(2E)-4-Ethoxy-4-oxo-2-butenoic acid

Basic Information

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CAS Number

2459-05-4

Molecular Formula

C6H8O4

Molecular Weight

144.13 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Physical Properties

Melting Point

66-68 °C

Boiling Point

147 °C/16 mmHg

Water Solubility

Soluble in water.

Flash Point

109.6 °C

Refractive Index

1.4500 (estimate)

SMILES

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CCOC(=O)C=CC(=O)O

InChI

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3+

InChIKey

XLYMOEINVGRTEX-ONEGZZNKSA-N

LogP

0.19029999999999997

Topological Polar Surface Area

63.60000000000001 Å²

Hydrogen Bond Donor/Acceptor

1 / 4

Complexity

159

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Hazard Class

Class IRRITANT Class IRRITANT

Synonyms & References

English

A937009
Tox21_301978
EINECS 219-544-7
CAS-3249-53-4
Fumaric acid, monoethyl ester
fumaric acid mono-ethyl ester
(~{Z})-4-ethoxy-4-oxidanylidene-but-2-enoic acid
CS-0030808
DTXSID1044485
CHEMBL1771637
2-Butenedioic acid (2E)-, 1-ethyl ester
LS-13140
HY-W019696
mono-Ethyl fumarate, certified reference material, TraceCERT(R)
3249-53-4
(E)-4-ethoxy-4-oxo-2-butenoic acid
2-Butenedioic acid (E)-, monoethyl ester
2459-05-4
Y3W849NG2N
NSC-524101
ETHYL FUMARATE [WHO-DD]
Q27294232
(2E)-4-ethoxy-4-oxobut-2-enoic acid
Monoethyl fumarate
NSC-244252
Fumaric acid, ethyl ester
NSC 524101
BDBM50342427
EN300-19541
Ethylhydrogenfumarat
Fumaric acid monoethyl ester

MDL Number

MFCD00002699

Customs Code

2918990090

FAQ

What are the physical and chemical properties of (2E)-4-Ethoxy-4-oxo-2-butenoic acid (CAS: 2459-05-4)?

(2E)-4-Ethoxy-4-oxo-2-butenoic acid is a white crystalline solid with a molecular weight of approximately 146.17 g/mol. It is slightly soluble in water and soluble in organic solvents like ethanol and acetone. The compound is known for its low reactivity under normal conditions but can undergo hydrolysis in the presence of water. It has a pKa of about 2.5, making it acidic. This compound is used in various applications due to its chemical stability and reactivity.

How is (2E)-4-Ethoxy-4-oxo-2-butenoic acid (CAS: 2459-05-4) typically synthesized?

The synthesis of (2E)-4-Ethoxy-4-oxo-2-butenoic acid typically involves the reaction of ethyl acetoacetate with ethanol in the presence of a catalytic amount of a strong acid like sulfuric acid. The product is then purified by recrystallization from water. This method provides good yields and high purity. The reaction is exothermic, and care must be taken to control the temperature to prevent side reactions.

What industries use (2E)-4-Ethoxy-4-oxo-2-butenoic acid (CAS: 2459-05-4)?

(2E)-4-Ethoxy-4-oxo-2-butenoic acid is used in pharmaceuticals, where it serves as a precursor in the synthesis of certain drug molecules. It is also utilized in the production of surfactants, sensors, and as a building block in the synthesis of monomers for polymers. Additionally, this compound finds application in the preparation of functional materials in the semiconductor industry.

What precautions should be taken when handling (2E)-4-Ethoxy-4-oxo-2-butenoic acid (CAS: 2459-05-4)?

When handling (2E)-4-Ethoxy-4-oxo-2-butenoic acid (CAS: 2459-05-4), ensure the use of appropriate personal protective equipment (PPE), including gloves and safety goggles. It should be stored in a dry, cool place away from moisture and heat sources. Spills should be cleaned up carefully using absorbent materials, and the area should be well-ventilated. Always refer to the safety data sheet (SDS) for detailed handling and emergency procedures. This compound is not flammable, but it should be handled with care due to its acidic nature and potential to undergo hydrolysis in the presence of water.