Conditions | Yield |
---|---|
With acetic anhydride; zinc In toluene at 40 - 86℃; for 48h; Reagent/catalyst; Inert atmosphere; chemoselective reaction; | 100% |
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In tetrahydrofuran; dichloromethane at 60℃; under 37503.8 Torr; for 24h; | 99% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.0833333h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With acetic anhydride at 80℃; for 2h; | 100% |
at 240℃; under 180 Torr; Rate constant; Equilibrium constant; var. temperature, var. pressure; | 97% |
2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In butryonitrile for 12h; Reflux; | 96% |
Conditions | Yield |
---|---|
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] In 1,4-dioxane at 90℃; under 43958.7 Torr; for 3h; | 98% |
Conditions | Yield |
---|---|
In toluene Irradiation (UV/VIS); (Ar); addn. of maleic anhydride to soln. of W-compd. in toluene portionwise, irradn. (500 W Hg-lamp, 550 nm, 58 h); removal of solid product by centrifugation, recrystn. (CH3CN); elem. anal.; | A 95% B 22% |
Conditions | Yield |
---|---|
With nitromethane; copper(l) chloride at 75℃; for 5h; Concentration; Temperature; | 91% |
oxirane
carbon monoxide
A
succinic acid anhydride
B
β-Propiolactone
Conditions | Yield |
---|---|
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere; | A 8% B 88% |
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere; | A 13% B 81% |
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 31029.7 Torr; for 3h; Glovebox; Inert atmosphere; | A 8 %Spectr. B 88 %Spectr. |
Conditions | Yield |
---|---|
With pyridine; 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; water In toluene for 0.5h; Ambient temperature; | 85% |
With diethyl ether; sodium acetate | |
With oxalic acid |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In water for 50h; pH=10; Reflux; | A 81% B 19% |
Conditions | Yield |
---|---|
With hydrogen at 180℃; under 7500.75 Torr; for 2h; Pressure; Temperature; | A n/a B 79.87% |
With hydrogen at 150℃; under 7500.75 Torr; | A n/a B 78.36% |
With hydrogen at 250℃; Conversion of starting material; |
tetrahydrofuran
A
4-butanolide
B
5-hydroxydihydrofuran-2(3H)-one
C
succinic acid anhydride
Conditions | Yield |
---|---|
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Inert atmosphere; | A 69% B 22% C 5% |
oxirane
carbon monoxide
A
succinic acid anhydride
B
acetaldehyde
Conditions | Yield |
---|---|
In 1,4-di-tert-butylbenzene at 20 - 80℃; under 10343.2 - 31029.7 Torr; for 0.666667h; | A 62.7% B 7.9% |
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] at 80℃; under 31029.7 Torr; for 2h; Catalytic behavior; Pressure; Reagent/catalyst; Glovebox; Inert atmosphere; | A 68.8 %Spectr. B 5.4 %Spectr. |
A
succinic acid anhydride
B
Ni(CO)2{1,2-bis(diphenylphosphino)ethane}
Conditions | Yield |
---|---|
With carbon monoxide In dichloromethane Schlenk tube contg. CH2Cl2 soln. of educt evacuated and 1 atm of CO introduced; analyzed by GLC, GC-mass, and IR; | A 55% B n/a |
Conditions | Yield |
---|---|
With titanium(IV) oxide In acetonitrile for 18h; UV-irradiation; Inert atmosphere; | A 16% B 54% |
Conditions | Yield |
---|---|
With triethyl phosphate; water; vanadium-containing catalyst at 393 - 455℃; Gas phase; | 51.5% |
With vanadium phosphorus oxide supported on TiO2 or SiO2; oxygen at 450℃; | |
With V-P-Co-O at 450℃; for 8.33333E-05h; Product distribution; Rate constant; various catalysts under different conditions; |
maleic anhydride
A
4-butanolide
B
succinic acid anhydride
C
butan-1-ol
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Autoclave; | A 49.73% B 35.07% C 12.66% |
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% |
maleic anhydride
Trimethylacetic acid
A
succinic acid anhydride
B
2-tert-butylsuccinic anhydride
Conditions | Yield |
---|---|
With titanium(IV) oxide In acetonitrile for 26h; UV-irradiation; Inert atmosphere; | A 20% B 16% |
2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione
A
succinic acid anhydride
Conditions | Yield |
---|---|
With water In acetone at 22℃; for 0.5h; | A n/a B 15% |
pyridine
diethyl ether
hydrogen cyanide
succinoyl dichloride
A
succinic acid anhydride
B
Succinyl Dicyanide
Conditions | Yield |
---|---|
at 20℃; Hydrogenation; |
tetrachloromethane
peroxydicuccinic acid
A
succinic acid anhydride
B
Adipic acid
chloroform
1,2-diisopropylidene-cyclobutane
A
Tetramethyl-[1,2,4,5]tetroxan
B
succinic acid anhydride
C
acetone
Conditions | Yield |
---|---|
at -20℃; bei der Ozonisation; |
(E)-1,2-dichloro-1-ethoxy-ethene
succinic acid
A
succinic acid anhydride
B
chloroacetic acid ethyl ester
Conditions | Yield |
---|---|
5-6 h Erhitzen der Schmelze; anschliessend Eindampfen mit konz. HCl; |
ethyl 3-(chloroformyl)propionate
A
succinic acid anhydride
B
chloroethane
Conditions | Yield |
---|---|
bei der Destillation unter vermindertem Druck; |
Conditions | Yield |
---|---|
at 300℃; |
Conditions | Yield |
---|---|
beim Schuetteln der waessr. Loesung von bernsteinsaurem Natrium; | |
at 120 - 150℃; unter Druck; |
pyrrolidine
succinic acid anhydride
4-oxo-4-(1-pyrrolidinyl)butanoic acid
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 100% |
In chloroform for 1h; Heating; | 83% |
With diethyl ether | |
Reflux; | |
In toluene for 2.5h; Reflux; |
Conditions | Yield |
---|---|
at 20℃; | 100% |
at 64 - 68℃; for 3.8h; | 98.5% |
at 70℃; for 2h; | 98% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere; | 100% |
at 120℃; | |
In pyridine at 20℃; |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere; | 100% |
With dmap In toluene at 110℃; for 1.5h; | 79.4% |
With pyridine | 42% |
succinic acid anhydride
Cholestanol
succinic acid mono-3β-cholestanyl ester
Conditions | Yield |
---|---|
With triethylamine In pyridine; dichloromethane for 144h; | 100% |
With dmap; triethylamine In ethyl acetate at 95℃; for 5h; | 47.8% |
With pyridine |
succinic acid anhydride
cyclohexylamine
4-(cyclohexylamine)-4-oxobutanoic acid
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; cyclohexylamine In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h; | 100% |
In 1,4-dioxane at 80℃; for 0.5h; | 90% |
In dichloromethane at 20℃; for 0.333333h; | 89% |
succinic acid anhydride
2-(3,4-dimethoxyphenyl)-ethylamine
N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
Conditions | Yield |
---|---|
With acetic acid for 24h; Reflux; | 100% |
Stage #1: succinic acid anhydride; 2-(3,4-dimethoxyphenyl)-ethylamine In ethyl acetate at 20℃; for 0.5h; Stage #2: With acetyl chloride In toluene for 1h; Reflux; | 84% |
With benzene und Erhitzen des Reaktionsprodukts mit Acetanhydrid unter Zusatz von wenig Pyridin; |
succinic acid anhydride
phenylhydrazine
4-oxo-4-(2-phenylhydrazinyl)butanoic acid
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 24h; | 100% |
With ethanol |
succinic acid anhydride
erythromycin
2'-O-(3-carboxypropanoyl) erythromycin
Conditions | Yield |
---|---|
In acetone at 50℃; | 100% |
With acetone | |
With dichloromethane |
succinic acid anhydride
tert-butylamine
4-(tert-butylamino)-4-oxobutanoic acid
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; tert-butylamine In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h; | 100% |
In dichloromethane at 20℃; for 1h; | 52% |
Stage #1: succinic acid anhydride; tert-butylamine In dichloromethane at 20℃; for 1h; Stage #2: With sodium hydroxide In water at 20℃; for 2h; Stage #3: With hydrogenchloride In water at 0℃; | 52% |
Conditions | Yield |
---|---|
With dmap In toluene for 5h; Heating; | 100% |
With dmap In toluene for 4h; Heating; | 90% |
With dmap In toluene for 4h; Reflux; | 89% |
succinic acid anhydride
2-(Trimethylsilyl)ethanol
4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid
Conditions | Yield |
---|---|
With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine In toluene for 1.5h; Heating; | 100% |
With dmap In toluene for 14h; Reflux; | 99% |
With pyridine In dichloromethane | 81% |
succinic acid anhydride
4-amino-phenol
4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
Conditions | Yield |
---|---|
With sodium dodecyl-sulfate In methanol; water at 20℃; for 0.583333h; | 100% |
With sodium dodecyl-sulfate In water | 87% |
In water at 50℃; | 86% |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 ,1977,p. 265.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Succinic anhydride, its cas register number is 108-30-5. It also can be called 2,5-Dioxotetrahydrofuran; Dihydro-2,5-diketotetrahydrofuran; Dihydro-2,5-furandione; Butanedioic anhydride; Succinic acid anhydride; Succinyloxide; Tetrahydro-2,5-dioxofuran; and SAA. It is an organic compound with the molecular formula C4H4O3. This colorless solid is the acid anhydride of succinic acid. Succinic anhydride is used as a sizing agent or wet strength additive in paper production.
Physical properties about Succinic anhydride are: (1)ACD/LogP: -0.89; (2)ACD/LogD (pH 5.5): -0.89; (3)ACD/LogD (pH 7.4): -0.89; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 7.81; (7)ACD/KOC (pH 7.4): 7.81; (8)#H bond acceptors: 3; (9)Index of Refraction: 1.47; (10)Molar Refractivity: 20.313 cm3; (11)Molar Volume: 72.755 cm3; (12)Polarizability: 8.053 10-24cm3; (13)Surface Tension: 47.7210006713867 dyne/cm; (14)Density: 1.375 g/cm3; (15)Flash Point: 122.071 °C; (16)Enthalpy of Vaporization: 49.871 kJ/mol; (17)Boiling Point: 260.999 °C at 760 mmHg; (18)Vapour Pressure: 0.0120000001043081 mmHg at 25°C
Preparation of Succinic anhydride: Succinic anhydride has been prepared from succinic acid with phosphorus pentachloride, phosphorus oxychloride, phosphorus pentoxide, thionyl chloride, acetyl chloride, or succinyl chloride; from barium or sodium succinate with benzoyl chloride, acetyl chloride, acetic anhydride, or benzophenone dichloride; from succinyl chloride and oxalic acid or sodium acetate; and from ethyl succinate and benzoyl chloride.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2;
(2)InChIKey=RINCXYDBBGOEEQ-UHFFFAOYSA-N;
(3)SmilesC1(OC(=O)CC1)=O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 1510mg/kg (1510mg/kg) | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0282-0433, |
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