638-10-8

Basic information

• Product Name: Ethyl 3,3-dimethylacrylate
• Synonyms: 3,3-DIMETHYLACRYLIC ACID ETHYL ESTER;3-METHYL-2-BUTENOIC ACID ETHYL ESTER;3-METHYLCROTONIC ACID ETHYL ESTER;ETHYL-SENECIOATE;ETHYL 3-METHYL-2-BUTENOATE;ETHYL 3-METHYLCROTONATE;ETHYL 3,3-DIMETHYLACRYLATE;ETHYL-BETA,BETA-DIMETHYL ACRYLATE
• CAS NO: 638-10-8
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 211-319-1
• Product Categories: ester series;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 638-10-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: -62.68°C (estimate)
• Boiling Point: 154-155 °C(lit.)
• Flash Point: 93 °F
• Appearance: liquid
• Density: 0.922 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.32mmHg at 25°C
• Refractive Index: n20/D 1.436(lit.)
• Water Solubility: Insoluble in water
• Stability: Stable. Flammable. Incompatible with acids, bases, oxidizing agents, reducing agents.
• CAS DataBase Reference: Ethyl 3,3-dimethylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3,3-dimethylacrylate(638-10-8)
• EPA Substance Registry System: Ethyl 3,3-dimethylacrylate(638-10-8)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-29-33-28-26
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: GQ5750000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 638-10-8(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Ethyl 3,3-dimethylacrylate was used in the synthesis of:3-benzylmercupto-3-methylbutanoic acid ethylestercis-2-cyano-3,3-dimethylcyclopropanecarboxylic acid, precursor for the synthesis of cis-pyrethroids1-[13CD3]-9-cis-retinoic acid

General Description

Ion-molecule reactions between the O=P(OCH3)2+phosphonium ions and ethyl 3,3-dimethylacrylate has been investigated by quadrupole ion trap mass spectrometery.

InChI:InChI=1/C7H12O2/c1-4-9-7(8)5-6(2)3/h5H,4H2,1-3H3

Synthetic route

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + acetone (67-64-1) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; Stage #2: acetone In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons olefination; Inert atmosphere;	90%
With n-butyllithium In tetrahydrofuran; hexane at -50 - 20℃;	89%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	88%

ethanol (64-17-5) + 3-Methylbutenoic acid (541-47-9) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
toluene-4-sulfonic acid In tetrachloromethane for 24h; Heating;	88.8%
With sulfuric acid for 16h; Reflux;	87%
With sulfuric acid for 10h; Heating;	72%

2-methyl-3-bromo-1-propene (1458-98-6) + carbon monoxide (201230-82-2) + sodium ethanolate (141-52-6) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
Na2PdCl4-dppe In ethanol at 50℃; for 2h;	87%

4-ethoxy-2-methylbut-3-yn-2-ol (20411-76-1) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With boron trifluoride diethyl etherate at -30℃; for 0.12h;	78%
With sulfuric acid
With hydrogen cation

acetone (67-64-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
at 35℃; under 6750540 Torr; for 24h;	75%
at 35℃; under 6750540 Torr; for 24h; Product distribution; Wittig reaction at high presure;
With benzoic acid

ethyl bromoacetate (105-36-2) + acetone (67-64-1) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With tributylstibine at 130℃; for 6h;	10%

1-ethyl-piperidine (766-09-6) + pyridine (110-86-1) + monoethyl isopropylidenemalonate (85738-78-9) → ethyl 3-methylbut-2-enoate (638-10-8) + 3-methyl-but-3-enoic acid ethyl ester (1617-19-2)

Conditions	Yield
at 111℃; Rate constant; Decarboxylation;

pyridine (110-86-1) + monoethyl isopropylidenemalonate (85738-78-9) + pyridinium picrate (1152-90-5) → ethyl 3-methylbut-2-enoate (638-10-8) + 3-methyl-but-3-enoic acid ethyl ester (1617-19-2)

Conditions	Yield
at 111℃; Rate constant; Decarboxylation;

pyridine (110-86-1) + monoethyl isopropylidenemalonate (85738-78-9) → ethyl 3-methylbut-2-enoate (638-10-8) + 3-methyl-but-3-enoic acid ethyl ester (1617-19-2)

Conditions	Yield
at 111℃; Rate constant; Decarboxylation;

diazoacetic acid ethyl ester (623-73-4) + dimethylketene (598-26-5) → 5-ethoxy-3,3-dimethyl-3H-furan-2-one (98558-46-4) + ethyl 3-methylbut-2-enoate (638-10-8)

diazoacetic acid ethyl ester (623-73-4) + dimethylketene (598-26-5) + ethyl acetate (141-78-6) → 5-ethoxy-3,3-dimethyl-3H-furan-2-one (98558-46-4) + ethyl 3-methylbut-2-enoate (638-10-8)

Ketene (463-51-4) + 2-acetoacetic acid (541-50-4) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With boric acid at 0 - 10℃; und anschliessenden Kochen;

ethyl 2-bromoisovalerate (609-12-1) → α-ethoxy-isovaleric acid ethyl ester (109989-35-7) + ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With ethanol; sodium ethanolate

ethyl 2-bromoisovalerate (609-12-1) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With N,N-diethylaniline
With quinoline at 170 - 175℃; weiteres Erhitzen auf 185-190grad;
With quinoline at 225℃;
Multi-step reaction with 2 steps 1: alcoholic KOH-solution 2: alcohol; concentrated sulfuric acid View Scheme

ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With phosphorus trichloride
With potassium pyrosulfate at 140 - 145℃;
With sulfuric acid

ethanol (64-17-5) + ethyl 3-bromo-3-methylbutyrate (6293-25-0) + sodium phenoxide (139-02-6) → ethyl 3-methylbut-2-enoate (638-10-8)

3-Methylbutenoic acid (541-47-9) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With ethanol; sulfuric acid
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 / 0.5 h / Ambient temperature 2: triphenylphosphine dibromide / 0.25 h / Ambient temperature 3: 2-oxo-3-trimethyltetrahydro-1,3-oxazole / 0.25 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 / 0.5 h / Ambient temperature 2: triphenylphosphine dibromide / 0.25 h / Ambient temperature 3: CH2Cl2 / 15 h / 15 °C View Scheme

1,3-dibromo-3-methyl-2-butanone (1518-06-5) → 3-Methylbutenoic acid (541-47-9) + ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With potassium hydroxide

ethyl 3-bromo-3-methylbutyrate (6293-25-0) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With sodium hydroxide; phenol
With sodium phenoxide; benzene

2,2-dimethyl-propane-1,1,3-tricarboxylic acid triethyl ester (861370-78-7) + sodium ethanolate (141-52-6) → ethyl 3-methylbut-2-enoate (638-10-8) + diethyl malonate (105-53-3)

Conditions	Yield
at 35℃; Gleichgewicht;
at 100℃; Gleichgewicht;

ethyl 2-acetyl-3-methylbut-2-enoate (35044-52-1) + ethanol (64-17-5) + ethyl iodide (75-03-6) → ethyl 3-methylbut-2-enoate (638-10-8) + ethyl acetate (141-78-6)

Conditions	Yield
With sodium ethanolate

ethyl bromoacetate (105-36-2) + acetone (67-64-1) → ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) + ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With zinc; benzene

bromo-isopropyl-malonic acid diethyl ester (38214-19-6) + N,N-dimethyl-aniline (121-69-7) → diethyl isopropylidenemalonate (6802-75-1) + ethyl 3-methylbut-2-enoate (638-10-8) + diethyl malonate (105-53-3)

Conditions	Yield
at 170 - 175℃;

diethyl ether (60-29-7) + β-benzoyloxy-isovaleric acid ethyl ester + sodium ethanolate (141-52-6) + oxalic acid diethyl ester (95-92-1) → ethyl 3-methylbut-2-enoate (638-10-8) + benzoic acid (65-85-0)

ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) + sodium ethanolate (141-52-6) + oxalic acid diethyl ester (95-92-1) → ethyl 3-methylbut-2-enoate (638-10-8)

acetone (67-64-1) + ethyl 1,1-dichloroacetate (535-15-9) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With amalgamated zinc; benzene

ethyl 3-bromo-3-methylbutyrate (6293-25-0) + sodium phenoxide (139-02-6) + benzene (71-43-2) → ethyl 3-methylbut-2-enoate (638-10-8)

(Z)-ethyl 3-acetoxybut-2-enoate (26805-39-0) + lithium dimethylcuprate (15681-48-8) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
In diethyl ether

3-methyl-but-3-enoic acid ethyl ester (1617-19-2) → ethyl 3-methylbut-2-enoate (638-10-8)

Conditions	Yield
With piperidine In tetrahydrofuran

Ethyl-3-methyl-3-nitrosobutanoat (52856-00-5) → ethyl 3-methylbut-2-enoate (638-10-8) + 3-methyl-but-3-enoic acid ethyl ester (1617-19-2) + Ethyl-3-methyl-3-nitrobutanoat (52856-07-2)

Conditions	Yield
In tetrachloromethane

ethyl 3-methylbut-2-enoate (638-10-8) → Ethyl isovalerate (108-64-5)

Conditions	Yield
With 1% Pd on activated carbon; hydrogen In water at 45℃; under 760.051 Torr; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;	100%
With C40H56FeN2Si4(2-); hydrogen In 1,2-dimethoxyethane at 80℃; under 7600.51 Torr; for 2h; Schlenk technique; Autoclave;	99%
Stage #1: ethyl 3-methylbut-2-enoate With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With hydrogen In tetrahydrofuran at 20℃; under 1500.15 Torr; for 3h;	87%

ethyl 3-methylbut-2-enoate (638-10-8) → 5,5-dimethylpyrazolidin-3-one (42953-82-2)

Conditions	Yield
With hydrazine hydrate In ethanol at 80℃; for 2h;	100%
With hydrazine hydrate In ethanol 1) r.t., 2) reflux;	78%
With hydrazine hydrate In ethanol at 20℃; for 6h; Reflux;	78%

ethyl 3-methylbut-2-enoate (638-10-8) + phenylmethanethiol (100-53-8) → ethyl 3-methyl-3-benzylthiobutanoate (377092-98-3)

Conditions	Yield
With sodium ethanolate In ethanol at 20 - 50℃; for 36h;	100%

ethyl 3-methylbut-2-enoate (638-10-8) + bis(pinacol)diborane (73183-34-3) → ethyl 3-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

Conditions	Yield
With 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; copper(l) chloride; sodium t-butanolate In tetrahydrofuran; methanol at 20℃; for 12h; Schlenk technique; Inert atmosphere;	99%
With methanol; [Pd2(μ-C9H7NPPh2)(μ-O2CCH3)]2; water; caesium carbonate In toluene at 25℃; for 6h; Inert atmosphere;
With tricyclohexylphosphine In methanol at 70℃; for 6h; Inert atmosphere; Schlenk technique;

ethyl 3-methylbut-2-enoate (638-10-8) + ethyl iodide (75-03-6) → 2-ethyl-3-methyl-but-3-enoic acid ethyl ester (18804-44-9)

Conditions	Yield
Stage #1: ethyl 3-methylbut-2-enoate With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃; for 1.5h; Inert atmosphere; Stage #2: ethyl iodide With lithium diisopropyl amide In tetrahydrofuran; hexane at 0 - 20℃; for 1.25h; Inert atmosphere;	98%

ethyl 3-methylbut-2-enoate (638-10-8) + (R)-2,2,2-trichloro-1-phenylethyl ((methylsulfonyl)oxy)carbamate (1391853-96-5) → ethyl 3-hydroxy-3-methyl-2-((((R)-2,2,2-trichloro-1-phenylethoxy)carbonyl)amino)butanoate

Conditions	Yield
Stage #1: (R)-2,2,2-trichloro-1-phenylethyl ((methylsulfonyl)oxy)carbamate With osmium(VIII) oxide; water In acetonitrile at 20℃; for 0.166667h; Stage #2: ethyl 3-methylbut-2-enoate In water; acetonitrile at 35℃; for 24h;	97%

ethyl 3-methylbut-2-enoate (638-10-8) + butyl magnesium bromide (693-04-9) → ethyl 3,3-dimethylheptanoate (51756-26-4)

Conditions	Yield
With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at -15℃;	95%
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran Ambient temperature; 0.5-1.5 h;	82%

ethyl 3-methylbut-2-enoate (638-10-8) + 1-propylmagnesium chloride (2234-82-4) → ethyl 3,3-dimethylhexanoate (116169-12-1)

Conditions	Yield
Stage #1: ethyl 3-methylbut-2-enoate With copper(l) iodide; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at -15 - -10℃; Further stages.;	95%

ethyl 3-methylbut-2-enoate (638-10-8) + phenylboronic acid-d2 (20469-72-1) → 3,3-dimethyl-2,3-dihydro-1H-inden-1-one-2,4-d2

Conditions	Yield
With palladium(II) trifluoroacetate; rac-2-((4R,5R)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)pyrimidine; oxygen In N,N-dimethyl acetamide at 80℃; for 24h; Schlenk technique;	95%

ethyl 3-methylbut-2-enoate (638-10-8) + phenylboronic acid (98-80-6) → 3,3-dimethylindan-1-one (26465-81-6)

Conditions	Yield
With palladium(II) trifluoroacetate; rac-2-((4R,5R)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)pyrimidine; oxygen In N,N-dimethyl acetamide at 80℃; for 24h; Schlenk technique;	95%

1-Bromopentane (110-53-2) + ethyl 3-methylbut-2-enoate (638-10-8) → ethyl 2-(2'-propenyl)heptanoate (59078-87-4)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) -78 deg C -> room temperature, 1 h;	94%
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran

ethyl 3-methylbut-2-enoate (638-10-8) + methyl iodide (74-88-4) → ethyl 2,3-dimethyl-3-butenoate (14387-99-6)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) -78 deg C -> room temperature, 1 h;	92%
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran

ethyl 3-methylbut-2-enoate (638-10-8) → 1,1,4,7-tetramethyl-3-indanone (54789-21-8)

Conditions	Yield
In para-xylene	92%

ethyl 3-methylbut-2-enoate (638-10-8) → 3-methyl-2-nitro-2-butenoate (18289-63-9)

Conditions	Yield
With nitric acid In water 1.) 0 deg C, 1.25 h; 2.) 0 deg C, 1.5 h; 3.) room temp., 1 h;	91%
With nitric acid In water at 0 - 20℃; Inert atmosphere;	89%
With water; nitric acid
With nitric acid unter Eiskuehlung;
With nitric acid

ethyl 3-methylbut-2-enoate (638-10-8) → 3-methyl-2-buten-1-ol (556-82-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	91%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3h; Inert atmosphere;	72%
With diisobutylaluminium hydride In toluene at -78 - 20℃;

ethyl 3-methylbut-2-enoate (638-10-8) → 3-methyl-3-sulfo-butyric acid ethyl ester

Conditions	Yield
With sodium hydrogensulfite In ethanol; water at 165℃; under 9000.72 Torr; for 1h; microwave irradiation;	91%

ethyl 3-methylbut-2-enoate (638-10-8) → ethyl (E)-4-hydroxy-3-methyl-2-butenoate (65527-85-7)

Conditions	Yield
With selenium(IV) oxide In ethanol for 24h; Heating;	90%
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / CCl4 / Heating 2: BaCO3 / dioxane; H2O / Heating View Scheme
With selenium(IV) oxide; ethanol at 120℃;

ethyl 3-methylbut-2-enoate (638-10-8) + N-cinnamylidene-p-anisidine (80542-40-1) → 3-Isopropylidene-1-(4-methoxy-phenyl)-4-phenyl-3,4-dihydro-1H-pyridin-2-one

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 12h; Ambient temperature;	90%

ethyl 3-methylbut-2-enoate (638-10-8) → [1,1-2H2]-3-methyl-2-butenol (6158-92-5)

Conditions	Yield
With lithium aluminium deuteride In diethyl ether for 1h; Heating;	90%
With lithium aluminium deuteride In diethyl ether at 0℃; for 1h; Inert atmosphere; Reflux;
With lithium aluminium deuteride In diethyl ether at 0℃; for 2h; Inert atmosphere; Reflux;
With lithium aluminium deuteride In diethyl ether at 0℃; for 2h; Inert atmosphere; Reflux;

(1E,4E)-1-Dimethylamino-5-(2,6,6-trimethyl-cyclohex-2-enyl)-penta-1,4-dien-3-one (883971-29-7) + ethyl 3-methylbut-2-enoate (638-10-8) → (E)-1-(2-Hydroxy-4-methyl-phenyl)-3-(2,6,6-trimethyl-cyclohex-2-enyl)-propenone

Conditions	Yield
Stage #1: ethyl 3-methylbut-2-enoate With lithium diisopropyl amide In 1,2-dimethoxyethane at -20℃; for 0.25h; Stage #2: (1E,4E)-1-Dimethylamino-5-(2,6,6-trimethyl-cyclohex-2-enyl)-penta-1,4-dien-3-one In 1,2-dimethoxyethane	90%

ethyl 3-methylbut-2-enoate (638-10-8) → ethyl 3-amino-3-methylbutanoate (85532-42-9)

Conditions	Yield
With ammonia In ethanol at 80℃; for 22h;	89%
With ammonia at 25℃;

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 598-26-5 dimethylketene 
• 141-78-6 ethyl acetate 
• 609-12-1 ethyl 2-bromoisovalerate 
• 6293-25-0 ethyl 3-bromo-3-methylbutyrate 
• 3278-34-0 ethyl 2-(ethoxythiocarbonylthio)acetate 
• 67-64-1 acetone 
• 64-17-5 ethanol 
• 10606-43-6 3-methylbut-2-enoyl bromide 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 23974-43-8 4-ethoxy-2,2-dimethyl-2,3-dihydro-azete 
• 448212-00-8 (Z)-ethyl-3-(4,4,5,5)-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate 
• 74-88-4 methyl iodide 
• 100-42-5 styrene 

Downstream Products

• 41438-17-9 5t-[2]furyl-3-methyl-penta-2c,4-dienoic acid 
• 81714-81-0 3-methyl-7t-phenyl-hepta-2c,4t,6-trienoic acid 
• 1000-86-8 2,4-Dimethyl-1,3-pentadiene 
• 6628-25-7 2-methyl-decan-4-one 
• 105540-08-7 5-((Ξ)-hexylidene)-4,4-dimethyl-dihydro-furan-2-one 
• 597-43-3 2,2-dimethylsuccinic acid 
• 4759-48-2 13-cis-retinoic acid 
• 302-79-4 all-trans-retinoic-acid 
• 302-79-4 9-cis-retinoic acid 
• 302-79-4 9,13-di-cis-retinoic acid 
• 4029-25-8 Ethyl 5,5-dimethylcyclohexane-1,3-dione-4-carboxylate 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 85532-42-9 ethyl 3-amino-3-methylbutanoate 
• 79405-51-9 dibromo-2,3 methyl-3 butanoate d'ethyle 

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