2082-81-7

Basic information

• Product Name: 1,4-Butanediol dimethacrylate
• Synonyms: 1,4-Butanediol bismethacrylate;Bismethacrylic acid 1,4-butanediyl;Bismethacrylic acid tetramethylene ester;Dimethacrylic acid 1,4-butanediyl;2-methylacrylic acid 4-methacryloyloxybutyl ester;4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate;1,4-Butanediol dimet;4-Butanediol diMethacrylate
• CAS NO: 2082-81-7
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• EINECS: 200-875-0
• Product Categories: Acrylic Monomers;C12 to C63Monomers;Carbonyl Compounds;Esters;Polyfunctional Acrylics
• Mol File: 2082-81-7.mol

Chemical Properties

• Melting Point: −117 °C(lit.)
• Boiling Point: 3-4 °C(lit.)
• Flash Point: 38 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.023 g/mL at 25 °C(lit.)
• Vapor Density: 2.09 (vs air)
• Vapor Pressure: 430 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 9.8(at 25℃)
• Water Solubility: 243mg/L at 20℃
• Merck: 14,9710
• BRN: 956566
• CAS DataBase Reference: 1,4-Butanediol dimethacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Butanediol dimethacrylate(2082-81-7)
• EPA Substance Registry System: 1,4-Butanediol dimethacrylate(2082-81-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 3-16-26-29-39-36/37/39
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 2
• RTECS: PA0350000
• F: 9-34
• HazardClass: 3
• PackingGroup: I
• Hazardous Substances Data: 2082-81-7(Hazardous Substances Data)

Usage

Uses

Used in Dental Industry:
1,4-Butanediol dimethacrylate is used as a cross-linking agent for dental composite materials, sealants, and prostheses. Its application is due to its ability to create strong and durable bonds, which are essential for the longevity and effectiveness of dental restorations.
However,

InChI:InChI=1/C12H18O4/c1-6-7-10(15-11(13)8(2)3)16-12(14)9(4)5/h10H,2,4,6-7H2,1,3,5H3

Synthetic route

Butane-1,4-diol (110-63-4) + poly(methacrylic acid) (79-41-4) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With cyclohexane; hydroquinone In water at 85 - 125℃;	98.83%
With sodium hydrogen sulfate In cyclohexane at 86℃; for 5h;	86.1%
With dicyclohexyl-carbodiimide In dichloromethane at -5℃; for 34h; Temperature;	77%
With sulfuric acid; benzene at 135℃; unter Entfernen des entstehenden Wassers;
With toluene-4-sulfonic acid; 1-Nitroso-2-naphthol

Butane-1,4-diol (110-63-4) + methacrylic acid methyl ester (80-62-6) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With sodium methylate; hydroquinone
With TEMPOL; oxygen; 4-methoxy-phenol; water; calcium oxide; lithium hydroxide at 70 - 96℃; Industry scale;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 4-methoxy-phenol; Amberlyst OH-form at 100 - 113℃; for 5h;

Butane-1,4-diol (110-63-4) + methacrylic acid methyl ester (80-62-6) → 4-methacryloyloxybutyl alcohol (997-46-6) + butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With 4-methoxy-phenol; zirconium acetylacetonate for 4h; Product distribution / selectivity; Heating / reflux;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 4-methoxy-phenol; zircornium(IV) n-propoxide; acetylacetone In propan-1-ol for 2h; Product distribution / selectivity; Heating / reflux;

2,3-Epoxypropyl methacrylate (106-91-2) + benzyltrismethylammonium methoxide (122-08-7) → butane-1,4-diyl di(methacrylate) (2082-81-7)

acryloyl chloride (814-68-6) + 3-Chloro-2-methylpropene (563-47-3) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
	7.3 g (95%)

acryloyl chloride (814-68-6) + 2-[3-(2-hydroxy-ethyl)-adamantan-1-yl]-ethanol (80121-65-9) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With triethylamine In benzene	7.0 g (95%)

5,7-dimethyl-1,3-bis(hydroxymethyl)adamantane + acryloyl chloride (814-68-6) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With hydrogenchloride; triethylamine In benzene	13.2 g (80%)

1,3-dimethyl-5,7-bis(2-hydroxyethyl)adamantane + acryloyl chloride (814-68-6) → butane-1,4-diyl di(methacrylate) (2082-81-7)

Conditions	Yield
With triethylamine In tetrahydrofuran; benzene	6.7 g (94%)

Butane-1,4-diol (110-63-4) + methacrylic acid methyl ester (80-62-6) → butane-1,4-diyl di(methacrylate) (2082-81-7) + 4-(3-methoxy-2-methylpropanoyloxy)butyl 2-methylprop-2-enoate + 4-(2-{[4-(2-methylprop-2-enoyloxy)butyl]oxycarbonyl}propoxy)butyl 2-methylprop-2-enoate

Conditions	Yield
With TEMPOL; oxygen; 4-methoxy-phenol; calcium oxide; lithium hydroxide at 70 - 96℃; Product distribution / selectivity; Industry scale;

styrene (292638-84-7) + butane-1,4-diyl di(methacrylate) (2082-81-7) → butane-1,4-diyl di(methacrylate)-crosslinked polystyrene; monomer(s): styrene; butane-1,4-diyl di(methacrylate)

Conditions	Yield
With Polyvinyl alcohol; dibenzoyl peroxide In toluene at 85℃; for 15h;	90%

tetrachloromethane (56-23-5) + butane-1,4-diyl di(methacrylate) (2082-81-7) → 2,4,4,4-Tetrachloro-2-methyl-butyric acid 4-(2,4,4,4-tetrachloro-2-methyl-butyryloxy)-butyl ester

Conditions	Yield
Cu catalyst

styrene (292638-84-7) + butane-1,4-diyl di(methacrylate) (2082-81-7) → styrene, butanediol dimethacrylate, copolymer of

Conditions	Yield
With Polyvinyl alcohol; dibenzoyl peroxide In water; toluene at 85℃; for 6h; Polymerization;

styrene (292638-84-7) + butane-1,4-diyl di(methacrylate) (2082-81-7) → 1,4-butanediol dimethacrylate cross-linked polystyrene; cross-linker content 1-4 mol. percent

Conditions	Yield
With dibenzoyl peroxide In toluene at 80℃; for 6h; Polymerization;

styrene (292638-84-7) + butane-1,4-diyl di(methacrylate) (2082-81-7) → polystyrene, cross-linked with 1,4-butanediol dimethacrylate, 2 percent cross-linking density; monomer(s): styrene; 1,4-butanediol dimethacrylate

Conditions	Yield
With Polyvinyl alcohol; dibenzoyl peroxide In water; toluene at 80℃; for 6h;

butane-1,4-diyl di(methacrylate) (2082-81-7) → poly(butane-1,4-diyl dimethacrylate); monomer(s): butane-1,4-diyl dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 60℃;

butane-1,4-diyl di(methacrylate) (2082-81-7) → poly(butane-1,4-diyl dimethacrylate), prepared by cross-linking polymerization in presence of cobalt(II) tetramethylhematoporphyrin; monomer(s): butane-1,4-diyl dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); cobalt(II) tetramethylhematoporphyrin at 60℃;

butane-1,4-diyl di(methacrylate) (2082-81-7) → poly[butane-1,4-diol dimethacrylate], photocured stereolithography; monomer(s): butane-1,4-diol dimethacrylate

Conditions	Yield
With Camphorquinone UV-irradiation;

3-(2',6'-dichloro-4'-nitrophenyl-azo)-9-(2'-hydroxyethyl)carbazole (151285-25-5) + 2-(2'-hydroxy-5'-(3-(methylacryloxy)propyl)-3-tert-butylphenyl)-5-chloro-2H-benzotriazol + acrylic acid n-butyl ester (141-32-2) + butane-1,4-diyl di(methacrylate) (2082-81-7) + 2-phenoxyethyl acrylate (48145-04-6) + 2-methyl-butyl acrylate (97-88-1) → poly(1,4-butanediol dimethacrylate-co-3-(2',6'-dichloro-4'-nitrophenylazo)-9-(2'-methacryloyloxyethyl)carbazole-co-ethylene glycol phenyl ether acrylate-co-2-(2'-hydroxy-5'-methacrylyloxypropyl-3'-tert-butylphenyl) - 5-chloro-2H-benzotriazole-co-n-butyl acrylate-co-n-butyl methacrylate)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 60 - 95℃; for 48h;

acrylic acid n-butyl ester (141-32-2) + butane-1,4-diyl di(methacrylate) (2082-81-7) + 2-phenoxyethyl acrylate (48145-04-6) + 2-methyl-butyl acrylate (97-88-1) → poly(1,4-butanediol dimethacrylate-co-ethylene glycol phenyl ether acrylate-co-n-butyl acrylate-co-n-butyl methacrylate)

Conditions	Yield
With 4-(5'-hydroxy-3'-methyl-1'-phenyl-4'-pyrazylylmethylene)-1-(4'-methacryloyloxymethylphenyl)-3-methyl-2-pyrazolin-5-one; 1-[4'-(4'-methacryloyloxyethylphenylazo)phenylazo]-2-naphthol; 2,2'-azobis(isobutyronitrile) at 60 - 95℃; for 48h; Air oven; vacuum oven;

t-butyl malonate (541-16-2) + butane-1,4-diyl di(methacrylate) (2082-81-7) → 1,1-di-tert-butyl 3-(4-((2,3-dimethylbut-2-enoyl)oxy)butyl) butane-1,1,3-tricarboxylate (1362862-16-5)

Conditions	Yield
Stage #1: butane-1,4-diyl di(methacrylate) With 18-crown-6 ether; potassium carbonate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: t-butyl malonate In tetrahydrofuran at 0 - 40℃; for 48.5h;

butane-1,4-diyl di(methacrylate) (2082-81-7) + (1,3,4)-triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene (166773-08-6) → BDMA(TPT)2

Conditions	Yield
With 4-methoxy-phenol In (2)H8-toluene at 80℃; for 6h; Temperature; Glovebox;

Upstream product

• 110-63-4 Butane-1,4-diol 
• 80-62-6 methacrylic acid methyl ester 
• 814-68-6 acryloyl chloride 
• 563-47-3 3-Chloro-2-methylpropene 
• 80121-65-9 2-[3-(2-hydroxy-ethyl)-adamantan-1-yl]-ethanol 
• 79-41-4 poly(methacrylic acid) 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 122-08-7 benzyltrismethylammonium methoxide 

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