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247715

Sigma-Aldrich

4-Amino-N-methylphthalimide

97%

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Empirical Formula (Hill Notation):
C9H8N2O2
CAS Number:
Molecular Weight:
176.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

mp

246-248 °C (lit.)

SMILES string

CN1C(=O)c2ccc(N)cc2C1=O

InChI

1S/C9H8N2O2/c1-11-8(12)6-3-2-5(10)4-7(6)9(11)13/h2-4H,10H2,1H3

InChI key

KMEBUNSLFRQSEM-UHFFFAOYSA-N

General description

The intermediate charge-transfer transients of 4-amino-N-methylphthalimide (4AMP) has been characterized by laser flash photolysis, steady-state and time-resolved fluorescence studies. 4AMP is a solvatochromic fluorescent dye. Transient solvation of 4AMP in binary supercritical fluids composed of 2-propanol and CO2 has been studied by frequency-domain fluorescence spectroscopy.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Characterization of the triplet charge-transfer state of 4-amino-N-methylphthalimide in aprotic and protic media by laser flash photolysis.
Aich S, et al.
J. Chem. Soc., Faraday, 93(17), 2991-2996 (1997)
Reversible excited-state transient solvation in binary supercritical fluids revealed by multifrequency phase and modulation fluorescence.
Betts TA and Bright FV.
Appl. Spectroscopy, 44(7), 1203-1209 (1990)
Axel G Griesbeck et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 2(2), 113-117 (2003-04-01)
The fluorescent 4,5-dimethoxyphthalimides 1-10 were applied as sensors for intra- and intermolecular photoinduced electron transfer processes. Strong intramolecular fluorescence quenching was detected for the thioether 2 and the tertiary amine 3. The fluorescence of the carboxylic acids 4-7 is pH-dependent

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