Product Name

  • Name

    ALLYLSUCCINIC ANHYDRIDE

  • EINECS
  • CAS No. 7539-12-0
  • Article Data5
  • CAS DataBase
  • Density 1.17
  • Solubility
  • Melting Point
  • Formula C7H8 O3
  • Boiling Point 143 °C / 17mmHg
  • Molecular Weight 140.139
  • Flash Point 115.9°C
  • Transport Information
  • Appearance
  • Safety Poison by skin contact. Moderately toxic by ingestion. A severe skin irritant. See also ANHYDRIDES and ALLYL COMPOUNDS. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Risk Codes R20/21/22; R36/37/38
  • Molecular Structure Molecular Structure of 7539-12-0 (ALLYLSUCCINIC ANHYDRIDE)
  • Hazard Symbols
  • Synonyms 2,5-Furandione,dihydro-3-(2-propenyl)- (9CI); Succinic anhydride, allyl- (6CI,7CI,8CI); Allysuccinic acid anhydride; Allylsuccinic acid anhydride; Allylsuccinic anhydride
  • PSA 43.37000
  • LogP 0.65220

Synthetic route

allyl succinic acid
5754-10-9

allyl succinic acid

allylsuccinic anhydride

allylsuccinic anhydride

Conditions
ConditionsYield
With acetyl chloride for 3h; Cyclization; Heating;85%
succinic acid anhydride

succinic acid anhydride

propene

propene

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

Conditions
ConditionsYield
With 4-methoxy-phenol; dimethyltin dichloride In toluene at 175 - 200℃; under 21307.1 - 32788.1 Torr; for 12 - 48h; Reactivity;41%
With 4-methoxy-phenol; Trichlorbutylstannan In toluene at 175℃; for 12h; Reactivity;
With 4-methoxy-phenol; dibutyltin chloride In toluene at 175℃; for 12h; Reactivity;
With 4-methoxy-phenol; cadmium(II) iodide In toluene at 200℃; for 12h; Reactivity;
maleic anhydride
108-31-6

maleic anhydride

propene
187737-37-7

propene

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

Conditions
ConditionsYield
With benzene at 250℃;
With benzene at 200℃;
maleic anhydride
108-31-6

maleic anhydride

propene
187737-37-7

propene

benzene
71-43-2

benzene

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

Conditions
ConditionsYield
at 250℃; under 54427.6 Torr;
3-((tert-butoxy)carbonyl)hex-5-enoic acid
308349-49-7

3-((tert-butoxy)carbonyl)hex-5-enoic acid

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C
2: 85 percent / AcCl / 3 h / Heating
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

3-(3-dimethylamino-propylcarbamoyl)-hex-5-enoic acid

3-(3-dimethylamino-propylcarbamoyl)-hex-5-enoic acid

Conditions
ConditionsYield
In dichloromethane at 25℃; for 18h;100%
methanol
67-56-1

methanol

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

dimethyl 2-(prop-2-en-1-yl)butanedioate
1069-40-5

dimethyl 2-(prop-2-en-1-yl)butanedioate

Conditions
ConditionsYield
With hydrogenchloride; silica gel In water at 70℃; Schlenk technique;100%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

3-(perfluorooctyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride

3-(perfluorooctyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 72℃; for 2h;99.6%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride
674786-54-0

3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 70 - 92℃; for 7h;99.6%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

allyl succinic acid
5754-10-9

allyl succinic acid

Conditions
ConditionsYield
With water at 110℃; Inert atmosphere; Schlenk technique;98.5%
With sodium carbonate
1,4-bis(dimethylsilyl)benzene
2488-01-9

1,4-bis(dimethylsilyl)benzene

allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

C4H4O3*C24H34O6Si2

C4H4O3*C24H34O6Si2

Conditions
ConditionsYield
Stage #1: 1,4-bis(dimethylsilyl)benzene; allylsuccinic anhydride With dihydrogen hexachloroplatinate In ethanol; toluene at 70℃;
Stage #2: 1,4-bis(dimethylsilyl)benzene In ethanol; toluene at 70 - 90℃; for 3.33333h;
95%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

n-butylguanidine hydrochloride
19341-56-1

n-butylguanidine hydrochloride

1,1'-((butylimino)methylene)bis(3-allylpyrrolidine-2,5-dione)

1,1'-((butylimino)methylene)bis(3-allylpyrrolidine-2,5-dione)

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 5h; Reagent/catalyst; Inert atmosphere;85%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

1,3,3,5,5-hexamethyltrisiloxane
1189-93-1

1,3,3,5,5-hexamethyltrisiloxane

4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

C36H50N2O6Si3

C36H50N2O6Si3

Conditions
ConditionsYield
Stage #1: allylsuccinic anhydride; 1,3,3,5,5-hexamethyltrisiloxane With platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane at 90 - 110℃; for 1.5h; Inert atmosphere;
Stage #2: 4-vinyl benzylamine In toluene at 20℃; for 0.5h;
Stage #3: With pyridine; acetic anhydride In toluene at 60℃; for 2h;
81%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

trimethoxysilylethyl-1,1,3,3-tetramethyldisiloxane
137407-65-9

trimethoxysilylethyl-1,1,3,3-tetramethyldisiloxane

C16H34O7Si3
1313483-76-9

C16H34O7Si3

Conditions
ConditionsYield
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane at 100 - 110℃; for 2h; Inert atmosphere;76.7%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

2-(3-bromopropyl)-succinic anhydride

2-(3-bromopropyl)-succinic anhydride

Conditions
ConditionsYield
With dibenzoyl peroxide In water; toluene67.3%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

anthranilic acid
118-92-3

anthranilic acid

2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid

2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid

Conditions
ConditionsYield
at 145 - 160℃; under 0.1 Torr;63%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(Z)-3-[2,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]dihydrofuran-2,5-dione
1325764-23-5

(Z)-3-[2,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]dihydrofuran-2,5-dione

Conditions
ConditionsYield
With (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 60℃; for 6h; Inert atmosphere;59%
With AlEt3; (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3) In toluene 2 equiv. B2pin2, 60°C, 6 h;59%
With (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 60℃; for 6h; Inert atmosphere; stereoselective reaction;52%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

((3-allylfuran-2,5-diyl)bis(oxy))bis(tert-butyldimethylsilane)

((3-allylfuran-2,5-diyl)bis(oxy))bis(tert-butyldimethylsilane)

Conditions
ConditionsYield
Stage #1: allylsuccinic anhydride With triethylamine In diethyl ether at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: t-butyldimethylsiyl triflate In diethyl ether at 0 - 23℃; Inert atmosphere;
53%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

aluminium trichloride
7446-70-0

aluminium trichloride

benzene
71-43-2

benzene

A

3-oxo-5c(?)-phenyl-cyclohexane-r-carboxylic acid methyl ester

3-oxo-5c(?)-phenyl-cyclohexane-r-carboxylic acid methyl ester

B

2-phenacyl-4-phenyl-valeric acid methyl ester

2-phenacyl-4-phenyl-valeric acid methyl ester

C

4-methyl-1-oxo-1,2,3,4-tetrahydro-<2>naphthyl>-acetic acid methyl ester

4-methyl-1-oxo-1,2,3,4-tetrahydro-<2>naphthyl>-acetic acid methyl ester

Conditions
ConditionsYield
Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol;
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

1H,1H,2H,2H-Perfluorodecanethiol
34143-74-3

1H,1H,2H,2H-Perfluorodecanethiol

3-[3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-propyl]-dihydro-furan-2,5-dione
577732-49-1

3-[3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-propyl]-dihydro-furan-2,5-dione

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 50 - 88℃; for 2h;31.0 g
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

2-perfluorohexylethanethiol
34451-26-8

2-perfluorohexylethanethiol

[3-(perfluorohexylethanethia)]prop-1-yl-2-butane-1,4-dioic acid anhydride
577732-47-9

[3-(perfluorohexylethanethia)]prop-1-yl-2-butane-1,4-dioic acid anhydride

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In hexane at 70℃; for 18h;4.3 mmol
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

1-(3-dimethylaminopropyl) 3-(prop-2-enyl)pyrrolidin-2, 5-dione

1-(3-dimethylaminopropyl) 3-(prop-2-enyl)pyrrolidin-2, 5-dione

Conditions
ConditionsYield
In toluene at 6 - 108℃; for 2.5h;
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

diethylaminopropylamine
104-78-9

diethylaminopropylamine

3-allyl-1-(3-diethylamino-propyl)-pyrrolidine-2,5-dione

3-allyl-1-(3-diethylamino-propyl)-pyrrolidine-2,5-dione

Conditions
ConditionsYield
In dichloromethane; toluene at 10 - 119℃; for 2h;
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

A

(S)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester

(S)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester

B

(R)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester

(R)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester

C

(S)-2-Allyl-succinic acid 1-(2,2,2-trifluoro-ethyl) ester

(S)-2-Allyl-succinic acid 1-(2,2,2-trifluoro-ethyl) ester

Conditions
ConditionsYield
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at -24℃;
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid 1-(3-phenyl-propyl)-piperidin-3-ylmethyl ester

2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid 1-(3-phenyl-propyl)-piperidin-3-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / 145 - 160 °C / 0.1 Torr
2: 94 percent / DCC
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

[(3R,5R)-2-Oxo-5-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-heptyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

[(3R,5R)-2-Oxo-5-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-heptyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99.6 percent / AIBN / 7 h / 70 - 92 °C
2: aq. KOH / 6.5 h / 25 °C
3: aq. H2SO4
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

[(3S,5R)-2-Oxo-5-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-heptyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

[(3S,5R)-2-Oxo-5-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-heptyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99.6 percent / AIBN / 7 h / 70 - 92 °C
2: aq. KOH / 6.5 h / 25 °C
3: aq. H2SO4
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

ethyl 2-[3-(perfluorohexyl)-E-2-propenyl]-1-oic acid-4-oate

ethyl 2-[3-(perfluorohexyl)-E-2-propenyl]-1-oic acid-4-oate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99.6 percent / AIBN / 7 h / 70 - 92 °C
2: aq. KOH / 6.5 h / 25 °C
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

[(perfluorohexylethanethia)propyl]-2-butane-1,4-dioic acid N,N-diethylamide

[(perfluorohexylethanethia)propyl]-2-butane-1,4-dioic acid N,N-diethylamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4.3 mmol / AIBN / hexane / 18 h / 70 °C
2: CH2Cl2 / 72 h / 25 °C
View Scheme
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

3-(3-dimethylamino-propylcarbamoyl)-6-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octylsulfanyl)-hexanoic acid

3-(3-dimethylamino-propylcarbamoyl)-6-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octylsulfanyl)-hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4.3 mmol / AIBN / hexane / 18 h / 70 °C
2: CH2Cl2 / 5.5 h / 18 - 25 °C
View Scheme

Allylsuccinic anhydride Chemical Properties

Molecular Formula: C7H8O3
Molar mass: 140.14 g/mol
EINECS: 231-412-0
Density: 1.149 g/cm3
Flash Point: 115.9 °C
Index of Refraction: 1.469
Boiling Point: 254 °C at 760 mmHg
Vapour Pressure: 0.0177 mmHg at 25°C
Product categories of Allylsuccinic anhydride (7539-12-0): Professional Olefins
Structure of Allylsuccinic anhydride (7539-12-0):

XLogP3-AA: 0.7
H-Bond Donor: 0
H-Bond Acceptor: 3
Systematic Name: 3-Allyltetrahydrofuran-2,5-dione 
SMILES: O=C1OC(=O)CC1C\C=C 
InChI: InChI=1/C7H8O3/c1-2-3-5-4-6(8)10-7(5)9/h2,5H,1,3-4H2 
InChIKey: WUMMIJWEUDHZCL-UHFFFAOYAU 
Std. InChI: InChI=1S/C7H8O3/c1-2-3-5-4-6(8)10-7(5)9/h2,5H,1,3-4H2 
Std. InChIKey: WUMMIJWEUDHZCL-UHFFFAOYSA-N

Allylsuccinic anhydride Toxicity Data With Reference

1.    

skn-rbt 10 mg/24H open SEV

    AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
2.    

orl-rat LD50:1070 mg/kg

    AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
3.    

skn-rbt LD50:320 mg/kg

    AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.

Allylsuccinic anhydride Safety Profile

Poison by skin contact. Moderately toxic by ingestion. A severe skin irritant. See also ANHYDRIDES and ALLYL COMPOUNDS. When heated to decomposition it emits acrid smoke and irritating fumes.
 

Risk Statements:
20:  Harmful by inhalation
21:  Harmful in contact with skin
22:  Harmful if swallowed 
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection

Allylsuccinic anhydride Specification

 Allylsuccinic anhydride (7539-12-0) also can be called 3-Allyl(dihydro)furan-2,5-dione ; 2,5-furandione, dihydro-3-(2-propen-1-yl)- and Succinic anhydride, allyl- .

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