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N-Methoxy-N-methylacetamide
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Name

N-Methoxy-N-methylacetamide

 EINECS 628-920-3
CAS No. 78191-00-1 Density 0.979 g/cm3
PSA 29.54000 LogP 0.02610
Solubility Soluble in water Melting Point N/A
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 Molecular Structure of 78191-00-1 (N-Methoxy-N-methylacetamide) Hazard Symbols R10:;
Synonyms

N,O-Dimethylacetohydroxamicacid;

Article Data 37

N-Methoxy-N-methylacetamide 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
135203-03-1

N-methoxy-N-methylacetamidine hydroiodide

78191-00-1

N-Methoxy-N-methylacetamide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With ozone In dichloromethane at 0℃;A 23%
B 9%
C 24%
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
ConditionsYield
With ozone In dichloromethane at 0℃;A 23%
B 9%
C 24%
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
ConditionsYield
With ozone In pentane at 0℃; Yields of byproduct given;A n/a
B 11%
75-36-5

acetyl chloride

78191-00-1

N-Methoxy-N-methylacetamide

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.

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