Ethyl 2-(ethoxymethylene)acetoacetate
- CAS No.
- 3788-94-1
- Chemical Name:
- Ethyl 2-(ethoxymethylene)acetoacetate
- Synonyms
- Ethyl (E)-2-(ethoxymethylene)-3-oxobutanoate;(Z)-ethyl 2-(ethoxyMethylene)-3-oxobutanoate;Ethyl (2E)-2-(ethoxymethylene)-3-oxobutanoate;2-(ethoxymethyL;Einecs 223-259-3;ene)-3-oxobutanoate;Ethyl 2-acetyl-3-ethoxyacrylate;Ethyl2-Acetyl-3-ethoxyacrylate>2-(ETHOXYMETHYLENE)-3-OXO-BUTANOIC;Ethyl-(ethoxymethylene)acetoacetate
- CBNumber:
- CB6475655
- Molecular Formula:
- C9H14O4
- Molecular Weight:
- 186.21
- MDL Number:
- MFCD06797311
- MOL File:
- 3788-94-1.mol
- MSDS File:
- SDS
| Boiling point | 266°C(lit.) |
|---|---|
| Density | 1.049±0.06 g/cm3(Predicted) |
| refractive index | 1.4730 to 1.4770 |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| form | powder to lump to clear liquid |
| color | Light yellow to Yellow to Orange |
| InChI | InChI=1S/C9H14O4/c1-4-12-6-8(7(3)10)9(11)13-5-2/h6H,4-5H2,1-3H3 |
| InChIKey | FNASCUBBFNCFQO-UHFFFAOYSA-N |
| SMILES | C(OCC)(=O)C(=COCC)C(=O)C |
| CAS DataBase Reference | 3788-94-1(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS05,GHS06,GHS02 |
|---|---|
| Signal word | Danger |
| Hazard statements | H301+H311+H331-H314-H335-H412-H226 |
| Precautionary statements | P501-P261-P273-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405 |
| HS Code | 2916399090 |
Ethyl 2-(ethoxymethylene)acetoacetate price More Price(56)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TCI Chemical | E1148 | Ethyl 2-Acetyl-3-ethoxyacrylate >98.0%(GC) | 3788-94-1 | 5g | $35 | 2026-04-30 | Buy |
| TCI Chemical | E1148 | Ethyl 2-Acetyl-3-ethoxyacrylate >98.0%(GC) | 3788-94-1 | 25g | $133 | 2026-04-30 | Buy |
| TRC | TRC-E900058-5G | Ethyl 2-(Ethoxymethylene)acetoacetate | 3788-94-1 | 5g | $78 | 2026-06-03 | Buy |
| TRC | TRC-E900058-1G | Ethyl 2-(Ethoxymethylene)acetoacetate | 3788-94-1 | 1g | $59 | 2026-06-03 | Buy |
| TRC | TRC-E900058-10G | Ethyl 2-(Ethoxymethylene)acetoacetate | 3788-94-1 | 10g | $109 | 2026-06-03 | Buy |
Ethyl 2-(ethoxymethylene)acetoacetate Chemical Properties, Uses, Production
Uses
Ethyl 2-(ethoxymethylene)acetoacetate is an active metabolite of leflunomide, a pyrimidine synthesis inhibitor with anti-inflammatory and immunomodulatory properties that reduces the number of activated central nervous system lymphocytes.
Application
Ethyl 2-(ethoxymethylene)acetoacetate is a mono-, di-, and trifunctional three-carbon electrophile in carbonyl reactions and cyclization reactions; a β-ketoester equivalent.
Preparation
Ethyl 2-(ethoxymethylene)acetoacetate is obtained by heating Ethyl Acetoacetate with Triethyl Orthoformate in Acetic Anhydride.
Synthesis
141-97-9
122-51-0
3788-94-1
Step a) Synthesis of the intermediate 2-(ethoxymethylene)-3-oxobutanoic acid ethyl ester: A mixed solution of ethyl acetoacetate (20 g, 154 mmol), triethyl orthoformate (51.1 mL, 307 mmol) and acetic anhydride (43.5 mL, 461 mmol) was heated and reacted for 5 hrs at 130 °C. After completion of the reaction, the mixture was cooled to room temperature. Subsequently, excess triethyl orthoformate and acetic anhydride were removed by concentration under reduced pressure. The residual acetic anhydride and triethyl orthoformate were further removed by distillation under reduced pressure (30 mbar, 30-70°C). Finally, the target product ethyl 2-(ethoxymethylene)-3-oxobutanoate was purified by distillation (6 mbar, 80 °C to 128 °C) as a viscous yellow oil (22.8 g, 80% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.59-7.69 (m, 1H), 4.17-4.34 (m, 4H), 2.29-2.44 (m, 3H), 1.25-1.44 (m, 6H).
storage
May be kept for a few weeks at 0 °C in the dark with addition of hydroquinone. The enol ether hydrolyses slowly in contact with water. Use in a fume hood.
References
[1] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 946 - 950
[2] Mendeleev Communications, 2016, vol. 26, # 1, p. 54 - 56
[3] Patent: WO2011/83316, 2011, A1. Location in patent: Page/Page column 52-53
[4] Letters in Drug Design and Discovery, 2016, vol. 13, # 9, p. 912 - 920
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3563 - 3567
Ethyl 2-(ethoxymethylene)acetoacetate Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Creasyn Finechem(Tianjin) Co., Ltd. | 022-83946278 13820372920 | sales@creasyn.com | China | 968 | 68 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Energy Chemical | 400-0056266 | sales8178@energy-chemical.com | China | 44850 | 61 |
| Shijiazhuang Sdyano Fine Chemical Co., Ltd. | 0311-89250318 13582355795 | master@sjzsdyn.com | China | 2776 | 65 |
| Wuhan Chemwish Technology Co., Ltd | 86-027-67849912 | sales@chemwish.com | China | 35884 | 56 |
| Capot Chemical Co., Ltd | +86 (0) 571 85 58 67 18 | China | 18187 | 66 | |
| JinYan Chemicals(ShangHai) Co.,Ltd. | 13817811078 | sales@jingyan-chemical.com | China | 9963 | 60 |
| Jia Xing Isenchem Co.,Ltd | 0573-85285100 18627885956 | isenchem@163.com | China | 9389 | 66 |
| Accela ChemBio Co.,Ltd. | 021-50795510 4000665055 | marketing@accelachem.com | China | 10972 | 64 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
View Latest Price from Ethyl 2-(ethoxymethylene)acetoacetate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-08-13 | Ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
|
1KG | 97% (GC) | 2000 | Shenzhen Nexcon Pharmatechs Ltd. | ||
 |
2026-06-30 | Ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
|
1kg | 98% | 1000kg | Shaanxi Dideu New Materials Co. Ltd | ||
 |
2025-09-16 | ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
|
1kg | 97% | 1 tons | Nanjing Kaitian Chemical Co., LTD |
-
- Ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
- 97% (GC)
- Shenzhen Nexcon Pharmatechs Ltd.
-
- Ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
- 98%
- Shaanxi Dideu New Materials Co. Ltd
-
- ethyl 2-(ethoxymethylene)acetoacetate
3788-94-1
- 97%
- Nanjing Kaitian Chemical Co., LTD
