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95330-46-4

95330-46-4

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Relevant articles and documentsAll total 2 Articles be found

A directed metalation of N-tert-butyl-N-methyl-2-methoxybenzamide. Short syntheses of 2-methoxy-6-methylbenzoic acid and lunularic acid

Reitz,Massey

, p. 1375 - 1379 (2007/10/02)

-

An Investigation into the Formation of Benzo- and Naphtho-pyrans by Cyclisation of ortho-Alkenyl(hydroxyalkyl)benzenes using either Cerium(IV) Ammonium Nitrate or Potassium t-Butoxide in Dimethylformamide

Giles, Robin G. F.,Green, Ivan R.,Pestana, J. Alexandre X.

, p. 2389 - 2396 (2007/10/02)

A series of ortho-alkenylbenzyl alcohols carrying methoxy substituents at appropriate positions on the aromatic ring have been synthesised.Each of these compounds has been treated separately with each of the title reagents.

Process route upstream and downstream products

Process route

N-methyl-tert-butylamine
14610-37-8

N-methyl-tert-butylamine

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; Ambient temperature;
97%
(2-methoxyphenyl)-tert-butylamino-methanone
88105-14-0

(2-methoxyphenyl)-tert-butylamino-methanone

methyl iodide
74-88-4

methyl iodide

1-(2-methoxyphenyl)pentan-1-one
20359-54-0

1-(2-methoxyphenyl)pentan-1-one

N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

N-tert-Butyl-N-methyl-2-methoxy-6-methylbenzamide
95330-45-3

N-tert-Butyl-N-methyl-2-methoxy-6-methylbenzamide

Conditions
Conditions Yield
With n-butyllithium; Multistep reaction. Yields of byproduct given; 1.) THF, hexane, -78 deg C (20 min), -10 deg C (30 min), 2.) -10 deg C (1 h), room temperature (1 h);
With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C (20 min), -10 deg C (30 min), 2.) -10 deg C (1 h), room temperature (1 h);
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

lunularic acid
23255-59-6

lunularic acid

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: Diisopropylamine, sec-Butyllithium (1.35 M in cyclohexane) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h; room temperature
3: CF3CO2H / 48 h / Heating
4: NaNO2/acetic acid / acetic anhydride / 0 °C
5: ethanolic KOH / Heating
6: 84 percent / BBr3 / CH2Cl2 / 1) -78 deg C, 1 h, 2) room temperature
With potassium hydroxide; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; boron tribromide; acetic acid; diisopropylamine; trifluoroacetic acid; sodium nitrite; In dichloromethane; acetic anhydride;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

2-methoxy-6-methyl-benzoic acid
6161-65-5

2-methoxy-6-methyl-benzoic acid

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: trifluoroacetic acid / 1) room temperature, 15 min, 2) reflux, 2 h
3: NaNO2/acetic acid / acetic anhydride / 0 °C
4: ethanolic KOH / diethyl ether / 0.5 h / Heating
With potassium hydroxide; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; acetic acid; trifluoroacetic acid; sodium nitrite; In diethyl ether; acetic anhydride;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

2-Methoxy-6-<2-(4-methoxyphenyl)ethyl>benzoic acid
36640-14-9

2-Methoxy-6-<2-(4-methoxyphenyl)ethyl>benzoic acid

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: Diisopropylamine, sec-Butyllithium (1.35 M in cyclohexane) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h; room temperature
3: CF3CO2H / 48 h / Heating
4: NaNO2/acetic acid / acetic anhydride / 0 °C
5: ethanolic KOH / Heating
With potassium hydroxide; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; acetic acid; diisopropylamine; trifluoroacetic acid; sodium nitrite; In acetic anhydride;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

C<sub>10</sub>H<sub>12</sub>N<sub>2</sub>O<sub>3</sub>
125023-39-4

C10H12N2O3

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: trifluoroacetic acid / 1) room temperature, 15 min, 2) reflux, 2 h
3: NaNO2/acetic acid / acetic anhydride / 0 °C
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; acetic acid; trifluoroacetic acid; sodium nitrite; In acetic anhydride;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

N-Methyl-N-nitroso-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide
125023-42-9

N-Methyl-N-nitroso-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: Diisopropylamine, sec-Butyllithium (1.35 M in cyclohexane) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h; room temperature
3: CF3CO2H / 48 h / Heating
4: NaNO2/acetic acid / acetic anhydride / 0 °C
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; acetic acid; diisopropylamine; trifluoroacetic acid; sodium nitrite; In acetic anhydride;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

2-methoxy-6,N-dimethylbenzamide
95330-31-7

2-methoxy-6,N-dimethylbenzamide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: trifluoroacetic acid / 1) room temperature, 15 min, 2) reflux, 2 h
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; trifluoroacetic acid;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

N-Methyl-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide
125023-41-8

N-Methyl-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: Diisopropylamine, sec-Butyllithium (1.35 M in cyclohexane) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h; room temperature
3: CF3CO2H / 48 h / Heating
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; diisopropylamine; trifluoroacetic acid;
N-tert-Butyl-N-methyl-2-methoxybenzamide
95330-46-4

N-tert-Butyl-N-methyl-2-methoxybenzamide

N-tert-Butyl-N-methyl-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide
125023-40-7

N-tert-Butyl-N-methyl-2-methoxy-6-<2-(4-methoxyphenyl)ethyl>benzamide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1) TMEDA, sec-Butyllithium (1.35 M in Cyclohexane) / 1) THf, -78 deg C, 1 h, 2) -78 deg C, 1 h; room temperature
2: Diisopropylamine, sec-Butyllithium (1.35 M in cyclohexane) / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 2 h; room temperature
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; diisopropylamine;

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