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467707

Sigma-Aldrich

3-Fluorophthalic anhydride

95%

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About This Item

Empirical Formula (Hill Notation):
C8H3FO3
CAS Number:
Molecular Weight:
166.11
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

solid

mp

158-161 °C (lit.)

SMILES string

Fc1cccc2C(=O)OC(=O)c12

InChI

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

InChI key

WWJAZKZLSDRAIV-UHFFFAOYSA-N

General description

3-Fluorophthalic anhydride undergoes reduction with NaBH4 to afford 4-fluorophthalide and 7-fluorophthalide. It can be synthesized starting from 3-nitrophthaloyl dichloride.

Application

3-Fluorophthalic anhydride may be used in the preparation of substituted benzamides with potential neuroleptic activity. It may be employed as starting reagent for the synthesis of 8-fluoro-10-methyl-1,2-benzanthracene.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of 8-Fluoro-10-methyl-1, 2-benzanthracene1.
Newman MS and Wiseman EH.
The Journal of Organic Chemistry, 26(9), 3208-3211 (1961)
A new synthesis of 3-fluorophthalic anhydride.
Passudetti M, et al.
Journal of Fluorine Chemistry, 50(2), 251-255 (1990)
Regioselectivity of metal hydride reductions of unsymmetrically substituted cyclic anhydrides. systems where" steric hindrance along the preferred reaction path" rationalization is not applicable.
Kayser MM and Morand P.
Canadian Journal of Chemistry, 58(23), 2484-2490 (1980)
Notes-Preparation of 3-Fluorophthalic Anhydride.
Heller A.
The Journal of Organic Chemistry, 25(5), 834-835 (1960)
M H Norman et al.
Journal of medicinal chemistry, 39(5), 1172-1188 (1996-03-01)
A series of substituted (4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)benzamide derivatives was prepared and evaluated as potential atypical antipsychotic agents. The target compounds were readily prepared from their benzoyl chloride, benzoic acid, or isatoic anhydride precursors, and they were evaluated in vitro for their ability

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