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1978-38-7 Usage

Chemical Properties

Deep brown liquid

Uses

2-Fluoro-N-methylaniline is an aniline derivative used in the preparation of various pharmaceutical compounds such as muscarinic agonists.

Check Digit Verification of cas no

The CAS Registry Mumber 1978-38-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,7 and 8 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1978-38:
(6*1)+(5*9)+(4*7)+(3*8)+(2*3)+(1*8)=117
117 % 10 = 7
So 1978-38-7 is a valid CAS Registry Number.

1978-38-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Fluoro-N-methylaniline

1.2 Other means of identification

Product number -
Other names N-methyl-o-fluoroaniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1978-38-7 SDS

1978-38-7Synthetic route

2-Fluoroaniline
348-54-9

2-Fluoroaniline

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
under 760.051 Torr; Reagent/catalyst; Molecular sieve; Reflux; Green chemistry;99.4%
N-methyl-N-(2-fluorophenyl)formamide
1272654-63-3

N-methyl-N-(2-fluorophenyl)formamide

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
With sulfuric acid; water at 80℃; for 5h;98.4%
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 130℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox;15 %Chromat.
N-(2-fluorophenyl)methanimine

N-(2-fluorophenyl)methanimine

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
With hydrogen at 120℃; under 7500.75 Torr; for 3h; Reagent/catalyst; Temperature; Pressure;96.6%
formaldehyd
50-00-0

formaldehyd

2-Fluoroaniline
348-54-9

2-Fluoroaniline

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Stage #1: formaldehyd; 2-Fluoroaniline With potassium hydroxide In methanol at 85℃; for 2h; Sealed tube;
Stage #2: With methanol; sodium tetrahydroborate at 0 - 85℃; for 1h; Reagent/catalyst; Temperature; Sealed tube;
95%
With methanol; sodium tetrahydroborate; sodium at 60℃; for 2h;65%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

methylamine
74-89-5

methylamine

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Stage #1: 2-Fluoroaniline With hydrogenchloride In water for 0.5h;
Stage #2: With sodium nitrite In water at -10 - 5℃; for 1.5h;
Stage #3: methylamine In water at 50℃; for 2.5h; Temperature;
95%
N-methyl-N-nosyl-o-fluoroaniline
900537-29-3

N-methyl-N-nosyl-o-fluoroaniline

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

2-(4-nitrophenylthio)acetic acid
3406-75-5

2-(4-nitrophenylthio)acetic acid

B

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;A n/a
B 88%
methanol
67-56-1

methanol

2-Fluoroaniline
348-54-9

2-Fluoroaniline

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
With [Cp*Ir(2-(1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazole)Cl][Cl]; caesium carbonate at 120℃; for 12h; Schlenk technique;87%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

methyl iodide
74-88-4

methyl iodide

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Stage #1: 2-Fluoroaniline With n-butyllithium In tetrahydrofuran; hexane at -50 - 20℃; for 1.25h;
Stage #2: methyl iodide In tetrahydrofuran; hexane for 5.25h; Further stages.;
80%
N-(2-fluorophenyl)formamide
824-48-6

N-(2-fluorophenyl)formamide

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
In tetrahydrofuran; methanol59%
Stage #1: N-(2-fluorophenyl)formamide With borane In tetrahydrofuran Heating;
Stage #2: With hydrogenchloride In methanol; ethanol Further stages.;
With hydrogenchloride; sodium hydroxide; borane In tetrahydrofuran; 1,4-dioxane at 0 - 60℃; for 4h; Under argon gas;
2-Fluoroaniline
348-54-9

2-Fluoroaniline

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / pyridine / CH2Cl2 / 20 °C
2: 100 percent / CH2Cl2 / 0.17 h / 20 °C
3: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: acetic anhydride / 2 h / 50 °C
1.2: 1 h / 20 °C
2.1: borane-THF / tetrahydrofuran / 2 h / 50 °C
2.2: 1 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Large scale
2: sodium hydride / mineral oil; tetrahydrofuran / 4 h / 0 °C / Large scale
3: ammonium hydroxide / water / 5 h / Reflux; Large scale
View Scheme
Multi-step reaction with 3 steps
1: toluene / 6 h / 88 - 110 °C
2: potassium carbonate / 4 h / 130 °C / 3000.3 - 4500.45 Torr / Autoclave
3: sulfuric acid; water / 5 h / 80 °C
View Scheme
N-(2-fluorophenyl)-4-nitrobenzenesulfonamide
1766-57-0

N-(2-fluorophenyl)-4-nitrobenzenesulfonamide

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / CH2Cl2 / 0.17 h / 20 °C
2: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C
View Scheme
formic acid
64-18-6

formic acid

2-Fluoroaniline
348-54-9

2-Fluoroaniline

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride at 0 - 50℃; Inert atmosphere;
Stage #2: 2-Fluoroaniline In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride; borane-THF
C13H13FN2O2S

C13H13FN2O2S

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Conditions
ConditionsYield
With ammonium hydroxide In water for 5h; Reflux; Large scale;646 g
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

(R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoyl chloride

(R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoyl chloride

C23H18F2N2O3

C23H18F2N2O3

Conditions
ConditionsYield
With sodium hydroxide In toluene at 20 - 25℃; for 3h; Reagent/catalyst;96.47%
(R)-(+)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propanoyl chloride
101053-90-1

(R)-(+)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propanoyl chloride

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

(R)-2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy)-N-(2-fluorophenyl)-N-methylpropionamide

(R)-2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy)-N-(2-fluorophenyl)-N-methylpropionamide

Conditions
ConditionsYield
With sodium hydroxide In toluene at 20 - 25℃; for 3.5h;96.46%
(2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid

(2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

metamifop

metamifop

Conditions
ConditionsYield
Stage #1: (2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid With trifluorormethanesulfonic acid; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1.5h;
Stage #2: 2-fluoro-N-methylaniline In dichloromethane at 20℃; for 3h; Solvent;
95.8%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

fenoxaprop-p-ethyl
66441-23-4, 71283-80-2

fenoxaprop-p-ethyl

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide
256412-89-2

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide

Conditions
ConditionsYield
With triethylamine In ethanol at 80℃; Solvent; Temperature; Reagent/catalyst;95%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

3-methyl-5H-1,4,2-dioxazol-5-one

3-methyl-5H-1,4,2-dioxazol-5-one

N'-(2-fluorophenyl)-N'-methylacetohydrazide
1604806-78-1

N'-(2-fluorophenyl)-N'-methylacetohydrazide

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In chloroform at 25℃; for 12h; Inert atmosphere; Sealed tube;95%
2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride
865352-01-8

2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

2-(2,2-difluoroethoxy)-N-(2-fluorophenyl)-N-methyl-6-(trifluoromethyl)benzenesulfonamide

2-(2,2-difluoroethoxy)-N-(2-fluorophenyl)-N-methyl-6-(trifluoromethyl)benzenesulfonamide

Conditions
ConditionsYield
With 3,5-Lutidine In dimethyl sulfoxide; toluene at 60 - 65℃; for 4.5h;94.36%
5-bromothiophene-2-carbonyl chloride
31555-60-9

5-bromothiophene-2-carbonyl chloride

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

5-bromo-N-(2-fluorophenyl)-N-methylthiophene-2-carboxamide
1396244-28-2

5-bromo-N-(2-fluorophenyl)-N-methylthiophene-2-carboxamide

Conditions
ConditionsYield
With triethylamine at 0℃; for 3h;94%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

phenazine-1-carboxylic acid chloride

phenazine-1-carboxylic acid chloride

N-(2-fluorophenyl)-N-methylphenazine-1-carboxamide

N-(2-fluorophenyl)-N-methylphenazine-1-carboxamide

Conditions
ConditionsYield
In dichloromethane at 0 - 5℃; for 1h;93%
With triethylamine In dichloromethane for 2h; Reflux;93%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

acetyl chloride
75-36-5

acetyl chloride

N-(2-fluorophenyl)-N-methylacetamide
120371-27-9

N-(2-fluorophenyl)-N-methylacetamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 17h; Inert atmosphere;91%
2-Bromo-6-[(S)-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-pyridine
867327-09-1

2-Bromo-6-[(S)-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-pyridine

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

C24H26FN3

C24H26FN3

Conditions
ConditionsYield
tris-(dibenzylideneacetone)dipalladium(0); CyJohnPhos In toluene at 20 - 80℃; for 2h;90.3%
(2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid

(2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide
256412-89-2

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide

Conditions
ConditionsYield
With oxalyl dichloride; triethylamine at 10 - 40℃; for 10h;90%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

N-methylaniline
100-61-8

N-methylaniline

Conditions
ConditionsYield
With sodium tetrafluoroborate; tetrabutylammonium tetrafluoroborate In 1-methyl-pyrrolidin-2-one at 60℃; for 3h; Electrochemical reaction; Green chemistry;87%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

2-Bromopropionic acid
598-72-1

2-Bromopropionic acid

N-(2-Fluorophenyl)-N-methyl-2-bromo-propionamide
256412-87-0

N-(2-Fluorophenyl)-N-methyl-2-bromo-propionamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In chloroform at 20℃; for 1h;87%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromo-N-(2-fluorophenyl)-N-methylacetamide
1339800-80-4

2-bromo-N-(2-fluorophenyl)-N-methylacetamide

Conditions
ConditionsYield
In dichloromethane at -10 - 20℃; for 17h; Inert atmosphere;86%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

Methacryloyl chloride
920-46-7

Methacryloyl chloride

N-(2-fluorophenyl)-N-methylmethacrylamide
1449116-83-9

N-(2-fluorophenyl)-N-methylmethacrylamide

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 0℃; Inert atmosphere; Sealed tube; Schlenk technique;85%
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;73%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;
With triethylamine In dichloromethane at 0 - 20℃; for 1h;
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

C21H20ClNO6

C21H20ClNO6

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide
256412-89-2

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]-N-(2-fluorophenyl)-N-methylpropanamide

Conditions
ConditionsYield
at 5 - 25℃; for 13h; Large scale;85%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

2-phenylimidazo[1,2-a]pyridine
4105-21-9

2-phenylimidazo[1,2-a]pyridine

2-fluoro-N-methyl-4-((2-phenylimidazo[1,2-a]pyridin-3-yl)thio)aniline

2-fluoro-N-methyl-4-((2-phenylimidazo[1,2-a]pyridin-3-yl)thio)aniline

Conditions
ConditionsYield
With sulfur; dimethyl sulfoxide at 110℃; for 12h; Sealed tube;83%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

isopropenylbenzene
98-83-9

isopropenylbenzene

C16H18FN

C16H18FN

Conditions
ConditionsYield
With C31H49N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 20 - 120℃; for 36h;82%
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 36h; Inert atmosphere; chemoselective reaction;82%
With 1,1,1,3',3',3'-hexafluoro-propanol; sodium acetate at 80℃; for 12h; chemoselective reaction;81%
2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

C8H7FN2S

C8H7FN2S

Conditions
ConditionsYield
With oxygen In tetrahydrofuran at 20℃; for 4h; Irradiation; chemoselective reaction;82%
rac-methoxyphenylacetic acid
7021-09-2

rac-methoxyphenylacetic acid

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

N-(2-fluorophenyl)-2-methoxy-N-methyl-2-phenylacetamide
1333643-96-1

N-(2-fluorophenyl)-2-methoxy-N-methyl-2-phenylacetamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere; optical yield given as %de;81%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

2-fluoro-N-methyl-N-(2-nitrophenyl)aniline
908242-57-9

2-fluoro-N-methyl-N-(2-nitrophenyl)aniline

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene for 16h; Heating;79%
1,6-dibromocyclohex-1-ene
17202-32-3

1,6-dibromocyclohex-1-ene

2-fluoro-N-methylaniline
1978-38-7

2-fluoro-N-methylaniline

N-(2-bromo-2-cyclohexenyl)-2-fluoro-N-methylaniline
475040-19-8

N-(2-bromo-2-cyclohexenyl)-2-fluoro-N-methylaniline

Conditions
ConditionsYield
Stage #1: 2-fluoro-N-methylaniline With n-butyllithium In tetrahydrofuran; hexane at -50 - 20℃; for 1h;
Stage #2: 1,6-dibromocyclohex-1-ene In tetrahydrofuran; hexane for 5.25h; Further stages.;
78%

1978-38-7Relevant articles and documents

Synthesis method of N-methyl o-fluoroaniline

-

Paragraph 0018; 0024; 0026-0041, (2021/05/29)

The invention relates to the field of preparation of pesticide and medical intermediates, and in particular, relates to a preparation method of N-methyl o-fluoroaniline, wherein the preparation method comprises the following steps: by taking o-fluoroaniline as a raw material and dimethyl carbonate as a reaction raw material and a reaction solvent, carrying out heat preservation reaction under the action of a basic catalyst; and after the reaction is finished, filtering to remove the catalyst, carrying out rectification separation on filtrate, and separating the solvent dimethyl carbonate from the product. Compared with the prior art, the novel synthesis method of N-methyl o-fluoroaniline provided by the invention has the following effective effects: only one-step reaction is needed, the selectivity is extremely high, the product quality is good, the selected methylation reagent dimethyl carbonate is low in toxicity, green and safe, the output of three wastes is low, and the novel synthesis method of N-methyl o-fluoroaniline is a green chemical process with extremely competitive power.

Synthesis method of N-methyl o-fluoroaniline

-

, (2020/09/23)

The invention discloses a synthesis method of N-methyl o-fluoroaniline, which comprises the following steps: an amidation reaction: by using o-fluoroaniline as a raw material, mixing o-fluoroaniline with toluene and formic acid, heating to react, and dehydrating while reacting to obtain N-(2-fluorophenyl) formamide; a methylation reaction: taking N-(2-fluorophenyl) formamide as a raw material, adding dimethyl carbonate and a catalyst, putting into an autoclave, and heating to carry out the methylation reaction so as to obtain N-methyl-N-formyl-2-fluoroaniline; and a hydrolysis reaction: takingN-methyl-N-formyl-2-fluoroaniline as a raw material, mixing the N-methyl-N-formyl-2-fluoroaniline with water and sulfuric acid, carrying out hydrolysis, and carrying out post-treatment to obtain theN-methyl o-fluoroaniline. The method has the advantages of easily available raw materials, low raw material cost, mild reaction conditions, greenness, safety, high total yield (up to 90%), and great industrial application prospect.

Manufacturing method for halogen substituted N-methylaniline

-

Paragraph 0025-0029; 0031-0032; 0033; 0034; 0043, (2019/09/05)

The present invention relates to a method for manufacturing halogen-substituted N-methylaniline from halogen-substituted aniline. When halogen-substituted N-methylaniline is manufactured by using the method of the present invention, it is possible to manufacture halogen-substituted N-methylaniline without using existing methoxide sodium which has low chemical stability and is expensive, by using a low-cost base having excellent chemical stability such as potassium hydroxide or sodium hydroxide. Therefore, it is possible to reduce costs in a manufacturing process and to produce N-methylaniline with a high yield and high purity, thereby being useful for mass production as a raw material for herbicide metamifop synthesis.COPYRIGHT KIPO 2019

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