propanedioic acid

• ChemBase ID: 1932
• Molecular Formular: C3H4O4
• Molecular Mass: 104.06146
• Monoisotopic Mass: 104.01095861
• SMILES: OC(=O)CC(=O)O
• Canonical SMILES: OC(=O)CC(=O)O
• InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
• InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propanedioic acid
• IUPAC Traditional name: malonic acid
• Synonyms: Malonic acid; Malonate Standard for IC; Propanedioic acid; Malonate; Dicarboxymethane; Carboxyacetic acid; Dicarboxylate; Dicarboxylic acid; Methanedicarboxylic acid; 1,3-Propanedioic acid; Dicarboxylic Acid C3; Propanediolic Acid; Metahnedicarboxylic Acid; Malonic acid; Propane-1,3-dioic acid; 缩苹果酸; 丙二酸

Database IDs

• CAS Number: 141-82-2
• EC Number: 231-791-2; 205-503-0
• MDL Number: MFCD00002707
• Beilstein Number: 1751370
• Merck Index: 145710
• PubChem SID: 24896631; 24872812; 46504875; 160965387
• PubChem CID: 867
• CHEBI ID: 30794
• CHEMBL: 7942
• Chemspider ID: 844
• DrugBank ID: DB02175
• Wikipedia Title: Malonic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.428424
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.4132009
• LogD (pH = 7.4): -5.336086
• Log P: -0.33111727
• Molar Refractivity: 18.9878 cm^3
• Polarizability: 7.6132627 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.6
• LOG S: 0.28
• Solubility (Water): 1.97e+02 g/l

PROPERTIES

Physical Property

• Solubility: Miscible in water
• Melting Point: 132-135 °C (dec.)(lit.); 132-136(dec.)°C; 132-136°C dec.; 135°C; 135–137 °C decomp.; 135-137°C
• Boiling Point: decomposes
• Flash Point: >110°C; 157°C(314°F); 172 °C; 341.6 °F
• Density: 1.619 g/cm^3; 1.62
• pKa: pK_a1=2.83; pK_a2=5.69

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Corrosive
• RTECS: OO0175000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1; nwg
• Risk Statements: 22-37/38-41; 22-41; R:22-36/37/38
• Safety Statements: 26-36/37/39; 26-36/39; S:25-26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H335-H318; H302-H318
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... SRC(6714)

Product Information

• Purity: ≥98.0% (T); ≥99.0%; ≥99.0% (T); 95+%; 99%
• Concentration: 1.000 g/L; in H2O
• Grade: analytical standard; certified reference material; puriss.; purum; ReagentPlus®; SAJ first grade; TraceCERT®
• Ignition Residue: ≤0.05%; ≤0.3%
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH2(COOH)2

DETAILS

MP Biomedicals - 05210871

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102238

Crystalline
Purity: 99%

DrugBank - DB02175

• Drug Groups: experimental
• External Links: Wikipedia

Sigma Aldrich - M1296

Packaging
100, 500 g in poly bottle
5 kg in poly drum
2.5 kg in poly bottle
5 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 68714

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 49323

General description
filtered through a 0.45 μm membrane filter
Preparation Note
prepared with malonic acid and H2O

REFERENCES

• Knoevenagel condensation with aldehydes yields substituted acrylic (e.g. cinnamic) acids; review: Org. React., 15, 204 (1967). For an example of the Doebner modification, using pyridine as solvent/base, see: Org. Synth. Coll., 3, 425 (1955); a catalytic amount of piperidine often gives superior results; see, e.g.: Org. Synth. Coll., 4, 327 (1963).