13641-96-8

Basic information

• Product Name: 2-IsocyanatoethylAcrylate
• Synonyms: 2-IsocyanatoethylAcrylate;2-Propenoic acid 2-isocyanatoethyl ester;2-isocyanatoethyl prop-2-enoate;2-Isocyanatoethyl Acrylate (stabilized with BHT);2-IsocyatoethylAcrylate
• CAS NO: 13641-96-8
• Molecular Formula: C₆H₇NO₃
• Molecular Weight: 141.12
• EINECS: 482-140-6
• Mol File: 13641-96-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: -25 °C
• Boiling Point: 200°Cat760mmHg
• Flash Point: 97°C(lit.)
• Appearance: /
• Density: 1.05
• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: 1.4470 to 1.4510
• CAS DataBase Reference: 2-IsocyanatoethylAcrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IsocyanatoethylAcrylate(13641-96-8)
• EPA Substance Registry System: 2-IsocyanatoethylAcrylate(13641-96-8)

Safety Data

• RIDADR: UN 2206 6.1/PG III
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13641-96-8(Hazardous Substances Data)

Usage

General Description

2-Isocyanatoethyl Acrylate is a chemical compound characterized by its strong reactivity and ability to act as a binding agent. It is classified as an acrylic monomer, which means it's often utilized in the creation of polymers or copolymers – complex molecules that form substances like plastics and resins. It is extensively used in industries related to coatings, paints, adhesives, and more. While the substance can be advantageous in several manufacturing processes, direct and prolonged exposure can lead to significant health risks such as skin or eye irritations and respiratory problems. As a result, proper handling and safety procedures are paramount when working with 2-Isocyanatoethyl Acrylate.

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

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

Relevant articles and documents

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.

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.

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