maleic acid
A
tetrahydrofuran
B
4-butanolide
C
methanol
D
Butane-1,4-diol
E
malic acid
F
succinic acid
G
acetic acid
H
butan-1-ol
Conditions | Yield |
---|---|
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity; | A 0.45% B 0.06% C 0% D 0.21% E 0.36% F 98.73% G 0.04% H 0.08% |
Conditions | Yield |
---|---|
With sodium; iron | 97% |
With water at 150 - 200℃; | |
With sodium hydroxide; water at 100℃; |
Conditions | Yield |
---|---|
With lanthanum(III) chloride at 116℃; for 19h; Product distribution; also with other alcohols; variation of reaction time, temperature and proportion of reagents; | A 3% B 95% |
methanol
lithium succinate
A
malic acid
B
2-methoxy succinic acid
Conditions | Yield |
---|---|
With lanthanum(III) chloride; trimethyl orthoformate In water at 150℃; for 6h; | A 1.5 % Chromat. B 91% |
maleic acid
A
tetrahydrofuran
B
4-butanolide
C
Butane-1,4-diol
D
4-hydroxybutanoic acid
E
malic acid
F
succinic acid
G
acetic acid
Conditions | Yield |
---|---|
With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2 at 110℃; Product distribution / selectivity; | A 1.27% B 4.78% C 1.55% D 1.24% E 0.48% F 90.6% G 0.08% |
maleic acid
A
tetrahydrofuran
B
4-butanolide
C
Butane-1,4-diol
D
malic acid
E
succinic acid
F
acetic acid
G
butan-1-ol
Conditions | Yield |
---|---|
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; for 96 - 238h; Product distribution / selectivity; | A 0.6% B 0.04% C 0.62% D 0.19% E 88.49% F 0.12% G 0.11% |
maleic acid
A
tetrahydrofuran
B
4-butanolide
C
Butane-1,4-diol
D
4-hydroxybutanoic acid
E
malic acid
F
succinic acid
G
terephthalic acid
H
acetic acid
I
propionic acid
J
(2E)-but-2-enedioic acid
Conditions | Yield |
---|---|
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2 at 110℃; for 170 - 1009h; Product distribution / selectivity; | A 0.86% B 4.34% C 0.28% D 1.24% E 0% F 85.51% G 0% H 0.04% I 0% J 0% |
Conditions | Yield |
---|---|
Stage #1: N-p-tolylphenylmaleimide With potassium carbonate; isopropyl alcohol for 1h; oxa-Michael addition; Heating; Stage #2: With hydrogenchloride; acetic acid for 10h; Heating; | 85% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; Product distribution / selectivity; | A 9% B 84% |
Conditions | Yield |
---|---|
With water at 190℃; for 1h; Temperature; Concentration; Time; Sealed tube; Green chemistry; | A n/a B 72% |
ethanol
lithium succinate
A
malic acid
B
(R,S)-ethoxybutanedioic acid
Conditions | Yield |
---|---|
With lanthanum(III) chloride; trimethyl orthoformate In water at 175℃; for 24h; | A 15.5 % Chromat. B 70% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water; acetonitrile at 20℃; | A 10% B 8% C 66% |
furfural
A
5-hydroxy-2-(5H)-furanone
B
formic acid
C
malic acid
D
maleic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 49.84℃; for 24h; Catalytic behavior; Temperature; Concentration; | A n/a B n/a C n/a D 57% |
5-hydroxymethyl-2-furfuraldehyde
A
glycolic Acid
B
malic acid
C
maleic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In water; acetic acid at 20℃; | A 55% B 29% C 14% |
furfural
A
2-furanoic acid
B
malic acid
C
succinic acid
D
maleic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; Product distribution / selectivity; | A 20% B 6% C 8% D 49% |
With dihydrogen peroxide; 5 weight percent methyltrioxorhenium on polystyrene In dichloromethane; water; acetonitrile at 20℃; Product distribution / selectivity; | A 10% B 11% C 10% D 44% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In water at 20℃; Product distribution / selectivity; | A 12% B 6% C 26% D 44% |
bromosuccinic acid
A
malic acid
B
sulfosuccinic acid
C
(2E)-but-2-enedioic acid
Conditions | Yield |
---|---|
heating, 18 h; | A n/a B 40% C n/a |
heating, 18 h; | A n/a B 40% C n/a |
furfural
A
5-hydroxy-2-(5H)-furanone
B
2-furanoic acid
C
formic acid
D
malic acid
E
succinic acid
F
2-buten-4-olide
G
maleic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide at 49.84℃; for 24h; | A n/a B n/a C n/a D n/a E 38% F 26% G 19.7% |
With dihydrogen peroxide In water at 49.84℃; for 3h; | A n/a B n/a C n/a D n/a E 12.2% F 16.9% G 7.3% |
furfural
A
5-hydroxy-2-(5H)-furanone
B
2-furanoic acid
C
formic acid
D
malic acid
E
succinic acid
F
2-buten-4-olide
G
maleic acid
H
(2E)-but-2-enedioic acid
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide In water at 49.84℃; for 3h; Reagent/catalyst; | A n/a B n/a C n/a D n/a E 9.1% F 16.6% G 34.4% H 5.8% |
5-hydroxymethyl-2-furfuraldehyde
A
glycolic Acid
B
5-hydroxymethyl-furan-2-carboxylic acid
C
malic acid
D
succinic acid
E
maleic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; | A 23% B 6% C 11% D 16% E 29% |
Conditions | Yield |
---|---|
With mercaptoethyl alcohol; tris(2,2’-bipyridine)ruthenium(II); Tris buffer; Paraquat; nicotinamide adenine dinucleotide phosphate; sodium hydrogencarbonate; manganese(ll) chloride In water under 767.6 Torr; for 8h; Irradiation; ferredoxin-NADP(1+) reductase, malic enzyme; | 24% |
With Tris buffer; Paraquat; NADP; 2-hydroxyethanethiol; cadmium(II) sulphide at 25℃; for 5h; Mechanism; Product distribution; Irradiation; malic enzyme, ferredoxin-NADP+-reductase; other photocatalyst; | |
With mercaptoethyl alcohol; tris(2,2’-bipyridine)ruthenium(II); malic enzyme; ferredoxin-NADP(+) reductase; Tris buffer; Paraquat; nicotinamide adenine dinucleotide phosphate; sodium hydrogencarbonate; manganese(ll) chloride In water under 767.6 Torr; Mechanism; Product distribution; Irradiation; rate of CO2 fixation as a function of illumination time; | |
With tris(2,2’-bipyridine)ruthenium(II); 1.9E-4 M MV(2+); NADP+; sodium hydrogencarbonate; 2-hydroxyethanethiol; manganese(ll) chloride; malic enzyme In water Irradiation; | |
With Tris buffer; Paraquat; NADP; 2-hydroxyethanethiol; cadmium(II) sulphide at 25℃; Irradiation; malic enzyme, ferredoxin-NADP+-reductase; |
Conditions | Yield |
---|---|
With water; palladium(II) bis(phosphine)monosulphide at 100℃; for 24h; | A 7% B 8% |
Conditions | Yield |
---|---|
With water for 0.333333h; argon plasma-jet; | 5.5% |
ethyl 2,3-dichloropropionate
ethanol
potassium cyanide
A
malic acid
B
(2E)-but-2-enedioic acid
Conditions | Yield |
---|---|
man kocht das Produkt mit Aetzkali; |
4,4,4-trichloro-3-hydroxybutyric acid
malic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide |
L-asparagine
A
malic acid
B
succinic acid
C
acetic acid
D
(2E)-but-2-enedioic acid
Conditions | Yield |
---|---|
bei der Einw. von Bac.fluorescens; Produkt5:Kohlendioxyd; |
Conditions | Yield |
---|---|
Gleichgewicht; |
Conditions | Yield |
---|---|
Dinatriumsalz reagiert.Hydrolysis; l(-)-chlorosuccinic acid; |
bromosuccinic acid
malic acid
Conditions | Yield |
---|---|
With water | |
With water; silver(l) oxide | |
With quinoline; water | |
With TlOH; water |
Conditions | Yield |
---|---|
With potassium disulphite; water at 100℃; | |
With potassium disulphite; water at 100℃; inactive sulfosuccinic acid; |
iodo-succinic acid
malic acid
Conditions | Yield |
---|---|
With silver(l) oxide des Lacton entsteht; | |
With silver(l) oxide des Lacton entsteht; |
malic acid
2,2-dimethoxy-propane
5(R,S)-Carboxymethyl-2,2-dimethyl-4-oxo-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
With pyridinium p-toluenesulfonate at 20℃; for 32h; | 90.7% |
With toluene-4-sulfonic acid In dichloromethane at 25℃; for 4h; | 52.4% |
Conditions | Yield |
---|---|
Stage #1: metformin hydrochloride With sodium hydroxide In water; acetonitrile at 20℃; Stage #2: malic acid In water; acetonitrile at 20℃; Product distribution / selectivity; | 100% |
Stage #1: metformin hydrochloride With sodium hydroxide In tetrahydrofuran; water at 20℃; Stage #2: malic acid In water; acetone at 20℃; Product distribution / selectivity; | 100% |
Stage #1: metformin hydrochloride With sodium hydroxide In water; acetonitrile at 20℃; Stage #2: malic acid In water; acetonitrile at 20℃; Product distribution / selectivity; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; | 100% |
In tetrahydrofuran Product distribution / selectivity; |
Conditions | Yield |
---|---|
With sulfuric acid at 110℃; for 3h; Inert atmosphere; Cooling with ice; | 100% |
With sulfuric acid at 80 - 90℃; for 3h; | 92% |
Stage #1: 2.6-diaminopyridine; malic acid With sulfuric acid at 110℃; Inert atmosphere; Cooling with ice; Stage #2: With ammonium hydroxide In water pH=8; Cooling with ice; | 87% |
malic acid
Conditions | Yield |
---|---|
In ethanol; dichloromethane at 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In methanol for 1h; Product distribution / selectivity; Reflux; | 99.51% |
In methanol at 40℃; | 93% |
In methanol at 20 - 40℃; for 2h; Large scale; | 93% |
malic acid
(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-ylpropyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one
(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one malate
Conditions | Yield |
---|---|
In methanol; water; acetonitrile at 20 - 50℃; Darkness; | 99% |
Conditions | Yield |
---|---|
In water at 95℃; | 99% |
2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione
malic acid
Conditions | Yield |
---|---|
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione With methylamine In ethanol; water at 60℃; for 2h; Stage #2: malic acid In ethanol; water | 98.8% |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 120℃; for 12h; | 98% |
With sulfuric acid at 110℃; for 3h; | 97% |
With sulfuric acid at 110℃; for 3h; Cooling with ice; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2.6-diaminopyridine; malic acid With sulfuric acid at 110℃; Stage #2: With sodium nitrite at 0 - 5℃; Cooling with ice; | 98% |
malic acid
tebuconazole
Conditions | Yield |
---|---|
In methanol at 20℃; | 98% |
malic acid
(R)-tylophorine
Conditions | Yield |
---|---|
In methanol; dichloromethane at 20℃; | A 98% B 97% |
malic acid
tegaserod
Conditions | Yield |
---|---|
In ethanol at 20 - 60℃; | 97.6% |
Conditions | Yield |
---|---|
With sulfuric acid at 115℃; for 1h; | 97% |
2,3,6,7-Tetramethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene
malic acid
NK-007
Conditions | Yield |
---|---|
In methanol; chloroform at 40 - 45℃; | 97% |
In methanol; chloroform | 97% |
In methanol; chloroform at 40 - 50℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
In n-heptane at 100 - 120℃; for 6h; Inert atmosphere; | 97% |
In n-heptane at 100 - 120℃; for 8h; Inert atmosphere; | 374 g |
Conditions | Yield |
---|---|
Stage #1: malic acid With trifluoroacetic anhydride at 0℃; for 3h; Inert atmosphere; Stage #2: benzyl alcohol at 20℃; for 4h; Inert atmosphere; | 96.7% |
Conditions | Yield |
---|---|
96% | |
In neat (no solvent) at 200℃; for 4h; Inert atmosphere; | 96.6% |
at 180℃; for 4h; Temperature; Inert atmosphere; | 88% |
malic acid
tegaserod
Conditions | Yield |
---|---|
In isopropyl alcohol at 20 - 75℃; for 20h; | 96.3% |
Conditions | Yield |
---|---|
With sulfuric acid | 96% |
With sulfuric acid at 20℃; -chloralide; |
Conditions | Yield |
---|---|
With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) at 110℃; Fischer-Speier Esterification; Flow reactor; | 96% |
With acetyl chloride at 20℃; Esterification; | 90% |
With carbon dioxide at 180℃; under 20686.5 Torr; for 5h; | 86.3% |
Conditions | Yield |
---|---|
With sulfuric acid; toluene-4-sulfonic acid In pentane for 36h; Heating; | 96% |
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 96% |
Conditions | Yield |
---|---|
In ethanol at 0℃; for 2h; Product distribution / selectivity; | 95.51% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4h; Heating; | 95% |
With 5-sulfosalicylic Acid In benzene |
The Molecular Structure of DL-Malic acid (CAS NO.617-48-1):
Empirical Formula: C4H6O5
Molecular Weight: 134.0874
IUPAC Name: 2-hydroxybutanedioic acid
Appearance: white crystalline powder
Nominal Mass: 134 Da
Average Mass: 134.0874 Da
Monoisotopic Mass: 134.021523 Da
Index of Refraction: 1.529
Molar Refractivity: 25.2 cm3
Molar Volume: 81.6 cm3
Surface Tension: 86.2 dyne/cm
Density: 1.641 g/cm3
Flash Point: 153.4 °C
Enthalpy of Vaporization: 63.43 kJ/mol
Boiling Point: 306.4 °C at 760 mmHg
Vapour Pressure: 7.19E-05 mmHg at 25°C
Product Categories: MalicAcidSeries
Solubility methanol: 0.1 g/mL, clear, colorless
Stability: Stable. Incompatible with strong oxidizing agents, strong bases, amines, alkali metals, carbonates
Synonyms: (+/-)-2-Hydroxysuccinic acid ; (+/-)-Hydroxybutanedioic acid ; (+/-)-Hydroxysuccinic acid ; Dl-2-hydroxybutanedioic acid ; Dl-hyroxybutanedioic acid ; Dl-hydroxysuccinic acid ; Dl-hydroxysucoinic acid ; Dl(+/-)-malic acid
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 50mg/kg (50mg/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. | |
mouse | LD50 | oral | 1600mg/kg (1600mg/kg) | Kodak Company Reports. Vol. #82-0458, | |
rat | LD50 | intraperitoneal | 100mg/kg (100mg/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. |
Hazard Codes: Xn
Risk Statements: 22-37/38-41-42/43-34
R22: Harmful if swallowed
R37/38: Irritating to respiratory system and skin
R41: Risk of serious damage to the eyes
R42/43: May cause sensitization by inhalation and skin contact
R34: Causes burns
Safety Statements: 26-39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S39: Wear eye / face protection
WGK Germany: 1
RTECS: ON7175000
Product Categories: MalicAcidSeries
Personal Protection:Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
Fire Fighting:Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing media: Use agent most appropriate to extinguish fire. In case of fire use water spray, dry chemical, carbon dioxide, or appropriate foam.
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