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524794

Sigma-Aldrich

3-Aminophthalimide

97%

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About This Item

Empirical Formula (Hill Notation):
C8H6N2O2
CAS Number:
2518-24-3
Molecular Weight:
162.15
MDL number:
MFCD00041853
UNSPSC Code:
12352100
PubChem Substance ID:
24874444

Assay

97%

mp

268.5-273.5 °C (lit.)

SMILES string

Nc1cccc2C(=O)NC(=O)c12

InChI

1S/C8H6N2O2/c9-5-3-1-2-4-6(5)8(12)10-7(4)11/h1-3H,9H2,(H,10,11,12)

InChI key

GQBONCZDJQXPLV-UHFFFAOYSA-N

General description

3-Aminophthalimide (API) is a stable precursor of luminol. API can be prepared by the hydrogenation of 3-nitrophthalimide and methanol in the presence of 10% Pd-C.

Application

3-Aminophthalimide may be used in direct chemiluminescent cellular bioassays. It may also be used in the preparation of 3-bromopthalimide.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

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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Certificates of Analysis (COA)

Lot/Batch Number
BCBP5195V
BCBB5078V
BCBB5078
1448218
01729KI

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A Study of the Aminophthalimidoacetic Acids1.
Caswell LR and Atkinson PC.
The Journal of Organic Chemistry, 29(11), 3151-3154 (1964)
Demetra Mavri-Damelin et al.
Bioconjugate chemistry, 20(2), 266-273 (2009-01-15)
We present a labeling system for direct chemiluminescence-based cellular bioassays using the stable pro-chemiluminescent, luminol precursor, 3-aminophthalimide (API). API-coupled reporter molecules are detected chemiluminometrically after treatment with hydrazine, which converts the API label to luminol. API derivatives containing a variety
177. Chemiluminescent organic compounds. Part VII. Substituted phthalaz-1: 4-diones. Effect of substituents on the luminescent power.
Drew HDK and Garwood RF.
Journal of the Chemical Society, 836-837 (1939)

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