2455-24-5

Basic information

• Product Name: Tetrahydrofurfuryl methacrylate
• Synonyms: METHACRYLIC ACID TETRAHYDROFURFURYL ESTER;2-METHYL-ACRYLIC ACID TETRAHYDRO-FURAN-2-YLMETHYL ESTER;TETRAHYDROFURFURYL METHACRYLATE;(TETRAHYDRO-2-FURANYL)METHYLMETHACRYLATE;2-methyl-2-propenoicaci(tetrahydro-2-furanyl)methylester;2-Propenoicacid,2-methyl-,(tetrahydro-2-furanyl)methylester;sartomersr203;sr203
• CAS NO: 2455-24-5
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• EINECS: 219-529-5
• Product Categories: FuransMonomers;Acrylic Monomers;Building Blocks;Heterocyclic Building Blocks;Methacrylate
• Mol File: 2455-24-5.mol

Chemical Properties

• Boiling Point: 52 °C0.4 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 1.044 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0094mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: 18.99g/L at 20℃
• Sensitive: Light Sensitive
• BRN: 117423
• CAS DataBase Reference: Tetrahydrofurfuryl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydrofurfuryl methacrylate(2455-24-5)
• EPA Substance Registry System: Tetrahydrofurfuryl methacrylate(2455-24-5)

Safety Data

• Statements: 10-36/37/38
• Safety Statements: 36
• RIDADR: 3272
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2455-24-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Tetrahydrofurfuryl methacrylate is used as methacrylic component in dental materials, such as crown and bridge products; in artificial nails.

InChI:InChI=1/C9H14O3/c1-7(2)9(10)12-6-8-4-3-5-11-8/h8H,1,3-6H2,2H3

Synthetic route

Tetrahydrofurfuryl alcohol (97-99-4) + methacrylic acid methyl ester (80-62-6) → (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5)

Conditions	Yield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; di(n-butyl)tin oxide In 2-Methylpentane; cyclohexane at 85 - 100℃; for 12h; Temperature;	95%
2-methyl-propan-2-ol; lanthanum tri-tert-butylate at 25℃; for 2h;	32 %Chromat.
sodium ethanolate	15 %Chromat.
With sulfuric acid; benzene

Tetrahydrofurfuryl alcohol (97-99-4) + methyl methacrylate (97-63-2) → (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5)

Conditions	Yield
With sulfuric acid

Tetrahydrofurfuryl alcohol (97-99-4) + poly(methacrylic acid) (79-41-4) → (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + diphenylphosphane (829-85-6) → C21H25O3P

Conditions	Yield
In 2-methyltetrahydrofuran at 90℃; for 4h; Inert atmosphere; Sealed tube; Green chemistry; regioselective reaction;	79%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + β-naphthaldehyde (66-99-9) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-(naphthalen-2-yl)-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	75%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 4-methoxy-benzaldehyde (123-11-5) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-4-(4-methoxyphenyl)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	74%

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + D,L-cis-phenylcyclopropylamine (34535-98-3) → (tetrahydrofuran-2-yl)methyl-1-methyl-2-(phenylamino)cyclopentanecarboxylate + (tetrahydrofuran-2-yl)methyl-1-methyl-2-(phenylamino)cyclopentanecarboxylate

Conditions	Yield
With C60H100N4O12Rh2 In hexane at 20℃; for 18h; Schlenk technique; Inert atmosphere;	A 11% B 74%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 3-methoxy-benzaldehyde (591-31-1) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-4-(3-methoxyphenyl)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	73%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + benzaldehyde (100-52-7) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-oxo-4-phenylbutanoate (1415690-09-3)

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	70%
With iron(II) chloride In decane; acetonitrile at 85℃; for 1h; Inert atmosphere;	61%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 4-fluorobenzaldehyde (459-57-4) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-4-(4-fluorophenyl)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	67%

5-Methylfurfural (620-02-0) + tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-(5-methylfuran-2-yl)-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	61%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + hydrazinecarboxylic acid methyl ester (6294-89-9) → 4-methyl-1-((tetrahydrofuran-2-yl)methyl) 2-(tert-butylperoxy)-2-methylsuccinate

Conditions	Yield
With iron(II) phthalocyanine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	60%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 1-naphthaldehyde (66-77-3) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-(naphthalen-1-yl)-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	51%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 4-chlorobenzaldehyde (104-88-1) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-4-(4-chlorophenyl)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	48%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + ortho-anisaldehyde (135-02-4) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-4-(2-methoxyphenyl)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	47%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 2-Phenylbenzaldehyde (1203-68-5) → (tetrahydrofuran-2-yl)methyl 4-([1,1'-biphenyl]-4-yl)-2-(tert-butylperoxy)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	47%

tert.-butylhydroperoxide (75-91-2) + 4-Trifluoromethylbenzaldehyde (455-19-6) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-oxo-4-(4-(trifluoromethyl)phenyl)butanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	44%

tert.-butylhydroperoxide (75-91-2) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + 4-bromo-benzaldehyde (1122-91-4) → (tetrahydrofuran-2-yl)methyl 4-(4-bromophenyl)-2-(tert-butylperoxy)-2-methyl-4-oxobutanoate

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In decane; 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	40%

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) + tris-(trimethylsilyl)silane (1873-77-4) → (tetrahydrofuran-2-yl)methyl2-((1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-yl)methyl)acrylate

Conditions	Yield
With Quinuclidine; pyridine; chloropyridinecobaloxime(III); (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In acetonitrile at 25℃; Schlenk technique; Irradiation; Inert atmosphere;	40%

2-methylacrylic acid 2-(benzyloxycarbonylamino)ethyl ester (107663-38-7) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): tetrahydrofurfuryl methacrylate; benzyl 2-(2-methylacryloyloxy)ethylcarbamate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

2-methylacrylic acid 2-(benzylcarbamoyloxy)ethyl ester (694483-26-6) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): tetrahydrofurfuryl methacrylate; 2-methylacrylic acid 2-(benzylcarbamoyloxy)ethyl ester

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

2-methylacrylic acid 2-(3-benzylureido)ethyl ester (110782-91-7) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): tetrahydrofurfuryl methacrylate; 2-methylacrylic acid 2-(3-benzylureido)ethyl ester

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): tetrahydrofurfuryl methacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): 2-hydroxyethyl methacrylate; tetrahydrofurfuryl methacrylate

Conditions	Yield
With dibenzoyl peroxide at 49.85 - 79.85℃; for 22h;

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → polymer; monomer(s): tetrahydrofurfur-2-yl methacrylate

Conditions	Yield
With methanesulfonic acid; 2,2-dimethoxy-2-phenylacetophenone at 25℃; for 0.0833333h; UV-irradiation;

2-methyl-1,4,5,6-tetrahydropyrimidine (4271-95-8) + (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5) → tetrahydrofurfuryl 3-(2-methyl-1,4,5,6-tetrahydropyrimidin-1-yl)-2-methylpropionate

Conditions	Yield
at 100℃; for 5h;

Upstream product

• 97-99-4 Tetrahydrofurfuryl alcohol 
• 97-63-2 methyl methacrylate 
• 80-62-6 methacrylic acid methyl ester 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 1415690-09-3 (tetrahydrofuran-2-yl)methyl 2-(tert-butylperoxy)-2-methyl-4-oxo-4-phenylbutanoate 

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