Product Name

  • Name

    Citraconic anhydride

  • EINECS 210-459-0
  • CAS No. 616-02-4
  • Article Data60
  • CAS DataBase
  • Density 1.334 g/cm3
  • Solubility Decomposes in water
  • Melting Point 6-10 °C(lit.)
  • Formula C5H4O3
  • Boiling Point 211.467 °C at 760 mmHg
  • Molecular Weight 112.085
  • Flash Point 96.766 °C
  • Transport Information UN 2810
  • Appearance clear colorless to very slightly yellow liquid
  • Safety 26-28A-36/37/39-45
  • Risk Codes 24-34-42/43
  • Molecular Structure Molecular Structure of 616-02-4 (Citraconic anhydride)
  • Hazard Symbols ToxicT
  • Synonyms Citraconicanhydride (6CI,8CI);2-Methyl-2-butenedioic anhydride;2-Methylmaleicanhydride;3-Methyl-2,5-furandione;3-Methylmaleic anhydride;Citraconic acidanhydride;Methylmaleic anhydride;Monomethylmaleic anhydride;NSC 6182;a-Methylmaleic anhydride;
  • PSA 43.37000
  • LogP 0.01610

Synthetic route

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
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%
citraconic acid
498-23-7

citraconic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
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
110-88-3

1,3,5-Trioxan

succinic acid anhydride
108-30-5

succinic acid anhydride

A

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

B

citraconic acid anhydride
616-02-4

citraconic acid anhydride

C

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor;A 7%
B 43%
C 16%
formaldehyd
50-00-0

formaldehyd

Dimethyl succinate
106-65-0

Dimethyl succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

C

citraconic acid anhydride
616-02-4

citraconic acid anhydride

D

carbon dioxide
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%
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

citraconic acid anhydride
616-02-4

citraconic acid anhydride

C

carbon dioxide
124-38-9

carbon dioxide

D

Dimethyl succinate
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%
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

Dimethyl succinate
106-65-0

Dimethyl succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

C

citraconic acid anhydride
616-02-4

citraconic acid anhydride

D

carbon dioxide
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%
(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
80818-24-2

(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

(Z)-(3-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
80818-11-7

(Z)-(3-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Reflux;A 9%
B n/a
C 22%
paraconic acid
498-89-5

paraconic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
bei der Destillation;
2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid
14556-16-2

2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
beim Destillieren;
2-bromo-3-methyl-succinic acid
7405-17-6

2-bromo-3-methyl-succinic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
at 210℃;
Mesaconic acid
498-24-8

Mesaconic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
With acetyl chloride at 100℃; beim Erhitzen im geschlossenen Rohr;
2-hydroxy-2-methylbutane-1,4-dioic acid
597-44-4

2-hydroxy-2-methylbutane-1,4-dioic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
at 83 - 89℃; under 15 Torr; Heating;4.9 g
methoxymethyl-succinic acid
81949-89-5

methoxymethyl-succinic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
at 210 - 230℃; durch Destillation;
at 210 - 230℃; beim Destillieren;
itaconic acid anhydride
2170-03-8

itaconic acid anhydride

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

citraconic acid anhydride
616-02-4

citraconic acid anhydride

itaconic acid anhydride
2170-03-8

itaconic acid anhydride

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
durch Destillation;
With 2,3-Dimethylaniline
bei der Destillation;
O-acetyl-tachysterol4

O-acetyl-tachysterol4

citraconic acid anhydride
616-02-4

citraconic acid anhydride

anthracene-citraconic anhydride adduct
51864-00-7

anthracene-citraconic anhydride adduct

propionic acid
802294-64-0

propionic acid

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

anthracene
120-12-7

anthracene

Conditions
ConditionsYield
at 142 - 143℃; Rate constant; Dissoziation;
at 131.5 - 143℃; Equilibrium constant; Dissoziation;
Mesaconic acid
498-24-8

Mesaconic acid

acetyl chloride
75-36-5

acetyl chloride

citraconic acid anhydride
616-02-4

citraconic acid anhydride

citric acid
77-92-9

citric acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
bei der Destillation;
2,5-bis<(trimethylsilyl)oxy>-3-methylfuran
77220-07-6

2,5-bis<(trimethylsilyl)oxy>-3-methylfuran

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
With bromine at -78℃; Rate constant; iodine at 0 deg C;
C5H5O7P(2-)

C5H5O7P(2-)

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; water for 0.333333h; Equilibrium constant; Ambient temperature; pH = 10.0;
citric acid
77-92-9

citric acid

A

diethyl 3-hydroxypentanedioate
638-18-6

diethyl 3-hydroxypentanedioate

B

Mesaconic acid
498-24-8

Mesaconic acid

C

1 propene 1,2,3 tricarboxylic acid
499-12-7

1 propene 1,2,3 tricarboxylic acid

D

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

E

citraconic acid anhydride
616-02-4

citraconic acid anhydride

F

itaconic acid anhydride
2170-03-8

itaconic acid anhydride

Conditions
ConditionsYield
With Sn/Pb solder at 150 - 210℃;
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With oxygen; P/Fe In water at 200℃; Yield given. Yields of byproduct given;
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

carbon dioxide
124-38-9

carbon dioxide

C

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With oxygen; P/Fe In water at 200℃; Product distribution; var. temp.;
(1R,2S,6R,7S)-2-Methyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(1R,2S,6R,7S)-2-Methyl-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

A

furan
110-00-9

furan

B

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
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;
cellulose

cellulose

A

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

B

cyclohexenone
930-68-7

cyclohexenone

C

citraconic acid anhydride
616-02-4

citraconic acid anhydride

D

3,4-dihydro-6-methyl-2H-pyran-2-one
3740-59-8

3,4-dihydro-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
With air at 400 - 450℃; Oxidation; Formation of xenobiotics;
anhydroaconitic acid

anhydroaconitic acid

citraconic acid anhydride
616-02-4

citraconic acid anhydride

Conditions
ConditionsYield
at 250℃;
aqueous citric acid

aqueous citric acid

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

itaconic acid anhydride
2170-03-8

itaconic acid anhydride

Conditions
ConditionsYield
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
18310-60-6, 53228-22-1, 71214-83-0, 136846-08-7, 147782-60-3

(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione

A

citraconic acid anhydride
616-02-4

citraconic acid anhydride

B

2endo-methyl-norborn-5-ene-2exo,3exo-dicarboxylic acid-anhydride

2endo-methyl-norborn-5-ene-2exo,3exo-dicarboxylic acid-anhydride

Conditions
ConditionsYield
at 200℃; unter Stickstoff;
methanol
67-56-1

methanol

citraconic acid anhydride
616-02-4

citraconic acid anhydride

citraconic acid dimethyl ester
617-54-9

citraconic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid for 12h; Heating;100%
With sulfuric acid Heating;90%
With sulfuric acid for 12h; Heating;75%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

1-(4-Methoxy-benzyl)-3-methyl-pyrrole-2,5-dione
215871-89-9

1-(4-Methoxy-benzyl)-3-methyl-pyrrole-2,5-dione

Conditions
ConditionsYield
With acetic acid at 100℃; for 5h;100%
In toluene for 13h; Heating;80%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione
18310-60-6, 53228-22-1, 71214-83-0, 136846-08-7, 147782-60-3

(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione

Conditions
ConditionsYield
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;
citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-amino-phenol
95-55-6

2-amino-phenol

2-hydroxy-β-methylmaleanilic acid

2-hydroxy-β-methylmaleanilic acid

Conditions
ConditionsYield
In acetone99%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

(-)-(R)-9-(1,2-dimethoxyethyl)anthracene
837366-23-1

(-)-(R)-9-(1,2-dimethoxyethyl)anthracene

C23H22O5

C23H22O5

Conditions
ConditionsYield
In toluene for 48h; Diels-Alder reaction; Heating;99%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

(R)-(+)-3-methyldihydrofuran-2,5-dione
83247-83-0

(R)-(+)-3-methyldihydrofuran-2,5-dione

Conditions
ConditionsYield
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
citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-benzylaniline
28059-64-5

2-benzylaniline

C18H15NO2
1098344-29-6

C18H15NO2

Conditions
ConditionsYield
With acetic acid for 48h; Reflux;99%
4-aminopyridine
504-24-5

4-aminopyridine

citraconic acid anhydride
616-02-4

citraconic acid anhydride

(Z)-2-Methyl-3-(pyridin-4-ylcarbamoyl)-acrylic acid

(Z)-2-Methyl-3-(pyridin-4-ylcarbamoyl)-acrylic acid

Conditions
ConditionsYield
In water at 20℃;98%
1,3-di(aminomethyl)benzene
1477-55-0

1,3-di(aminomethyl)benzene

citraconic acid anhydride
616-02-4

citraconic acid anhydride

1,3-bis(citraconimidomethyl)benzol
119462-56-5

1,3-bis(citraconimidomethyl)benzol

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

citraconic acid anhydride
616-02-4

citraconic acid anhydride

citraconic acid dimethyl ester
84569-14-2

citraconic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid97%
ethene
74-85-1

ethene

citraconic acid anhydride
616-02-4

citraconic acid anhydride

1-methyl-3-oxabicyclo[3.2.0]heptane-2,4-dione
64197-91-7

1-methyl-3-oxabicyclo[3.2.0]heptane-2,4-dione

Conditions
ConditionsYield
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
616-02-4

citraconic acid anhydride

C16H12N4S2
1610505-50-4

C16H12N4S2

3-methyl-1-[2-phenyl-5-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-ylamino]-1H-pyrrole-2,5-dione

3-methyl-1-[2-phenyl-5-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-ylamino]-1H-pyrrole-2,5-dione

Conditions
ConditionsYield
In chloroform at 80℃; for 18h;96%
In chloroform at 80℃;
citraconic acid anhydride
616-02-4

citraconic acid anhydride

2,2'-dimethylbenzidine
84-67-3

2,2'-dimethylbenzidine

C24H20N2O4

C24H20N2O4

Conditions
ConditionsYield
With acetic acid In toluene for 1h; Inert atmosphere; Reflux;96%
methanol
67-56-1

methanol

citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-hydroxy-5-chloro-aniline
95-85-2

2-hydroxy-5-chloro-aniline

Methyl α-(6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)acetate
104662-88-6

Methyl α-(6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)acetate

Conditions
ConditionsYield
With triethylamine for 5h; Heating;95%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

benzylamine
100-46-9

benzylamine

1-Benzyl-3-methyl-2,5-dihydropyrrole-2,5-dione
73383-82-1

1-Benzyl-3-methyl-2,5-dihydropyrrole-2,5-dione

Conditions
ConditionsYield
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
616-02-4

citraconic acid anhydride

anthranilic acid
118-92-3

anthranilic acid

2-(3-methyl-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid
553636-63-8

2-(3-methyl-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

Conditions
ConditionsYield
at 140℃; for 20h;95%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-methyl-4-oxo-but-2-enoic acid

4-[N'-(2-hydroxy-benzoyl)-hydrazino]-2-methyl-4-oxo-but-2-enoic acid

Conditions
ConditionsYield
In ethyl acetate95%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

citraconic acid anhydride
616-02-4

citraconic acid anhydride

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(cyclohexylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate
1229316-21-5

dimethyl 2-(cyclohexylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h; regiospecific reaction;95%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

(9S)-9-Methyl-1-phenylbicyclo<4.3.0>nona-1(2),3(4)-diene
126971-21-9

(9S)-9-Methyl-1-phenylbicyclo<4.3.0>nona-1(2),3(4)-diene

A

C21H22O3
142746-85-8

C21H22O3

B

C21H22O3
142746-84-7

C21H22O3

Conditions
ConditionsYield
In dichloromethane under 4875390 Torr; for 240h; Ambient temperature;A 1%
B 94%
(3E)-1,3-pentadien-2-yl(pyridine)bis(diphenylglyoximato)cobalt(III)

(3E)-1,3-pentadien-2-yl(pyridine)bis(diphenylglyoximato)cobalt(III)

citraconic acid anhydride
616-02-4

citraconic acid anhydride

endo-cis-(1,3,3a,4,7,7a-hexahydro-7,7a-dimethyl-1,3-dioxoisobenzofuran-5-yl)pyridinebis(diphenylglyoximato)cobalt(III)

endo-cis-(1,3,3a,4,7,7a-hexahydro-7,7a-dimethyl-1,3-dioxoisobenzofuran-5-yl)pyridinebis(diphenylglyoximato)cobalt(III)

Conditions
ConditionsYield
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
119072-55-8, 7188-38-7

tert-butylisonitrile

citraconic acid anhydride
616-02-4

citraconic acid anhydride

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(tert-butylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate
1229316-23-7

dimethyl 2-(tert-butylimino)-8-methyl-7-oxo-1,6-dioxaspiro[4.4]nona-3,8-diene-3,4-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h; regiospecific reaction;94%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

4-[1-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-methyl-4-oxo-but-2-enoic acid

4-[1-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-methyl-4-oxo-but-2-enoic acid

Conditions
ConditionsYield
With triethylamine In chloroform for 0.0833333h;94%
L-valine
72-18-4

L-valine

citraconic acid anhydride
616-02-4

citraconic acid anhydride

(S)-3-methyl-2-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid
1448189-60-3

(S)-3-methyl-2-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid

Conditions
ConditionsYield
With acetic acid at 120℃; for 1h; Microwave irradiation; Sealed tube;94%
In acetic acid at 120℃; for 1h; Microwave irradiation;94%
2-amino-3-methylphenol
2835-97-4

2-amino-3-methylphenol

citraconic acid anhydride
616-02-4

citraconic acid anhydride

C12H11NO3
1613169-59-7

C12H11NO3

Conditions
ConditionsYield
In toluene for 2h; Reflux;94%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-phenoxyaniline
2688-84-8

2-phenoxyaniline

C17H13NO3
1033000-78-0

C17H13NO3

Conditions
ConditionsYield
With acetic acid for 48h; Reflux;93%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

N-(3-aminopropyl)cinnamamide

N-(3-aminopropyl)cinnamamide

N-[3-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propyl]cinnamamide

N-[3-(3-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propyl]cinnamamide

Conditions
ConditionsYield
With acetic acid for 12h; Reflux;93%
citraconic acid anhydride
616-02-4

citraconic acid anhydride

4-methoxy-aniline
104-94-9

4-methoxy-aniline

A

(Z)-(4-(4-methoxyphenylamino)-2-methyl-4-oxo)but-2-enoic acid
80818-22-0

(Z)-(4-(4-methoxyphenylamino)-2-methyl-4-oxo)but-2-enoic acid

B

(Z)-3-(4-Methoxy-phenylcarbamoyl)-3-methyl-acrylic acid
80818-09-3

(Z)-3-(4-Methoxy-phenylcarbamoyl)-3-methyl-acrylic acid

Conditions
ConditionsYield
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
67-56-1

methanol

citraconic acid anhydride
616-02-4

citraconic acid anhydride

2-hydroxy-5-nitroaniline
99-57-0

2-hydroxy-5-nitroaniline

(2-Methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid methyl ester
104662-90-0

(2-Methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid methyl ester

Conditions
ConditionsYield
With triethylamine Heating;92%

CITRACONIC ANHYDRIDE Chemical Properties

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/cm
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 Uses

 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 Production

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 . 

CITRACONIC ANHYDRIDE Toxicity Data With Reference


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.

 

CITRACONIC ANHYDRIDE Safety Profile

 

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 Specification

Citraconic anhydride (616-02-4) is crystallization.

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