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; |
malonic acid dihydrazide
carbon disulfide
A
malonic acid
B
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% |
malonic acid dimethyl ester
A
malonic acid
B
Malonic acid monomethyl ester
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% |
Conditions | Yield |
---|---|
With iron disulphate; dihydrogen peroxide at 2℃; | A 16% B 12% C 58% |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate at 0℃; for 0.05h; | A 8.5% B 57% |
With potassium hydroxide; potassium permanganate In water at 0℃; for 0.05h; Product distribution; Mechanism; | A 8.5% B 57% |
5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion
A
6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene
B
cycl-isopropylidene malonate
C
tartronic acid
D
malonic acid
E
2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; water for 3.5h; Product distribution; Irradiation; | A 14% B 5% C 12% D 6% E 56% |
ethyl malonamate
A
acetamide
B
malonic acid
C
hydrogen ethyl malonate
D
acetic acid
Conditions | Yield |
---|---|
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 1h; Hydrolysis; | A n/a B n/a C 53% D n/a |
2,5-dihydroxy-1,4-benzoquinone
A
malonic acid
B
carbon dioxide
C
acetic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 39.99℃; for 0.333333h; Kinetics; Thermodynamic data; Mechanism; Temperature; Time; | A 52.1% B n/a C n/a |
methanol
cycl-isopropylidene malonate
indan-1,2,3-trione hydrate
A
malonic acid
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate; indan-1,2,3-trione hydrate With montmorillonite K10 clay In methanol at 20℃; for 0.0833333h; Stage #2: methanol In ethyl acetate | A n/a B 40% |
Conditions | Yield |
---|---|
Sonication; | A 40% B 30% C 13% |
cyclohexa-1,4-diene
malonic acid
Conditions | Yield |
---|---|
With ozone In methanol for 1h; Product distribution; Heating; followed by reaction with aq. H2O2 / HCOOH; | 30% |
With formic acid; dihydrogen peroxide; ozone 1.) methanol, -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; |
D-glucose
A
formic acid
B
glycolic Acid
C
L-Lactic acid
D
malonic acid
E
succinic acid
F
oxalic acid
G
acetic acid
H
propionic acid
I
2-oxo-propionic acid
J
maleic acid
Conditions | Yield |
---|---|
With sodium silicate; water at 300℃; under 64356.4 Torr; for 0.0166667h; Reagent/catalyst; Sealed tube; | A n/a B n/a C 30% D n/a E n/a F n/a G n/a H n/a I n/a J n/a |
cycl-isopropylidene malonate
ethanol
indan-1,2,3-trione hydrate
A
malonic acid
B
ethyl (2'-hydroxyindane-1',3'-dione-2'-yl)acetate
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate; indan-1,2,3-trione hydrate With montmorillonite K10 clay In ethanol at 20℃; for 0.0833333h; Stage #2: ethanol In ethyl acetate | A n/a B 25% |
cyclohexene
A
pentanal
B
Succinic semialdehyde
C
malonic acid
D
oxalic acid
Conditions | Yield |
---|---|
With ozone at 24.85℃; Product distribution; in dark; | A 17.05% B 6.9% C 6.88% D 6.16% |
Conditions | Yield |
---|---|
With water for 0.833333h; argon plasma-jet; | 13% |
Conditions | Yield |
---|---|
With potassium hydroxide |
mucobromic acid
malonic acid
Conditions | Yield |
---|---|
With barium dihydroxide beim Kochen; |
propene
malonic acid
Conditions | Yield |
---|---|
With potassium permanganate |
Conditions | Yield |
---|---|
With water | |
With water In diethyl ether C3O2 dissolved in ether;; | |
With water; hydrogenchloride In water | |
With water In water during hours;; | >99 |
With water In water |
Conditions | Yield |
---|---|
With oxygen in Gegenwart einer dialysierten Enzymloesung aus Schweineherz und von MnCl2; |
malonic acid
Conditions | Yield |
---|---|
With nitric acid |
Conditions | Yield |
---|---|
With acetic acid at 20℃; for 1h; | 100% |
With acetic acid |
5-methylthiophene-2-carboxaldehyde
malonic acid
(E)-3-(5-methyl-2-thienyl)-2-propenoic acid
Conditions | Yield |
---|---|
With piperidine; pyridine Heating; | 100% |
With piperidine; pyridine Reflux; | 66% |
With piperidine; pyridine Heating / reflux; | 66% |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
zirconium(IV) oxide; molybdenum at 84.85℃; for 6h; Esterification; | 95% |
iodine for 15h; Heating; | 94% |
malonic acid
(1S,2R,5S)-(+)-menthol
Malonsaeure-bis<(1R)-menthyl>ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In diethyl ether for 2h; Ambient temperature; | 100% |
at 100℃; Einleiten von HCl; |
Conditions | Yield |
---|---|
With pyridine In ethanol for 1.75h; Knoevenagel condensation; Inert atmosphere; Reflux; | 100% |
With ammonium acetate for 0.0666667h; Irradiation; | 95% |
Stage #1: malonic acid; 4-nitrobenzaldehdye With piperidine; pyridine Knoevenagel-Doebner reaction; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice; optical yield given as %de; | 95% |
Conditions | Yield |
---|---|
With piperidine; pyridine | 100% |
With piperidine; pyridine at 115℃; for 3h; Knoevenagel Condensation; | 93% |
With pyridine for 1h; Heating; | 82% |
Conditions | Yield |
---|---|
Stage #1: malonic acid; cyclohexanecarbaldehyde With piperidine; pyridine at 20 - 80℃; for 6h; Doebner reaction; Stage #2: With hydrogenchloride In water Cooling with ice; | 100% |
With piperidine; pyridine | 97% |
With piperidine; pyridine |
4-Trifluoromethylbenzaldehyde
malonic acid
4-(trifluoromethyl)cinnamic acid
Conditions | Yield |
---|---|
With pyridine; aniline In toluene for 18h; Doebner Modification; Reflux; | 100% |
With pyridine; ammonium acetate at 85℃; for 5h; Darkness; | 65.36% |
3-formyl-5,5'-dimethyl-2,2'-bithiophene
malonic acid
Conditions | Yield |
---|---|
With piperidine; pyridine for 2h; Heating; | 100% |
malonic acid
3-methoxy-4-methylbenzaldehyde
3-(3-Methoxy-4-methylphenyl)-2-propenoic acid
Conditions | Yield |
---|---|
Stage #1: malonic acid; 3-methoxy-4-methylbenzaldehyde With piperidine; pyridine for 2.5h; Heating / reflux; Stage #2: With hydrogenchloride In water | 100% |
In piperidine; pyridine for 2.5h; Heating / reflux; | 100% |
With piperidine; pyridine for 5h; Heating; | 99.7% |
malonic acid
1-methoxypyrene-8-carboxaldehyde
Conditions | Yield |
---|---|
With piperidine; pyridine 1.) from 80 deg C to 85 deg C, 30 min, 2.) reflux, 4 h; | 100% |
Conditions | Yield |
---|---|
copper(I) oxide In dimethyl sulfoxide at 110 - 120℃; for 1.5h; Product distribution / selectivity; | 100% |
copper(I) oxide In N,N-dimethyl-formamide at 110 - 120℃; for 1.5h; Product distribution / selectivity; | 100% |
In neat (no solvent) at 141℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔF(excit.); further solvent; |
Conditions | Yield |
---|---|
With pyridine; glycine at 80℃; for 3h; Catalytic behavior; Reagent/catalyst; Sealed tube; | 100% |
With triton-B adsorbed on flyash In neat (no solvent) for 0.0152778h; Microwave irradiation; Green chemistry; | 96% |
Stage #1: malonic acid With triethylamine In toluene Knoevenagel Condensation; Stage #2: 4-hydroxy-benzaldehyde With piperidine In toluene for 2h; Knoevenagel Condensation; Reflux; | 88% |
malonic acid
methyl 4-formylbenzoate
4-(2-carboxyvinyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With piperidine; pyridine at 120℃; for 12h; | 100% |
With piperidine In pyridine at 100 - 120℃; for 19h; | 99.39% |
With piperidine; pyridine at 80 - 100℃; for 4h; | 91.6% |
With piperidine; pyridine at 110℃; for 2h; | 75% |
With piperidine; pyridine for 5h; Reflux; | 36% |
malonic acid
[tert-Butoxycarbonyl-(2-formyl-phenyl)-amino]-acetic acid methyl ester
(E)-3-[2-(tert-Butoxycarbonyl-methoxycarbonylmethyl-amino)-phenyl]-acrylic acid
Conditions | Yield |
---|---|
With piperidine; pyridine for 1h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With piperidine; pyridine for 2.5h; Heating / reflux; Neat (no solvent); | 100% |
With piperidine; pyridine for 2.5h; Heating / reflux; | 100% |
With piperidine; pyridine at 100℃; Condensation; |
Conditions | Yield |
---|---|
With pyridine; aniline In toluene for 18h; Doebner Modification; Reflux; | 100% |
With triton-B adsorbed on flyash In neat (no solvent) for 0.0125h; Microwave irradiation; Green chemistry; | 96% |
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100 - 110℃; for 1.25h; Knoevenagel-Doebner-Stobbe Reaction; | 95% |
malonic acid
2-(vinyloxy)ethyl isothiocyanate
Conditions | Yield |
---|---|
at 65 - 100℃; for 0.166667h; | 100% |
4-Bromothiophen-2-aldehyde
malonic acid
trans-3-(4-bromothiophen-2-yl)propenoic acid
Conditions | Yield |
---|---|
With piperidine; pyridine at 100℃; | 100% |
Stage #1: 4-Bromothiophen-2-aldehyde; malonic acid With piperidine; pyridine at 100℃; for 24h; Stage #2: With hydrogenchloride In water pH=3; | 100% |
piperidine In pyridine at 100℃; for 22h; Knoevenagel reaction; | 96% |
malonic acid
3-methoxy-4-methylbenzaldehyde
Conditions | Yield |
---|---|
Stage #1: malonic acid; 3-methoxy-4-methylbenzaldehyde With piperidine; pyridine for 11h; Heating / reflux; Stage #2: With hydrogenchloride In water | 100% |
malonic acid
(-)-8-phenylmenthol
Bis<(1S,2R,4R)-2-methyl-5-(1-methyl-1-phenylethyl)cyclohexyl>malonate
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 0.5h; | 100% |
malonic acid
Methyl 3-formylbenzoate
(E)-3-(3-methoxycarbonylphenyl)acrylic acid
Conditions | Yield |
---|---|
With PYRIMIDINE In N,N-dimethyl-formamide at 90℃; for 10h; Inert atmosphere; | 100% |
With piperidine; pyridine Knoevenagel Condensation; Reflux; | 75% |
With piperidine; pyridine at 80℃; for 4h; | 72% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; | 100% |
In tetrahydrofuran Product distribution / selectivity; |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: (E)-3-[5,10,15,20-tetrakis(3,5-dimethylphenyl)porphyrin-2-yl]-2-propenal; malonic acid With ammonium acetate; acetic acid at 70℃; for 3h; Stage #2: zinc diacetate at 70℃; for 0.25h; | 100% |
Conditions | Yield |
---|---|
In water; acetone for 0.166667h; | 100% |
malonic acid
3-[4-(1-ethoxycarbonylpiperidin-4-ylidene)-9,10-dihydro-4H-1-thiabenzo[f]azulen-2-yl]acrylic acid
Conditions | Yield |
---|---|
With piperidine; hydrogenchloride In pyridine Reflux; | 100% |
malonic acid
methyl 2,3-O-isopropylidene-α-D-mannopyranoside-4,6-cyclic sulfate
Conditions | Yield |
---|---|
Stage #1: malonic acid; methyl-2,3-O-isopropylidene-4,6-cyclic sulfate-α-D-mannopyranoside With sodium hydride In N,N-dimethyl-formamide Stage #2: In tetrahydrofuran; methanol regioselective reaction; | 100% |
Conditions | Yield |
---|---|
at 100℃; | 100% |
at 20℃; for 24h; | |
at 50 - 120℃; | |
at 80℃; |
Conditions | Yield |
---|---|
With piperidine; pyridine at 95℃; | 100% |
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 (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.
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 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 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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