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108-30-5

Basic Information
CAS No.: 108-30-5
Name: 2,5-Furandione,dihydro-
Molecular Structure:
Molecular Structure of 108-30-5 (2,5-Furandione,dihydro-)
Formula: C4H4O3
Molecular Weight: 100.07
Synonyms: Succinicanhydride (8CI);2,5-Diketotetrahydrofuran;Butanedioic anhydride;Dihydro-2,5-furandione;NSC 8518;Rikacid SA;Succinic acid anhydride;Succinylanhydride;Succinyl oxide;Tetrahydro-2,5-dioxofuran;Tetrahydro-2,5-furandione;Succinic anhydride;
EINECS: 203-570-0
Density: 1.375 g/cm3
Melting Point: 118-120 °C(lit.)
Boiling Point: 261 °C at 760 mmHg
Flash Point: 122.1 °C
Solubility: water: <0.1 g/100 mL at 21 oC (decomposes)
Appearance: fine white crystalline solid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36/37-22
Safety: 25
Transport Information:
PSA: 43.37000
LogP: -0.15000
Synthetic route
108-31-6

maleic anhydride

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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%
110-15-6

succinic acid

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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%
201230-82-2

carbon monoxide

75-56-9, 16033-71-9

methyloxirane

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] In 1,4-dioxane at 90℃; under 43958.7 Torr; for 3h;98%
108-31-6

maleic anhydride

WH2(η-cyclopentadienyl)2

A

108-30-5

succinic acid anhydride

B

(C5H5)2W(C4H2O3)

Conditions
ConditionsYield
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%
638-32-4

succinamic acid

18698-97-0

ortho-bromophenylacetic acid

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
With nitromethane; copper(l) chloride at 75℃; for 5h; Concentration; Temperature;91%
75-21-8

oxirane

201230-82-2

carbon monoxide

A

108-30-5

succinic acid anhydride

B

57-57-8

β-Propiolactone

Conditions
ConditionsYield
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.
543-20-4

succinoyl dichloride

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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
147-85-3

L-proline

A

123-56-8

Succinimide

B

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In water for 50h; pH=10; Reflux;A 81%
B 19%
108-31-6

maleic anhydride

A

96-48-0

4-butanolide

B

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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;
109-99-9

tetrahydrofuran

A

96-48-0

4-butanolide

B

50768-69-9

5-hydroxydihydrofuran-2(3H)-one

C

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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%
75-21-8

oxirane

201230-82-2

carbon monoxide

A

108-30-5

succinic acid anhydride

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
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.

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2)

A

108-30-5

succinic acid anhydride

B

15793-01-8

Ni(CO)2{1,2-bis(diphenylphosphino)ethane}

Conditions
ConditionsYield
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
108-31-6

maleic anhydride

625-45-6

2-methoxyacetic acid

A

108-30-5

succinic acid anhydride

B

(methoxymethyl)succinic anhydride

Conditions
ConditionsYield
With titanium(IV) oxide In acetonitrile for 18h; UV-irradiation; Inert atmosphere;A 16%
B 54%
106-97-8

n-butane

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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;
108-31-6

maleic anhydride

A

96-48-0

4-butanolide

B

108-30-5

succinic acid anhydride

C

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Autoclave;A 49.73%
B 35.07%
C 12.66%
50-00-0

formaldehyd

106-65-0

Dimethyl succinate

A

108-30-5

succinic acid anhydride

B

3878-55-5

methyl hydrogen succinate

C

616-02-4

citraconic acid anhydride

D

124-38-9

carbon dioxide

Conditions
ConditionsYield
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%
110-88-3

1,3,5-Trioxan

3878-55-5

methyl hydrogen succinate

A

108-30-5

succinic acid anhydride

B

616-02-4

citraconic acid anhydride

C

124-38-9

carbon dioxide

D

106-65-0

Dimethyl succinate

Conditions
ConditionsYield
With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor;A 9%
B 23%
C 15%
D 30%
110-88-3

1,3,5-Trioxan

106-65-0

Dimethyl succinate

A

108-30-5

succinic acid anhydride

B

3878-55-5

methyl hydrogen succinate

C

616-02-4

citraconic acid anhydride

D

124-38-9

carbon dioxide

Conditions
ConditionsYield
With gamma-alumina at 380℃; under 3750.38 Torr; Temperature; Pressure; Stobbe Condensation; Autoclave; Flow reactor;A 8%
B 19%
C 26%
D 18%
108-31-6

maleic anhydride

75-98-9

Trimethylacetic acid

A

108-30-5

succinic acid anhydride

B

52685-36-6

2-tert-butylsuccinic anhydride

Conditions
ConditionsYield
With titanium(IV) oxide In acetonitrile for 26h; UV-irradiation; Inert atmosphere;A 20%
B 16%
145178-53-6

2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione

A

108-30-5

succinic acid anhydride

B

(Z)-2,3-bis(trimethylsilyl)succinic anhydride

Conditions
ConditionsYield
With water In acetone at 22℃; for 0.5h;A n/a
B 15%
110-86-1

pyridine

60-29-7

diethyl ether

74-90-8

hydrogen cyanide

543-20-4

succinoyl dichloride

A

108-30-5

succinic acid anhydride

B

63979-84-0

Succinyl Dicyanide

108-31-6

maleic anhydride

141-78-6

ethyl acetate

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
at 20℃; Hydrogenation;
56-23-5

tetrachloromethane

123-23-9

peroxydicuccinic acid

A

108-30-5

succinic acid anhydride

B

124-04-9

Adipic acid

67-66-3

chloroform

3642-16-8

1,2-diisopropylidene-cyclobutane

A

1073-91-2

Tetramethyl-[1,2,4,5]tetroxan

B

108-30-5

succinic acid anhydride

C

67-64-1

acetone

Conditions
ConditionsYield
at -20℃; bei der Ozonisation;
42345-82-4

(E)-1,2-dichloro-1-ethoxy-ethene

110-15-6

succinic acid

A

108-30-5

succinic acid anhydride

B

105-39-5

chloroacetic acid ethyl ester

110-15-6

succinic acid

A

108-30-5

succinic acid anhydride

B

502-50-1

4-Ketopimelic acid

Conditions
ConditionsYield
5-6 h Erhitzen der Schmelze; anschliessend Eindampfen mit konz. HCl;
14794-31-1

ethyl 3-(chloroformyl)propionate

A

108-30-5

succinic acid anhydride

B

75-00-3

chloroethane

Conditions
ConditionsYield
bei der Destillation unter vermindertem Druck;
77341-67-4

L-menthylsuccinic acid

A

108-30-5

succinic acid anhydride

B

89-78-1

menthol

Conditions
ConditionsYield
at 300℃;
144-62-7

oxalic acid

543-20-4

succinoyl dichloride

108-30-5

succinic acid anhydride

110-15-6

succinic acid

108-24-7

acetic anhydride

108-30-5

succinic acid anhydride

Conditions
ConditionsYield
beim Schuetteln der waessr. Loesung von bernsteinsaurem Natrium;
at 120 - 150℃; unter Druck;
123-75-1

pyrrolidine

108-30-5

succinic acid anhydride

69338-35-8

4-oxo-4-(1-pyrrolidinyl)butanoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃;100%
In chloroform for 1h; Heating;83%
With diethyl ether
Reflux;
In toluene for 2.5h; Reflux;
108-30-5

succinic acid anhydride

67-56-1

methanol

3878-55-5

methyl hydrogen succinate

Conditions
ConditionsYield
at 20℃;100%
at 64 - 68℃; for 3.8h;98.5%
at 70℃; for 2h;98%
108-30-5

succinic acid anhydride

143-28-2

oleoyl alcohol

20060-41-7

oleyl hemisuccinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
at 120℃;
In pyridine at 20℃;
108-30-5

succinic acid anhydride

36653-82-4

1-Hexadecanol

50893-80-6

hexadecanol monosuccinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With dmap In toluene at 110℃; for 1.5h;79.4%
With pyridine42%
108-30-5

succinic acid anhydride

80-97-7

Cholestanol

84597-57-9

succinic acid mono-3β-cholestanyl ester

Conditions
ConditionsYield
With triethylamine In pyridine; dichloromethane for 144h;100%
With dmap; triethylamine In ethyl acetate at 95℃; for 5h;47.8%
With pyridine
108-30-5

succinic acid anhydride

108-91-8

cyclohexylamine

21451-32-1

4-(cyclohexylamine)-4-oxobutanoic acid

Conditions
ConditionsYield
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%
108-30-5

succinic acid anhydride

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

39662-45-8

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide

Conditions
ConditionsYield
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;
108-30-5

succinic acid anhydride

100-63-0

phenylhydrazine

14580-01-9

4-oxo-4-(2-phenylhydrazinyl)butanoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;100%
With ethanol
108-30-5

succinic acid anhydride

114-07-8

erythromycin

20057-07-2

2'-O-(3-carboxypropanoyl) erythromycin

Conditions
ConditionsYield
In acetone at 50℃;100%
With acetone
With dichloromethane
108-30-5

succinic acid anhydride

75-64-9

tert-butylamine

6622-06-6

4-(tert-butylamino)-4-oxobutanoic acid

Conditions
ConditionsYield
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%
108-30-5

succinic acid anhydride

107-18-6

allyl alcohol

3882-09-5

4-(allyloxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap In toluene for 5h; Heating;100%
With dmap In toluene for 4h; Heating;90%
With dmap In toluene for 4h; Reflux;89%
108-30-5

succinic acid anhydride

2916-68-9

2-(Trimethylsilyl)ethanol

93790-78-4

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid

Conditions
ConditionsYield
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 dichloromethane81%
108-30-5

succinic acid anhydride

123-30-8

4-amino-phenol

62558-67-2

4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid

Conditions
ConditionsYield
With sodium dodecyl-sulfate In methanol; water at 20℃; for 0.583333h;100%
With sodium dodecyl-sulfate In water87%
In water at 50℃;86%
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Consensus Reports

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.

Specification

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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