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87-41-2

Basic Information
CAS No.: 87-41-2
Name: Phthalide
Article Data: 561
Cas Database
Molecular Structure:
Molecular Structure of 87-41-2 (Phthalide)
Formula: C8H6O2
Molecular Weight: 134.134
Synonyms: Phthalolactone;Phthalide(6CI,8CI);1-Phthalanone;2-Benzofuran-1(3H)-one;2-Hydroxymethylbenzoic acid g-lactone;3H-Isobenzofuran-1-one;NSC 1469;
EINECS: 201-744-0
Density: 1.265 g/cm3
Melting Point: 71-74 °C(lit.)
Boiling Point: 289.999 °C at 760 mmHg
Flash Point: 124.844 °C
Solubility: sparingly soluble in water
Appearance: White to light beige crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36-36/37/38
Safety: 26-36-24/25-37/39
PSA: 26.30000
LogP: 1.35700
Synthetic route
612-14-6

phthalyl alcohol

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
643-79-8

o-phthalic dicarboxaldehyde

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
201230-82-2

carbon monoxide

5159-41-1

2-iodobenzyl alcohol

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
95-47-6

o-xylene

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

Conditions
ConditionsYield
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

Reaxys ID: 11463934

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

C

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
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

Reaxys ID: 11463934

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

Conditions
ConditionsYield
With oxygen at 340 - 360℃;A 0.01%
B 100%
With oxygen at 340 - 360℃;A 0.01%
B 100%
Reaxys ID: 11464679

Reaxys ID: 11464679

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

C

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 354 - 357℃;A 0.2%
B 100%
C 0.15%
88-95-9

Phthaloyl dichloride

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
496-14-0

1,3-dihydroisobenzofuran

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
85-44-9

phthalic anhydride

87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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%
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    Specifications Classification: Acaricide, Biological Pesticide, Fungicide, Herbicide, Insecticide, Molluscicide, Nematicide, Plant Growth Regulator, Rodenticide, Agrochemicals CAS No.: 87-41-2 Other Names: Phthalide MF: C8H6O2 EINECS No.: 2

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Phthalide, with the CAS registry number 87-41-2, is also known as 1(3H)-Isobenzofuranone. Its EINECS registry number is 201-744-0. This chemical's molecular formula is C8H6O2 and molecular weight is 134.13. What's more, its IUPAC name is called 3H-2-Benzofuran-1-one. Phthalide is a lactone that serves as the core chemical structure for a variety of more complex chemical compounds including dyes, fungicides and natural oils.

Physical properties about Phthalide are: (1)ACD/LogP: 1.029; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.03; (4)ACD/LogD (pH 7.4): 1.03; (5)ACD/BCF (pH 5.5): 3.56; (6)ACD/BCF (pH 7.4): 3.56; (7)ACD/KOC (pH 5.5): 86.43; (8)ACD/KOC (pH 7.4): 86.43; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 35.551 cm3; (15)Molar Volume: 106.065 cm3; (16)Polarizability: 14.094×10-24 cm3; (17)Surface Tension: 47.17 dyne/cm; (18)Density: 1.265 g/cm3; (19)Flash Point: 124.844 °C; (20)Enthalpy of Vaporization: 52.934 kJ/mol; (21)Boiling Point: 289.999 °C at 760 mmHg; (22)Vapour Pressure: 0.0020 mmHg at 25 °C.

Preparation of Phthalide: this chemical can be prepared by 2-methyl-benzoic acid. This reaction needs reagents sodium bromate, sodium hydrogen sulfite and solvents ethyl acetate, H2O at temperature of 20 °C. The reaction time is 40 hours. The yield is 63 %.

Phthalide can be prepared by 2-methyl-benzoic acid.

Uses of Phthalide: (1)it is mainly used as intermediates in organic synthesis; (2) it is used to produce other chemicals. For example, it can react with methylmagnesium bromide to get 2-(a-hydroxy-isopropyl)-benzyl alcohol. The reaction occurs with diethyl ether at temperature of 20 °C. The yield is 100 %.

Phthalide can react with methylmagnesium bromide to get 2-(a-hydroxy-isopropyl)-benzyl alcohol.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. You must avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1OCc2ccccc12
(2) InChI: InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
(3) InChIKey: WNZQDUSMALZDQF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD intraperitoneal > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 25, 1953.

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