2499-95-8

Basic information

• Product Name: N-HEXYL ACRYLATE
• Synonyms: hexyl2-propenoate;ACRYLIC ACID N-HEXYL ESTER;HEXYL ACRYLATE;HEXYLAND2-ETHYLBUTYLACRYLATE;n-Hexyl acrylate, 95%, stab. with hydroquinone;Hexyl Acrylate (stabilized with HQ);HEXYL ACRYLATE, 96%, STABILIZED;Hexyl acrylate, stabilized
• CAS NO: 2499-95-8
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• EINECS: 219-698-5
• Product Categories: AcrylateCarbonyl Compounds;Acrylic Monomers;C8 to C9;Esters;Monomers;Acrylate;Acrylic Monomers;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Materials Science;Organic Building Blocks;Polymer Science
• Mol File: 2499-95-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -45°C
• Boiling Point: 88-90 °C24 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: /
• Density: 0.888 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.51mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: 57.4mg/L at 20℃
• BRN: 1757327
• CAS DataBase Reference: N-HEXYL ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HEXYL ACRYLATE(2499-95-8)
• EPA Substance Registry System: N-HEXYL ACRYLATE(2499-95-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-43-51/53
• Safety Statements: 24-26-37-61
• RIDADR: 3082
• WGK Germany: 2
• RTECS: AT1450000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 2499-95-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

General Description

Poly(hexyl acrylate-co-1,4-butanediol diacrylate-co-[2-(acryloyloxy)ethyl]trimethyl ammonium chloride) can be prepared by the photopolymeirzation of hexyl acrylate and several other components. These polyacrylate-based monolithics were designed to be used for capillary electrochromatography (CEC). Mutagenicity of this acrylate ester was evaluated by the Salmonella-microsome test.

InChI:InChI=1/C9H16O2/c1-3-5-6-7-8-11-9(10)4-2/h4H,2-3,5-8H2,1H3

Synthetic route

hexyl 2-propenyl ether (3295-94-1) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; magnesium acetate In decane; butyl butyrate at 0℃; chemoselective reaction;	91%

acryloyl chloride (814-68-6) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	83.4%
With triethylamine In tetrahydrofuran at 10 - 20℃; for 3h;	81%
With potassium carbonate In tetrahydrofuran
With triethylamine In chloroform at 10℃; for 12h;

acrylic acid-6-iodohexyl ester (133122-99-3) → n-hexyl acrylate (2499-95-8) + 1,11-dioxacycloisocosane (797-29-5) + oxecan-2-one (6008-27-1)

Conditions	Yield
With sodium cyanoborohydride In methanol for 3h; Ambient temperature; Irradiation; Yields of byproduct given;	A n/a B n/a C 74%
With sodium cyanoborohydride In methanol for 3h; Ambient temperature; Irradiation; Yield given;	A n/a B n/a C 74%

acrylic acid (79-10-7) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Reflux;	62.6%
With alkanesulfonic acid; toluene at 120℃;
With zirconium(IV) oxychloride at 50℃; for 24h;	61 % Chromat.

vinyl acrylate (2177-18-6) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea;	40%
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea; transesterification, other alcohols; also with vinyl methacrylate;	40%

acrylic acid methyl ester (292638-85-8) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

1,6-hexanediol (629-11-8) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 47percent HBr / toluene / Heating 2: NaI / acetone / Ambient temperature 3: p-TolSO3H / benzene / Heating 4: NaBH3CN / methanol / 3 h / Ambient temperature; Irradiation View Scheme

1-bromo-6-hexanol (4286-55-9) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaI / acetone / Ambient temperature 2: p-TolSO3H / benzene / Heating 3: NaBH3CN / methanol / 3 h / Ambient temperature; Irradiation View Scheme

1-iodohexan-6-ol (40145-10-6) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-TolSO3H / benzene / Heating 2: NaBH3CN / methanol / 3 h / Ambient temperature; Irradiation View Scheme

hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; magnesium acetate / decane; butyl butyrate / 0 °C View Scheme

ethyl acrylate (140-88-5) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
In neat (no solvent) at 79.84℃; for 5h;

ethyl acrylate (140-88-5) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8) + ethyl 3-(hexyloxy)propanoate (14144-59-3)

Conditions	Yield
In neat (no solvent) at 79.84℃; for 1h; Reagent/catalyst; Solvent; Temperature;

n-hexyl acrylate (2499-95-8) + diethyl malonate (105-53-3) → 2-ethoxycarbonyl-pentanedioic acid 1-ethyl ester 5-hexyl ester

Conditions	Yield
Mg-La mixed oxides In N,N-dimethyl-formamide at 24.85℃; for 3.5h; Michael addition;	99%

Hexanethiol (111-31-9) + n-hexyl acrylate (2499-95-8) → C15H30O2S (1236160-83-0)

Conditions	Yield
With hexan-1-amine at 20℃; for 3h; Kinetics; Reagent/catalyst; Thio-Michael reaction; Neat (no solvent);	99%
With Dimethyl(phenyl)phosphine In neat (no solvent) for 0.5h; Reagent/catalyst; Michael Addition;

Nitroethane (79-24-3) + n-hexyl acrylate (2499-95-8) → 4-nitro-pentanoic acid hexyl ester

Conditions	Yield
Mg-La mixed oxides In N,N-dimethyl-formamide for 3.5h; Michael addition;	98%

n-hexyl acrylate (2499-95-8) + butyl 3-mercaptopropionate (16215-21-7) → C16H30O4S

Conditions	Yield
With cyclohexanone; 1-(9-fluorenylmethoxycarbonyl)-diethylamine for 0.0833333h; Reagent/catalyst; Irradiation;	98%

benzenesulfonamide (98-10-2) + n-hexyl acrylate (2499-95-8) → N,N-di((2-carbo-n-hexyloxy)ethyl)benzenesulfonamide

Conditions	Yield
With potassium fluoride; tetrabutylammomium bromide at 130℃; for 0.233333h; Microwave irradiation; Neat (no solvent);	97%

n-hexyl acrylate (2499-95-8) + 4-Iodobenzenesulphonyl Fluoride (4241-66-1) → hexyl (E)-3-(4-(fluorosulfonyl)phenyl)acrylate

Conditions	Yield
With tetrabutyl-ammonium chloride; palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; Sealed tube;	97%

n-hexyl acrylate (2499-95-8) + 1,6-diiodopyrene (76656-52-5) → di-n-hexyl 1,6-pyrenedipropenoate (658858-93-6)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 120℃; for 6h;	94%

n-hexyl acrylate (2499-95-8) + 1-iodosinomenine (945761-25-1) → C28H37NO6

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 85℃; for 0.333333h; Time; Heck Reaction;	94%

n-hexyl acrylate (2499-95-8) + benzamide (55-21-0) → hexyl 3-benzamidopropanoate (1116115-87-7)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate for 0.25h; aza-Michael addition; microwave irradiation;	93%

2,3-dibromothiophen (3140-93-0) + n-hexyl acrylate (2499-95-8) → C22H32O4S

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 48h; Heck reaction;	92%

2,3-dibromothiophen (3140-93-0) + n-hexyl acrylate (2499-95-8) → dihexyl (2E,2'E)-3,3'-(thiophene-2,3-diyl)diacrylate (1184839-42-6)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 48h; Heck Reaction; Inert atmosphere;	92%

n-hexyl acrylate (2499-95-8) + benzenesufonyl hydrazide (80-17-1) → hexyl 3-(phenylsulfonyl)propanoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 75℃; for 3h; Michael Addition; Green chemistry;	92%

benzenesulfonamide (98-10-2) + n-hexyl acrylate (2499-95-8) → hexyl 3-(phenylsulfonamido)propanoate + N,N-di((2-carbo-n-hexyloxy)ethyl)benzenesulfonamide

Conditions	Yield
With aluminum oxide; potassium fluoride; tetrabutylammomium bromide at 110℃; for 0.166667h; Michael condensation; Microwave irradiation;	A 91% B 6%
With 1-n-butyl-3-methylimidazolim bromide; zinc(II) oxide at 110℃; for 0.0833333h; Michael addition reaction; microwave irradiation;	A 85% B 9%

n-hexyl acrylate (2499-95-8) + 2-naphthalenesulphonamide (1576-47-2) → hexyl 3-(naphthalene-2-suylfonamido)propanoate + dihexyl 3,3'-(naphthalene-2-sulfonylazanediyl)dipropanoate

Conditions	Yield
With aluminum oxide; potassium fluoride; tetrabutylammomium bromide at 110℃; for 0.166667h; Michael condensation; Microwave irradiation;	A 91% B 6%

n-hexyl acrylate (2499-95-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → hexyl 3-tosylpropanoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 75℃; for 3h; Michael Addition; Green chemistry;	90%

spiro[1,3-dioxolane-2,3'-indolin]-2'-one (6714-68-7) + n-hexyl acrylate (2499-95-8) → C19H25NO5 (1380216-32-9)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 80 - 90℃; for 1h; Michael condensation; neat (no solvent);	89%

2,3-dibromofuran (30544-34-4) + n-hexyl acrylate (2499-95-8) → dihexyl (2E,2'E)-3,3'-(furan-2,3-diyl)diacrylate (1338800-56-8)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 36h; Heck reaction; Inert atmosphere;	88%

n-hexyl acrylate (2499-95-8) + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) → C16H33NO7

Conditions	Yield
In 1,4-dioxane; water at 50℃; for 5h;	86%

2,3-dibromo-5-(ethoxycarbonyl)furan (54113-42-7) + n-hexyl acrylate (2499-95-8) → dihexyl (2E,2'E)-3,3'-[5-(ethoxycarbonyl)furan-2,3-diyl]diacrylate (1338800-62-6)

Conditions	Yield
With palladium diacetate; triethylamine; XPhos In N,N-dimethyl-formamide at 100℃; for 24h; Heck reaction; Inert atmosphere;	85%

n-hexyl acrylate (2499-95-8) + 1.3′,3′,6′,6′-tetramethyl-3′,4′,6′,7′-tetrahydrospiro[indoline-3, 9′-xanthene]-1′, 2, 8′ (2′H, 5′H)-trione (123055-54-9) → hexyl 3-(3',3',6',6'-tetramethyl-1',2,8'-trioxo-1',2',3',4',5',6',7',8'-octahydrospiro[indoline-3,9'-xanthen]-1-yl)propanoate

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate for 0.0333333h; Michael Addition; Heating; Green chemistry;	85%

8-methylquinoline (611-32-5) + n-hexyl acrylate (2499-95-8) → hexyl 4-(quinolin-8-yl)butanoate

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,1,1,3',3',3'-hexafluoro-propanol; Trimethylacetic acid at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; regioselective reaction;	85%

n-hexyl acrylate (2499-95-8) + benzaldehyde (100-52-7) → 3-phenyl-3-hydroxy-2-methylene-propanoic acid hexyl ester (144261-66-5)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 216h; Ambient temperature;	82%

C68H85N4O2B + n-hexyl acrylate (2499-95-8) → n-hexyl (E)-3-[5,10,15-tris(3,5-di-tert-butylphenyl)porphyrin-2-yl]prop-2-enoate

Conditions	Yield
With [Rh(OH)(cod)]2 In 1,4-dioxane; water at 100℃; for 16h; Heck-type addition; Inert atmosphere;	82%

n-hexyl acrylate (2499-95-8) + 2,3-dibromo-1-methyl-1H-indole (128746-62-3) → di(n-hexyl) 9-methyl-2,9-dihydro-1H-carbazole-2,3-dicarboxylate (1186316-09-5)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 48h; domino Heck reaction - 6ϖ-electrocyclization; Inert atmosphere;	81%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 48h; domino two-fold Heck/6ϖ-electrocyclization reaction; Inert atmosphere;	81%

n-hexyl acrylate (2499-95-8) → n-hexyl propionate (2445-76-3)

Conditions	Yield
With C51H71CoN4O14(1+)*ClO4(1-); trifluoroacetic acid In acetonitrile at 20℃; Electrolysis; Inert atmosphere;	81%
With methanol for 24h; UV-irradiation;	60%
With [Rh(OH)(cod)]2; 2-(hex-1-yn-1-yl)phenol at 90℃; for 6h;
With C18H9BF6*C4H8O; hydrogen In dichloromethane-d2 at -196.16 - 25℃; under 3000.3 Torr; for 36h; Inert atmosphere; Schlenk technique; Glovebox;	> 95 %Spectr.

N-Bromosuccinimide (128-08-5) + n-hexyl acrylate (2499-95-8) → (E)-hexyl 2-bromo-3-(2,5-dioxopyrrolidin-1-yl)acrylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 12h; stereoselective reaction;	81%

n-hexyl acrylate (2499-95-8) + phenylboronic acid (98-80-6) → n-hexyl cinnamate (3488-00-4)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate; copper(II) sulfate; palladium dichloride In water at 85℃; for 10h; Heck Reaction; Schlenk technique; stereoselective reaction;	81%

2,3,5,6-tetrabromo-1-methyl-1H-indole (25055-55-4) + n-hexyl acrylate (2499-95-8) → di(n-hexyl) 6,7-bis((E)-3-(hexyloxy)-3-oxoprop-1-enyl)-9-methyl-2,9-dihydro-1H-carbazole-2,3-dicarboxylate (1314799-02-4)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 120℃; for 48h; domino two-fold Heck/6ϖ-electrocyclization reaction; Inert atmosphere;	80%

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 111-27-3 hexan-1-ol 
• 814-68-6 acryloyl chloride 
• 140-88-5 ethyl acrylate 
• 3295-94-1 hexyl 2-propenyl ether 
• 40145-10-6 1-iodohexan-6-ol 
• 4286-55-9 1-bromo-6-hexanol 
• 629-11-8 1,6-hexanediol 
• 133122-99-3 acrylic acid-6-iodohexyl ester 
• 2177-18-6 vinyl acrylate 
• 79-10-7 acrylic acid 

Downstream Products

• 132876-44-9 1-(2-Hexyloxycarbonyl-ethyl)-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic acid methyl ester 
• 1116115-87-7 hexyl 3-benzamidopropanoate 
• 1039027-47-8 di-n-hexyl 3,3'-[10,20-bis(3,5-di-tertbutylphenyl)porphyrinate(zinc)-5,15-diyl]dipropanoate 
• 1232327-00-2 C₂₀H₂₄F₅NO₃ 
• 1174935-74-0 C₂₇H₃₁BF₂N₂O₂ 

Relevant articles and documents

Ε - propionic acid is oneself ester base - ε - caprolactone and its preparation method (by machine translation)

The invention discloses Epsilon-propionic-n-hexyl-Epsilon-caprolactone, having a structural formula shown as below. The invention further discloses a preparing method of the Epsilon-propionic-n-hexyl-Epsilon-caprolactone. The preparing method includes allowing an acidic compound and an alcoholic compound to esterify in organic solvent through an acid catalyst to obtain an n-hexyl acrylate compound, and allowing addition and Baeyer-Villiger oxidation of the n-hexyl acrylate compound and an alkene compound in the organic solvent through a basic catalyst and the acidic catalyst to obtain the Epsilon-propionic-n-hexyl-Epsilon-caprolactone compound. The Epsilon-propionic-n-hexyl-Epsilon-caprolactone is a novel Epsilon-lactone compound having characteristic fragrance of alcoholic sweet rice wine and belongs to latest research achievements on Epsilon-lactone compounds having characteristic fragrance at home and abroad.

Transesterification of acrylates by heterogeneous basic catalysis

Different solid basic catalysts including CsF/αAl2O 3, KF/αAl2O3, Ca(NO3) 2/γAl2O3, NaNO3/γAl 2O3, LiNO3/γAl2O3 were evaluated for the transesterification of ethyl acrylate by n-hexanol. All of them are active and selective in the transesterification reaction under mild conditions and without solvent, using a 1/1 molar ratio of reactants. Ca/γAl2O3 was shown to be the most selective of this set of catalysts and it could be recycled three times without lost of selectivity.

Nanostructure formation in aqueous solution of amphiphilic copolymers of 2-(N,N-dimethylaminoethyl)methacrylate and alkylacrylate: Characterization, antimicrobial activity, DNA binding, and cytotoxicity studies

Three amphiphilic random copolymers poly(2-(dimethylaminoethyl) methacrylate-co-alkylacrylate) (where, alkyl = hexyl, octyl, dodecyl) with 16 mol% hydrophobic substitution were synthesized. Surface tension, viscosity, fluorescence probe, dynamic light scattering (DLS), as well as transmission electron microscopic (TEM) techniques were utilized to investigate self-assembly formation by the hydrophobically modified polymers (HMPs) in pH 5. Formation of hydrophobic domains through inter-polymer chain interaction of the copolymer in dilute solution was confirmed by fluorescence probe studies. Average hydrodynamic diameter of the copolymer aggregates at different polymer concentration was measured by DLS studies. The copolymer with shorter hydrophobic chain exhibits larger hydrodynamic diameter in dilute solution, which decreased with either increase of concentration or increase of hydrophobic chain length. TEM images of the dilute solutions of the copolymers with shorter as well as with longer hydrophobic chain exhibit spherical aggregates of different sizes. The antimicrobial activity of the copolymers was evaluated by measuring the minimum inhibitory concentration value against one Gram-positive bacterium Bacillus subtilis and one Gram-negative bacterium Escherichia coli. The copolymer with the octyl group as pendent hydrophobic chain was found to be more effective in killing these microorganisms. The interaction of the cationic copolymers with calf-thymus DNA was studied by fluorescence quenching method. The polymer-DNA binding was found to be purely electrostatic in nature. The hydrophobes on the polymer backbone were found to have a significant influence on the binding process. Biocompatibility studies of the copolymers in terms of cytotoxicity measurements were finally performed at different concentrations of the HMPs to evaluate their potential application in biomedical fields.