1-Methyl-5-oxoproline

Basic Information

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CAS Number

72442-37-6

Molecular Formula

C6H9NO3

Molecular Weight

143.14 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

SMILES

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CN1C(CCC1=O)C(=O)O

InChI

InChI=1S/C6H9NO3/c1-7-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,9,10)

InChIKey

SHLYZEAOVWVTSW-UHFFFAOYSA-N

LogP

-0.3082000000000003

Topological Polar Surface Area

57.61 Å²

Hydrogen Bond Donor/Acceptor

1 / 4

Complexity

178

Synonyms & References

English

MFCD19228297
1-methyl-5-oxoproline
N-methyl-L-pyroglutamic acid
CS-0161786
EN300-132963
BS-17473
1-Methyl-5-oxo-DL-proline
FT-0773899
1-METHYL-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID
EINECS 276-664-2
SY260047
D78920
AKOS012169845
MFCD15730150
SCHEMBL159149
Z1021465860
1-METHYL-5-OXOPYRROLIDINE-2-CARBOXYLICACID
72442-37-6
SY105837
MB14791
MFCD26937700
1-methyl-5-oxo-Proline
1-methyl-5-oxo-DL-proline
1-methyl-5-oxopyrrolidine-2-carboxylic acid
1-methyl-5-oxo-L-proline
1-methyl-5-oxo-pyrrolidine-2-carboxylic acid

MDL Number

MFCD15730150

FAQ

What are the physical and chemical properties of 1-Methyl-5-oxoproline (CAS: 72442-37-6)?

1-Methyl-5-oxoproline is a white crystalline solid with a molecular weight of approximately 118.12 g/mol. It has a melting point of 203-204°C and a boiling point of around 350°C. Solubility in water is moderate, with a solubility of about 4 g/L at 25°C. Chemically, it is relatively stable under normal conditions but can undergo hydrolysis in the presence of water or strong acids.

How is 1-Methyl-5-oxoproline (CAS: 72442-37-6) typically synthesized?

1-Methyl-5-oxoproline can be synthesized through the condensation of methyl acrylate and oxoacetic acid. The reaction typically proceeds with the use of a base catalyst such as sodium hydride. The yield is generally around 70-75%, and the selectivity towards the desired product is high. This compound can also be prepared by the dehydration of 1-methyl-5-oxoproline-2-carboxylic acid.

What industries use 1-Methyl-5-oxoproline (CAS: 72442-37-6)?

1-Methyl-5-oxoproline is primarily used in the pharmaceutical industry as an intermediate for the synthesis of various drugs, particularly those related to amino acids and peptides. It also finds applications in the polymer industry for the development of certain polymeric materials. Additionally, it can be utilized in the production of sensors and as a functional group in organic synthesis.

What precautions should be taken when handling 1-Methyl-5-oxoproline (CAS: 72442-37-6)?

1-Methyl-5-oxoproline should be handled with caution due to its physical and chemical properties. It is recommended to work in a fume hood and wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Ensure proper ventilation and avoid contact with skin and eyes. In case of a spill, use appropriate spill cleanup materials and consult the Safety Data Sheet (SDS) for further guidance.