m-xylene
A
5-methoxylindole
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | A 62% B 61% |
m-xylene
A
3,5-dimethylaminoaniline
B
2,4-Xylidine
C
2,6-dimethylaniline
Conditions | Yield |
---|---|
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 1h; | A 2% B 58% C 15% |
With hydrogenchloride; aluminium trichloride; sodium azide In various solvent(s) at 20℃; | |
With sodium azide; trifluorormethanesulfonic acid at 20℃; Ultrasonic irradiation; | |
Stage #1: m-xylene With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h; Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube; Overall yield = 60 percent; Overall yield = 72 mg; |
Conditions | Yield |
---|---|
With hydrogenchloride; PPA; hydroxylamine |
Conditions | Yield |
---|---|
With alkaline sodium hypobromite |
2-amino-4,6-dimethylbenzene-1,3-dicarbonitrile
A
2-amino-4,6-dimethyl benzamide
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With sulfuric acid |
3,5-dimethyl-cyclohex-2-enone oxime
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With hydrogenchloride at 170℃; |
3,5-Dimethylphenol
A
bis-(3,5-dimethylphenyl)-amine
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With ammonium chloride at 350℃; under 36775.4 Torr; |
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride | |
With iron; acetic acid | |
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
at 350℃; under 117681 Torr; |
3,5-Dimethylphenol
A
bis-(3,5-dimethylphenyl)-amine
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
at 350℃; under 36775.4 - 44130.5 Torr; |
1,2,3-triethylbenzene
bis-(3,5-dimethyl-cyclohex-2-enylidene)-hydrazine
3,5-dimethylaminoaniline
hydrogenchloride
4-(3,5-dimethyl-phenylazo)-3,5-dimethyl-aniline
A
3,5-dimethylaminoaniline
B
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
In chloroform-d1 not isolated; detected by NMR; |
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With 3,6-dimethyl-1,2,4,5-tetrazine; formic acid In acetonitrile at 20℃; for 1h; Reagent/catalyst; Solvent; | |
With 3,6-dimethyl-1,2,4,5-tetrazine; formic acid In acetonitrile at 20℃; for 1h; Reagent/catalyst; Solvent; |
Conditions | Yield |
---|---|
With pyridine In acetonitrile at 20℃; for 1h; Reagent/catalyst; |
3,5-dimethylaminoaniline
p-toluenesulfonyl chloride
N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With silica gel at 20℃; | 95% |
With triethylamine In dichloromethane at 0 - 20℃; | 82% |
3,5-dimethylaminoaniline
Trimethylacetic acid
N-(3,5-dimethylphenyl)pivalamide
Conditions | Yield |
---|---|
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating; | 100% |
3,5-dimethylaminoaniline
dimethyl acetylenedicarboxylate
dimethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate
Conditions | Yield |
---|---|
at 20℃; for 0.133333h; Michael addition; | 100% |
In diethyl ether at 0℃; | 75% |
4-methoxy-benzaldehyde
3,5-dimethylaminoaniline
3,5-dimethyl-N-(4-methoxybenzylidene)aniline
Conditions | Yield |
---|---|
at 20℃; | 100% |
With acetic acid In methanol at 20℃; |
Ethyl oxalyl chloride
3,5-dimethylaminoaniline
2-(3,5-dimethylphenylamino)-2-oxoacetic acidethyl ester
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1.5h; Inert atmosphere; | 100% |
With triethylamine In tetrahydrofuran at 0 - 20℃; | 68% |
3,5-dimethylaminoaniline
3-(3,5-dimethyl-phenylamino)-propionamide
Conditions | Yield |
---|---|
With ammonia In methanol at 80℃; | 100% |
2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h; | 100% |
{4-[6-formyl-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester
3,5-dimethylaminoaniline
{4-[6-[(3,5-dimethylphenylamino)methyl]-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In acetonitrile at 20℃; for 12h; | 100% |
3,5-dimethylaminoaniline
1,2-dibromobenzene
N,N'-di(3,5-dimethylphenyl)benzene-1,2-diamine
Conditions | Yield |
---|---|
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene | 100% |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere; | 100 %Chromat. |
β-(1-naphthyl)nitroethylene
3,5-dimethylaminoaniline
C20H20N2O2
Conditions | Yield |
---|---|
at 20℃; for 0.1h; Michael addition; neat (no solvent); | 100% |
1-nitro-2-(2-nitrovinyl)benzene
3,5-dimethylaminoaniline
C16H17N3O4
Conditions | Yield |
---|---|
at 20℃; for 0.1h; Michael addition; neat (no solvent); | 100% |
Conditions | Yield |
---|---|
at 20℃; for 0.1h; Michael addition; neat (no solvent); | 100% |
3-nitro-β-nitrostyrene
3,5-dimethylaminoaniline
3,5-dimethyl-N-[2-nitro-1-(3-nitro-phenyl)-ethyl]-aniline
Conditions | Yield |
---|---|
at 20℃; for 0.1h; Michael addition; neat (no solvent); | 100% |
1-chloro-4-(2-nitrovinyl)benzene
3,5-dimethylaminoaniline
C16H17ClN2O2
Conditions | Yield |
---|---|
at 20℃; for 0.1h; Michael addition; neat (no solvent); | 100% |
3,5-dimethylaminoaniline
acetylenedicarboxylic acid diethyl ester
diethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate
Conditions | Yield |
---|---|
at 20℃; for 0.15h; Michael addition; | 100% |
benzaldehyde
3,5-dimethylaminoaniline
3,5-dimethyl-N-benzylideneaniline
Conditions | Yield |
---|---|
at 20℃; | 100% |
In methanol | 99% |
In ethanol for 3h; Reflux; |
4-methyl-benzaldehyde
3,5-dimethylaminoaniline
3,5-dimethyl-N-(4-methylbenzylidene)aniline
Conditions | Yield |
---|---|
at 20℃; | 100% |
4-chlorobenzaldehyde
3,5-dimethylaminoaniline
3,5-dimethyl-N-(4-chlorobenzylidene)aniline
Conditions | Yield |
---|---|
at 20℃; | 100% |
In neat (no solvent) at 20℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere; |
3,5-dimethylaminoaniline
4-bromo-benzaldehyde
3,5-dimethyl-N-(4-bromobenzylidene)aniline
Conditions | Yield |
---|---|
at 20℃; | 100% |
Conditions | Yield |
---|---|
at 20℃; | 100% |
2-bromo-butyryl bromide
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 99% |
Stage #1: acetic anhydride; 3,5-dimethylaminoaniline In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water pH=12 - 14; Cooling with ice; | 99% |
Stage #1: acetic anhydride; 3,5-dimethylaminoaniline In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water pH=12 - 14; Cooling with ice; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 201℃; for 1h; | 99% |
Stage #1: 3,5-dimethylaminoaniline With potassium carbonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride for 2h; Inert atmosphere; | 99% |
With potassium carbonate In dichloromethane at 20℃; for 2.5h; Cooling with ice; | 98.8% |
4-hydroxyphenylacetate
3,5-dimethylaminoaniline
N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h; | 99% |
With boric acid In toluene for 18h; Heating; | 95% |
With pyridine; FI-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 60℃; for 0.75h; Sealed tube; | 86% |
2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate
3,5-dimethylaminoaniline
Conditions | Yield |
---|---|
With perchloric acid In ethanol at 105℃; for 1.5h; | 99% |
1-(tert-butoxycarbonyl)-L-proline
3,5-dimethylaminoaniline
(S)-tert-butyl 2-((3,5-dimethylphenyl)carbamoyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With chloroformic acid ethyl ester; triethylamine In dichloromethane at 20℃; for 1h; | 99% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h; | 85% |
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 12h; Ambient temperature; | 65% |
para-chlorotoluene
3,5-dimethylaminoaniline
3,5-dimethyl-N-p-tolylbenzenamine
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere; | 99% |
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium hydroxide; sodium t-butanolate In water at 110℃; for 22h; Buchwald-Hartwig amination; Inert atmosphere; chemoselective reaction; | 95% |
With sodium t-butanolate; [Na2PdCl4]; dicyclohexyl-(9-ethyl-9H-fluoren-9-yl)phosphane*HBF4 In toluene at 120℃; for 12h; Buchwald-Hartwig coupling reaction; | |
With sodium t-butanolate; palladium diacetate; dicyclohexyl(9-ethyl-9H-fluorene-9-yl)-phosphine·HBF4 In toluene at 120℃; for 12h; Product distribution / selectivity; Buchwald-Hartwig Amination; |
1. | mmo-sat 1 mg/plate | EMMUEG Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1. | ||
2. | orl-rat LD50:707 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 . | ||
3. | orl-mus LD50:421 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 . |
Suspected carcinogen. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also XYLIDINE; 2,3-XYLIDINE; 2,4-XYLIDINE; 2,5-XYLIDINE; 2,6-XYLIDINE; 3,4-XYLIDINE; 2,4-XYLIDINE HYDROCHLORIDE; 2,5-XYLIDINE HYDROCHLORIDE.
Hazard Codes:T,N
Risk Statements:
23: Toxic by inhalation
24: Toxic in contact with skin
25: Toxic if swallowed
33: Danger of cumulative effects
51: Toxic to aquatic organisms
53: May cause long-term adverse effects in the aquatic environment
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
37: Wear suitable gloves
39: Wear eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61: Avoid release to the environment. Refer to special instructions safety data sheet
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