13641-96-8

Usage

Uses

Used in Coatings Industry:
2-Isocyanatoethyl Acrylate is used as a component in the formulation of coatings for its strong reactivity and ability to bind with other materials, enhancing the durability and performance of the final product.
Used in Paints Industry:
2-Isocyanatoethyl Acrylate is used as a key ingredient in paint formulations, contributing to the paint's adhesion, flexibility, and overall quality.
Used in Adhesives Industry:
2-Isocyanatoethyl Acrylate is used as a binding agent in adhesives, providing strong and durable bonds between various materials.
Used in Plastics Industry:
2-Isocyanatoethyl Acrylate is used in the production of plastics, where its reactivity and ability to form polymers contribute to the creation of versatile and durable plastic materials.
Used in Resins Industry:
2-Isocyanatoethyl Acrylate is used in the synthesis of resins, where its reactivity and binding properties are essential for creating strong and stable resin compounds.
Note: While 2-Isocyanatoethyl Acrylate offers numerous benefits in various industries, it is essential to follow proper handling and safety procedures due to its potential health risks, such as skin or eye irritations and respiratory problems.

InChI:InChI=1/C6H7NO3/c1-2-6(9)10-4-3-7-5-8/h2H,1,3-4H2

Synthetic route

3-chloropropionic acid (2-isocyanatoethyl) ester (98134-34-0) → acrylic acid 2-isocyanatoethyl ester (13641-96-8)

Conditions	Yield
With triethylamine In toluene at 50℃; for 6h; Product distribution / selectivity;	87%
With strongly basic ion-exchange resin In toluene at 50℃; for 6h; not specified; Product distribution / selectivity;	86%
With N,N,N,N,-tetramethylethylenediamine In toluene at 50℃; for 6h; Product distribution / selectivity;	86%

2-(N,N-diethylureido)ethyl acrylate → acrylic acid 2-isocyanatoethyl ester (13641-96-8)

Conditions	Yield
With hydrogenchloride; 2,6-di-tert-butyl-4-methyl-phenol In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 3h;	60.7%

2-(methylurea)ethyl acrylate → acrylic acid 2-isocyanatoethyl ester (13641-96-8)

Conditions	Yield
With Bu2SnL2 In toluene at 300℃;	20%

quinoline (91-22-5) + 3-chloropropionic acid (2-isocyanatoethyl) ester (98134-34-0) → acrylic acid 2-isocyanatoethyl ester (13641-96-8)

Conditions	Yield
With 9,10-phenanthrenequinone

3-azido-3-oxopropyl acrylate (869583-47-1) → acrylic acid 2-isocyanatoethyl ester (13641-96-8)

Conditions	Yield
In chloroform for 2h; Heating / reflux;
In chloroform for 2h; Heating / reflux;

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + N-phenyl-N-(3-trimethoxysilylpropyl)amine (3068-76-6) → 3,3-dimethoxy-8-oxo-7-phenyl-2-oxa-7,9-diaza-3-silaundecan-11-yl acrylate

Conditions	Yield
at 45℃;	100%

(3-(N-ethylamino)isobutyl) trimethoxysilane + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → 7-ethyl-3,3-dimethoxy-5-methyl-8-oxo-2-oxa-7,9-diaza-3-silaundecan-11-yl acrylate

Conditions	Yield
at 65℃;	100%

(4-amino-3,3-dimethylbutyl)trimethoxysilane (157923-74-5) + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → 3,3-dimethoxy-6,6-dimethyl-9-oxo-2-oxa-8,10-diaza-3-siladodecan-12-yl acrylate

Conditions	Yield
at 75℃;	100%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + nonaethylene glycol (3386-18-3) → 31-hydroxy-4-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-3-azahentriacontyl acrylate

Conditions	Yield
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Flow reactor;	99.8%
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h;

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) → C9H9F6NO4

Conditions	Yield
With dibutyltin(II) dilaurate; 10H-phenothiazine at 60℃; for 24h; Temperature; Reagent/catalyst; Inert atmosphere; Green chemistry;	99.7%

ethyl methyl ketone oxime (96-29-7) + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → 2-(O-[1'-methylpropylideneamino]carboxyamino)ethyl acrylate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol at 10 - 20℃; for 6h;	99%
With 2,6-di-tert-butyl-4-methyl-phenol at 10 - 20℃; for 6h; Temperature; Enzymatic reaction;

acrylic acid 2-isocyanatoethyl ester (13641-96-8) → N,N'-<2-(2-propenoic acid) ethyl ester> urea

Conditions	Yield
With water; triethylamine In toluene at 20℃; for 13h;	98%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one (91526-18-0) → 2-[[[(5-methyl-1,3-dioxolen-2-one-4-yl)methoxy]carbonyl]amino]ethyl acrylate

Conditions	Yield
With dibutyltin(II) dilaurate; 4-methoxy-phenol at 60 - 80℃;	98%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + C23H41N5O8 → 2-((2-(3,5-bis(2-(hexylcarbamoyloxy)ethyl)-2,4,6-trioxo-1,3,5-triazinan-1-yl)ethoxy)carbonylamino)ethyl acrylate

Conditions	Yield
With dibutyltin dilaurate In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;	97%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 1-((4-bromophenyl)thio)-3-(phenylthio)propan-2-ol → 2-((((1-((4-bromophenyl)thio)-3-(phenylthio)propan-2-yl)oxy)carbonyl)amino)ethyl acrylate

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;	96%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione (5395-50-6) → 1,3,4,6-tetrakis(2-acryloyloxyethylcarbamoyloxy)methylglycoluril

Conditions	Yield
With dibutyltin dilaurate In dichloromethane at 20℃; for 24h;	95%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-ethanol (16111-07-2) → C26H27N3O7

Conditions	Yield
With dibutyltin dilaurate In dichloromethane at 25 - 50℃;	92%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 4-(9-phenyl-9H-fluorene-9-yl)phenol (169169-72-6) → C31H25NO4

Conditions	Yield
Stage #1: acrylic acid 2-isocyanatoethyl ester; 4-(9-phenyl-9H-fluorene-9-yl)phenol In ethyl acetate at 70℃; for 3.5h; Stage #2: With dibutyltin dilaurate In ethyl acetate for 2h;	92%

3,5-dimethyl-1H-pyrazole (67-51-6) + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl acrylate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 10℃; for 3h;	90%
With 4-methoxy-phenol at 15 - 40℃; for 2.5h; Product distribution / selectivity;

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + C27H22O2 → C33H29NO5

Conditions	Yield
Stage #1: acrylic acid 2-isocyanatoethyl ester; C27H22O2 In ethyl acetate at 75℃; for 8.5h; Stage #2: With dibutyltin dilaurate In ethyl acetate for 5h;	88.6%

1,6-hexanediol (629-11-8) + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → C18H28N2O8

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethyl acetate at 55℃; for 2h; Inert atmosphere;	86.7%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene (367279-75-2) → C38H48N2O8

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	86%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + C27H30N2O6S → C39H44N4O12S

Conditions	Yield
In N,N-dimethyl-formamide for 8h;	85%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 3-hydroxypropyltriphenylsilane (2509-34-4) → Triphenylsilylpropoxycarbonylaminoethyl Acrylate

Conditions	Yield
With dibutyltin(II) dilaurate In hexane; water; ethyl acetate; toluene	81%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 3-hydroxypropyltriphenylsilane (2509-34-4) → 2-({[3-(triphenylsilyl)propoxy]carbonyl}amino)ethyl acrylate

Conditions	Yield
With dibutyltin dilaurate In toluene at 70℃; for 6h; Inert atmosphere;	81%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 1,3-diaminoadamantane (10303-95-4) → C22H32N4O6

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere;	79%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 2-methoxy-5-((5,6,7-trimethoxychroman-3-yl)-methyl)phenol → 2-(((2-methoxy-5-((5,6,7-trimethoxychroman-3-yl)methyl)phenoxy)carbonyl)amino)ethyl acrylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	75%

phthalimide (136918-14-4) + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → 2-[(phthalimido)carbonylamino]ethyl acrylate

Conditions	Yield
Stage #1: phthalimide With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: acrylic acid 2-isocyanatoethyl ester In tetrahydrofuran for 24.5h;	72%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 9-Fluorenylmethanol (24324-17-2) → C20H19NO4 (909781-41-5)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In benzene for 9h; Heating / reflux;	71%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + C27H33N2O2(1+)*C2F6NO4S2(1-) → C39H47N4O8(1+)*C2F6NO4S2(1-)

Conditions	Yield
With dibutyltin(II) dilaurate; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran-d8; water; ethyl acetate at 20℃; for 24h;	71%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)disulfide → C30H50N4O8S2

Conditions	Yield
With dibutyltin dilaurate In N,N-dimethyl acetamide at 20℃; for 5h;	71%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + ethanolamine (141-43-5) + rhodamine B sulfonyl chloride (62796-29-6) → C35H42N4O10S2

Conditions	Yield
Stage #1: ethanolamine; rhodamine B sulfonyl chloride With dmap; triethylamine In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere; Stage #2: acrylic acid 2-isocyanatoethyl ester With dibutyltin dilaurate In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	70%

C24H56O12Si4 + acrylic acid 2-isocyanatoethyl ester (13641-96-8) → C48H84N4O24Si4

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dioctyltin(IV) oxide In ethyl acetate at 80℃; for 5h; Inert atmosphere;	68.7%

acrylic acid 2-isocyanatoethyl ester (13641-96-8) + 2-(1-benzyl-5-(6-methylpyridin-2-yl)-1H-1,2,3-triazol-4-yl)ethan-1-ol → 2-(((2-(1-benzyl-4-(6-methylpyridin-2-yl)-1H-1,2,3-triazol-5-yl)ethoxy)carbonyl)amino)ethyl acrylate

Conditions	Yield
With dibutyltin dilaurate In dichloromethane at 20℃; for 48h; Inert atmosphere;	62.7%

Upstream product

• 91-22-5 quinoline 
• 98134-34-0 3-chloropropionic acid (2-isocyanatoethyl) ester 
• 75-44-5 phosgene 
• 141-43-5 ethanolamine 
• 625-36-5 2-chloropropionyl chloride 
• 869583-47-1 3-azido-3-oxopropyl acrylate 

Relevant academic research and scientific papers

COMPOSITION, PRODUCTION METHOD FOR COMPOSITION, AND PRODUCTION METHOD FOR UNSATURATED COMPOUND

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A), [in-line-formulae](R1—COO)n—R2—(NCO)m??(1)[/in-line-formulae] [in-line-formulae](R1—COO)n—R2—(R3—R1)m??(2)[/in-line-formulae] wherein in general formulae (1) and (2), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R1 and R2 in the general formula (1) are the same as R1 and R2 in the general formula (2); in general formula (2), R3 is —NHC(═O)—; and n and m each represent an integer of one or two.

The ethylenically unsaturated group-containing isocyanate compound

PROBLEM TO BE SOLVED: To provide a production method capable of obtaining an ethylenically unsaturated group-containing isocyanate compound with high yield, which is excellent in safety to human bodies or environments without using phosgene and in which the production processes and production facilities are simplified.SOLUTION: There is a method for producing an ethylenically unsaturated group-containing isocyanate compound which produces a compound having an ethylenically unsaturated bond and an isocyanate group in the molecule using an amino alcohol as a raw material, wherein the method has a step of producing a cyclic compound having a urethane bond in the molecule as an intermediate.

STABILIZED ISOCYANATE GROUP-CONTAINING ETHYLENICALLY UNSATURATED COMPOUND

An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl group which may have a substituent.

STABILIZED ISOCYANATE GROUP-CONTAINING ETHYLENICALLY UNSATURATED COMPOUND

An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization, a multimerization reaction and a discoloration reaction of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl halide group or an amino alkyl group which may have a substituent.

BIODEGRADABLE OCULAR IMPLANTS AND METHODS FOR TREATING OCULAR CONDITIONS

Biodegradable ocular implants are described. The ocular implants include a bioactive agent that can be released within the eye to treat an ocular condition or indication. The implants can be used for the administration of a bioactive agent over prolonged periods of time. In some aspects the implants are formed of a matrix of natural biodegradable polysaccharides.

METHOD FOR PRODUCING (METH)ACRYLATE DERIVATIVE HAVING ISOCYANATE GROUP

The invention aims to provide a method whereby (meth)acrylate derivatives having an isocyanate group can be obtained in high yield by dehydrochlorination of 3-chloropropionate derivatives having an isocyanate group under industrially advantageous and mild conditions, and the content of residual hydrolyzable chlorine can be reduced. A method for producing a (meth)acrylate derivative having an isocyanate group comprises performing dehydrochlorination of a 3-chloropropionate derivative having an isocyanate group in the presence of a basic nitrogen compound having a tertiary nitrogen, the tertiary nitrogen of the basic nitrogen compound having