2478-10-6

Basic information

• Product Name: 4-Hydroxybutyl acrylate
• Synonyms: 4-Hydroxybutyl acrylate ,98%;4-Hydroxybutyl acrylate 90%, contains 50 ppm monomethyl ether hydroquinone as inhibitor, 300 ppm hydroquinone as inhibitor;4-Hydroxybutyl acrylate, stabilized with &ap:500ppm 4-methoxyphenol;1,4-Butanediolmonoacrylate;2-Propenoicacid,4-hydroxybutylester;4-Hydroxybutyl2-propenoate;4-HYDROXYBUTYL ACRYLATE;ACRYLIC ACID 4-HYDROXYBUTYL ESTER
• CAS NO: 2478-10-6
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• EINECS: 219-606-3
• Product Categories: AcrylateCarbonyl Compounds;Acrylic Monomers;C6 to C7;Esters;Monomers
• Mol File: 2478-10-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: -112°C
• Boiling Point: 95 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear liquid
• Density: 1.041 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 0-6°C
• PKA: 14.99±0.10(Predicted)
• Water Solubility: soluble
• BRN: 1756545
• CAS DataBase Reference: 4-Hydroxybutyl acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybutyl acrylate(2478-10-6)
• EPA Substance Registry System: 4-Hydroxybutyl acrylate(2478-10-6)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 20/21/22-36/37/38-51/53
• Safety Statements: 26-37/39-38-61-36/37/39-29
• RIDADR: 2922
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2478-10-6(Hazardous Substances Data)

Usage

Description

4-Hydroxybutyl acrylate (HBA) is a clear liquid monomer synthesized by the esterification of acrylic acid with 1,4-butanediol over a catalyst such as Amberlyst 15. It is known for its properties of luster, chemical, and scratch resistance, making it a valuable component in various applications.

Uses

Used in Membrane Systems:
4-Hydroxybutyl acrylate is used as a monomer for the fabrication of membrane systems for controlled release of transdermal drug delivery systems. Its chemical and scratch resistance properties contribute to the durability and effectiveness of these systems.
Used in Pharmaceutical Industry:
4-Hydroxybutyl acrylate is used as a component in the preparation of poly(2-hydroxy-3-phenoxypropylacrylate, 4-hydroxybutyl acrylate, dibutyl maleate) membranes. These membranes are utilized in the pharmaceutical industry for drug delivery applications, taking advantage of HBA's luster and resistance properties to enhance the performance and longevity of the delivery systems.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H12O3/c1-2-7(9)10-6-4-3-5-8/h2,8H,1,3-6H2

Synthetic route

Butane-1,4-diol (110-63-4) + acrylic acid methyl ester (292638-85-8) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With 10H-phenothiazine; dioctyltin(IV) oxide In cyclohexane at 85℃; for 10h; Concentration; Reagent/catalyst;	98.3%

vinyloxybutyl acrylate → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With toluene-4-sulfonic acid at 40℃; under 225.023 Torr; for 1h;	91%

Butane-1,4-diol (110-63-4) + acrylic acid (79-10-7) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With toluene-4-sulfonic acid; 4-methoxy-phenol; hydroquinone In cyclohexane at 60 - 120℃; Temperature;	82.5%
toluene-4-sulfonic acid
With 10H-phenothiazine; sulfuric acid In cyclohexane at 85℃; for 12h;
With toluene-4-sulfonic acid; hydroquinone

4-((4-methoxybenzyl)oxy)butyl acrylate → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 3h; Irradiation; Green chemistry;	45%

Butane-1,4-diol (110-63-4) + acetylene (74-86-2) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With acetic acid; tetracarbonyl nickel

1,4-Butanediol diacrylate (1070-70-8) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With phosphate buffer; carboxylesterase from Brevibacterium linens IFO 12171 In water at 30℃; pH=7.0; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

Butane-1,4-diol (110-63-4) + acrolein (107-02-8) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
Stage #1: acrolein With tert-butylhypochlorite In tetrachloromethane at 30℃; for 3.33333h; Stage #2: Butane-1,4-diol In tetrachloromethane at 25℃; for 1.5h;

Butane-1,4-diol (110-63-4) + acrylic acid methyl ester (292638-85-8) → 4-hydroxybutyl acrylate (2478-10-6) + 1,4-Butanediol diacrylate (1070-70-8)

Conditions	Yield
With Novozyme 435 In tert-Amyl alcohol at 50℃; for 120h; Inert atmosphere; Molecular sieve; Enzymatic reaction;
With Novozyme 435 In 2-methyl-2-butanol at 50℃; for 24h; Enzymatic reaction;

Butane-1,4-diol (110-63-4) + acryloyl chloride (814-68-6) → 4-hydroxybutyl acrylate (2478-10-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
With triethylamine

4-hydroxybutyl acrylate (2478-10-6) + bis(trichloromethyl) carbonate (32315-10-9) → 4-(chlorocarbonyloxy)butyl prop-2-enoate (185756-32-5)

Conditions	Yield
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane at -5 - 20℃; for 22.5h; Inert atmosphere;	100%
With N,N-diethylaniline In ethyl acetate at 5℃; for 3h;	273 g

4-hydroxybutyl acrylate (2478-10-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-tert-butyldimethylsilyloxy-1-butyl acrylate (756480-45-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	98%

4-hydroxybutyl acrylate (2478-10-6) + acetylacetone (123-54-6) → C19H32O8 (1108203-14-0)

Conditions	Yield
With N,N,N',N'-tetramethylguanidine at 40℃; for 4h; Michael Condensation;	98%

Methyltrichlorosilane (75-79-6) + 4-hydroxybutyl acrylate (2478-10-6) → C22H36O9Si

Conditions	Yield
With hydroquinone at 100℃; for 2.5h; Large scale;	92.1%

succinic acid anhydride (108-30-5) + 4-hydroxybutyl acrylate (2478-10-6) → 4-(4-(acryloyloxy)butoxy)-4-oxobutanoic acid (136153-20-3)

Conditions	Yield
With dmap In dichloromethane at 25℃; for 48h; Inert atmosphere; Darkness;	92%

4-hydroxybutyl acrylate (2478-10-6) → C32H52O12Si

Conditions	Yield
With tetrachlorosilane; hydroquinone at 100℃; for 2.5h; Large scale;	90.1%

oenanthic acid (111-14-8) + 4-hydroxybutyl acrylate (2478-10-6) → 4-(heptanoyloxy)butyl acrylate (1370407-32-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Cooling with ice;	90%

4-hydroxybutyl acrylate (2478-10-6) + 4-<7-<4-<(dimethylthexylsilyl)oxy>phenyl>heptylidene>benzoic acid (162380-33-8) → (acrylyloxy)-1,4-tetramethylene 4-<7-<4-<(dimethylthexylsilyl)oxy>phenyl>heptylidene>benzoate (162380-34-9)

Conditions	Yield
With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane for 25h;	88.2%

4-hydroxybutyl acrylate (2478-10-6) + cyanoacetic acid (372-09-8) → C10H13NO4 (45162-96-7)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 2h;	88%

4-hydroxybutyl acrylate (2478-10-6) + 2-[(4-methoxybenzyl)oxy]-3-nitropyridine (350848-02-1) → 4-((4-methoxybenzyl)oxy)butyl acrylate

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333h;	87%

4-hydroxybutyl acrylate (2478-10-6) + benzaldehyde (100-52-7) → (4-hydroxybutyl)-2-(α-hydroxybenzyl)acrylate (130977-36-5)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 72h; Ambient temperature;	85%

4-hydroxybutyl acrylate (2478-10-6) + (2-dimethylamino-1-(4-morpholinophenyl)-2-(4-carboxyphenylmethyl)butan-1-one) → C31H40N2O6

Conditions	Yield
Stage #1: 4-hydroxybutyl acrylate; (2-dimethylamino-1-(4-morpholinophenyl)-2-(4-carboxyphenylmethyl)butan-1-one) With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 2h; Stage #2: With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h;	83%

4-hydroxybutyl acrylate (2478-10-6) + rhodamine B (81-88-9) → Cl(1-)*C35H41N2O5(1+)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	80.2%

4-hydroxybutyl acrylate (2478-10-6) + (4-(tert-butyl)benzyl)(trifluoromethyl)sulfane → (E)-2-(3-(4-hydroxybutoxy)-3-oxoprop-1-en-1-yl)-4-(tert-butyl)benzyl trifluoromethyl sulfane

Conditions	Yield
With [2,2]bipyridinyl; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate at 80℃; for 12h; Sealed tube;	80%

4-hydroxybutyl acrylate (2478-10-6) + 4-<(2R)-2-cyano-7-<4-<<<4'-(pentyloxy)-4-biphenyl>carbonyl>oxy>phenyl>heptylidene>benzoic acid (151608-77-4) → (acrylyloxy)-1,4-tetramethylene-4-<(2R)-2-cyano-7-<4-<<<4'-(pentyloxy)-4-biphenyl>carbonyl>oxy>phenyl>heptylidene>benzoate

Conditions	Yield
With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane for 24h;	78.5%

4-hydroxybutyl acrylate (2478-10-6) + 4‑((4,5‑diphenyl)‑1H‑imidazol‑2‑yl)benzoic acid (5496-35-5) → C29H26N2O4

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 10.5h; Cooling with ice;	76.44%

4-hydroxybutyl acrylate (2478-10-6) + cyclopenta-1,3-diene (542-92-7) → 4-hydroxybutyl-bicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions	Yield
Stage #1: 4-hydroxybutyl acrylate With dmap; 1-ClCOOCH2CH2O-2-MeO-4-HOCOCH2-5-BzNHCH2-C6H2; dacarbazine In pyridine; N,N-dimethyl-formamide at 0 - 20℃; for 25h; Esterification; Stage #2: cyclopenta-1,3-diene In tetrahydrofuran at 60℃; for 15h; Cycloaddition; Diels-Alder reaction; Stage #3: With penicillin G acylase In methanol at 37℃; for 48h; pH=7.0; Substitution; Product release;	75%

4-hydroxybutyl acrylate (2478-10-6) + 2,5-bis-(4-butoxybenzoyloxy)-benzoic acid (205689-93-6) → 2,5-bis-(4-butoxybenzoyloxy)benzoic acid 4-acryloyloxybutyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	75%

4-hydroxybutyl acrylate (2478-10-6) + N-((2-chloro-1,1,2,2-tetrafluoroethyl)sulfinyl)-2-methyl-2-phenylpropionamide → 1-[2-(4-hydroxylbutoxyl)-2-oxoethyl]-4,4-dimethyl-1,4-dihydroisoquinolin-3(2H)-one

Conditions	Yield
With silver(I) acetate; palladium diacetate; sodium carbonate at 80℃; Schlenk technique; Sealed tube;	74%

4-hydroxybutyl acrylate (2478-10-6) + 1-benzylsulfanyl-4-methyl-benzene (5023-60-9) → C21H24O3S

Conditions	Yield
With silver tetrafluoroborate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate at 80℃; for 12h;	72%

4-hydroxybutyl acrylate (2478-10-6) + N-((2-chloro-1,1,2,2-tetrafluoroethyl)sulfinyl)pivalamide → 4-hydroxybutyl 2-(4,4-dimethyl-5-oxopyrrolidin-2-yl)acetate

Conditions	Yield
With silver(I) acetate; palladium diacetate; sodium carbonate at 120℃; Schlenk technique;	70%

4-hydroxybutyl acrylate (2478-10-6) + 4-hydroxy-benzaldehyde (123-08-0) → C14H16O4

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 10.5h; Cooling with ice;	67%

4-hydroxybutyl acrylate (2478-10-6) + C45H56O6 → 4-[2-(3,4,5-trihexyloxyphenyl)vinyl]benzoic acid 4'-(4-acryloyloxybutoxy)biphenyl-4-ylester

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 70℃; for 12h; Mitsunobu Displacement; Inert atmosphere;	66%

2-bromomethylfuran (4437-18-7) + 4-hydroxybutyl acrylate (2478-10-6) → C14H18O6

Conditions	Yield
Stage #1: 4-hydroxybutyl acrylate With carbon dioxide; N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide at 30℃; under 7500.75 Torr; for 1h; Autoclave; Stage #2: 2-bromomethylfuran With carbon dioxide In N,N-dimethyl-formamide at 30℃; under 22502.3 Torr; for 24h; Autoclave;	65%

isobornyl methacrylate (16868-12-5) + styrene (292638-84-7) + 2-hydroxypropyl methacrylate (923-26-2) + 4-hydroxybutyl acrylate (2478-10-6) + methacrylic acid methyl ester (80-62-6) + 2-methyl-butyl acrylate (97-88-1) → poly(n-bytyl methacrylate-co-4-hydroxybutyl acrylate-co-2-hydroxypropyl methacrylate-co-isobornyl methacrylate-co-methyl methacrylate-co-styrene)

Conditions	Yield
Stage #1: isobornyl methacrylate; styrene; 2-hydroxypropyl methacrylate; 4-hydroxybutyl acrylate; methacrylic acid methyl ester; 2-methyl-butyl acrylate In acetic acid butyl ester; ethyl acetate at 110℃; for 5h; Stage #2: With tert-butyl peroxyacetate; azobis(2-cyanobutane) In acetic acid butyl ester; ethyl acetate for 6.5h; Heating / reflux;	60.4%

4-hydroxybutyl acrylate (2478-10-6) + 4-methyl-benzaldehyde (104-87-0) → 2-(Hydroxy-p-tolyl-methyl)-acrylic acid 4-hydroxy-butyl ester

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 144h; Ambient temperature;	60%

4-hydroxybutyl acrylate (2478-10-6) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → Acrylic acid 4-(2'-hydroxy-[1,1']binaphthalenyl-2-yloxy)-butyl ester

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate Ambient temperature;	60%

Upstream product

• 7434-86-8 2-ethenyl-1,3-dioxepane 
• 110-63-4 Butane-1,4-diol 
• 292638-85-8 acrylic acid methyl ester 
• 814-68-6 acryloyl chloride 
• 107-02-8 acrolein 
• 1070-70-8 1,4-Butanediol diacrylate 
• 79-10-7 acrylic acid 
• 74-86-2 acetylene 

Downstream Products

• 110-63-4 Butane-1,4-diol 
• 157525-13-8 C₉H₁₃ClO₄ 
• 297132-04-8 4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoic acid 
• 185756-32-5 4-(chlorocarbonyloxy)butyl prop-2-enoate 

Relevant articles and documents

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