Ethyl 2-(ethoxymethylene)acetoacetate
- Product Name
- 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;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;ETHYL A-(ETHOXYMETHYLENE)ACETOACETATE
- CBNumber
- CB6475655
- Molecular Formula
- C9H14O4
- Formula Weight
- 186.21
- MOL File
- 3788-94-1.mol
Ethyl 2-(ethoxymethylene)acetoacetate Property
- 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
- HS Code
- 2916399090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H226Flammable liquid and vapour
H314Causes severe skin burns and eye damage
H335May cause respiratory irritation
H412Harmful to aquatic life with long lasting effects
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242Use only non-sparking tools.
P243Take precautionary measures against static discharge.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P273Avoid release to the environment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P370+P378In case of fire: Use … for extinction.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P403+P235Store in a well-ventilated place. Keep cool.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- E1148
- Product name
- Ethyl 2-Acetyl-3-ethoxyacrylate
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $33
- Updated
- 2025/07/31
- Product number
- E1148
- Product name
- Ethyl 2-Acetyl-3-ethoxyacrylate
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $127
- Updated
- 2025/07/31
- Product number
- E900058
- Product name
- Ethyl2-(Ethoxymethylene)acetoacetate
- Packaging
- 1g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 067173
- Product name
- Ethyl 2-Acetyl-3-ethoxyacrylate
- Packaging
- 1g
- Price
- $12
- Updated
- 2021/12/16
- Product number
- 067173
- Product name
- Ethyl 2-Acetyl-3-ethoxyacrylate
- Packaging
- 5g
- Price
- $30
- Updated
- 2021/12/16
Ethyl 2-(ethoxymethylene)acetoacetate Chemical Properties,Usage,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
Raw materials
Preparation Products
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View Lastest Price from Ethyl 2-(ethoxymethylene)acetoacetate manufacturers
- Product
- Ethyl 2-(ethoxymethylene)acetoacetate 3788-94-1
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 97% (GC)
- Supply Ability
- 2000
- Release date
- 2025-06-11
- Product
- Ethyl 2-(ethoxymethylene)acetoacetate 3788-94-1
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20t
- Release date
- 2024-07-15
- Product
- ethyl 2-(ethoxymethylene)acetoacetate 3788-94-1
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 97%
- Supply Ability
- 1 tons
- Release date
- 2022-12-06