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125733

Sigma-Aldrich

Phthalic anhydride

ReagentPlus®, 99%

Synonym(s):

1,2-Benzenedicarboxylic anhydride, 1,3-Isobenzofurandione, Phthalic acid anhydride

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About This Item

Empirical Formula (Hill Notation):
C8H4O3
CAS Number:
Molecular Weight:
148.12
Beilstein:
118515
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

vapor density

5.1 (vs air)

Quality Level

vapor pressure

<0.01 mmHg ( 20 °C)

product line

ReagentPlus®

Assay

99%

form

flakes

autoignition temp.

1058 °F

expl. lim.

10.4 %

bp

284 °C (lit.)

mp

131-134 °C (lit.)

functional group

anhydride
ester

SMILES string

O=C1OC(=O)c2ccccc12

InChI

1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H

InChI key

LGRFSURHDFAFJT-UHFFFAOYSA-N

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General description

Phthalic anhydride is an industrially important chemical. It can be prepared from o-xylene or naphthalene. It is widely used for the industrial preparation of plasticizers for PVC (polyvinyl chloride).
Phthalic anhydride can be synthesized via oxidation of o-xylene, in the presence of V2O5/TiO2 monolithic catalyst supported by aluminium honeycomb.

Application

Phthalic anhydride may be used in the synthesis of the following compounds:
  • pthalimide
  • phenolphthalein
  • anthracene

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

305.6 °F - DIN 51758

Flash Point(C)

152 °C - DIN 51758

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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"Conductive monolithic catalysts: development and industrial pilot tests for the oxidation of o-xylene to phthalic anhydride"
Groppi G, et al.
Industrial & Engineering Chemistry Research, 51(22), 7590-7596 (2011)
Phthalic anhydride from o-xylene catalysis: science and engineering.
Nikolov V, et al.
Catalysis Reviews: Science and Engineering, 33(3-4), 319-374 (1991)
Eagleson M.
Concise Encyclopedia Chemistry, 77-77 (1994)
Chuan-Fu Liu et al.
Journal of agricultural and food chemistry, 55(6), 2399-2406 (2007-02-27)
Homogeneous modification of cellulose, isolated with 10% KOH from delignified sugarcane bagasse, was performed in room-temperature ionic liquid 1-allyl-3-methylinidazolium chloride with phthalic anhydride in the absence of catalyst. The results showed the degree of substitution of phthalated cellulosic derivatives, ranging
Yuichi Kajita et al.
Journal of the American Chemical Society, 130(51), 17226-17227 (2008-12-04)
An intermolecular nickel-catalyzed addition reaction has been developed where phthalic anhydrides react with alkynes to afford substituted isocoumarins. A mechanistic rationale is proposed, implying reductive elimination of Ni(0) promoted by ZnCl(2) cocatalyst as the key step of the catalytic cycle.

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