Conditions | Yield |
---|---|
With calcium In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; under 750.075 Torr; for 1.5h; Reagent/catalyst; | 99.3% |
Stage #1: 2-methylenesuccinic acid With acetic anhydride at 80℃; Stage #2: at 230℃; under 262.526 Torr; for 4h; | 94% |
4Cs(1+)*SiW12O40(4-) = Cs4{SiW12O40} at 170 - 200℃; under 50 - 100 Torr; for 5.5h; Product distribution / selectivity; | 92.5% |
Conditions | Yield |
---|---|
With trifluoroacetic anhydride at 20℃; Inert atmosphere; | 99% |
With niobium(V) oxide hydrate In o-xylene at 160℃; for 72h; Inert atmosphere; Molecular sieve; | 94% |
With phosphorus pentoxide In chloroform for 48h; Reflux; | 80% |
1,3,5-Trioxan
succinic acid anhydride
A
methyl hydrogen succinate
B
citraconic acid anhydride
C
carbon dioxide
Conditions | Yield |
---|---|
With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor; | A 7% B 43% C 16% |
formaldehyd
Dimethyl succinate
A
succinic acid anhydride
B
methyl hydrogen succinate
C
citraconic acid anhydride
D
carbon dioxide
Conditions | Yield |
---|---|
With gamma-alumina In methanol; water at 380℃; under 3750.38 Torr; Kinetics; Concentration; Temperature; Stobbe Condensation; Autoclave; Flow reactor; | A 8% B 18% C 30% D 10% |
1,3,5-Trioxan
methyl hydrogen succinate
A
succinic acid anhydride
B
citraconic acid anhydride
C
carbon dioxide
D
Dimethyl succinate
Conditions | Yield |
---|---|
With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor; | A 9% B 23% C 15% D 30% |
1,3,5-Trioxan
Dimethyl succinate
A
succinic acid anhydride
B
methyl hydrogen succinate
C
citraconic acid anhydride
D
carbon dioxide
Conditions | Yield |
---|---|
With gamma-alumina at 380℃; under 3750.38 Torr; Temperature; Pressure; Stobbe Condensation; Autoclave; Flow reactor; | A 8% B 19% C 26% D 18% |
(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
A
citraconic acid anhydride
B
(Z)-(3-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
C
4-nitro-aniline
Conditions | Yield |
---|---|
In tetrahydrofuran for 24h; Reflux; | A 9% B n/a C 22% |
Conditions | Yield |
---|---|
bei der Destillation; |
2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid
citraconic acid anhydride
Conditions | Yield |
---|---|
beim Destillieren; |
Conditions | Yield |
---|---|
at 210℃; |
Conditions | Yield |
---|---|
With acetyl chloride at 100℃; beim Erhitzen im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 83 - 89℃; under 15 Torr; Heating; | 4.9 g |
methoxymethyl-succinic acid
citraconic acid anhydride
Conditions | Yield |
---|---|
at 210 - 230℃; durch Destillation; | |
at 210 - 230℃; beim Destillieren; |
Conditions | Yield |
---|---|
durch Destillation; | |
With 2,3-Dimethylaniline | |
bei der Destillation; |
citraconic acid anhydride
anthracene-citraconic anhydride adduct
propionic acid
A
citraconic acid anhydride
B
anthracene
Conditions | Yield |
---|---|
at 142 - 143℃; Rate constant; Dissoziation; | |
at 131.5 - 143℃; Equilibrium constant; Dissoziation; |
Conditions | Yield |
---|---|
bei der Destillation; |
2,5-bis<(trimethylsilyl)oxy>-3-methylfuran
citraconic acid anhydride
Conditions | Yield |
---|---|
With bromine at -78℃; Rate constant; iodine at 0 deg C; |
citraconic acid anhydride
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; water for 0.333333h; Equilibrium constant; Ambient temperature; pH = 10.0; |
citric acid
A
diethyl 3-hydroxypentanedioate
B
Mesaconic acid
C
1 propene 1,2,3 tricarboxylic acid
D
2-methylenesuccinic acid
E
citraconic acid anhydride
F
itaconic acid anhydride
Conditions | Yield |
---|---|
With Sn/Pb solder at 150 - 210℃; |
Conditions | Yield |
---|---|
With oxygen; P/Fe In water at 200℃; Yield given. Yields of byproduct given; |
2-oxo-propionic acid
A
citraconic acid anhydride
B
carbon dioxide
C
acetic acid
Conditions | Yield |
---|---|
With oxygen; P/Fe In water at 200℃; Product distribution; var. temp.; |
Conditions | Yield |
---|---|
With lithium perchlorate In diethyl ether Rate constant; Equilibrium constant; Ambient temperature; t1/2 = 4.4 h; | |
at 40℃; Equilibrium constant; Rate constant; t1/2 = 3.3 h; | |
at 20℃; Equilibrium constant; Rate constant; t1/2 = 52 h; |
A
(2-furyl)methyl alcohol
B
cyclohexenone
C
citraconic acid anhydride
D
3,4-dihydro-6-methyl-2H-pyran-2-one
Conditions | Yield |
---|---|
With air at 400 - 450℃; Oxidation; Formation of xenobiotics; |
citraconic acid anhydride
Conditions | Yield |
---|---|
at 250℃; |
Conditions | Yield |
---|---|
under 30 - 40 Torr; Eintragen in ein auf 300grad erhitztes Kupfergefaess; |
(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione
A
citraconic acid anhydride
Conditions | Yield |
---|---|
at 200℃; unter Stickstoff; |
Conditions | Yield |
---|---|
With sulfuric acid for 12h; Heating; | 100% |
With sulfuric acid Heating; | 90% |
With sulfuric acid for 12h; Heating; | 75% |
citraconic acid anhydride
4-methoxy-benzylamine
1-(4-Methoxy-benzyl)-3-methyl-pyrrole-2,5-dione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 5h; | 100% |
In toluene for 13h; Heating; | 80% |
citraconic acid anhydride
cyclopenta-1,3-diene
(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione
Conditions | Yield |
---|---|
In Petroleum ether at 20℃; Diels-Alder Cycloaddition; | 99% |
In chloroform at 0 - 20℃; Diels-Alder Cycloaddition; Darkness; | 92% |
With lithium perchlorate In diethyl ether for 3h; Ambient temperature; | 90% |
With bis(trifluoromethane)sulfonimide lithium In acetone at 25℃; for 2.5h; Cycloaddition; Diels-Alder reaction; | 99 % Spectr. |
In diethyl ether at 20℃; for 16h; |
Conditions | Yield |
---|---|
In acetone | 99% |
Conditions | Yield |
---|---|
In toluene for 48h; Diels-Alder reaction; Heating; | 99% |
citraconic acid anhydride
(R)-(+)-3-methyldihydrofuran-2,5-dione
Conditions | Yield |
---|---|
With bis(norbornadiene)rhodium(l)tetrafluoroborate; C46H38F6FeN2P2S(2+); hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 1.16667h; Glovebox; Autoclave; enantioselective reaction; | 99% |
With 1,4-dihydronicotinamide adenine dinucleotide; sodium phosphate buffer; Marchantia polymorpha p68 reductase at 35℃; for 4h; pH=7.0; | |
With C31H42IrNOP(1+)*C32H12BF24(1-); hydrogen In dichloromethane at 20℃; under 7500.75 Torr; for 18h; Pressure; Autoclave; High pressure; enantioselective reaction; | n/a |
Conditions | Yield |
---|---|
With acetic acid for 48h; Reflux; | 99% |
Conditions | Yield |
---|---|
In water at 20℃; | 98% |
1,3-di(aminomethyl)benzene
citraconic acid anhydride
1,3-bis(citraconimidomethyl)benzol
Conditions | Yield |
---|---|
With acetic acid In toluene at 110℃; for 5h; Temperature; Reagent/catalyst; Solvent; | 97.5% |
With acetic acid at 110℃; for 4h; Temperature; Time; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid | 97% |
ethene
citraconic acid anhydride
1-methyl-3-oxabicyclo[3.2.0]heptane-2,4-dione
Conditions | Yield |
---|---|
With thio-xanthene-9-one In ethyl acetate at 25℃; under 9000.9 Torr; for 0.00833333h; Concentration; Solvent; Flow reactor; UV-irradiation; | 96% |
With thio-xanthene-9-one In ethyl acetate at 25℃; under 9000.9 Torr; for 10h; Catalytic behavior; Concentration; Solvent; Time; UV-irradiation; Flow reactor; | 96% |
With benzophenone In acetone at 10 - 15℃; for 6h; Irradiation; | 69% |
citraconic acid anhydride
C16H12N4S2
Conditions | Yield |
---|---|
In chloroform at 80℃; for 18h; | 96% |
In chloroform at 80℃; |
Conditions | Yield |
---|---|
With acetic acid In toluene for 1h; Inert atmosphere; Reflux; | 96% |
methanol
citraconic acid anhydride
2-hydroxy-5-chloro-aniline
Methyl α-(6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)acetate
Conditions | Yield |
---|---|
With triethylamine for 5h; Heating; | 95% |
citraconic acid anhydride
benzylamine
1-Benzyl-3-methyl-2,5-dihydropyrrole-2,5-dione
Conditions | Yield |
---|---|
at 20 - 120℃; Inert atmosphere; Neat (no solvent); | 95% |
With acetic acid for 2h; Heating; | 92% |
With acetic acid for 12h; Heating; | 90% |
citraconic acid anhydride
anthranilic acid
2-(3-methyl-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid
Conditions | Yield |
---|---|
at 140℃; for 20h; | 95% |
Conditions | Yield |
---|---|
In ethyl acetate | 95% |
Cyclohexyl isocyanide
citraconic acid anhydride
dimethyl acetylenedicarboxylate
dimethyl 2-(cyclohexylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; regiospecific reaction; | 95% |
citraconic acid anhydride
(9S)-9-Methyl-1-phenylbicyclo<4.3.0>nona-1(2),3(4)-diene
A
C21H22O3
B
C21H22O3
Conditions | Yield |
---|---|
In dichloromethane under 4875390 Torr; for 240h; Ambient temperature; | A 1% B 94% |
citraconic acid anhydride
Conditions | Yield |
---|---|
In tetrahydrofuran the anhydride is added to the starting complex in THF, stored at -20°C for 6 d; the solvent is removed, the crude solid is triturated with ether, driedin vac., elem. anal.; | 94% |
tert-butylisonitrile
citraconic acid anhydride
dimethyl acetylenedicarboxylate
dimethyl 2-(tert-butylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; regiospecific reaction; | 94% |
citraconic acid anhydride
emetine dihydrochloride
Conditions | Yield |
---|---|
With triethylamine In chloroform for 0.0833333h; | 94% |
L-valine
citraconic acid anhydride
(S)-3-methyl-2-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid
Conditions | Yield |
---|---|
With acetic acid at 120℃; for 1h; Microwave irradiation; Sealed tube; | 94% |
In acetic acid at 120℃; for 1h; Microwave irradiation; | 94% |
Conditions | Yield |
---|---|
In toluene for 2h; Reflux; | 94% |
Conditions | Yield |
---|---|
With acetic acid for 48h; Reflux; | 93% |
citraconic acid anhydride
Conditions | Yield |
---|---|
With acetic acid for 12h; Reflux; | 93% |
citraconic acid anhydride
4-methoxy-aniline
A
(Z)-(4-(4-methoxyphenylamino)-2-methyl-4-oxo)but-2-enoic acid
B
(Z)-3-(4-Methoxy-phenylcarbamoyl)-3-methyl-acrylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; Reflux; regioselective reaction; | A 92% B n/a |
In diethyl ether at 10 - 15℃; for 0.5h; Yield given; | |
In diethyl ether at 10 - 15℃; for 0.5h; Yields of byproduct given. Title compound not separated from byproducts; |
methanol
citraconic acid anhydride
2-hydroxy-5-nitroaniline
(2-Methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine Heating; | 92% |
IUPAC Name: 3-Methylfuran-2,5-dione(616-02-4)
Synonyms: 2,5-Furanedione, 3-methyl ; 3-Methyl-2,5-furandione ; 3-Methyl-5-furandione ; 3-methyl-furan-2,5-dione ; 3-Methylmaleic anhydride ; 3-Methylmaleicanhydride ; Alpha-Methylmaleic anhydride ; Alpha-methylmaleicanhydride
CAS: 616-02-4
MF: C5H4O3
MW: 112.08
MS:
EINECS: 210-459-0
Product Categories: Rubber & Plastic Auxiliary Agent ; Anhydride Monomers ; Monomers ; Polymer Science ; Carbonyl Compounds ; Carboxylic Acid Anhydrides ; Organic Building Blocks
Mol File: 616-02-4.mol
MP:6-10 °C(lit.)
Surface Tension: 42.9 dyne/cm
Density: 1.333 g/cm3
Flash Point: 96.8 °C
Enthalpy of Vaporization: 44.78 kJ/mol
Boiling Point: 211.5 °C at 760 mmHg
Vapour Pressure: 0.182 mmHg at 25°C
Refractive index n20/D 1.471(lit.)
storage temp: Store at RT.
Water Solubility: decomposes
Sensitive: Moisture Sensitive
BRN : 1835
Citraconic anhydride (616-02-4) used as raw materials in the production of organic synthesis (preparation clothing Ping acid, clothing Ping acid amide).
Citraconic anhydride (616-02-4) is also known as butyrolactone - β - carboxylic acid, tetrahydrofuran oxo-3-carboxylic acid. Gain Citraconic anhydride (Citraconic anhydride) by the way of distillation .React with alkali to get itamalic acid,and then with hydrobromic acid to produce methyl bromide succinic acid,which heated with Ammonia of methanol ,producing HOOCCH(CH2OH) CH2CONH2 ,then treat with Silver oxide Ag2O for the product of succinic acid methyl bromide .
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | skin | 1mL/kg (1mL/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. | |
rabbit | LD50 | skin | 218mg/kg (218mg/kg) | Shell Chemical Company. | |
rat | LD50 | oral | 2600mg/kg (2600mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. |
Hazard Codes: T
Risk Statements: 23/24/25-36/37/38-42/43-34
23/24/25: Toxic by inhalation, in contact with skin and if swallowed
36/37/38: Citraconic anhydride (616-02-4) is irritating to eyes, respiratory system and skin
42/43: May cause sensitization by inhalation and skin contact
34: Causes burns
Safety Statements: 26-36/37/39-45-28
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
RTECS: GE6825000
F: 10-21
HazardClass: 6.1
PackingGroup: III
HS Code: 29171990
Citraconic anhydride (616-02-4) is crystallization.
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