Dibutyl 2-methylenesuccinate

Basic Information

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CAS Number

2155-60-4

Molecular Formula

C13H22O4

Molecular Weight

242.31 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

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Boiling Point

190°C/60mmHg

Flash Point

>230 °F

Refractive Index

n20/D 1.444(lit.)

SMILES

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CCCCOC(=O)CC(=C)C(=O)OCCCC

InChI

InChI=1S/C13H22O4/c1-4-6-8-16-12(14)10-11(3)13(15)17-9-7-5-2/h3-10H2,1-2H3

InChIKey

OGVXYCDTRMDYOG-UHFFFAOYSA-N

LogP

2.619300000000001

Topological Polar Surface Area

52.6 Å²

Hydrogen Bond Donor/Acceptor

0 / 4

Complexity

258

Safety Information

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Hazard Statement

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H413 May cause long lasting harmful effects to aquatic life
Hazardous to the aquatic environment, long-term hazard

Synonyms & References

English

Itaconic Acid Dibutyl Ester
dibutylitaconate
bis(butyl) itaconate
AKOS015916161
NSC-5251
NSC-8487
Dibutyl itaconate, 96%
Succinic acid, methylene-, dibutyl ester
I0201
NS00021060
dibutyl 2-methylidenebutanedioate
NSC5251
Itaconic acid di-n-butyl ester
AI3-15511
NSC 8487
MFCD00027211
NSC8487
Dibutyl itaconate(stabilized with HQ)
Butanedioic acid, 2-methylene, dibutyl ester
Dibutyl 2-methylenesuccinate #
Dibutyl itaconate
2155-60-4
CS-0187350
A879029
Butanedioic acid, 2-methylene-, 1,4-dibutyl ester
Butanedioic acid, methylene-, dibutyl ester
1,4-dibutyl 2-methylidenebutanedioate
SCHEMBL194857
Itaconic acid, dibutyl ester
Butanedioic acid,2-methylene-, 1,4-dibutyl ester
NSC 5251

MDL Number

MFCD00027211

Customs Code

2917190090

FAQ

What are the physical and chemical properties of Dibutyl 2-methylenesuccinate (CAS: 2155-60-4)?

Dibutyl 2-methylenesuccinate (CAS: 2155-60-4) is a colorless or slightly yellow liquid. It has a molecular weight of approximately 250.4 g/mol and a boiling point of 251-253°C. The compound is slightly soluble in water but highly soluble in organic solvents. It is known for its reactivity towards nucleophiles and can undergo esterification and ester hydrolysis reactions.

How is Dibutyl 2-methylenesuccinate (CAS: 2155-60-4) typically synthesized?

Dibutyl 2-methylenesuccinate (CAS: 2155-60-4) can be synthesized by the esterification of succinic anhydride with n-butanol. The reaction typically involves the use of a Lewis acid catalyst such as aluminum chloride. The process is carried out under mild conditions to achieve high yield and selectivity. The product can be purified by recrystallization or distillation.

What industries use Dibutyl 2-methylenesuccinate (CAS: 2155-60-4)?

Dibutyl 2-methylenesuccinate (CAS: 2155-60-4) is primarily used in the pharmaceutical industry as a precursor for the synthesis of certain bioactive compounds. It is also utilized in the polymer industry as a plasticizer. Additionally, it has applications in the production of sensors and as a chemical intermediate in semiconductor manufacturing due to its reactivity and functional groups.

What precautions should be taken when handling Dibutyl 2-methylenesuccinate (CAS: 2155-60-4)?

When handling Dibutyl 2-methylenesuccinate (CAS: 2155-60-4), it is important to use appropriate Personal Protective Equipment (PPE), such as gloves, goggles, and a lab coat. The compound should be stored in a cool, dry place away from heat and open flames. Fume hoods should be used when mixing or reacting with the compound. In case of spills, the area should be immediately cleaned up, and the chemical safety data sheet (SDS) should be consulted for specific spill disposal procedures.