1,3-dihydro-2-benzofuran-1,3-dione

• ChemBase ID: 103476
• Molecular Formular: C8H4O3
• Molecular Mass: 148.11556
• Monoisotopic Mass: 148.01604399
• SMILES: O=C1OC(=O)c2ccccc12
• Canonical SMILES: O=C1OC(=O)c2c1cccc2
• InChI: InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H
• InChIKey: LGRFSURHDFAFJT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dihydro-2-benzofuran-1,3-dione
• IUPAC Traditional name: phthalic anhydride; Pan
• Synonyms: Isobenzofuran-1,3-dione; 1,3-Isobenzofurandione; PHTHALIC ANHYDRIDE; Phthalic anhydride; Isobenzofuran-1,3-dione; 2,5-Isobenzofurandione; Benzene-1,2-dicarboxylic anhydride; Phthalic anhydride, ACS; 邻苯二甲酸酐; 邻苯二甲酸酐, ACS

Database IDs

• CAS Number: 85-44-9
• EC Number: 201-607-5
• MDL Number: MFCD00005918
• Beilstein Number: 118515
• Merck Index: 147372
• PubChem SID: 24859242; 24847534; 162090905; 24887514
• PubChem CID: 6811
• CHEBI ID: 36605
• Chemspider ID: 6552
• Wikipedia Title: Phthalic_anhydride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4225837
• LogD (pH = 7.4): 1.4225837
• Log P: 1.4225837
• Molar Refractivity: 37.365 cm^3
• Polarizability: 14.102598 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.62 g/100g (20—25 °C); ; 19.0 g/100g (100 °C); ; reacts slowly in water
• Apperance: Flaky Crystals; white flakes
• Melting Point: 129-133 °C; 130-133 °C; 130-134°C; 131 °C; 131 °C; 131-133°C; 131-134 °C(lit.)
• Boiling Point: 284 °C; 284 °C(lit.); 295 °C subl.; 295°C subl.
• Flash Point: 152 °C (closed cup and DIN 51758); 152 °C; 152°C(305°F); 305.6 °F
• Auto Ignition Point: 1058 °F; 580 °C
• Density: 1.527 g/cm^3 at 4 °C; 1.53; 1.53 g/cm^3, solid
• Vapor Pressure: <0.01 mmHg ( 20 °C); 2.7 E-4 hPa at 20 °C
• Vapor Density: 5.1 (vs air); 5.10 (air = 1)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Moisture Sensitive
• RTECS: TI3150000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2214; UN2214
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-37/38-41-42/43; R:22-37/38-41-42/43; R22, R37/38, R41, R42/43
• Safety Statements: 23-24/25-26-37/39-46; S:23-26-46-24/25-37/39; S2, S23, S24/25, S26, S37/39, S46
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 156
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  1

  3

  0
• Explode Limits: 10.4 %
• GHS Hazard statements: H302-H315-H317-H318-H334-H335; H334-H317-H318-H315-H302-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311; P285-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥99%; ≥97.0% (NT); ≥99%; ≥99.0%; ≥99.0% (T); 95+%; 99%; 99.0-100.2%
• Grade: ACS reagent; puriss.; purum; ReagentPlus®; SAJ first grade
• Ignition Residue: ≤0.01%
• Impurities: ~2% phthalic acid
• Cation Traces: Fe: ≤5 ppm; heavy metals (as Pb): ≤5 ppm
• Antion Traces: chloride (Cl-): ≤0.002%; sulfate (SO42-): ≤0.003%
• Empirical Formula (Hill Notation): C8H4O3

DETAILS

MP Biomedicals - 02151877

Crystalline
Purity: 99+%
Useful N-protecting reagent.

Sigma Aldrich - 320064

Packaging
2.5 kg in poly drum
25, 500 g in glass bottle

Sigma Aldrich - 125733

Packaging
1 kg in poly bottle
2.5 kg in poly drum
16 kg in fiber drum
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Can be used for the dehydration of nitro aldols to nitroalkenes; see, e.g.: Org. Synth. Coll., 7, 396 (1990).
• For examples of formation of phthalimides from amines, see: Org. Synth. Coll., 4, 106 (1963); 5, 973 (1973). As an alternative to hydrazinolysis, ɑ-amino acids can also be quantitatively recovered from their phthaloyl derivatives by prolonged reaction with aqueous methylamine at room temperature: Can. J. Chem., 48, 3572 (1970).
• Reaction with H₂O₂ gives monoperphthalic acid, useful in peroxidation reactions; see, e.g.: Org. Synth. Coll.,3, 619 (1955); 5, 805 (1973). With urea hydrogen peroxide, provides a superior system for converting N-heteroaromatics and tert-amines to their N-oxides: Chem. Ber., 125, 1965 (1992)