- Malonic acid
- Malonic acid bis(2,4,6-trichlorophenyl) ester
- Malonic acid disodium salt monohydrate
- Malonic acid, (trifluoromethyl)-, dimethyl ester
- Malonic acid, ethylmethyl-
- Malonic acid, ethylphenyl-, 2-(diethylamino)ethyl ethyl ester
- Malonic acid,(3-isothiazolylmethyl)methyl-, diethyl ester (7CI,8CI)
- Malonic dihydrazide
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Cas Database |
| Name |
Malonic acid |
EINECS | 205-503-0 |
| CAS No. | 141-82-2 | Density | 1.546 g/cm3 |
| PSA | 74.60000 | LogP | -0.45430 |
| Solubility | water: 1400 g/L (20 °C) | Melting Point |
132-135 °C (dec.)(lit.) |
| Formula | C3H4O4 | Boiling Point | 386.808 °C at 760 mmHg |
| Molecular Weight | 104.062 | Flash Point | 201.905 °C |
| Transport Information | N/A | Appearance | Crystalline |
| Safety | 26-36/39-37/39-36 | Risk Codes | 20/22-41-36/37/38-22 |
| Molecular Structure |
|
Hazard Symbols |
 Xn, Xi
|
| 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; |
Article Data | 303 |
Malonic acid Synthetic route
| Conditions | Yield |
|---|---|
| With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry; | 99% |
| With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h; | 93% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water | 97% |
| With sodium hydroxide elektrochemische Oxydation, am besten an einer Nickelanode; |
| Conditions | Yield |
|---|---|
| With water at 70 - 80℃; | 97% |
| With water; sodium hydroxide In methanol at 80℃; for 1h; |
| Conditions | Yield |
|---|---|
| With acetic acid In water at 70 - 80℃; Reagent/catalyst; | 95% |
| With hydrogen ethyl malonate; sulfuric acid at 70℃; under 175 Torr; Abdestillieren des entstehenden Aethanols; | |
| With malonic acid; sulfuric acid at 70℃; under 175 Torr; Abdestillieren des entstehenden Aethanols; |
- 3815-86-9
malonic acid dihydrazide
- 75-15-0
carbon disulfide
A
- 141-82-2
malonic acid
B
- 1072-71-5
2,5-Dimercapto-1,3,4-thiadiazole
| Conditions | Yield |
|---|---|
| Stage #1: malonic acid dihydrazide; carbon disulfide With potassium hydroxide In ethanol for 3h; Rearrangement; cyclization; Heating; Stage #2: With hydrogenchloride In ethanol Hydrolysis; ring cleavage; | A n/a B 90% |
| Conditions | Yield |
|---|---|
| With niobium(V) oxide; water In neat (no solvent) for 30h; Reflux; Inert atmosphere; | 82% |
| Conditions | Yield |
|---|---|
| Stage #1: malonic acid dimethyl ester With potassium hydroxide; water In acetonitrile at 0℃; for 1h; Stage #2: With hydrogenchloride; water In acetonitrile Product distribution / selectivity; | A n/a B 81% |
| Stage #1: malonic acid dimethyl ester With water; potassium hydroxide at 0℃; for 1.5h; Stage #2: Acidic aq. solution; | A 9.8% B 76% |
| Conditions | Yield |
|---|---|
| Stage #1: diethyl malonate With water; potassium hydroxide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: In tetrahydrofuran; water Acidic conditions; | A 8.3% B 76.9% |
| Stage #1: diethyl malonate With water; potassium hydroxide at 0℃; for 6h; Stage #2: Acidic aq. solution; | A 36.6% B 35.6% |
| Conditions | Yield |
|---|---|
| With phosphotungstic acid; dihydrogen peroxide; cetylpyridinium bromide In water at 85℃; for 5h; Concentration; Green chemistry; | A 49.8% B 60.7% |
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 18h; | 60% |
Malonic acid Chemical Properties
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
Malonic acid 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.
Malonic acid 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, |
Malonic acid 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.
Malonic acid 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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