Dimethyl malonate - ≥98% , CAS No.108-59-8

CAS: 108-59-8 Cat. No.: D103051 Molecular Weight: 132.11 Beilstein Registry Number: 774261 EC Number: 203-597-8

GRADE & PURITY ≥98%

Synonyms

NCGC00248011-02 | CH2(CO2CH3)2 | Dimethyl malonate | HY-Y1787 | malonic acid dimethylester | J-002165 | PROPANEDIOIC ACID,DIMETHYL ESTER (MALONIC ACID,DIMETHYL ESTER) | EM8Y79998C | MFCD00008460 | NCGC00248011-01 | STL146546 | Dimethyl 1,3-propanedioate

Storage

Room temperature

Shipped In

Normal

Overview

Dimethyl Malonate is a diester derivative of Malonic Acid. It is also a precursor in the synthesis of Barbituric Acids.
A diester derivative of Malonic Acid.

Specifications

Synonyms

NCGC00248011-02 | CH2(CO2CH3)2 | Dimethyl malonate | HY-Y1787 | malonic acid dimethylester | J-002165 | PROPANEDIOIC ACID, DIMETHYL ESTER (MALONIC ACID, DIMETHYL ESTER) | EM8Y79998C | MFCD00008460 | NCGC00248011-01 | STL146546 | Dimethyl 1, 3-propanedioate

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488180614
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180614
• Canonical Smiles: COC(=O)CC(=O)OC
• IUPAC Name: dimethyl propanedioate
• InChIKey: BEPAFCGSDWSTEL-UHFFFAOYSA-N
• INCHI: 1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3
• Isomeric SMILES: COC(=O)CC(=O)OC
• WGK Germany: 1
• RTECS: OO0950000
• Molecular Weight: 132.11
• Beilstein: 774261
• Reaxy-Rn: 774261
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=774261&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Dicarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Dicarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Dicarboxylic acids and derivatives
• Alternative Parents: 1,3-dicarbonyl compounds Methyl esters Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1,3-dicarbonyl compound - Dicarboxylic acid or derivatives - Methyl ester - Carboxylic acid ester - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
• 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.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DLD-1 (17511 Activities)

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DMS-273 (14108 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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RXF 631 (11415 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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SNB-78 (14240 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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XF498 (12972 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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HOP-18 (11577 Activities)

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HOP-92 (41141 Activities)

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NCI-H460 (60772 Activities)

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SF-268 (49410 Activities)

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IGROV-1 (47897 Activities)

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KM-20L2 (14967 Activities)

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LOX IMVI (44321 Activities)

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HOP-62 (47048 Activities)

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LXFL 529 (14112 Activities)

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M19-MEL (15326 Activities)

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Malme-3M (44254 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in organic solvents such as alcohol and ether, slightly soluble in water.
• Sensitivity: Moisture & Air & Light sensitive.
• Refractive Index: 1.4149
• Flash Point(°F): 185 °F
• Flash Point(°C): 90℃
• Boil Point(°C): 181.4°C
• Melt Point(°C): -62°C
• Molecular Weight: 132.110 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 132.042 Da
• Monoisotopic Mass: 132.042 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 104.000
• 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

References

1. Yongliang Ding, Jiangjun Zhou, Lieshun Cai, Zhongkai Wang, Feng Jiang.  (2023)  Humidity-sensitive and fluorescent bio-based polyhydroxylamides toward sustainable adhesives.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2023.117423]

2. Zhang Yuanwen, Zheng Yueming, Wu Qingqing, Tian Fuyun, Ma Chuanjun, Xu Haiyan, Zhan Li, Gao Zhaobing, Zhao Guilong, Ti Huihui.  (2022)  Study on structure-activity relationship (SAR) of simplified mirogabalin derivatives as voltage-gated calcium channel α2δ ligands for the treatment of chronic neuropathic pain.  MEDICINAL CHEMISTRY RESEARCH,  32  (2): (288-313).  [PMID:] [10.1007/s00044-022-03006-6]

3. Yuqing Shen, Chaoping Yuan, Xianyi Zhu, Qin Chen, Shenjun Lu, Haibo Xie.  (2021)  Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction.  GREEN CHEMISTRY,  23  (24): (9922-9934).  [PMID:] [10.1039/D1GC03148A]

4. Shuai Sun, Yijiao Xue, Xiaodong Xu, Liping Ding, Zhen Jiang, Linghui Meng, Pingan Song, Yongping Bai.  (2021)  Highly Stretchable, Ultratough, and Strong Polyesters with Improved Postcrystallization Optical Property Enabled by Dynamic Multiple Hydrogen Bonds.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.0c02628]

5. Jie Yao, Yan Wang, Suleiman Sabo Bello, Guangwen Xu, Lei Shi.  (2020)  Regulation of Brønsted acid sites in H-MOR for selective methyl methoxyacetate synthesis.  APPLIED ORGANOMETALLIC CHEMISTRY,  34  (11): (e5925).  [PMID:] [10.1002/aoc.5925]

6. Fei Xia, Zhongtian Du, Junxia Liu, Yangyang Ma, Jie Xu.  (2016)  Catalytic oxidative C–C bond cleavage route of levulinic acid and methyl levulinate.  RSC Advances,  6  (76): (72744-72749).  [PMID:] [10.1039/C6RA16149A]

7. Abbas Tanver, Mu-Hua Huang, Yunjun Luo, Syed Khalid, Tariq Hussain.  (2015)  Energetic interpenetrating polymer network based on orthogonal azido–alkyne click and polyurethane for potential solid propellant.  RSC Advances,  5  (79): (64478-64485).  [PMID:] [10.1039/C5RA10467J]

8. Xie Tianyu, Hu Wenbo, You Lin, Wang Xin.  (2024)  Design, synthesis and biological evaluation of thienopyridine derivatives as c-Met kinase inhibitors.  MOLECULAR DIVERSITY,      [PMID:39356364] [10.1007/s11030-024-10998-3]