87-41-2

Basic information

• Product Name: Phthalide
• Synonyms: 1,3-Dihydrobenzo[C]furan-2-one;2-Benzofuran-1(3H)-one;2-Hydroxymethylbenzoic acid, gamma-lactone;Phthalolactone;1-PHTHALANONE;1-OXOPHTHALAN;2-BENZOFURAN-(3H)-ONE;1-ISOBENZOFURANONE
• CAS NO: 87-41-2
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• EINECS: 201-744-0
• Product Categories: Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks
• Mol File: 87-41-2.mol
• Article Data: 561

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 290 °C(lit.)
• Flash Point: 152 °C
• Appearance: White to light beige/Crystalline Powder
• Density: 1.1
• Vapor Pressure: 0.00213mmHg at 25°C
• Refractive Index: 1.5360 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: sparingly soluble
• BRN: 114632
• CAS DataBase Reference: Phthalide(CAS DataBase Reference)
• NIST Chemistry Reference: Phthalide(87-41-2)
• EPA Substance Registry System: Phthalide(87-41-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-36-24/25-37/39
• WGK Germany: 3
• RTECS: TI3520000
• TSCA: Yes
• Hazardous Substances Data: 87-41-2(Hazardous Substances Data)

Usage

Description

White powder; sweet tonka, coumarin, powdery, coconut, phenolic, lactonic aroma.

Uses

Phthalide may be used in scaffolds for the design of high potency monoamine oxidase (MAO) inhibitors.

Definition

ChEBI: A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.

Aroma threshold values

Low strength odor, Tonka type.

Taste threshold values

Sweet coumarin, coconut, creamy, anisic, green vegetable, floral taste at 100 ppm in water.

Synthesis Reference(s)

Chemistry Letters, 23, p. 1149, 1994The Journal of Organic Chemistry, 68, p. 9423, 2003 DOI: 10.1021/jo0350763Tetrahedron Letters, 7, p. 6097, 1966

Flammability and Explosibility

Notclassified

Pharmacology

Systemic fungicide giving effective preventive control of the rice blast fungus in rice as foliar spray.

Purification Methods

Crystallise phthalide from water (75mL/g) and dry it in air on filter paper. [Beilstein 17/10 V 7.]

Toxicity evaluation

Mammalian toxicology. Oral: Acute oral LD50 for rats and mice >10000 mg/kg. Skin and eye: Acute percutaneous LD50 for rats and mice >10000 mg/kg. Not a shaved skin irritant, eye irritant (rabbits). Inhalation LC50 (4 h) for rats >4.1 mg/L air. NOEL: (2 yr) for rats 2000, mice 100 mg/kg diet.

InChI:InChI=1/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2

Synthetic route

phthalyl alcohol (612-14-6) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With (CH3)5C5*Ir(-OCH2C(C6H5)2NH-) In acetone at 20℃; for 4h;	100%
With sodium bromate; hydrogen bromide In acetic acid at 35℃; for 5h;	99%
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 20℃; for 2h;	99%

o-phthalic dicarboxaldehyde (643-79-8) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With calcium oxide In benzene at 39.84℃; for 0.25h; Tishchenko reaction;	100%
[La2(tBu2pz)6] In benzene-d6 at 21℃; Tishchenko reaction;	100%
With [(ImDippN)Th{N(SiMe3)2}3] In benzene-d6 at 20℃; for 6h;	100%

carbon monoxide (201230-82-2) + 2-iodobenzyl alcohol (5159-41-1) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 60℃; under 760 Torr; for 72h;	100%
With N-ethyl-N,N-diisopropylamine; C50H42O2P2Pd2; triphenylphosphine In toluene at 60℃; for 1.66667h; Conversion of starting material;	100%
With triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium dichloride In toluene at 80℃; under 760.051 Torr; for 4h;	97%

o-xylene (95-47-6) → 2-benzofuran-1(3H)-one (87-41-2) + phthalic anhydride (85-44-9)

Conditions	Yield
With oxygen at 340 - 360℃; Product distribution / selectivity;	A 0.01% B 100%
With oxygen at 340 - 360℃;	A 0.1% B 100%
With oxygen at 340 - 360℃;	A 0.03% B 100%

Reaxys ID: 11463934 → 2-benzofuran-1(3H)-one (87-41-2) + phthalic anhydride (85-44-9) + [1,4]naphthoquinone (130-15-4)

Conditions	Yield
With oxygen at 340 - 360℃; Product distribution / selectivity;	A 0.01% B 100% C 0.02%
With oxygen at 340 - 360℃;	A 0.03% B 100% C 0.05%
With oxygen at 340 - 360℃;	A 0.01% B 100% C 0.01%

Reaxys ID: 11463934 → 2-benzofuran-1(3H)-one (87-41-2) + phthalic anhydride (85-44-9)

Conditions	Yield
With oxygen at 340 - 360℃;	A 0.01% B 100%
With oxygen at 340 - 360℃;	A 0.01% B 100%

Reaxys ID: 11464679 → 2-benzofuran-1(3H)-one (87-41-2) + phthalic anhydride (85-44-9) + [1,4]naphthoquinone (130-15-4)

Conditions	Yield
With oxygen at 354 - 357℃;	A 0.2% B 100% C 0.15%

Phthaloyl dichloride (88-95-9) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h;	99%
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h; other catalysts: Co(acac)2, Ni(acac)2; same reaction of iso- and terephthaloyl chloride;	99%
With tricyclohexylborane at 300℃; for 2h;	11.5%

1,3-dihydroisobenzofuran (496-14-0) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 0.25h;	99%
With oxygen In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 24h; Irradiation;	99%
With tert.-butylhydroperoxide; 0.5C34H18N16(4-)*2H2O*2Cu(1+)*C3H7NO In water at 20℃; for 6h; Reagent/catalyst; Time; Sonication;	97%

phthalic anhydride (85-44-9) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane at -78℃; for 1h;	98%
With lithium borohydride In tetrahydrofuran for 0.25h;	91%
With 4-butanolide; cyclohexane; hydrogen at 180℃; under 30003 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Autoclave;	89.6%

1,3-dihydroisobenzofuran (496-14-0) → 2-benzofuran-1(3H)-one (87-41-2) + 1,3-dihydroisobenzofuran-1-ol (59868-79-0)

Conditions	Yield
With cobalt(III) acetylacetonate; oxygen In ethyl acetate at 70℃; for 24h;	A 98% B 1%

7,7a-dihydro-3H-3a,6-epoxyisobenzofuran-1(6H)-one → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With methanesulfonic acid; acetic anhydride at 80℃; Temperature; Reagent/catalyst;	98%
With sulfuric acid; acetic anhydride at 0 - 80℃; for 1h;

o-carboxybenzaldehyde (119-67-5) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With (dipyridylamine)Cp*IrOSO3; hydrogen In water at 130℃; under 3750.38 Torr; for 32h;	97%
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In water at 80℃; for 2h; chemoselective reaction;	91%
With sodium tetrahydroborate; nickel(II) phthalocyanine In PEG-400 at 20℃; for 0.333333h; chemoselective reaction;	87%
With iodine; phosphorous acid In 1,2-dichloro-ethane at 60℃; for 13h; Inert atmosphere; Schlenk technique;	86%
Multi-step reaction with 2 steps 1: fluorobenzene / 0.5 h / 46 °C / Microwave irradiation 2: potassium carbonate / fluorobenzene / 0.17 h / 155 °C View Scheme

2-iodobenzyl alcohol (5159-41-1) + terephthalaldehyde, (623-27-8) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
Stage #1: terephthalaldehyde, With palladium 10% on activated carbon; sodium carbonate In isopropyl alcohol at 110℃; for 24h; Inert atmosphere; Stage #2: 2-iodobenzyl alcohol With triphenylphosphine In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 100℃; for 24h; Catalytic behavior; Solvent; Temperature; Inert atmosphere;	97%
Stage #1: terephthalaldehyde, With palladium 10% on activated carbon; sodium carbonate In isopropyl alcohol at 120℃; for 24h; Inert atmosphere; Stage #2: 2-iodobenzyl alcohol With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Inert atmosphere;	85%

2-hydroxymethyl-benzoic acid hydrazide (51707-35-8) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With t-butyldimethylsiyl triflate; N,N-dimethyl-formamide at 20℃; for 20h;	97%

2-(bromomethyl)benzoic acid (7115-89-1) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
Stage #1: 2-(bromomethyl)benzoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h; Stage #2: With methyl iodide In acetone at 20℃; for 4h;	96%
With cesium fluoride In acetonitrile for 10h; Heating;	80%
With sodium hydroxide anschl. Ansaeuern;
In gas at 380℃; Mechanism; Thermodynamic data; Ea(excit.);

benzo[c]thiophene-1,3-dione (5698-59-9) → 2-benzofuran-1(3H)-one (87-41-2) + 3-hydroxy-2-thiophthalide

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1.5h;	A n/a B 96%

carbon monoxide (201230-82-2) + o-bromobenzyl alcohol (18982-54-2) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 2.5h; Irradiation;	95%
With potassium carbonate; F-CH2Co(CO)4 In methanol at 25℃;	84%
With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l); triethylamine In toluene at 100℃; under 900.09 Torr; for 12h;	82 %Chromat.

styrene oxide (96-09-3) + o-bromobenzyl alcohol (18982-54-2) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With 5%-palladium/activated carbon; sodium fluoride In 1,4-dioxane at 150℃; for 24h;	94%

styrene (292638-84-7) + o-bromobenzyl alcohol (18982-54-2) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With 5%-palladium/activated carbon; sodium fluoride; 3-chloro-benzenecarboperoxoic acid In 1,4-dioxane at 150℃; for 24h;	94%

4,7-dihyrophthalide (21483-54-5) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 14h; Ambient temperature;	92%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + ethanol (64-17-5) + o-bromobenzyl alcohol (18982-54-2) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With dmap; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 0.5h; Microwave irradiation;	92%

phthalyl alcohol (612-14-6) → 2-benzofuran-1(3H)-one (87-41-2) + butanedial (638-37-9)

Conditions	Yield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h;	A 92% B 8%

Diethyl phthalate (84-66-2) → 2-benzofuran-1(3H)-one (87-41-2) + phthalyl alcohol (612-14-6)

Conditions	Yield
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;	A 9% B 91%
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;	A 8% B 91%
With diisobutylaluminium hydride In dichloromethane; toluene at -30 - 20℃; for 1h; Inert atmosphere; regioselective reaction;	A 68% B 10%
With diisobutylaluminium hydride In dichloromethane; toluene at -30 - 20℃; for 1h; Temperature; Inert atmosphere; regioselective reaction;	A 30% B 60%

2-(hydroxymethyl)benzoic acid (612-20-4) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With oxygen In water at 80℃; for 12h; Reagent/catalyst; Sealed tube;	90%
With copper(II) oxide; zinc In water at 250℃; for 2h;	17%
With water

2-[(Diisopropoxy-methyl-silanyl)-methyl]-benzoic acid methyl ester (85719-69-3) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With peracetic acid; potassium fluoride In N,N-dimethyl-formamide for 18h; Ambient temperature;	90%

benzoic acid (65-85-0) + 1,2-dibromomethane (74-95-3) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With dipotassium hydrogenphosphate; palladium diacetate at 140℃; for 36h;	90%
With dipotassium hydrogenphosphate; palladium diacetate at 130℃; for 36h;	87%
With palladium diacetate for 36h; Alkaline conditions; Heating;

(2-methoxyphenyl)methanol (612-16-8) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With tungsten(VI) oxide monohydrate; dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 24h;	90%

3-chloro-1(3H)-isobenzofuranone (6295-21-2) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With triethylamine; nickel In tetrahydrofuran	89%
With hydrogen In Pt on charcoal; 5,5-dimethyl-1,3-cyclohexadiene
With sodium acetate; palladium In acetic acid

o-phthalic dicarboxaldehyde (643-79-8) + phenylboronic acid (98-80-6) → 2-benzofuran-1(3H)-one (87-41-2) + 3-phenylphthalide (5398-11-8)

Conditions	Yield
With potassium carbonate; 1,2-bis-(diphenylphosphino)ethane; cobalt(II) iodide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	A 10% B 89%
With 1,10-Phenanthroline; potassium carbonate; cobalt(II) chloride In acetonitrile at 80℃; for 12h; Inert atmosphere;	A 65% B 36%

2-benzofuran-1(3H)-one (87-41-2) + methylmagnesium bromide (75-16-1) → α,α-dimethyl-o-xylene α,α'-diol (55549-01-4)

Conditions	Yield
at -78 - 20℃;	100%
In tetrahydrofuran; diethyl ether at 30℃; for 12.5h;	88%
unter Wasserabgabe entsteht 1.1-Dimethyl-phthalan;

2-benzofuran-1(3H)-one (87-41-2) + methylamine (74-89-5) → 2-methylisoindolin-1-one (5342-91-6)

Conditions	Yield
In water at 220℃; under 114000 Torr; for 4h;	100%
With ethanol at 220℃;
In 5,5-dimethyl-1,3-cyclohexadiene

2-benzofuran-1(3H)-one (87-41-2) → phthalyl alcohol (612-14-6)

Conditions	Yield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.25h;	100%
With dimethyl zinc(II); sodium hydride In tetrahydrofuran at 0℃; for 6h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; under 760.051 Torr; for 16h; Inert atmosphere;	99%

2-benzofuran-1(3H)-one (87-41-2) + phenylmethanethiol (100-53-8) → 2-<(Benzylthio)methyl>benzoic acid (1218-59-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil for 45h; Reflux;	100%
With sodium hydride In N,N-dimethyl-formamide for 24h; Heating;	99%
	58%
With sodium ethanolate In ethanol

methanol (67-56-1) + 2-benzofuran-1(3H)-one (87-41-2) → o-(chloromethyl)benzoic acid methyl ester (34040-62-5)

Conditions	Yield
Stage #1: 2-benzofuran-1(3H)-one With boron trifluoride diethyl etherate; N-benzyl-N,N,N-triethylammonium chloride In xylene at 100℃; Stage #2: With thionyl chloride In xylene at 100 - 132℃; for 3h; Stage #3: methanol at 50 - 60℃; for 2h;	100%
Stage #1: 2-benzofuran-1(3H)-one With chloro(triphenyl)phosphonium chloride at 180℃; for 2h; Stage #2: methanol With pyridine for 1h;
With pyridine; dichlorotriphenylphosphorane at 180℃;

2-benzofuran-1(3H)-one (87-41-2) → lithium 3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Conditions	Yield
In tetrahydrofuran; hexane	100%

2-benzofuran-1(3H)-one (87-41-2) + 2,6-difluorobenzaldehyde (437-81-0) → 2-(2,6-difluorophenyl)-1,3-dioxoindane

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	100%

2-benzofuran-1(3H)-one (87-41-2) + methylamine (74-89-5) → 2-(hydroxymethyl)-N-methylbenzamide (39976-03-9)

Conditions	Yield
In methanol for 36h;	99.5%

2-benzofuran-1(3H)-one (87-41-2) + p-methoxybenzyl chloride (824-94-2) → 4-methoxybenzyl 2-(hydroxymethyl)benzoate

Conditions	Yield
Stage #1: 2-benzofuran-1(3H)-one With sodium hydroxide In water at 20℃; for 3h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 80℃; for 1h;	99%
Stage #1: 2-benzofuran-1(3H)-one With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 80℃; for 1h;

2-benzofuran-1(3H)-one (87-41-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1,2-bis(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)benzene

Conditions	Yield
With ToMMgMe at 24.84℃; for 1h;	99%
With C12H36MgN2Si4 In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	99%
With C42H50Mg2N4 In neat (no solvent) at 25℃; for 1h; Glovebox; Schlenk technique; Inert atmosphere;	99 %Spectr.

2-benzofuran-1(3H)-one (87-41-2) + tert-Butoxybis(dimethylamino)methane (5815-08-7) → 3-isobenzofuran-1(3H)-one (89968-08-1)

Conditions	Yield
at 135℃; for 0.5h;	98%

2-benzofuran-1(3H)-one (87-41-2) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → tetra-n-butylammonium 2-(hydroxymethyl)benzoate (93612-81-8)

Conditions	Yield
for 0.5h;	98%
With water for 1.5h; Heating;	39 g
In water for 1.5h; Heating;

2-benzofuran-1(3H)-one (87-41-2) + butyraldehyde (123-72-8) → 3-hydroxybutyl phthalide (168288-19-5)

Conditions	Yield
Stage #1: 2-benzofuran-1(3H)-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: butyraldehyde In tetrahydrofuran	98%
With lithium diisopropyl amide 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1-2 h; Yield given. Multistep reaction;

2-benzofuran-1(3H)-one (87-41-2) + N-butylamine (109-73-9) → N-butyl-2-hydroxymethylbenzamide (39976-06-2)

Conditions	Yield
In neat (no solvent) at 40℃; for 3h;	98%

2-benzofuran-1(3H)-one (87-41-2) → α-carboxy-α'-hydroxy-o-xylene sodium salt

Conditions	Yield
With sodium hydroxide In water for 2h; Reflux;	98%

2-benzofuran-1(3H)-one (87-41-2) → 3-Bromophthalide (6940-49-4)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane	97%
With N-Bromosuccinimide In tetrachloromethane for 0.666667h; Bromination; Irradiation;	94%
With N-Bromosuccinimide In tetrachloromethane for 0.666667h; Irradiation;	94%

2-benzofuran-1(3H)-one (87-41-2) → 1,3-dihydroisobenzofuran-1-ol (59868-79-0)

Conditions	Yield
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1.5h;	97%
With diisobutylaluminium hydride	91%
With diisobutylaluminium hydride In dichloromethane at -78℃;	70%

Upstream product

• 85-41-6 O-Phthalimide 
• 7440-66-6 ZINC 
• 7758-98-7 Copper(II) sulfate 

Downstream Products

• 135186-78-6 PYRIFTALID 
• 119-67-5 2-Carboxybenzaldehyde 
• 724-98-1 2-(Phenoxymethyl)benzoic acid 
• 602-25-5 1,4-DICHLOROANTHRAQUINONE 
• 7115-89-1 2-(Bromomethyl)benzoic acid 

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