999-59-7

Basic information

• Product Name: Methyl N,N-dimethylaminoacrylate
• Synonyms: Methyl 3-(N,N-Dimethylamino)Acrylate;3-(Dimethylamino)-acrylic acid methyl ester;Methyl 3-(dimethylamino)acrylate;3-(Dimethylamino)propenoic acid methyl ester;Methyl N,N-dimethylaminoacrylate;(E)-methyl 3-(dimethylamino)acrylate;methyl (E)-3-(dimethylamino)acrylate
• CAS NO: 999-59-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Mol File: 999-59-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 48-49 °C
• Boiling Point: 163.6 °C at 760 mmHg
• Flash Point: 61.7 °C
• Appearance: /
• Density: 0.979 g/cm³
• Vapor Pressure: 2.05mmHg at 25°C
• Refractive Index: 1.449
• PKA: 6.58±0.70(Predicted)
• CAS DataBase Reference: Methyl N,N-dimethylaminoacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl N,N-dimethylaminoacrylate(999-59-7)
• EPA Substance Registry System: Methyl N,N-dimethylaminoacrylate(999-59-7)

Safety Data

• Hazardous Substances Data: 999-59-7(Hazardous Substances Data)

Usage

General Description

Methyl N,N-dimethylaminoacrylate is a chemical compound with the molecular formula C7H13NO2. It is a colorless liquid with a fruity odor, and it is used as a monomer in the production of polymers and resins. This chemical is classified as an acrylate and has applications in the manufacture of adhesives, coatings, and sealants. Methyl N,N-dimethylaminoacrylate is also used as a crosslinking agent in the production of copolymers, and it can be polymerized to form polymethyl methacrylate, a clear and shatter-resistant plastic. However, it is important to handle this compound with care, as it is considered a hazardous substance and can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C6H11NO2/c1-7(2)5-4-6(8)9-3/h4-5H,1-3H3/b5-4+

Synthetic route

dimethyl amine (124-40-3) + propynoic acid methyl ester (922-67-8) → methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7)

Conditions	Yield
In diethyl ether at 20℃; for 1h;	100%
With benzene

diethylamine (109-89-7) + propynoic acid methyl ester (922-67-8) → methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7)

Conditions	Yield
In diethyl ether at 20℃; for 1h;	100%

acetic acid methyl ester (79-20-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7)

Conditions	Yield
In toluene at 110℃; Inert atmosphere;

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + N-benzyloxyamine (622-33-3) → methyl 3-(benzyloxyimino)propanoate (561068-87-9)

Conditions	Yield
With camphor-10-sulfonic acid In xylene for 24h; Heating;	93%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + C13H10O3 (1241667-97-9) → methyl 3-acetyl-5-(2-hydroxybenzoyl)benzoate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 3h; regioselective reaction;	92%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + C13H9ClO4 (55593-92-5) → dimethyl 5-(5-chloro-2-hydroxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 3h; regioselective reaction;	86%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 3-Formylchromone (17422-74-1) → dimethyl 5-(2-hydroxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; regioselective reaction;	85%
With indium(III) triflate In acetonitrile at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent;	85%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 6-nitro-4-oxo-4H-chromene-3-carbaldehyde (42059-80-3) → dimethyl 5-(2-hydroxy-5-nitrobenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 7h; regioselective reaction;	84%
With indium(III) triflate In acetonitrile at 20℃; for 7h;	84%

6-fluorochromone-3-carboxaldehyde (69155-76-6) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → dimethyl 5-(5-fluoro-2-hydroxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;	83%

dichloroacethyl chloride (79-36-7) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → methyl 2-dichloroacetyl-3-dimethylaminoacrylate

Conditions	Yield
Stage #1: dichloroacethyl chloride; methyl 3-(N,N-dimethylamino)-2-propenoate In toluene at 0 - 20℃; for 0.5h; Stage #2: With sodium hydroxide In water; toluene at 0 - 20℃; for 3 - 3.33333h;	82.3%

3-formyl-6-methylchromone (42059-81-4) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → dimethyl 5-(2-hydroxy-5-methylbenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;	82%

6-bromo-4-oxo-4H-chromene-3-carbaldehyde (52817-12-6) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → dimethyl 5-(5-bromo-2-hydroxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 8h; regioselective reaction;	82%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 6-chloro-7-methyl-4-oxo-4H-chromene-3-carbaldehyde (64481-12-5) → dimethyl 5-(5-chloro-2-hydroxy-4-methylbenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 9h; regioselective reaction;	81%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + C14H12O5 → dimethyl 5-(2-hydroxy-5-methoxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 5h; regioselective reaction;	81%

3-formyl-6-isopropylchromone (49619-58-1) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → dimethyl 5-(2-hydroxy-5-isopropylbenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 9h; regioselective reaction;	78%
With indium(III) triflate In acetonitrile at 20℃; for 9h;	78%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + C13H8Br2O4 → dimethyl 5-(3,5-dibromo-2-hydroxybenzoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 5h; regioselective reaction;	78%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + C15H25N5O → N2-[4-[4-(dimethylamino)-1-piperidyl]-2-methoxyphenyl]amino-4(1H)-pyrimidone

Conditions	Yield
In toluene Reflux;	77.3%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 6,7-methylenedioxychromone-3-carboxaldehyde → dimethyl 5-(6-hydroxybenzo[d][1,3]dioxole-5-carbonyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 60℃; for 12h; regioselective reaction;	76%
With indium(III) triflate In acetonitrile at 60℃; for 12h;	76%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 4-oxo-4H-1-naphtho<2,3-c>pyran-3-carboxaldehyde (57051-28-2) → dimethyl 5-(1-hydroxy-2-naphthoyl)isophthalate

Conditions	Yield
With indium(III) triflate In acetonitrile at 20℃; for 10h; regioselective reaction;	75%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 1-(4-cyanophenyl)guanidine (5637-42-3) → 4-((4-hydroxypyrimidin-2-yl)amino)benzonitrile (189956-45-4)

Conditions	Yield
In toluene at 117℃; for 26h;	75%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 2,2-difluoroacetaldehyde oxime → methyl 3-(difluoromethyl)isoxazole-4-carboxylate

Conditions	Yield
Stage #1: 2,2-difluoroacetaldehyde oxime With N-chloro-succinimide In chloroform at 20℃; Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate In chloroform at 20℃; regioselective reaction;	73%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + (1-phenylcycloprop-2-en-1-yl)methyl acetate (682760-57-2) → methyl (E)-3-formyl-5-phenylhexa-3,5-dienoate

Conditions	Yield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 20℃; Inert atmosphere;	52%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + urea (57-13-6) → uracil (66-22-8)

Conditions	Yield
Stage #1: urea In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 4h; Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate With polyoxyethylene lauryl ether phosphate sodium salt In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 110℃; for 6h; Temperature; Time; Solvent; Reagent/catalyst;	30%

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + benzene (71-43-2) → 1,3,5-tris-(methoxycarbonyl)benzene (2672-58-4)

Conditions	Yield
With hydrogen bromide

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + methyl 2-nitroacetate (2483-57-0) → 4-methoxycarbonylmethyl-2-oxy-4,5-dihydro-isoxazole-3,5-dicarboxylic acid dimethyl ester (53183-90-7)

Conditions	Yield
In methanol

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 4-dimethylamino-benzaldehyde (100-10-7) → 2-Methoxycarbonyl-3-<4-dimethylamino-phenyl>-prop-2-enyl-dimethylimmonium

Conditions	Yield
With pyridinium perchlorate

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 3-dimethylaminoacrolein (927-63-9) → 4-Methoxycarbonyl-5-dimethylamino-penta-2,4-dienyl-dimethylimonium

Conditions	Yield
With pyridinium perchlorate

9H-fluorene (86-73-7) + methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) → C17H14O2

Conditions	Yield
Stage #1: 9H-fluorene In tetrahydrofuran at -78 - 0℃; Stage #2: methyl 3-(N,N-dimethylamino)-2-propenoate In tetrahydrofuran at -78 - 0℃;

methyl 3-(N,N-dimethylamino)-2-propenoate (999-59-7) + 2,3,4,5-tetrafluorobenzoyl chloride (94695-48-4) → methyl 2-(2,3,4,5-tetrafluorophenyl)formyl-3-(N,N-dimethylamino)acrylate

Conditions	Yield
With triethylamine In toluene at 53℃; Temperature; Solvent; Reagent/catalyst;

Upstream product

• 79-20-9 acetic acid methyl ester 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 922-67-8 propynoic acid methyl ester 
• 69819-66-5 N-methylpyrrole-2-carbaldehyde N,N-dimethylhydrazone 
• 506-59-2 N,N-dimethylammonium chloride 
• 3853-06-3 methyl 3-(dimethylamino)propionate 
• 20180-31-8 N,N-dimethyl(dimethylphenylsilyl)amine 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 922-69-0 1,1-dimethoxyethylene 
• 68-12-2 N,N-dimethyl-formamide 
• 96-32-2 bromoacetic acid methyl ester 
• 26387-66-6 3-dimethylamino-2-bromo-2-propenal 
• 927-63-9 (E)-3-(dimethylamino)acrolein 

Downstream Products

• 1257649-33-4 dimethyl 1-methoxy-2-phenyl-1H-pyrrole-3,4-dicarboxylate 
• 1257649-36-7 3-ethyl 4-methyl 1-methoxy-2-(4-nitrophenyl)-1H-pyrrole-3,4-dicarboxylate 
• 1257649-37-8 3-ethyl 4-methyl 1-methoxy-2-(4-methoxyphenyl)-1H-pyrrole-3,4-dicarboxylate 
• 1257649-42-5 3-ethyl 4-methyl 2-benzyl-1-methoxy-1H-pyrrole-3,4-dicarboxylate 
• 1257649-45-8 dimethyl 2-cyclohexyl-1-methoxy-1H-pyrrole-3,4-dicarboxylate 

Relevant articles and documents

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