Product Name

  • Name

    5-Carboxyphthalide

  • EINECS 225-343-5
  • CAS No. 4792-29-4
  • Article Data12
  • CAS DataBase
  • Density 1.502
  • Solubility
  • Melting Point
  • Formula C9H6 O4
  • Boiling Point 481.1 °C at 760 mmHg
  • Molecular Weight 178.144
  • Flash Point 206.3 °C
  • Transport Information
  • Appearance White to off white odorless powder
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 4792-29-4 (5-Carboxyphthalide)
  • Hazard Symbols Xi,Xn
  • Synonyms 5-Phthalancarboxylicacid, 1-oxo- (8CI); 1,4-Benzenedicarboxylic acid, (hydroxymethyl)-, g-lactone; 5-Carboxyphthalide;Phthalide-5-carboxylic acid
  • PSA 63.60000
  • LogP 1.05520

Synthetic route

terephthalic acid
100-21-0

terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With sulfuric acid; paraformaldehyde In water82%
With hydrogenchloride; sodium hydroxide; sulfur trioxide In 1,3,5-Trioxan; water
With hydrogenchloride; sodium hydroxide; sulfur trioxide In 1,3,5-Trioxan; water
formaldehyd
50-00-0

formaldehyd

terephthalic acid
100-21-0

terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide at 100 - 150℃; for 5 - 6h;76.4%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

terephthalic acid
100-21-0

terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
at 27 - 130℃; for 3h; Product distribution / selectivity; Industry scale; Neat (no solvent);60%
1-oxo-1,3-dihydroisobenzofuran-5-carboxamide
85118-25-8

1-oxo-1,3-dihydroisobenzofuran-5-carboxamide

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With sodium hydroxide anschliessend Ansaeuern;
hydroxymethyl-terephthalic acid
23405-34-7

hydroxymethyl-terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
at 110℃;
2-formyl-4-carboxybenzoic acid
69526-90-5

2-formyl-4-carboxybenzoic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With sodium hydroxide
phthalide-dicarboxylic acid-(3.5)

phthalide-dicarboxylic acid-(3.5)

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
at 240℃;
5-amino-3H-isobenzofuran-1-one
65399-05-5

5-amino-3H-isobenzofuran-1-one

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: copper (II)-sulfate; potassium cyanide / ueber eine wss. Diazoniumsalz-Loesung
2: aqueous sulfuric acid
3: aq. NaOH solution / anschliessend Ansaeuern
View Scheme
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous sulfuric acid
2: aq. NaOH solution / anschliessend Ansaeuern
View Scheme
With sulfuric acid In water Reflux;
2-dichloromethyl-4-trichloromethyl-benzoyl chloride

2-dichloromethyl-4-trichloromethyl-benzoyl chloride

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: calcium carbonate; water
2: NaOH-solution
View Scheme
m-xylene
108-38-3

m-xylene

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: iron chloride; carbon disulfide
2: sodium hypobromite / 0 °C
3: thionyl chloride
5: calcium carbonate; water
6: NaOH-solution
View Scheme
2,4-dimethylbenzoyl chloride
21900-42-5

2,4-dimethylbenzoyl chloride

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: calcium carbonate; water
3: NaOH-solution
View Scheme
2,4-dimethylacetophenone.
89-74-7

2,4-dimethylacetophenone.

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hypobromite / 0 °C
2: thionyl chloride
4: calcium carbonate; water
5: NaOH-solution
View Scheme
2,4-dimethyl-benzoic acid
611-01-8

2,4-dimethyl-benzoic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride
3: calcium carbonate; water
4: NaOH-solution
View Scheme
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

terephthalic acid
100-21-0

terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sulfur trioxide In water
With hydrogenchloride; sulfur trioxide; sodium hydrogencarbonate In water
With hydrogenchloride; sulfur trioxide; sodium hydrogencarbonate In water; acetic acid
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

NaHCO3are

NaHCO3are

terephthalic acid
100-21-0

terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

Conditions
ConditionsYield
With hydrogenchloride; sulfur trioxide In water; acetic acid
...Expand
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

5-(hydroxymethyl)isobenzofuran-1(3H)-one
65006-89-5

5-(hydroxymethyl)isobenzofuran-1(3H)-one

Conditions
ConditionsYield
Stage #1: 5-carboxyphtalide With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water
Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=2;		94%
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2 h / 20 °C
2: sodium tetrahydroborate / tetrahydrofuran; water / 0.08 h / 20 °C
View Scheme
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

pentafluorophenyl trifloroacetate
14533-84-7

pentafluorophenyl trifloroacetate

C15H5F5O4
1374215-44-7

C15H5F5O4

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 20℃; for 2h;93%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride
227954-90-7

(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide at 60℃; for 3 - 5h; Product distribution / selectivity; Heating / reflux;91%
With thionyl chloride
With thionyl chloride In N,N-dimethyl-formamide; toluene
With thionyl chloride In N,N-dimethyl-formamide for 6h; Heating / reflux;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 80℃; for 1h; Heating / reflux;
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

methyl iodide
74-88-4

methyl iodide

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
23405-32-5

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 0.5h;91%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;15%
methanol
67-56-1

methanol

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
23405-32-5

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate

Conditions
ConditionsYield
With thionyl chloride at 5℃; for 2h; Reflux;90%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-carboxyphtalide With ethyl phosphate; ammonium carbonate In acetonitrile at 0 - 25℃; for 6h;
Stage #2: at 90 - 95℃; for 12h;		89.5%
With thionyl chloride; SULFAMIDE In sulfolane; water
With thionyl chloride; SULFAMIDE In sulfolane; water
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

butan-1-ol
71-36-3

butan-1-ol

5-butoxycarbonylphthalide

5-butoxycarbonylphthalide

Conditions
ConditionsYield
With sulfuric acid In toluene at 80 - 110℃;88.3%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

2-Amino-2-methyl-1-propanol
124-68-5

2-Amino-2-methyl-1-propanol

4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline
265137-37-9

4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline

Conditions
ConditionsYield
Stage #1: 5-carboxyphtalide With chloroformic acid ethyl ester; triethylamine In acetone at -10 - 13℃; for 0.5h;
Stage #2: 2-Amino-2-methyl-1-propanol In acetone at -10 - 20℃;
Stage #3: With thionyl chloride; ammonia more than 3 stages;		66.8%
Stage #1: 5-carboxyphtalide With thionyl chloride In ISOPROPYLAMIDE at 60 - 80℃; for 6.5h;
Stage #2: 2-Amino-2-methyl-1-propanol With potassium carbonate In tetrahydrofuran at 0 - 10℃; for 0.5h;
Stage #3: With thionyl chloride; ammonia more than 3 stages;		59.8%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

N-(3-hydroxypropyl)-1-oxo-1,3-dihydroisobenzofuran-5-carboxamide
1359020-78-2

N-(3-hydroxypropyl)-1-oxo-1,3-dihydroisobenzofuran-5-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;52%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

C10H14N2O2S*ClH
627898-14-0

C10H14N2O2S*ClH

5-{2-[((2-phenoxyethyl)thio)methyl]-1,3,4-oxadiazol-5-yl}phthalide
627899-11-0

5-{2-[((2-phenoxyethyl)thio)methyl]-1,3,4-oxadiazol-5-yl}phthalide

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; 4-(N,N-Dimethylamino)triphenylphosphine In acetonitrile at 20℃;51%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

thiophenol
108-98-5

thiophenol

2-Phenylsulfanylmethyl-terephthalic acid

2-Phenylsulfanylmethyl-terephthalic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

diluted NaOH-solution

diluted NaOH-solution

hydroxymethyl-terephthalic acid
23405-34-7

hydroxymethyl-terephthalic acid

5-carboxyphtalide
4792-29-4

5-carboxyphtalide

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
23405-32-5

methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride
2: methanol
View Scheme
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

5-ethoxycarbonylphthalide
23405-31-4

5-ethoxycarbonylphthalide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride
2: ethanol
View Scheme
With trichlorophosphate In ethanol
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

2-Phenylsulfanylmethyl-terephthaloyl dichloride
67666-77-7

2-Phenylsulfanylmethyl-terephthaloyl dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / dimethylformamide
2: SOCl2
View Scheme

5-Carboxyphthalide Chemical Properties

IUPAC Name: 1-Oxo-3H-2-benzofuran-5-carboxylic acid
Synonyms of 5-Carboxyphthalide (CAS NO.4792-29-4): Phthalide-5-carboxylic acid ; 1,3-Dihydro-1-oxo-5-isobenzofurancarboxylic acid ; 1-Oxo-5-phthalancarboxylic acid
CAS NO: 4792-29-4
Molecular Formula: C9H6O4
Molecular Weight: 178.14
Molecular Structure:
EINECS: 225-343-5
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 52.6 Å2
Index of Refraction: 1.635
Molar Refractivity: 42.48 cm3
Molar Volume: 118.5 cm3
Surface Tension: 66.3 dyne/cm
Density: 1.502 g/cm3
Flash Point: 206.3 °C
Enthalpy of Vaporization: 78.55 kJ/mol
Boiling Point: 481.1 °C at 760 mmHg
Vapour Pressure: 4.57E-10 mmHg at 25°C
SMILES: O=C(O)c1ccc2C(=O)OCc2c1
InChI: InChI=1/C9H6O4/c10-8(11)5-1-2-7-6(3-5)4-13-9(7)12/h1-3H,4H2,(H,10,11)
InChIKey: QTWUWCFGWYYRRL-UHFFFAOYAG
Std. InChI: InChI=1S/C9H6O4/c10-8(11)5-1-2-7-6(3-5)4-13-9(7)12/h1-3H,4H2,(H,10,11)
Std. InChIKey: QTWUWCFGWYYRRL-UHFFFAOYSA-N
Product Categories of 5-Carboxyphthalide (CAS NO.4792-29-4): blocks;Carboxes

5-Carboxyphthalide Safety Profile

Hazard Codes: IrritantXi
Hazard Note: Irritant

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