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Sigma-Aldrich

4-Fluorophthalic anhydride

97%

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About This Item

Empirical Formula (Hill Notation):
C8H3FO3
CAS Number:
319-03-9
Molecular Weight:
166.11
MDL number:
MFCD00191363
UNSPSC Code:
12352100
PubChem Substance ID:
24883115
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

mp

75-79 °C (lit.)

SMILES string

Fc1ccc2C(=O)OC(=O)c2c1

InChI

1S/C8H3FO3/c9-4-1-2-5-6(3-4)8(11)12-7(5)10/h1-3H

InChI key

XVMKZAAFVWXIII-UHFFFAOYSA-N

General description

4-Fluorophthalic anhydride is a fluorinated building block commonly used in chemical synthesis for the preparation of polyimide, pesticides, herbicides, and fungicides. It can be synthesized by treating 4-chlorophthalic anhydride with potassium fluoride.

Application

4-Fluorophthalic anhydride can be used as a reactant to prepare:
  • 4-amino substituted phthalimides applicable as potential fluorescent probes and fluorescent bioactive compounds.
  • 4,4′-bis(4-fluorophthalimido)diphenyl ether monomer, which is used in the synthesis of cardo polymers via nucleophilic substitution polymerization reaction.
  • Asymmetric polyimides by a solution polycondensation reaction.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of cardo containing asymmetric poly (ether-naphthalimide-phthalimide) s
Mushtaq N, et al.
Polymer International, 66(11), 1633-1639 (2017)
Synthesis of high performance phenolphthalein-based cardo poly (ether ketone imide) s via aromatic nucleophilic substitution polymerization
Liu Jiangtao, et al.
Polymer, 70, 30-37 (2015)
Saturated vapor pressure of 4-fluorophthalic anhydride and 4-chlorophthalic anhydride and isobaric vapor-liquid phase equilibrium of 4-fluorophthalic anhydride+ 4-chlorophthalic anhydride: Measurement and modeling
LiRongRong, et al.
Fluid Phase Equilibria, 396, 35-42 (2015)
Efficient one-step synthesis of 4-amino substituted phthalimides and evaluation of their potential as fluorescent probes
Kindahl T and Chorell E
Organic & Biomolecular Chemistry, 12(25), 4461-4470 (2014)
Vu H Nguyen et al.
EJNMMI research, 3(1), 80-80 (2013-12-18)
Sigma2 (σ2) receptors are highly expressed in cancer cell lines and in tumours. Two novel selective 18F-phthalimido σ2 ligands, 18F-SIG343 and 18F-SIG353, were prepared and characterised for their potential tumour imaging properties. Preparation of 18F-SIG343 and 18F-SIG353 was achieved via
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