Lot numbers can be found on the outside label of a product:
Dimethyl 2-methylmaleate
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CAS No. 617-54-9
- Cat. No. CS-0149232
- Purity≥95%
- MDL No.MFCD10698758
*For research and further manufacturing use only, not for direct human use.
Structure of 617-54-9
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General Information
- CAS No. 617-54-9
- Cat. No. CS-0149232
- Purity ≥95%
- MDL No. MFCD10698758
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₇H₁₀O₄
- Molecular Weight 158.15
- Synonym(s) Citraconic acid, dimethyl ester
- SMILES O=C(OC)/C(C)=C\C(OC)=O
Description
Dimethyl 2-methylmaleate is a bench-stable diester featuring a sterically hindered alkene and electron-deficient double bond. This structure enables efficient Diels-Alder cycloadditions, serving as a reactive dienophile in synthetic routes to complex cyclic frameworks. The methyl substituent enhances solubility in common organic solvents while maintaining high reactivity under thermal conditions.
Application
Dimethyl 2-methylmaleate serves as a versatile diester building block in synthetic organic chemistry, enabling efficient access to substituted maleic anhydride derivatives and cyclic systems. Its conjugated diene functionality facilitates Diels-Alder reactions with high regio- and stereoselectivity, while the methyl substituent enhances steric control and product differentiation. The compound exhibits good bench stability, ease of purification, and compatibility with standard reaction conditions, making it a practical choice for the synthesis of heterocycles and functionalized intermediates in medicinal chemistry and materials science workflows.
Synthesis
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Route1
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67-56-1 -
In-stock
498-23-7 - ~97%
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In-stock
617-54-9
References
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Jaoui; Kleindienst; Lewandowski; Edney Analytical Chemistry, 2004 , vol. 76, # 16 p. 4765 - 4778
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Route2
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75-16-1
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In-stock
762-42-5 - ~92%
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In-stock
617-54-9
References
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Adlington, Robert M.; Baldwin, Jack E.; Cox, Rhona J.; Pritchard, Gareth J. Synlett, 2002 , # 5 p. 820 - 822
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Route3
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In-stock
498-23-7
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74-88-4
- ~51%
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In-stock
617-54-9
References
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Mangan, David; Miskelly, Iain; Moody, Thomas S. Advanced Synthesis and Catalysis, 2012 , vol. 354, # 11-12 p. 2185 - 2190,6 Title/Abstract Full Text Show Details Mangan, David; Miskelly, Iain; Moody, Thomas S. Advanced Synthesis and Catalysis, 2012 , vol. 354, # 11-12 p. 2185 - 2190
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS02
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Signal Word : Danger
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UN#: 1993
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Class : 3
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Packing Group : Ⅲ
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Hazard Statements : H227
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Precautionary Statements : P210-P280-P501
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Quality Control
Computational Chemistry Data
- TPSA 52.6
- LogP 0.2787
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 2
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