3775-90-4

Basic information

• Product Name: 2-(TERT-BUTYLAMINO)ETHYL METHACRYLATE
• Synonyms: 2-Propenoicacid,2-methyl-,2-[(1,1-dimethylethyl)amino]ethylester;Ageflex FM-4;ageflexfm-4;butylaminoethylmethacrylate;Ethanol, 2-(tert-butylamino)-, methacrylate;ethanol,2-(tert-butylamino)-methacrylate(ester);Methacrylic acid, 2-(tert-butylamino)ethyl ester;methacrylicacid,2-(tert-butylamino)ethylester
• CAS NO: 3775-90-4
• Molecular Formula: C₁₀H₁₉NO₂
• Molecular Weight: 185.26
• EINECS: 223-228-4
• Product Categories: Acrylic Monomers;C10 to C11Monomers;Carbonyl Compounds;Esters;Methacrylate;Acrylic Monomers;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Materials Science;Monomers;Organic Building Blocks;Polymer Science
• Mol File: 3775-90-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 100～105℃/12 mm
• Boiling Point: 82 °C10 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: clear, colourless up to yellowish liquid
• Density: 0.914 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.097mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Solubility: Slightly soluble in water
• PKA: 8.99±0.10(Predicted)
• Water Solubility: 18g/L at 25℃
• CAS DataBase Reference: 2-(TERT-BUTYLAMINO)ETHYL METHACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TERT-BUTYLAMINO)ETHYL METHACRYLATE(3775-90-4)
• EPA Substance Registry System: 2-(TERT-BUTYLAMINO)ETHYL METHACRYLATE(3775-90-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 26
• RIDADR: 1760
• WGK Germany: 1
• RTECS: OZ3500000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3775-90-4(Hazardous Substances Data)

Usage

Safety Profile

Poison by intraperitoneal route. See also ESTERS and AMINES. Combustible when exposed to heat or flame. To fight fire, use alcohol foam, water spray or mist, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C10H19NO2/c1-7(2)9(12)13-8(3)11-10(4,5)6/h8,11H,1H2,2-6H3

Synthetic route

2-[(1,1-dimethylethyl)amino]-ethanol (4620-70-6) + methacrylic acid methyl ester (80-62-6) → 2-tert-butylaminoethyl methacrylate (3775-90-4)

2-tert-butylaminoethyl methacrylate (3775-90-4) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 10-(tert-butyl)-4,4-diethoxy-9-oxo-3-oxa-8,10-diaza-4-siladodecan-11-yl methacrylate

Conditions	Yield
at 45℃;	100%

2-tert-butylaminoethyl methacrylate (3775-90-4) + diphenylphosphane (829-85-6) → C22H30NO2P

Conditions	Yield
In 2-methyltetrahydrofuran at 90℃; for 4h; Inert atmosphere; Sealed tube; Green chemistry; regioselective reaction;	89%

2-tert-butylaminoethyl methacrylate (3775-90-4) + (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)oxirane (38565-53-6) → 2-methyl-acrylic acid 2-[tert-butyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxy-undecyl)-amino]-ethyl ester

Conditions	Yield
With hydroquinone at 150℃; for 17h;	84%

2-tert-butylaminoethyl methacrylate (3775-90-4) + acryloyl chloride (814-68-6) → C13H21NO3 (1604699-42-4)

Conditions	Yield
With triethylamine In dichloromethane at -10 - 20℃; for 2h; Inert atmosphere;	80%

phosgene (75-44-5) + 2-(4-aminophenyl)benzothiazole (6278-73-5) + 2-tert-butylaminoethyl methacrylate (3775-90-4) → C24H27N3O3S

Conditions	Yield
Stage #1: phosgene; 2-(4-aminophenyl)benzothiazole In chloroform; toluene Reflux; Stage #2: 2-tert-butylaminoethyl methacrylate In dichloromethane for 0.0166667h;	52%

2-tert-butylaminoethyl methacrylate (3775-90-4) + cyanogen chloride (506-77-4) → 1-(tert-butyl-cyano-amino)-2-methacryloyloxy-ethane (86239-80-7)

Conditions	Yield
With potassium carbonate

2-tert-butylaminoethyl methacrylate (3775-90-4) + methacrylic acid methyl ester (80-62-6) → copolymer; monomer(s): methyl methacrylate; (tert-butylamino)ethyl methacrylate

Conditions	Yield
With N-propyl 2-pyridinylmethanimine; copper(I) bromide In toluene at 90℃;

poly(methacrylic acid) (79-41-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + methyl methacrylate (97-63-2) + Methacrylamide (79-39-0) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-tert-butylaminoethyl methacrylate-co-ethyl methacrylate-co-methacrylamide-co-methacrylic acid)

Conditions	Yield
Stage #1: poly(methacrylic acid); 2-tert-butylaminoethyl methacrylate; methyl methacrylate; Methacrylamide; acrylic acid In ethanol; water at 65 - 70℃; for 9h; Stage #2: With tert-butyl peroxypivalate In ethanol; water at 70 - 80℃; for 2.5h; Stage #3: With N-methyl-3-hydroxypropylamine In ethanol; water for 0.166667h;

poly(methacrylic acid) (79-41-4) + tert-Butyl acrylate (1663-39-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-methacrylic acid-co-N-(tert-butyl)-aminoethyl methacrylate-co-tert-butyl acrylate)

Conditions	Yield
Stage #1: poly(methacrylic acid); tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;
Stage #1: poly(methacrylic acid); tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;

1-ethenyl-2-pyrrolidinone (88-12-0) + tert-Butyl acrylate (1663-39-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-(tert-butyl) aminomethyl methacrylate-co-tert-butyl acrylate-co-vinylpyrrolidone)

Conditions	Yield
Stage #1: 1-ethenyl-2-pyrrolidinone; tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With 2-(N,N-dimethylamino)ethanol; α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 63 - 65℃; for 7h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 65 - 80℃; for 2.5h; Stage #3: With 2-(N,N-dimethylamino)ethanol In ethanol; water at 40℃; pH=8.0; Product distribution / selectivity;
Stage #1: 1-ethenyl-2-pyrrolidinone; tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With 2-(N,N-dimethylamino)ethanol; α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 63 - 65℃; for 7h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 65 - 80℃; for 2.5h; Stage #3: With 2-(N,N-dimethylamino)ethanol In ethanol; water at 40℃; pH=8.0; Product distribution / selectivity;

1-ethenyl-2-pyrrolidinone (88-12-0) + tert-Butyl acrylate (1663-39-4) + N-tert-Butylacrylamide (107-58-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-tert-butylarylamide-co-N-(tert-butyl) aminomethyl methacrylate-co-tert-butyl acrylate-co-vinylpyrrolidone)

Conditions

Yield

Stage #1: 1-ethenyl-2-pyrrolidinone; tert-Butyl acrylate; N-tert-Butylacrylamide; 2-tert-butylaminoethyl methacrylate; acrylic acid With 2-(N,N-dimethylamino)ethanol; α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 63 - 65℃; for 7h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 65 - 80℃; for 2.5h; Stage #3: With 2-(N,N-dimethylamino)ethanol In ethanol; water at 40℃; pH=8.0; Product distribution / selectivity;

tert-Butyl acrylate (1663-39-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-(tert-butyl)-aminoethyl methacrylate-co-tert-butyl acrylate)

Conditions	Yield
Stage #1: tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;
Stage #1: tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;

tert-Butyl acrylate (1663-39-4) + tert-Butyl methacrylate (585-07-9) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-(tert-butyl) aminoethyl methacrylate-co-tert-butyl acrylate-tert-butyl methacrylate)

Conditions	Yield
Stage #1: tert-Butyl acrylate; tert-Butyl methacrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;

tert-Butyl acrylate (1663-39-4) + N-tert-Butylacrylamide (107-58-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-tert-butylacrylamide-co-N-(tert-butyl) aminoethyl methacrylate-co-tert-butyl acrylate)

Conditions	Yield
Stage #1: tert-Butyl acrylate; N-tert-Butylacrylamide; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;
Stage #1: tert-Butyl acrylate; N-tert-Butylacrylamide; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;
Stage #1: tert-Butyl acrylate; N-tert-Butylacrylamide; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With 2-Amino-2-methyl-1-propanol In ethanol; water for 0.166667h; Product distribution / selectivity;

N-tert-octylacrylamide + tert-Butyl acrylate (1663-39-4) + 2-tert-butylaminoethyl methacrylate (3775-90-4) + acrylic acid (79-10-7) → poly(acrylic acid-co-N-(tert-butyl) aminoethyl methacrylate-co-N-tert-octylacrylamide-co-tert-butyl acrylate)

Conditions	Yield
Stage #1: N-tert-octylacrylamide; tert-Butyl acrylate; 2-tert-butylaminoethyl methacrylate; acrylic acid With α,α'-azodiizobutyramidine-dihydrochloride In ethanol; water at 70 - 73℃; for 9h; Stage #2: With tert-butyl peroxyisobutyrate In ethanol; water at 70 - 80℃; for 4.66667h; Stage #3: With triethanolamine In ethanol; water for 0.166667h; Product distribution / selectivity;

2-tert-butylaminoethyl methacrylate (3775-90-4) → poly(2-(tert-butylamino)ethyl methacrylate)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In propan-1-ol; butanone at 60℃; for 5h;

2-tert-butylaminoethyl methacrylate (3775-90-4) + 2-methyl-butyl acrylate (97-88-1) → poly(2-(tert-butylamino)ethyl methacrylate-co-n-butyl methacrylate)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In propan-1-ol; butanone at 60℃; for 5h;

2-tert-butylaminoethyl methacrylate (3775-90-4) + isophorone diisocyanate (4098-71-9) → C22H37N3O4

Conditions	Yield
at 30℃;

5-furfurylidene-2,2-dimethyl-[1,3]dioxane-4,6-dione (15875-49-7) + 2-tert-butylaminoethyl methacrylate (3775-90-4) → 2-(tert-butyl ((1E,3Z)-5-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-4-hydroxypenta-1,3-dien-1-yl)amino)ethyl methacrylate

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;	1.67 g

2-tert-butylaminoethyl methacrylate (3775-90-4) + C70H116N4O23 → C90H154N6O27

Conditions	Yield
With hydroquinone In dichloromethane at 5 - 20℃; for 14h;	215 g

Upstream product

• 4620-70-6 2-[(1,1-dimethylethyl)amino]-ethanol 
• 80-62-6 methacrylic acid methyl ester 

Relevant articles and documents

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