Conditions | Yield |
---|---|
With copper (II) carbonate hydroxide; phenylsilane; cyclohexyldiphenylphosphine In acetonitrile at 60℃; for 12h; | 99% |
In toluene for 0.0833333h; Reflux; | 96% |
In toluene at 88 - 108℃; | 96% |
N,N-dimethyl-formamide
N-methylaniline
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With zinc(II) phthalocyanine; carbon dioxide; phenylsilane at 25℃; under 3750.38 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Autoclave; chemoselective reaction; | 99% |
With 1H-imidazole; nickel oxinate at 150℃; | 85% |
With t-butyldimethylsiyl triflate at 20℃; for 24h; | 82% |
With 1,2,4-Triazole; 8-quinolinol; copper(II) choride dihydrate at 150℃; | 74% |
With methyl benzylphosphonic chloride at 130℃; for 3.5h; | 59% |
Conditions | Yield |
---|---|
With copper(II) acetate dihydrate; phenylsilane; 1,2-bis-(diphenylphosphino)ethane In toluene at 25℃; under 760.051 Torr; for 2h; | 99% |
With Zn(salen); phenylsilane at 25℃; under 3750.38 Torr; for 7h; Reagent/catalyst; Pressure; Temperature; | 99% |
With Al(salen); phenylsilane at 100℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Pressure; Temperature; Autoclave; | 99% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; | 99% |
Conditions | Yield |
---|---|
With formaldehyd; sodium hydroxide In ethanol; water at 27℃; for 9h; | 97% |
With ethanol; oxalic acid anschliessend man erhitzt das abgeschiedene Salz bis zur Beendung der Gasentwicklung auf 160-180grad; |
N-phenylthioacetamide
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.5h; | 97% |
With triphenyltin(IV) hydroxide In benzene-d6 at 90℃; for 3h; | 50% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 27℃; for 9h; | 97% |
With sodium hydroxide In water; toluene at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; chemoselective reaction; | 94% |
With sodium hydroxide In water at 25℃; for 6h; | 93% |
Conditions | Yield |
---|---|
With phenylsilane; C19H37N2(1+)*Br(1-) In neat (no solvent) at 20℃; under 3750.38 Torr; for 6h; Autoclave; | 95% |
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 100℃; under 22502.3 Torr; for 20h; Autoclave; | 70% |
diethylzinc at 100℃; under 34200 Torr; for 18h; | 30% |
With Wilkinson's catalyst; copper diacetate; lithium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; under 760.051 Torr; for 36h; Schlenk technique; |
N,N-dimethyl-aniline
triethyl phosphite
A
triethyl phosphate
B
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; oxygen In 1,2-dichloro-ethane; acetonitrile at 25℃; for 24h; Schlenk technique; Irradiation; | A n/a B 95% |
Conditions | Yield |
---|---|
With Cu/Al2O3; dihydrogen peroxide In water at 50℃; for 12h; Green chemistry; | 95% |
methanol
N-methylaniline
A
N-methyl-N-phenylformamide
B
Formanilid
Conditions | Yield |
---|---|
With lithium hydroxide In water for 4h; Air; Reflux; | A 94% B 5% |
Conditions | Yield |
---|---|
With methanol; lithium hydroxide In water at 80℃; for 4h; | A 94% B 5% |
carbon dioxide
N-methylaniline
A
N,N-dimethyl-aniline
B
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 4h; Time; Sealed tube; | A 94% B 8% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 110℃; under 760.051 Torr; for 48h; Mechanism; Solvent; Reagent/catalyst; Schlenk technique; | A 92% B 8% |
With phenylsilane; C23H23O2P In acetonitrile at 100℃; under 15001.5 Torr; for 24h; | A 8% B 91% |
Conditions | Yield |
---|---|
With potassium fluoride on basic alumina In acetonitrile at 20℃; for 18h; | 93% |
With sodium ethanolate at 50℃; Riemer-Tiemann reaction; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With copper(II) acetate dihydrate; nickel(II) chloride hexahydrate; sodium perchlorate; caesium carbonate In dimethyl sulfoxide at 20℃; Reagent/catalyst; Solvent; Electrolysis; | 93% |
Conditions | Yield |
---|---|
at 60℃; for 15h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In dichloromethane for 1h; Ambient temperature; | 91.2% |
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With hydrogenchloride; diethyl ether In diethyl ether at -78℃; for 0.5h; | 91% |
Conditions | Yield |
---|---|
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 25℃; for 48h; | 91% |
at 50℃; | 80% |
(formyloxy)(acetoxy)phenylmethane
N-methylaniline
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 1h; | 91% |
Conditions | Yield |
---|---|
With Silphos at 20℃; for 12h; | 90% |
With N1-(3-(trimethoxysilyl)propyl)ethane-1,2-diamine-sulfamic acid supported on mesoporous silica SBA-15 In neat (no solvent) at 50℃; Green chemistry; | 90% |
With immobilized H2SO4 on activated charcoal at 54℃; for 1.33333h; | 90% |
3-phenyl-2-azido-N-(2-iodophenyl)-N-methylpropanamide
A
3-benzyl-1-methyl-2(1H)-quinoxalinone
B
N-methyl-N-phenyl-carbamoyl cyanide
C
phenylacetonitrile
D
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; | A n/a B n/a C 80% D 89% |
α,α,α-iodinefluoroacetophenone
N-methylaniline
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With water; sodium hydroxide In acetonitrile at 20℃; for 0.166667h; | 89% |
chloroform
N-(3-methylbut-2-enyl)-N-methylaniline
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide at 20℃; for 4h; | 88% |
Conditions | Yield |
---|---|
With air In 1,2-dimethoxyethane at 20℃; under 760.051 Torr; Solvent; Irradiation; | 87% |
With FeIII(meso-tetrakis(o,o,m,m-tetrafluoro-p-(dimethylamino)phenyl)porphyrinato)OTf; dihydrogen peroxide; acetic acid In methanol; water at 20℃; for 2h; Reagent/catalyst; chemoselective reaction; | 82% |
With benzyl(triethyl)ammoniumpermanganate In dichloromethane | 78% |
2-(1-adamantyl)-2-azido-N-(2-iodophenyl)-N-methylacetamide
A
3-((1s,3s)-adamantan-1-yl)-1-methylquinoxalin-2(1H)-one
B
1-adamantanecarbonitrile
C
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; | A n/a B 86% C 84% |
Conditions | Yield |
---|---|
With TEMPO; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 12h; | A 71% B 86% |
2-azido-N-(2-iodophenyl)-N-methyltridecanamide
A
1-methyl-3-undecyl-2(1H)-quinoxalinone
B
N-methyl-N-phenylformamide
C
undecyl cyanide
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 110℃; | A 13% B 80% C 85% |
Conditions | Yield |
---|---|
With copper (I) acetate; caesium carbonate; XPhos In water; N,N-dimethyl-formamide at 110℃; for 12h; Reagent/catalyst; Solvent; Schlenk technique; | 85% |
With water In N,N-dimethyl-formamide at 110℃; for 6h; Mechanism; Solvent; Time; Temperature; Reagent/catalyst; Schlenk technique; | 84% |
With copper (I) acetate; caesium carbonate; XPhos In N,N-dimethyl-formamide at 110℃; for 12h; Reagent/catalyst; Solvent; | 82% |
formamide
N-methylaniline
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With sulfated tungstate at 100℃; for 60h; Green chemistry; | 84% |
With [Mn((N'1E,N'2E)-N'1,N'2-bis(phenyl(pyridin-2-yl)methylene)oxalohydrazide(-H))(OAc)(H2O)]2*6H2O In neat (no solvent) at 120℃; for 24h; | 83% |
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 100℃; for 1.5h; Microwave irradiation; | 75% |
2-carbethoxyindole
N-methyl-N-phenylformamide
ethyl 3-formyl-1H-indole-2-carboxylate
Conditions | Yield |
---|---|
With trichlorophosphate In 1,2-dichloro-ethane for 1.5h; Heating / reflux; | 100% |
With trichlorophosphate In 1,2-dichloro-ethane Vilsmeier-Haack reaction; Heating; | 86% |
Stage #1: N-methyl-N-phenylformamide With chlorophosphonic acid at 20℃; for 0.25h; Stage #2: 2-carbethoxyindole In 1,2-dichloro-ethane for 1.5h; Heating / reflux; | 66% |
With 1,2-dichloro-ethane; trichlorophosphate Behandeln des Reaktionsgemisches mit wss. Natriumacetat; |
6,7,8-trimethoxy-1,4-dimethylcarbazole
N-methyl-N-phenylformamide
3-formyl-6,7,8-trimethoxy-1,4-dimethylcarbazole
Conditions | Yield |
---|---|
With trichlorophosphate for 3.5h; Heating; | 100% |
With trichlorophosphate In Trichloroethylene for 3.5h; Heating; | 99% |
3-fluorobromobenzene
N-methyl-N-phenylformamide
2-bromo-6-fluorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With hydrogenchloride; n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - -70℃; for 2.5h; Stage #2: N-methyl-N-phenylformamide In tetrahydrofuran; hexanes at -78 - -70℃; for 2h; | 100% |
N-methyl-N-phenylformamide
p-aminoethylbenzoate
N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine
Conditions | Yield |
---|---|
With thionyl chloride In toluene at 20℃; for 19.5h; Reagent/catalyst; | 99.4% |
In water; toluene for 5h; Solvent; Reflux; | 92.2% |
2-butylthiophene
N-methyl-N-phenylformamide
5-butylthiophene-2-carboxaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate | 99% |
With trichlorophosphate |
Conditions | Yield |
---|---|
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction; | 99% |
7-Methyl-imidazo[1,2-a]pyridine
N-methyl-N-phenylformamide
7-methylimidazo<1,2-a>pyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In ethanol at 80℃; for 11h; Reagent/catalyst; | 98.8% |
8-methyl-2-phenylimidazo[1,2-a]pyridine
N-methyl-N-phenylformamide
8-methyl-2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In chlorobenzene at 80℃; for 10h; Reagent/catalyst; | 98.6% |
2-methylimidazo[1,2-a]pyridine
N-methyl-N-phenylformamide
2-Methylimidazo<1,2-a>pyridin-3-carboxaldehyd
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In toluene at 70℃; for 12h; Reagent/catalyst; | 98.3% |
N-methyl-N-phenylformamide
1,4-Dimethoxy-2-[(3-methoxybenzyl)thio]benzol
2,5-Dimethoxy-4-[(3-methoxybenzyl)thio]benzaldehyd
Conditions | Yield |
---|---|
Stage #1: N-methyl-N-phenylformamide; 1,4-Dimethoxy-2-[(3-methoxybenzyl)thio]benzol With trichlorophosphate at 15 - 60℃; Vilsmeier-formylation; Stage #2: With water for 0.5h; | 98% |
N-methyl-N-phenylformamide
methyl 4-methyl-1H-indole-2-carboxylate
methyl 3-formyl-4-methylindole-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.25h; Stage #2: methyl 4-methyl-1H-indole-2-carboxylate In 1,2-dichloro-ethane for 2.5h; Heating; Further stages.; | 98% |
Conditions | Yield |
---|---|
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: ferrocene at 20℃; Inert atmosphere; | 98% |
With phosphorus oxychloride In neat (no solvent) anilide and P-compd. stirring at room temp. for 30 min, Fe-compd. addn.,mixt. stirring at room temp. for 3 d, quenching by pouring onto ice, aq . layer extn. after 2 h with Et2O, org. layer drying (MgSO4), vac. concn.; residue flash column chromy. (SiO2, petrol/E2O 7:3 to 5:5), recrystn. (hot petroleum); | 87% |
With trichlorophosphate In neat (no solvent) Vilsmeyer formylation; double mol amt. of formylation mixt., few days at ambient temp.;; | 81% |
2-isopropoxynaphthalene
N-methyl-N-phenylformamide
2-iso-Propoxynaphthalin-1-carbaldehyd
Conditions | Yield |
---|---|
Stage #1: 2-isopropoxynaphthalene; N-methyl-N-phenylformamide With trichlorophosphate at 0 - 75℃; for 12h; Vilsmeier-Haack reaction; Stage #2: With water; sodium hydroxide Vilsmeier-Haack reaction; | 98% |
p-methoxybenzyl chloride
N-methyl-N-phenylformamide
4-methoxy-N-methyl-N-phenylbenzenemethanamine
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique; | 98% |
With potassium hydroxide In water at 50℃; for 3h; Green chemistry; | 80% |
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With 1-(4-sulfonylbutyl)pyridinium p-toluenesulfonate; tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2] In 1-methyl-pyrrolidin-2-one at 100℃; for 8h; Reagent/catalyst; | 97.9% |
Conditions | Yield |
---|---|
With 1,3-Dimethoxybenzene; trichlorophosphate In dichloromethane at 40℃; for 24h; Product distribution; other carboxamides, var. solvents, var. temp., var. time, var. reagents mole ratio; | 97% |
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 100℃; under 37503.8 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Pressure; Temperature; Autoclave; Glovebox; | 94% |
With aluminum oxide; potassium fluoride for 0.333333h; microwave irradiation; | 80% |
1,4-dimethoxy-2,3-methylenedioxybenzene
N-methyl-N-phenylformamide
4,7-dimethoxy-benzo[1,3]dioxole-5-carbaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at 0 - 20℃; for 3h; Vilsmeier-Haack Formylation; | 97% |
With trichlorophosphate for 48h; Ambient temperature; | 87% |
n-Methylformanilide (93-61-8) is also named as Formamide,N-methyl-N-phenyl- ; Formanilide, N-methyl- ; Methylphenylformamide ; FORMIC ACID N-METHYLANILIDE ; METHYLFORMANILIDE and so on. n-Methylformanilide (93-61-8) is usually clear, colorless liquid. Its product categories are acids and esters.
CAS: 93-61-8
Molecular Formula: C8H9NO
Molecular Weight: 135.16
Molecular structure:
EINECS: 202-262-3
Water Solubility: immiscible
Melting point: 8-13 °C(lit.)
Boiling Point: 243 °C at 760 mmHg
Index of Refraction: 1.567
Flash Point: 126.7 °C
BRN: 636496
Polarizability: 16.15 10-24cm3
Surface Tension: 42.3 dyne/cm
Enthalpy of Vaporization: 48 kJ/mol
Vapour Pressure: 0.0329 mmHg at 25 °C
Surface Tension: 42.3 dyne/cm
Density: 1.083 g/cm3
n-Methylformanilide (93-61-8) is commonly used as organic intermediates.
RTECS#: CAS# 93-61-8: None listed
LD50/LC50: RTECS: Not available.
Carcinogenicity: N-METHYLFORMANILIDE, 99% - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated.
Hazard Codes: Xn,Xi
Risk Statements: 22-43-38
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R38:Irritating to skin.
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 2
HS Code: 29242995
Chemical Stability: Stable under normal temperatures and pressures.
Conditions to Avoid: Incompatible materials, strong oxidants.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization Has not been reported.
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