Methyl acetoacetate(MAA) - CP, ≥98% , CAS No.105-45-3

CAS: 105-45-3 Cat. No.: M108599 Molecular Weight: 116.12 Beilstein Registry Number: 506727 EC Number: 203-299-8

GRADE & PURITY CP, ≥98%

Synonyms

CAS-105-45-3 | s3091 | Tox21_200162 | 3-Oxobutyric Acid Methyl Ester | 3-oxo-butyric acid methyl ester | AKOS000118978 | BDBM50502126 | METHYL ACETOACETATE [MI] | InChI=1/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H | Acetoacetate methyl ester | DTXCID706716 | HSDB

Storage

Room temperature

Shipped In

Normal

Overview

Methyl acetoacetate undergoes asymmetric hydrogenation to form (R)-(-)-methyl-3-hydroxybutyrate in the presence of enantioselective Ni/SiO2 catalysts. It undergoes Pechmann reactions with phenols in various ionic liquids.
Methyl acetoacetate was used in development of a simple and cost effective method for monitoring of trace formaldehyde in air. It was used to study the substrate specificity of NADPH-dependent diacetyl reductase in Escherichia coli.

Specifications

Synonyms

CAS-105-45-3 | s3091 | Tox21_200162 | 3-Oxobutyric Acid Methyl Ester | 3-oxo-butyric acid methyl ester | AKOS000118978 | BDBM50502126 | METHYL ACETOACETATE [MI] | InChI=1/C5H8O3/c1-4(6)3-5(7)8-2/h3H2, 1-2H | Acetoacetate methyl ester | DTXCID706716 | HSDB

Specifications & Purity

CP, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

CP

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504751445
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751445
• Canonical Smiles: CC(=O)CC(=O)OC
• IUPAC Name: methyl 3-oxobutanoate
• InChIKey: WRQNANDWMGAFTP-UHFFFAOYSA-N
• INCHI: 1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
• Isomeric SMILES: CC(=O)CC(=O)OC
• WGK Germany: 1
• RTECS: AK5775000
• UN Number: 1993
• Packing Group: I
• Molecular Weight: 116.12
• Beilstein: 506727
• Reaxy-Rn: 506727
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=506727&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Keto acids and derivatives
      • Subclass Beta-keto acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Keto acids and derivatives
• Subclass: Beta-keto acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Beta-keto acids and derivatives
• Alternative Parents: Fatty acid methyl esters 1,3-dicarbonyl compounds Methyl esters Ketones Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Beta-keto acid - Fatty acid ester - Fatty acid methyl ester - 1,3-dicarbonyl compound - Fatty acyl - Methyl ester - Carboxylic acid ester - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Easily soluble in water.
• Sensitivity: Moisture sensitive.
• Refractive Index: 1.418
• Flash Point(°F): 158 °F
• Flash Point(°C): 67℃
• Boil Point(°C): 169-170°C
• Melt Point(°C): -80°C
• Molecular Weight: 116.110 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047 Da
• Monoisotopic Mass: 116.047 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 106.000
• 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

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2. Peilan Luo, Menglin Ye, Wenli Zhou, Pingping Wan, Zhongyun Ma, Zhongxian Qiu, Jilin Zhang, Ru-Shi Liu, Shixun Lian.  (2022)  Simultaneous construction of impermeable dual-shell stabilizing fluoride phosphors for white light-emitting diodes.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2022.134951]

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4. Chao Ding, Weili Wei, Hanjun Sun, Jinhua Ding, Jinsong Ren, Xiaogang Qu.  (2014)  Reduced graphene oxide supported chiral Ni particles as magnetically reusable and enantioselective catalyst for asymmetric hydrogenation.  CARBON,      [PMID:] [10.1016/j.carbon.2014.08.022]

5. He Liu, Shixi Wang, Meng Xu, Kaiyue Zhang, Qian Gao, Hualei Wang, Dongzhi Wei.  (2024)  Engineering an (R)-selective transaminase for asymmetric synthesis of (R)-3-aminobutanol.  BIOORGANIC CHEMISTRY,      [PMID:38492494] [10.1016/j.bioorg.2024.107264]

6. Canglong Li, Hongli Qi, Jie Huang, Dongping Chen, Yuanzi Cheng, Minghan Xu, Zihao Jiang, Huaming Yu, Yang Huang, Guanghui Li, Yuejiao Chen.  (2025)  Enabling highly reversible Zn anode via an interfacial preferentially adsorbed additive containing nucleophilic groups.  Microstructures,  5  (2): (N).  [PMID:] [10.20517/microstructures.2024.114]

7. He Gao, Haiyan Ma, Ling Yan, Shiqi Li, Longbin Xu.  (2026)  Sequential and selective fluorescent detection of sulfur pollutants in environmental water using a dual-channel probe.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2026.145563]