N-Methoxy-N-methylacetamide supplier

Name
N-Methoxy-N-methylacetamide
EINECS 628-920-3
CAS No. 78191-00-1
Article Data37
CAS DataBase
Density 0.979 g/cm³
Solubility Soluble in water
Melting Point
Formula C₄H₉NO₂
Boiling Point 92 °C at 760 mmHg
Molecular Weight 103.121
Flash Point 9.4 °C
Transport Information UN 1993 3/PG 3
Appearance clear colorless liquid
Safety 16
Risk Codes 10
Molecular Structure
Hazard Symbols R10:;
Synonyms N,O-Dimethylacetohydroxamicacid;
PSA 29.54000
LogP 0.02610

Synthetic route

: 457948-95-7
2-(4-fluorophenyl)-N-methoxy-N-methylacetamide

: 3536-96-7
vinylmagnesium chloride

A: 860642-35-9
1-(4-fluorophenyl)but-3-en-2-one

B: 119114-45-3
2-(4-fluorophenyl)-N-methoxyacetamide

C: C12H16FNO2

D: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
Stage #1: 2-(4-fluorophenyl)-N-methoxy-N-methylacetamide; vinylmagnesium chloride In tetrahydrofuran; toluene at -30℃; for 2h; Stage #2: With acetic anhydride In tetrahydrofuran; toluene at -30℃; for 0.5h; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene at -30 - 10℃;	A 100% B n/a C n/a D n/a

...Expand

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 75-36-5
acetyl chloride

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	98%
With triethylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;	83%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: acetyl chloride In dichloromethane at 0 - 22℃;	78%

: 123-86-4
acetic acid butyl ester

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: acetic acid butyl ester In tetrahydrofuran at 20℃; for 2h;	91%

: 434-45-7
1,1,1-trifluoroacetophenone

: 4,4,4-trifluoro-1-(N-methoxy-N-methylamino)-1-methyl-1-(trimethylsiloxyl)-2-butyne

A: 78191-00-1
N-Methoxy-N-methylacetamide

B: 2,4-Diphenyl-5-[2,2,2-trifluoro-eth-(Z)-ylidene]-2,4-bis-trifluoromethyl-[1,3]dioxolane

Conditions

Conditions	Yield
Stage #1: 4,4,4-trifluoro-1-(N-methoxy-N-methylamino)-1-methyl-1-(trimethylsiloxyl)-2-butyne With tetrabutyl ammonium fluoride In tetrahydrofuran; diethyl ether at -15℃; for 0.166667h; Stage #2: 2,2,2-Trifluoroacetophenone In tetrahydrofuran; diethyl ether at 20℃; for 1h;	A n/a B 85%

...Expand

: 135203-03-1
N-methoxy-N-methylacetamidine hydroiodide

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
With potassium hydroxide for 2h; Heating;	62%

: 77-78-1
dimethyl sulfate

: N-acetyl-N-methylhydroxylamine, sodium salt

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
In water at 20℃; for 17h;	61%

: 3376-35-0
Methylether von Acetonoxim

A: 78191-00-1
N-Methoxy-N-methylacetamide

B: 189824-63-3
3,3,11,11-Tetramethyl-1,2,4,9,10,12-hexaoxa-dispiro[4.2.4.2]tetradecane

C: 3,3-Dimethyl-1,2,4-trioxa-spiro[4.5]decan-8-one

Conditions

Conditions	Yield
With ozone In dichloromethane at 0℃;	A 23% B 9% C 24%

...Expand

: 3376-35-0
Methylether von Acetonoxim

: 637-88-7
1,4-Cyclohexanedione

A: 78191-00-1
N-Methoxy-N-methylacetamide

B: 189824-63-3
3,3,11,11-Tetramethyl-1,2,4,9,10,12-hexaoxa-dispiro[4.2.4.2]tetradecane

C: 3,3-Dimethyl-1,2,4-trioxa-spiro[4.5]decan-8-one

Conditions

Conditions	Yield
With ozone In dichloromethane at 0℃;	A 23% B 9% C 24%

...Expand

: 3376-35-0
Methylether von Acetonoxim

: 67-64-1
acetone

A: 78191-00-1
N-Methoxy-N-methylacetamide

B: 15592-50-4
3,3,5,5-tetramethyl-1,2,4-trioxolane

Conditions

Conditions	Yield
With ozone In pentane at 0℃; Yields of byproduct given;	A n/a B 11%

...Expand

: 75-36-5
acetyl chloride

: 78191-00-1
N-Methoxy-N-methylacetamide

: 75-36-5
acetyl chloride

: 1117-97-1
N,0-dimethylhydroxylamine

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
With pyridine In chloroform

: 67442-07-3
2-chloro-N-methoxy-N-methylacetamide

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
Stage #1: 2-chloro-N-methoxy-N-methylacetamide With 3-mercaptophenol; potassium carbonate In N,N-dimethyl-formamide at 23℃; for 2h; Stage #2: With tetra-(n-butyl)ammonium iodide; potassium carbonate; Merrifield resin In N,N-dimethyl-formamide at 50℃; for 2h; Stage #3: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene-d6 at 150℃; for 0.166667h; microwave irradiation;

: C12H15FMgNO2

A: 860642-35-9
1-(4-fluorophenyl)but-3-en-2-one

B: 119114-45-3
2-(4-fluorophenyl)-N-methoxyacetamide

C: C12H16FNO2

D: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
With acetic anhydride at -30℃; for 0.5h;

...Expand

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 64-19-7
acetic acid

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
Stage #1: acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 23℃; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 2h;

: 77-78-1
dimethyl sulfate

: sodium acetohydroxamate

: 78191-00-1
N-Methoxy-N-methylacetamide

Conditions

Conditions	Yield
With sodium hydroxide at 25℃; for 5h;

: 78191-00-1
N-Methoxy-N-methylacetamide

: 898229-76-0
4-cyclopropyl-4-(2,2-dimethylhydrazono)butan-2-one

Conditions

Conditions	Yield
Stage #1: 2-(1-cyclopropylethylidene)-1,1-dimethylhydrazine With n-butyllithium; diisopropylamine In tetrahydrofuran; pentane at -78 - 0℃; for 0.583333h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; pentane at -78 - 0℃; for 0.5h;	100%

: 51608-60-7
N-(benzylidene)-p-methylbenzenesulfonamide

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1262117-66-7
N-methoxy-N-methyl-3-phenyl-3-(tosylamino)propanamide

Conditions

Conditions	Yield
With triisopropylsilyl trifluoromethanesulfonate; triethylamine In toluene at 20℃; for 12h; Mannich type reaction;	100%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 77893-68-6
2-bromo-3-chlorothiophene

: 1403468-44-9
1-(5-bromo-3-chlorothiophen-2-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 2-bromo-3-chlorothiophene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 0.5h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at -78℃; for 0.5h;	100%

: 2510-23-8
3-Ethynylpyridine

: 78191-00-1
N-Methoxy-N-methylacetamide

: 4-(pyridin-3-yl)but-3-yn-2-one

Conditions

Conditions	Yield
Stage #1: 3-Ethynylpyridine With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 18h; Inert atmosphere;	100%

: 42365-04-8
triphenylacetaldehyde

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1356445-91-4
(RS)-3-hydroxy-N-methoxy-N-methyl-4,4,4-triphenylbutanamide

Conditions

Conditions	Yield
Stage #1: N-Methoxy-N-methylacetamide With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: triphenylacetaldehyde In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere;	99%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 7531-76-2
1-(4,5-dimethylthiazol-2-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 4,5-Dimethylthiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.16667h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 2.16667h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water for 0.5h;	98%

: C19H29FN3OP

: 78191-00-1
N-Methoxy-N-methylacetamide

: C23H38FN4O3P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	98%

: 740842-73-3
1,1-dimethylethyl 7-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1283016-79-4
1,1-dimethylethyl 7-acetyl-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,1-dimethylethyl 7-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78 - 20℃;	97%

: C20H32N3OP

: 78191-00-1
N-Methoxy-N-methylacetamide

: C24H41N4O3P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	96%

: 36049-90-8
2-lithio-1,3-dithiane

: 78191-00-1
N-Methoxy-N-methylacetamide

: 58277-26-2
1-(1,3-dithian-2-yl)-1-ethanone

Conditions

Conditions	Yield
With ammonium chloride In tetrahydrofuran at -78 - 0℃;	95%

: 1694-31-1
tert-butyl acetoacetate

: 78191-00-1
N-Methoxy-N-methylacetamide

: 116967-26-1
3,5-dioxoheptenoic acid t-butyl ester

Conditions

Conditions	Yield
Stage #1: tert-butyl acetoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran; hexane; mineral oil at -10℃; for 0.5h; Inert atmosphere; Stage #3: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane; mineral oil at -40 - 20℃; for 2h; Inert atmosphere;	95%
With lithium diisopropyl amide In tetrahydrofuran	93%

: C19H29N4O3P

: 78191-00-1
N-Methoxy-N-methylacetamide

: C23H38N5O5P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	95%

: C19H29BrN3OP

: 78191-00-1
N-Methoxy-N-methylacetamide

: C23H38BrN4O3P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	95%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 34943-06-1
1-benzylaziridine-2-carboxylic acid ethyl ester

: 1326628-20-9
1-benzyl-N-methoxy-N-methylaziridine-2-carboxamide

Conditions

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran Inert atmosphere;	95%

: 556-96-7
5-bromo-1,3-xylene

: 78191-00-1
N-Methoxy-N-methylacetamide

: 5379-16-8
3,5-dimethylacetophenone

Conditions

Conditions	Yield
Stage #1: 5-bromo-1,3-xylene With iodine; magnesium In tetrahydrofuran at 80℃; for 2h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at 80℃; for 2h;	95%

: 319-04-0
7-Bromo-1-fluoronaphthalene

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1-(8-fluoro-2-naphthyl)ethanone

Conditions

Conditions	Yield
Stage #1: 7-Bromo-1-fluoronaphthalene With n-butyllithium In tetrahydrofuran at -70℃; for 1h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at -70℃; for 0.333333h; Inert atmosphere;	95%

: 3581-89-3
5-methylthiazole

: 78191-00-1
N-Methoxy-N-methylacetamide

: 59303-17-2
1-(5-methylthiazol-2-yl)ethan-1-on

Conditions

Conditions	Yield
Stage #1: 5-methylthiazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at -78 - 0℃; for 0.6h; Inert atmosphere;	94%
Stage #1: 5-methylthiazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran at 0℃; for 1.5h;	51%
Stage #1: 5-methylthiazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.25h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; diethyl ether; hexane at 20℃; for 1h;	43.2%
Stage #1: 5-methylthiazole With n-butyllithium In diethyl ether at -78℃; for 0.25h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; diethyl ether at -78 - 20℃;

: 1350349-82-4
2-bromo-5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)thiazole

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1350349-83-5
1-(5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)thiazol-2-yl)ethanone

Conditions

Conditions	Yield
Stage #1: 2-bromo-5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)thiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 2h;	94%
Stage #1: 2-bromo-5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)thiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 2h;	94%

: 629-05-0
n-octyne

: 78191-00-1
N-Methoxy-N-methylacetamide

: 91658-50-3
dec-3-yn-2-one

Conditions

Conditions	Yield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at 20℃; for 4h;	93%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 3.5h; Inert atmosphere;	86%
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78 - 20℃; for 4h; Inert atmosphere;	64%

: C20H32N3O2P

: 78191-00-1
N-Methoxy-N-methylacetamide

: C24H41N4O4P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	93%

: C19H29ClN3OP

: 78191-00-1
N-Methoxy-N-methylacetamide

: C23H38ClN4O3P

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	93%

: 23074-36-4
2-bromobutene

: 78191-00-1
N-Methoxy-N-methylacetamide

: 4359-77-7
3-ethyl-3-buten-2-one

Conditions

Conditions	Yield
Stage #1: 2-bromobutene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1.33333h; Stage #2: N-Methoxy-N-methylacetamide In diethyl ether; pentane at -78℃; for 1h;	93%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 100-52-7
benzaldehyde

: 80783-99-9, 124931-15-3, 113474-86-5
N-methoxy-N-methylcinnamamide

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 16h; Mukaiyama Aldol Addition; Inert atmosphere;	93%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 147438-60-6
(E)-(2R,3R)-3-Methoxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-4-enal

: (E)-(4S,5R)-3-Hydroxy-5-methoxy-8-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-6-enoic acid methoxy-methyl-amide

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h;	92%

: 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole

: 78191-00-1
N-Methoxy-N-methylacetamide

: 1-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-indol-5-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;	92%

: 78191-00-1
N-Methoxy-N-methylacetamide

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 155849-96-0
N-methoxy-N-methyl3-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-2-yl>-3-hydroxypropanamide

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran	91%
With n-butyllithium; diisopropylamine 1.) hexane, THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 3 h; Yield given. Multistep reaction;

: 78191-00-1
N-Methoxy-N-methylacetamide

: 107-02-8
acrolein

: 1143516-73-7
3-hydroxypent-4-enoic acid methoxymethylamide

Conditions

Conditions	Yield
Stage #1: N-Methoxy-N-methylacetamide With lithium diisopropyl amide Stage #2: acrolein at -78℃;	91%

N-Methoxy-N-methylacetamide Specification

The IUPAC name of this chemical is N-methoxy-N-methylacetamide. With the CAS registry number 78191-00-1, it is also named as Acetamide, N-methoxy-N-methyl-. The product's categories are hydroxylamines, hydroxylamines (N-substituted), hydroxylamines (O-substituted), amides, carbonyl compounds and organic building blocks. In addiotion, it is clear colorless liquid which is soluble in water. And this chemical is flammable, so people should keep it away from sources of ignition.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.31; (4)ACD/LogD (pH 7.4): -0.31; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 16.06; (8)ACD/KOC (pH 7.4): 16.06; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.409; (13)Molar Refractivity: 26.07 cm³; (14)Molar Volume: 105.2 cm³; (15)Polarizability: 10.33×10^-24 cm³; (16)Surface Tension: 27.7 dyne/cm; (17)Enthalpy of Vaporization: 33.18 kJ/mol; (18)Vapour Pressure: 52.7 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 103.063329; (21)MonoIsotopic Mass: 103.063329; (22)Topological Polar Surface Area: 29.5; (23)Heavy Atom Count: 7.

Preparation of N-Methoxy-N-methylacetamide: It can be obtained by N-methoxy-N-methylacetamidine hydroiodide with 6 M aq. potassium hydroxide under heating. The reaction time is 2 hours. The yield is 62%.

Uses of N-Methoxy-N-methylacetamide: It can react with 2-Lithio-1,3-dithian to get 1-[1,3]dithian-2-yl-ethanone. This reaction needs reagent aq. ammonium chloride and solvent tetrahydrofuran at temperature of -78 - 0 °C. The yield is 95%.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(N(OC)C)C;
2. InChI: InChI=1/C4H9NO2/c1-4(6)5(2)7-3/h1-3H3.

Product Name

N-Methoxy-N-methylacetamide

Synthetic route

N-Methoxy-N-methylacetamide Specification

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