Conditions | Yield |
---|---|
With sulfuric acid; paraformaldehyde In water | 82% |
With hydrogenchloride; sodium hydroxide; sulfur trioxide In 1,3,5-Trioxan; water | |
With hydrogenchloride; sodium hydroxide; sulfur trioxide In 1,3,5-Trioxan; water |
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide at 100 - 150℃; for 5 - 6h; | 76.4% |
chlorosulfuric acid chloromethyl ester
terephthalic acid
5-carboxyphtalide
Conditions | Yield |
---|---|
at 27 - 130℃; for 3h; Product distribution / selectivity; Industry scale; Neat (no solvent); | 60% |
1-oxo-1,3-dihydroisobenzofuran-5-carboxamide
5-carboxyphtalide
Conditions | Yield |
---|---|
With sodium hydroxide anschliessend Ansaeuern; |
hydroxymethyl-terephthalic acid
5-carboxyphtalide
Conditions | Yield |
---|---|
at 110℃; |
2-formyl-4-carboxybenzoic acid
5-carboxyphtalide
Conditions | Yield |
---|---|
With sodium hydroxide |
5-carboxyphtalide
Conditions | Yield |
---|---|
at 240℃; |
5-amino-3H-isobenzofuran-1-one
5-carboxyphtalide
Conditions | Yield |
---|---|
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
5-carboxyphtalide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: aq. NaOH solution / anschliessend Ansaeuern View Scheme | |
With sulfuric acid In water Reflux; |
5-carboxyphtalide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: calcium carbonate; water 2: NaOH-solution View Scheme |
Conditions | Yield |
---|---|
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
5-carboxyphtalide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: calcium carbonate; water 3: NaOH-solution View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium hypobromite / 0 °C 2: thionyl chloride 4: calcium carbonate; water 5: NaOH-solution View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride 3: calcium carbonate; water 4: NaOH-solution View Scheme |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With hydrogenchloride; sulfur trioxide In water; acetic acid |
5-carboxyphtalide
5-(hydroxymethyl)isobenzofuran-1(3H)-one
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 20℃; for 2h; | 93% |
5-carboxyphtalide
(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride
Conditions | Yield |
---|---|
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
methyl iodide
methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide for 0.5h; | 91% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 15% |
methanol
5-carboxyphtalide
methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
Conditions | Yield |
---|---|
With thionyl chloride at 5℃; for 2h; Reflux; | 90% |
5-carboxyphtalide
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With sulfuric acid In toluene at 80 - 110℃; | 88.3% |
5-carboxyphtalide
2-Amino-2-methyl-1-propanol
4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline
Conditions | Yield |
---|---|
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
propan-1-ol-3-amine
N-(3-hydroxypropyl)-1-oxo-1,3-dihydroisobenzofuran-5-carboxamide
Conditions | Yield |
---|---|
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
C10H14N2O2S*ClH
5-{2-[((2-phenoxyethyl)thio)methyl]-1,3,4-oxadiazol-5-yl}phthalide
Conditions | Yield |
---|---|
With tetrachloromethane; triethylamine; 4-(N,N-Dimethylamino)triphenylphosphine In acetonitrile at 20℃; | 51% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide |
5-carboxyphtalide
hydroxymethyl-terephthalic acid
5-carboxyphtalide
methyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride 2: methanol View Scheme |
5-carboxyphtalide
5-ethoxycarbonylphthalide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride 2: ethanol View Scheme | |
With trichlorophosphate In ethanol |
5-carboxyphtalide
2-Phenylsulfanylmethyl-terephthaloyl dichloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: SOCl2 View Scheme |
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
Hazard Codes: Xi
Hazard Note: Irritant
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