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
• Article Data: 15

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

Description

Sensitization to 1,4-butanediol dimethacrylate (BUDMA) was reported in dental technieians, with cross reactivity to methylmethacrylate.

Uses

cross-linking methacrylic monomer for use in dental-composite materials, sealants, prostheses, etc.

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 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 122-08-7 benzyltrismethylammonium methoxide 
• 79-41-4 poly(methacrylic acid) 

Relevant articles and documents

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