7539-12-0

Basic information

• Product Name: ALLYLSUCCINIC ANHYDRIDE
• Synonyms: (2-PROPENYL)BUTANEDIOIC ANHYDRIDE;ALLYLSUCCINIC ANHYDRIDE;4-PENTENE-1,2-DICARBOXYLIC ANHYDRIDE;allyl-succinicanhydrid;3-allyl(dihydro)furan-2,5-dione;2,3,4,5-Tetrahydro-3-(2-propenyl)furan-2,5-dione;2-Allylsuccinic anhydride;3-Allylfuran-2,5(3H,4H)-dione
• CAS NO: 7539-12-0
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• EINECS: 231-412-0
• Mol File: 7539-12-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 143 °C / 17mmHg
• Flash Point: 115.9°C
• Appearance: /
• Density: 1.17
• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: 1.4700-1.4720
• CAS DataBase Reference: ALLYLSUCCINIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLSUCCINIC ANHYDRIDE(7539-12-0)
• EPA Substance Registry System: ALLYLSUCCINIC ANHYDRIDE(7539-12-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• RTECS: WN1050000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 7539-12-0(Hazardous Substances Data)

Usage

General Description

ALLYLSUCCINIC ANHYDRIDE is a chemical compound with the molecular formula C7H8O3. It is a colorless liquid with a pungent odor, and it is soluble in water and most organic solvents. Allylsuccinic anhydride is primarily used as a chemical intermediate in the production of various polymers and resins. It is also used as a crosslinking agent in the preparation of adhesives and coatings. In addition, it has applications in the synthesis of pharmaceuticals and agricultural chemicals. However, it is important to handle allylsuccinic anhydride with care, as it is corrosive and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation.

InChI:InChI=1/C7H8O3/c1-2-3-5-4-6(8)10-7(5)9/h2,5H,1,3-4H2

Synthetic route

allyl succinic acid (5754-10-9) → allylsuccinic anhydride

Conditions	Yield
With acetyl chloride for 3h; Cyclization; Heating;	85%

succinic acid anhydride + propene → allylsuccinic anhydride (7539-12-0)

Conditions	Yield
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) + propene (187737-37-7) → allylsuccinic anhydride (7539-12-0)

Conditions	Yield
With benzene at 250℃;
With benzene at 200℃;

maleic anhydride (108-31-6) + propene (187737-37-7) + benzene (71-43-2) → allylsuccinic anhydride (7539-12-0)

Conditions	Yield
at 250℃; under 54427.6 Torr;

3-((tert-butoxy)carbonyl)hex-5-enoic acid (308349-49-7) → allylsuccinic anhydride (7539-12-0)

Conditions	Yield
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) + 1-amino-3-(dimethylamino)propane (109-55-7) → 3-(3-dimethylamino-propylcarbamoyl)-hex-5-enoic acid

Conditions	Yield
In dichloromethane at 25℃; for 18h;	100%

methanol (67-56-1) + allylsuccinic anhydride (7539-12-0) → dimethyl 2-(prop-2-en-1-yl)butanedioate (1069-40-5)

Conditions	Yield
With hydrogenchloride; silica gel In water at 70℃; Schlenk technique;	100%

allylsuccinic anhydride (7539-12-0) + 1-iodoheptadecafluorooctane (507-63-1) → 3-(perfluorooctyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 72℃; for 2h;	99.6%

allylsuccinic anhydride (7539-12-0) + n-perfluorohexyl iodide (355-43-1) → 3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride (674786-54-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70 - 92℃; for 7h;	99.6%

allylsuccinic anhydride (7539-12-0) → allyl succinic acid (5754-10-9)

Conditions	Yield
With water at 110℃; Inert atmosphere; Schlenk technique;	98.5%
With sodium carbonate

1,4-bis(dimethylsilyl)benzene (2488-01-9) + allylsuccinic anhydride (7539-12-0) → C4H4O3*C24H34O6Si2

Conditions	Yield
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) + n-butylguanidine hydrochloride (19341-56-1) → 1,1'-((butylimino)methylene)bis(3-allylpyrrolidine-2,5-dione)

Conditions	Yield
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) + 1,3,3,5,5-hexamethyltrisiloxane (1189-93-1) + 4-vinyl benzylamine (1520-21-4) → C36H50N2O6Si3

Conditions	Yield
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) + trimethoxysilylethyl-1,1,3,3-tetramethyldisiloxane (137407-65-9) → C16H34O7Si3 (1313483-76-9)

Conditions	Yield
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane at 100 - 110℃; for 2h; Inert atmosphere;	76.7%

allylsuccinic anhydride (7539-12-0) → 2-(3-bromopropyl)-succinic anhydride

Conditions	Yield
With dibenzoyl peroxide In water; toluene	67.3%

allylsuccinic anhydride (7539-12-0) + anthranilic acid (118-92-3) → 2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid

Conditions	Yield
at 145 - 160℃; under 0.1 Torr;	63%

allylsuccinic anhydride (7539-12-0) + bis(pinacol)diborane (73183-34-3) → (Z)-3-[2,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]dihydrofuran-2,5-dione (1325764-23-5)

Conditions	Yield
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) + t-butyldimethylsiyl triflate (69739-34-0) → ((3-allylfuran-2,5-diyl)bis(oxy))bis(tert-butyldimethylsilane)

Conditions	Yield
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) + aluminium trichloride (7446-70-0) + benzene (71-43-2) → 3-oxo-5c(?)-phenyl-cyclohexane-r-carboxylic acid methyl ester + 2-phenacyl-4-phenyl-valeric acid methyl ester + 4-methyl-1-oxo-1,2,3,4-tetrahydro-<2>naphthyl>-acetic acid methyl ester

Conditions	Yield
Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol;

allylsuccinic anhydride (7539-12-0) + 1H,1H,2H,2H-Perfluorodecanethiol (34143-74-3) → 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)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 50 - 88℃; for 2h;	31.0 g

allylsuccinic anhydride (7539-12-0) + 2-perfluorohexylethanethiol (34451-26-8) → [3-(perfluorohexylethanethia)]prop-1-yl-2-butane-1,4-dioic acid anhydride (577732-47-9)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In hexane at 70℃; for 18h;	4.3 mmol

allylsuccinic anhydride (7539-12-0) + 1-amino-3-(dimethylamino)propane (109-55-7) → 1-(3-dimethylaminopropyl) 3-(prop-2-enyl)pyrrolidin-2, 5-dione

Conditions	Yield
In toluene at 6 - 108℃; for 2.5h;

allylsuccinic anhydride (7539-12-0) + diethylaminopropylamine (104-78-9) → 3-allyl-1-(3-diethylamino-propyl)-pyrrolidine-2,5-dione

Conditions	Yield
In dichloromethane; toluene at 10 - 119℃; for 2h;

allylsuccinic anhydride (7539-12-0) + 2,2,2-trifluoroethanol (75-89-8) → (S)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester + (R)-2-Allyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester + (S)-2-Allyl-succinic acid 1-(2,2,2-trifluoro-ethyl) ester

Conditions	Yield
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at -24℃;

allylsuccinic anhydride (7539-12-0) → 2-(3-allyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid 1-(3-phenyl-propyl)-piperidin-3-ylmethyl ester

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

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

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

Conditions	Yield
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

Upstream product

• 108-31-6 maleic anhydride 
• 187737-37-7 propene 
• 5754-10-9 allyl succinic acid 
• 108-30-5 succinic acid anhydride 
• 71-43-2 benzene 
• 308349-49-7 3-((tert-butoxy)carbonyl)hex-5-enoic acid 

Relevant articles and documents

PROCESS FOR MAKING ALLYL SUCCINIC ANHYDRIDE

A process for the production of allyl succinic anhydride comprising reacting a mixture of propene with maleic anhydride in the presence of a catalyst comprised of an alkyl tin chloride as provided. The process an be run efficiently at temperatures below about 200°C without and the formation of polymer or decomposition by-products.

Organopolysiloxanes having bifunctional terminal siloxane units

The present invention relates to the organopolysiloxanes having the formula where R is optionally substituted C1 - to C18 -hydrocarbon radicals, R1 is an optionally substituted C6 - to C15 -hydrocarbon radical having at least one phenyl ring, R2 is a C1 - to C3 -hydrocarbon radical, X is a hydrogen atom or an organic or organosilicon functional group bonded via a divalent, optionally substituted C2 - to C15 -hydrocarbon radical, with one or more methylene units of the hydrocarbon radical being able to be replaced by oxygen atoms bonded on both sides to carbon atoms, a is an integer of at least 1 and b, c, d and e are each 0 or a positive integer, and the sum of a, b, c, d and e is at least 3, and the process for the preparation thereof.