5411-63-2

Basic information

• Product Name: 2-ButenaMide, N,N-diethyl-3-Methyl-
• Synonyms: 2-ButenaMide, N,N-diethyl-3-Methyl-;N,N-diethyl-3-methyl-2-Butenamide;N,N-diethyl-3-methylbut-2-enamide
• CAS NO: 5411-63-2
• Molecular Formula: C9H17NO
• Molecular Weight: 155.23738
• Mol File: 5411-63-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 259.3°Cat760mmHg
• Flash Point: 109°C
• Appearance: /
• Density: 0.887g/cm³
• Vapor Pressure: 0.0131mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 2-ButenaMide, N,N-diethyl-3-Methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ButenaMide, N,N-diethyl-3-Methyl-(5411-63-2)
• EPA Substance Registry System: 2-ButenaMide, N,N-diethyl-3-Methyl-(5411-63-2)

Safety Data

• Hazardous Substances Data: 5411-63-2(Hazardous Substances Data)

Usage

Description

2-ButenaMide, N,N-diethyl-3-Methyl-, also known as 2-Butenamide, N,N-diethyl-3-methyl-, is a chemical compound with the molecular formula C10H19NO. It is an amide derivative characterized by a butenamide structure, featuring two ethyl groups and a methyl group. 2-ButenaMide, N,N-diethyl-3-Methylis recognized for its versatile reactivity and potential as a building block in the synthesis of various compounds, making it a valuable component in organic synthesis and pharmaceutical research.

Uses

Used in Organic Synthesis:
2-ButenaMide, N,N-diethyl-3-Methylis used as a reactant in organic synthesis for its ability to participate in a wide range of chemical reactions, facilitating the creation of diverse organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, 2-ButenaMide, N,N-diethyl-3-Methylserves as a key intermediate, contributing to the development of new drugs and medicinal compounds due to its structural properties and reactivity.
Used in Agrochemical Development:
2-ButenaMide, N,N-diethyl-3-Methylis utilized in the development of agrochemicals, where its chemical properties are harnessed to create effective products for agricultural applications.
Used as a Precursor in Dye and Pigment Synthesis:
2-ButenaMide, N,N-diethyl-3-Methylis also used as a precursor in the synthesis of dyes and pigments, where its chemical structure plays a crucial role in determining the color and properties of the final products.
Used in Biological Activity and Medicinal Property Studies:
2-ButenaMide, N,N-diethyl-3-Methylhas been studied for its potential biological activity and medicinal properties, indicating its possible use in the discovery and development of new therapeutic agents.

InChI:InChI=1/C9H17NO/c1-5-10(6-2)9(11)7-8(3)4/h7H,5-6H2,1-4H3

Synthetic route

3,3-Dimethylacryloyl chloride (3350-78-5) + diethylamine (109-89-7) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
	90%
With diethyl ether

n-butyllithium (109-72-8, 29786-93-4) + N,N-diethyl-1,2,2-trichlorovinylamine (686-10-2) + acetone (67-64-1) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
(i), (ii) /BRN= 635680/, (iii) (hydrolysis); Multistep reaction;

2-methylallylmagnesium chloride (5674-01-1) + 2,2-Dimethyl-but-3-enoic acid diethylamide → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;
With lithium diisopropyl amide In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;

carbon monoxide (201230-82-2) + diethylamine (109-89-7) + 3-Chloro-2-methylpropene (563-47-3) → diethyl-methallyl-amine (19737-36-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6) + 4-Methyl-2-oxo-pent-3-enoic acid diethylamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In benzene under 76000 Torr; Ambient temperature;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + bis(pinacol)diborane (73183-34-3) → N,N-diethyl-3-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanamide

Conditions	Yield
With methanol; water; caesium carbonate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 7h;	80%

triethylsilyl chloride (994-30-9) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-04-6) + (E)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-05-7)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran at -78℃; for 18.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 21% B 47%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-2,4-dimethoxybenzene (7051-13-0) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide In tetrahydrofuran -78 deg C, 1 h, rt;	46%

chloro-trimethyl-silane (75-77-4) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-02-4) + (E)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-03-5) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 17.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 39% B 35% C n/a

3-methoxyphenyl bromide (2398-37-0) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxyphenyl bromide In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	35%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

3,3-Dimethylacryloyl chloride (3350-78-5) + diethylamine (109-89-7) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
	90%
With diethyl ether

n-butyllithium (109-72-8, 29786-93-4) + N,N-diethyl-1,2,2-trichlorovinylamine (686-10-2) + acetone (67-64-1) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
(i), (ii) /BRN= 635680/, (iii) (hydrolysis); Multistep reaction;

2-methylallylmagnesium chloride (5674-01-1) + 2,2-Dimethyl-but-3-enoic acid diethylamide → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;
With lithium diisopropyl amide In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;

carbon monoxide (201230-82-2) + diethylamine (109-89-7) + 3-Chloro-2-methylpropene (563-47-3) → diethyl-methallyl-amine (19737-36-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6) + 4-Methyl-2-oxo-pent-3-enoic acid diethylamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In benzene under 76000 Torr; Ambient temperature;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + bis(pinacol)diborane (73183-34-3) → N,N-diethyl-3-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanamide

Conditions	Yield
With methanol; water; caesium carbonate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 7h;	80%

triethylsilyl chloride (994-30-9) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-04-6) + (E)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-05-7)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran at -78℃; for 18.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 21% B 47%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-2,4-dimethoxybenzene (7051-13-0) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide In tetrahydrofuran -78 deg C, 1 h, rt;	46%

chloro-trimethyl-silane (75-77-4) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-02-4) + (E)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-03-5) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 17.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 39% B 35% C n/a

3-methoxyphenyl bromide (2398-37-0) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxyphenyl bromide In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	35%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 4-Bromoveratrole (2859-78-1) → 5,6-dimethoxy-2-methyl-4-naphthol (106914-41-4)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 4-Bromoveratrole In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	31%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol (160538-97-6) + 8-bromo-5-(methoxymethoxy)-3-methyl-1-naphthalenol + N,N-diethyl-2-[2-bromo-5-(methoxymethoxy)phenyl]-3-methyl-3-butenoic acid amide + N,N-diethyl-2-[5-bromo-2-(methoxymethoxy)phenyl]-3-methyl-3-butenoic acid amide

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Metallation; Stage #2: 2,4-dibromo-1-(methoxymethoxy)benzene With lithium cyclohexylisopropylamide In tetrahydrofuran; hexane at 0℃; for 14h; Cycloaddition; Condensation; Further byproducts given;	A 31% B 7% C n/a D n/a

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N-cyclohexylisopropylamine (1195-42-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → α-naphthol (90-15-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	29%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol (160538-97-6)

Conditions	Yield
With lithium cyclohexylisopropylamide	21%
With lithium cyclohexylisopropylamide In tetrahydrofuran at -78 - 0℃; for 24h;	20%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → 5,6,7-trimethoxy-2-methyl-4-naphthol (6395-25-1)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-3,4,5-trimethoxybenzene In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	21%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,2'-dimethoxy-3,3',5,5'-tetrabromobiphenyl (855255-50-4) → 4,4'-dibromodiospyrol

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 3,3',5,5'-tetrabromo-2,2'-dimethoxybiphenyl In tetrahydrofuran at -78 - 20℃;	20%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + Limettin (487-06-9) → 1,3-Dimethoxy-9-methyl-benzo[c]chromen-6-one

Conditions	Yield
With trichlorophosphate	13%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-diethyl-3-methylbutanamide (533-32-4) + 2-isopropyl-3,3-dimethyl-glutaric acid bis-diethylamide

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-Diethyl-2,3-dibrom-3-methyl-buttersaeureamid (91367-35-0)

Conditions	Yield
With bromine In tetrachloromethane

bromobenzene (108-86-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 3-methylnaphthalen-1-ol (13615-40-2)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-bromoanisole (578-57-4) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9) + N,N-diethyl-2-isopropenyl-2-(3'-methoxyphenyl)acetamide (106914-38-9)

Conditions	Yield
With lithium cyclohexylisopropylamide Product distribution; multistep reaction: 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, thenn room temp., overnight. Investigation of different reagents and compounds;
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given;
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 9-bromophenanthrene (573-17-1) → 3-Methyl-triphenylen-1-ol (106914-42-5)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-bromo-2-(methoxymethoxy)benzene (68314-54-5) → 8-methoxymethoxy-3-methyl-1-naphthalenol (106914-40-3)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-chloro-1,4-dimethoxybenzene (2100-42-7) → 5,8-dimethoxy-3-methylnaphthalen-1-ol (50559-08-5)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-3,5-dimethoxybenzene (7051-16-3) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-chloro-5-methylanisole (73909-16-7) → 1-Hydroxy-8-methoxy-3,6-dimethyl-naphthalin (778-99-4)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 2-isopropyl-3,3-dimethyl-glutaric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: aqueous hydrochloric acid View Scheme

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-Diethyl-2,3-di-S-acetyl-3-methyl-buttersaeureamid (92158-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CCl4 2: Py / benzene View Scheme

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → C9H16NO(1-)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - -20℃; for 1.25h; Inert atmosphere;

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 109-89-7 diethylamine 
• 109-72-8 n-butyllithium 
• 686-10-2 N,N-diethyl-1,2,2-trichlorovinylamine 
• 67-64-1 acetone 
• 201230-82-2 carbon monoxide 
• 563-47-3 3-Chloro-2-methylpropene 
• 5674-01-1 2-methylallylmagnesium chloride 

Downstream Products

• 533-32-4 N,N-diethyl-3-methylbutanamide 
• 13615-40-2 3-methylnaphthalen-1-ol 
• 22273-56-9 4-hydroxy-5-methoxy-2-methyl-naphthalene 
• 106914-38-9 N,N-diethyl-2-isopropenyl-2-(3'-methoxyphenyl)acetamide 
• 160538-97-6 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol 
• 90-15-3 α-naphthol 

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