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58279

Isatoic anhydride

Name: Isatoic anhydride
Brand: SIAL

technical, ≥94% (HPLC)

Synonym(s):

3,1-Benzoxazine-2,4(1H)-dione, Anthranilic acid N-carboxylic acid anhydride

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About This Item

Empirical Formula (Hill Notation):

C₈H₅NO₃

CAS Number:

118-48-9

Molecular Weight:

163.13

Beilstein:

136786

EC Number:

204-255-0

MDL number:

MFCD00006700

UNSPSC Code:

12162002

PubChem Substance ID:

329758412

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vapor density

5.6 (vs air)

grade

technical

Assay

≥94% (HPLC)

mp

233 °C (dec.) (lit.)

SMILES string

O=C1Nc2ccccc2C(=O)O1

InChI

1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)

InChI key

TXJUTRJFNRYTHH-UHFFFAOYSA-N

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Other Notes

Review[1]; Reagent for 2-aminobenzoylations[2]

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G.M. Coppola

Synthesis, 505-505 (1980)

M.C. Venuti

Synthesis, 266-266 (1982)

Fluorescence properties of o-aminobenzoyl-labeled proteins.

J E Churchich

Analytical biochemistry, 213(2), 229-233 (1993-09-01)

Isatoic anhydride reacts with nucleophile groups of proteins to yield o-aminobenzoyl protein conjugates. The fluorescence emitted by the chromophore decays in a multiexponential manner with average fluorescence lifetimes ranging from 9.9 to 10.7 ns. The steady emission anisotropy, measured upon

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones by three-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe(3)O(4) nanoparticles in water.

Zhan-Hui Zhang et al.

Journal of combinatorial chemistry, 12(5), 643-646 (2010-08-06)

A simple and efficient protocol for one-pot three-component coupling of isatoic anhydride, amines, and aldehydes in water using magnetically recoverable Fe(3)O(4) nanoparticles is reported. This methodology results in the synthesis of a variety of 2,3-dihydroquinazolin-4(1H)-ones in high yields. The catalyst

Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison.

Christine Hiu-Tung Chen et al.

Molecular diversity, 9(4), 353-359 (2005-11-29)

Reactions using fluorous reagents and scavengers are compared side-by-side with their solid-supported counterparts. Fluorous triphenylphosphine is used in the bromination reaction of alcohols, fluorous thiol is used as an electrophile scavenger for alpha-bromoketones, fluorous isatoic anhydride is used as a

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