Basic information
- Name:
Malonic acid
- CAS No.:
141-82-2
- Molecular Structure:
- Formula:
- C3H4O4
- Synonyms:
- Dicarboxymethane;Carboxyacetic acid;Malonic acid （Electronical grade）;Malonicacid;Malonic acid(medicine grade);Malonic Acid (P516);USAF EK-695;Propanedioic acid Malonic Acid;Propanedioic acid (9CI);Methanedicarboxylic acid;1,3-Propanedioic acid;Malonic acid;propanedioec acid;
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Chemistry
Molecular Structure of Malonic acid (CAS NO. 141-82-2):
IUPAC Name: Propanedioic acid
Molecular Formula: C3H4O4
Molecular Weight: 104.061460 g/mol
XLogP3: -0.8
H-Bond Donor: 2
H-Bond Acceptor: 4
Canonical SMILES: C(C(=O)O)C(=O)O
InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N
Index of Refraction: 1.478
Molar Refractivity: 19.07 cm3
Molar Volume: 67.3 cm3
Surface Tension: 70.5 dyne/cm
Density: 1.546 g/cm3
Flash Point: 201.9 °C
Enthalpy of Vaporization: 69.8 kJ/mol
Boiling Point: 386.8 °C at 760 mmHg
Vapour Pressure: 4.66E-07 mmHg at 25 °C
Melting Point: 132-135 °C (dec.)(lit.)
Water Solubility: 1400 g/L (20 ºC)
Storage Temp.: Store at RT.
BRN: 1751370
EINECS: 205-503-0
Product Categories: Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
Uses
Malonic acid (141-82-2) is used as building block in chemical synthesis. frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid. Its esters are also used for the -CH2COOH synthon in the malonic ester synthesis.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 300mg/kg (300mg/kg) | National Technical Information Service. Vol. AD277-689, | |
| mouse | LD50 | oral | 4gm/kg (4000mg/kg) | Biochemical Journal. Vol. 34, Pg. 1196, 1940. | |
| rabbit | LDLo | skin | 10gm/kg (10000mg/kg) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 22-3/1971, | |
| rat | LC50 | inhalation | > 8900mg/m3/1H (8900mg/m3) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 22-3/1971, | |
| rat | LD50 | intraperitoneal | 1500mg/kg (1500mg/kg) | "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4937, 1982. | |
| rat | LD50 | oral | 1310mg/kg (1310mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 22-3/1971, |
Safety Profile
Safety Information of Malonic acid (CAS NO. 141-82-2):
Hazard Codes: Xn,Xi 
Risk Statements: 20/22-41-36/37/38-22
R20/22: Harmful by inhalation and if swallowed
R41: Risk of serious damage to the eyes
R36/37/38: Irritating to eyes, respiratory system and skin
R22:Harmful if swallowed
Safety Statements: 26-36/39-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S37/39:Wear suitable gloves and eye/face protection
S36/39:Wear suitable protective clothing and eye/face protection
S36:Wear suitable protective clothing
RIDADR: 3261
WGK Germany: 1
RTECS: OO0175000
PackingGroup: III
HS Code: 29171910
When heated to decomposition it emits acrid smoke and irritating vapors.
Specification
Malonic acid with cas registry number of 141-82-2 is is a carboxylic acid, also called for AI3-15375 ; Carboxyacetic acid ; Dicarboxymethane ; Kyselina malonova ; Kyselina malonova [Czech] ; MALONIC ACID ; Methanedicarboxylic acid ; NSC 8124 ; Propanedioic acid ; USAF EK-695 . It can be prepared in this way: Sodium carbonate generates the sodium salt which is then reacted with sodium cyanide to provide the cyano acetic acid salt via a nucleophilic substitution. The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate and acidification affords malonic acid.
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