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Meldrum’s acid - 98%, high purity , CAS No.2033-24-1
Basic Description
Synonyms
2,6-dione | AKOS000119035 | m-DIOXANE-4,6-DIONE, 2,2-DIMETHYL- | Meldrum inverted exclamation mark s acid | STK397458 | 2.2-dimethyl-1,3-dioxane-4,6-dione | NSC71902 | NSC-71902 | AM20090153 | 2, 2-dimethyl-1,3-dioxane-4, 6-dione | cycl-Isopropylidene mal
Specifications & Purity
≥98%
Storage Temp
Store at 2-8°C,Argon charged
Shipped In
Wet ice
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description
2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.
Usually used in the synthesis of macrocyclic β-keto lactone,4-pyridyl-substituted heterocycles,2-substituted indoles, isofraxidin.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Organic oxygen compounds
Class
Organooxygen compounds
Subclass
Ethers
Intermediate Tree Nodes
Acetals
Direct Parent
Ketals
Alternative Parents
Dicarboxylic acids and derivatives 1,3-dioxanes 1,3-dicarbonyl compounds Lactones Carboxylic acid esters Oxacyclic compounds Organic oxides Hydrocarbon derivatives
Molecular Framework
Aliphatic heteromonocyclic compounds
Substituents
Ketal - 1,3-dicarbonyl compound - Dicarboxylic acid or derivatives - Meta-dioxane - Lactone - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic heteromonocyclic compound
Description
This compound belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
External Descriptors
Not available
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Names and Identifiers
IUPAC Name
2,2-dimethyl-1,3-dioxane-4,6-dione
INCHI
InChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
InChIKey
GXHFUVWIGNLZSC-UHFFFAOYSA-N
Smiles
CC1(OC(=O)CC(=O)O1)C
Isomeric SMILES
CC1(OC(=O)CC(=O)O1)C
WGK Germany
3
RTECS
JH0800000
Molecular Weight
144.13
Beilstein
117310
Reaxy-Rn
117310
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=117310&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Solubility
Soluble in water. Slightly soluble in ethanol and chloroform.
Sensitivity
heat sensitive
Melt Point(°C)
95°C
Molecular Weight
144.120 g/mol
XLogP3
0.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Exact Mass
144.042 Da
Monoisotopic Mass
144.042 Da
Topological Polar Surface Area
52.600 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
164.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Yingze Li, Nuo Xu, Hanxiong Lyu, Naiyu Jiang, Hongyan Zhang, Nan Zhou, Dongxing Zhang.
(2023)
Enhanced mechanical and tribological properties of carbon fiber/PEEK composites by hydroxylated boron nitride nanosheets and polyetherimide sizing agents. COMPOSITES SCIENCE AND TECHNOLOGY,
232
(109851).
2.
Jiang Nan, Zhou Xue, Zhong Tianyuan, Wang Guang.
(2023)
A new pyrene-based “turn-on” fluorescent probe for highly selective detection of hypochlorite in aqueous solution and in living cells. CHEMICAL PAPERS,
77
(1):
(197-205).
3.
Nuo Xu, Shaohua Chen, Yingze Li, Naiyu Jiang, Ting Zheng, Nick Goossens, Jef Vleugels, Dongxing Zhang, David Seveno.
(2022)
A hybrid 1D/2D coating strategy with MXene and CNT towards the interfacial reinforcement of carbon fiber/poly(ether ether ketone) composite. COMPOSITES PART B-ENGINEERING,
246
(110278).
4.
Yuying Bian, Xinhui Song, Yuxin Han, Guang Wang, Hongmei Qiao.
(2024)
Carboxyl functionalized covalent organic framework material for selective adsorption of methylene blue in aqueous solutions. TETRAHEDRON LETTERS,
150
(155281).
5.
Naiyu Jiang, Yingze Li, Qiao Wang, Nan Zhou, Hongyan Zhang, Xiaohu Zou, Dongxing Zhang.
(2024)
Constructing coordination-connected flexible-rigid structures for the interfacial enhancement of CF/polyetheretherketone composites. Surfaces and Interfaces,
53
(104964).
6.
Nan Zhou, Yingze Li, Long Xia, Naiyu Jiang, Hongyan Zhang, Hua Yao, Xiaohu Zou, Wenbo Liu, Dongxing Zhang.
(2025)
Electrostatic assembly induced cross-dimensional nano-interface design for enhanced mechanical and electromagnetic interference shielding properties of CF/PEEK composites. COMPOSITES SCIENCE AND TECHNOLOGY,
265
(111155).
7.
Jianwei Hou, Xinghai Hao, Jiali Xu, Geoffrey I.N. Waterhouse, Chunhua Ni, Zhiming Zhang, Liangmin Yu.
(2024)
Fluorescent zinc acrylate resins containing coumarin structures with enhanced antifouling performance. PROGRESS IN ORGANIC COATINGS,
194
(108597).
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7 Citations
H2408604