Maleic anhydride-d2
Overview
Description
Maleic anhydride-d2, also known as 2,5-Furandione-3,4-d2, is an organic compound with a specific deuterium isotope . It has the empirical formula C4D2O3 and a molecular weight of 100.07 . It is used in various laboratory chemicals .
Synthesis Analysis
The synthesis of this compound involves various chemical reactions. For instance, it can be used in the copolymerization of styrene and maleic anhydride to form polypropylene . Another synthesis route involves the dehydration of 1-butanol to 1-butene, followed by the oxidation of butenes to maleic anhydride .
Molecular Structure Analysis
The molecular structure of this compound is derived from the electron-deficient conjugated double bond and the cyclic anhydride functionality present . The bond angles and bond lengths for maleic anhydride are depicted in Fig. 2.1, and this results in a very compact and particularly planar structure .
Chemical Reactions Analysis
This compound can participate in a variety of chemical reactions due to its activated double bond. It can take part in Michael reactions, electrophilic addition, formation of Diels–Alder adducts, alkylation and acylation reactions, sulfonation, halogenations, reduction, photodimerization, hydroformylation, or free-radical polymerization reactions to generate poly-anhydride copolymers .
Physical and Chemical Properties Analysis
This compound appears as a powder with a boiling point of 200 °C (lit.) and a melting point of 51-56 °C (lit.) .
Scientific Research Applications
Reversible Blocking of Amino Groups : Maleic anhydride has been utilized for the reversible blocking of amino groups in biochemical research. This application is significant in protein chemistry and enzymology. Dixon and Perham (1968) investigated the effects of introducing methyl groups into maleic anhydride molecules, which can be extended to introduce pyruvoyl groups (Dixon & Perham, 1968).
Reactive Polymers in Diagnostics : Maleic anhydride-co-methyl vinyl ether copolymers have potential applications in diagnostics. These copolymers are used for linking oligodeoxyribonucleotides to make oligonucleotide-copolymer conjugates, showcasing its significance in molecular biology and bioengineering (Ladavière et al., 1997).
Maleic Anhydride in Protein Modification : Butler et al. (1969) demonstrated that maleic anhydride reacts rapidly and specifically with amino groups of proteins and peptides. This finding is pivotal for understanding protein structure and function (Butler et al., 1969).
Industrial Applications and Production : Hood and Musa (2016) explored the diverse chemistries and commercial applications of maleic anhydride, noting its critical role in various industrial processes (Hood & Musa, 2016).
Photolysis of Maleic Anhydride : Research by Marshall et al. (2019) investigated the UV and infrared absorption spectra and photolysis of maleic anhydride, highlighting its environmental and atmospheric chemistry relevance (Marshall et al., 2019).
Grafting onto Poly(L-lactic Acid) : The grafting of maleic anhydride onto poly(L-lactic acid) and its effects on physical and mechanical properties were investigated, suggesting applications in polymer science and materials engineering (Hwang et al., 2012).
- chemical production and environmental science (Agirre et al., 2020).
- Antimicrobial Polymers : Nagaraja et al. (2019) reviewed the development of antimicrobial polymers involving maleic anhydride, demonstrating its significance in microbiology and pharmaceutical sciences (Nagaraja et al., 2019).
Mechanism of Action
Target of Action
Maleic anhydride-d2, a derivative of maleic anhydride, is a versatile compound that can participate in a variety of chemical reactions due to its electron-deficient conjugated double bond and cyclic anhydride functionality . Its primary targets include various organic molecules that can undergo reactions such as Michael reactions, electrophilic addition, formation of Diels–Alder adducts, alkylation and acylation reactions, sulfonation, halogenations, reduction, photodimerization, hydroformylation, or free-radical polymerization reactions .
Mode of Action
The activated double bond in this compound allows it to take part in a variety of reactions. For instance, it can participate in Michael reactions, electrophilic addition, and the formation of Diels–Alder adducts . Additionally, the reactive anhydride functionality permits a whole host of organic reactions like esterification, amidation, imidation, hydrolysis, decarboxylation, and metal chelation .
Biochemical Pathways
This compound can affect various biochemical pathways. For instance, it can participate in the formation of poly-anhydride copolymers through free-radical polymerization reactions . It can also be involved in the biosynthesis of maleidrides, a family of polyketide-based dimeric natural products isolated from fungi .
Pharmacokinetics
Maleic anhydride derivatives have been used in the development of intelligent drug delivery systems . The content of maleic anhydride in the polymer had a major influence on the drug release rate and it could be used to control the release .
Result of Action
The molecular and cellular effects of this compound’s action can vary depending on the specific reaction it is involved in. For instance, in the context of antimicrobial polymers, the content of maleic anhydride in the polymer can inhibit the growth of certain bacteria within 8–16 hours .
Action Environment
The action, efficacy, and stability of this compound can be influenced by various environmental factors. For instance, the production of maleic anhydride has to face ever-increasing governmental scrutiny, fierce pricing pressures, and tremendous technical requirements . Moreover, the choice of technological routes for the production of maleic anhydride can also impact its environmental performance .
Safety and Hazards
Future Directions
Recent research has focused on the development of maleic anhydride-d2 polymers for various applications. For instance, they have been used in lithium metal batteries due to their high energy density and superior safety characteristics . Future research directions include further exploration of the versatile S-MI/MA copolymers .
Properties
IUPAC Name |
3,4-dideuteriofuran-2,5-dione | |
---|---|---|
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H/i1D,2D | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI Key |
FPYJFEHAWHCUMM-QDNHWIQGSA-N | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=O)OC1=O | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
[2H]C1=C(C(=O)OC1=O)[2H] | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C4H2O3 | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID80514711 | |
Record name | (~2~H_2_)Furan-2,5-dione | |
Source | EPA DSSTox | |
URL | https://comptox.epa.gov/dashboard/DTXSID80514711 | |
Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
100.07 g/mol | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
CAS No. |
33225-51-3 | |
Record name | (~2~H_2_)Furan-2,5-dione | |
Source | EPA DSSTox | |
URL | https://comptox.epa.gov/dashboard/DTXSID80514711 | |
Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Record name | Maleic anhydride-d2 | |
Source | European Chemicals Agency (ECHA) | |
URL | https://echa.europa.eu/information-on-chemicals | |
Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
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Retrosynthesis Analysis
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Strategy Settings
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Model | Template_relevance |
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Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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