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4-(Bromomethyl)-7-(diethylamino)coumarin

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4-(Bromomethyl)-7-(diethylamino)coumarin Basic information

Product Name:
4-(Bromomethyl)-7-(diethylamino)coumarin
Synonyms:
  • 4-(Bromomethyl)-7-(diethylamino)coumarin
  • 2H-1-Benzopyran-2-one, 4-(bromomethyl)-7-(diethylamino)-
CAS:
1256259-14-9
MF:
C14H16BrNO2
MW:
310.19
Mol File:
1256259-14-9.mol
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4-(Bromomethyl)-7-(diethylamino)coumarin Chemical Properties

Boiling point:
435.8±45.0 °C(Predicted)
Density 
1.407±0.06 g/cm3(Predicted)
pka
3.21±0.20(Predicted)
form 
powder to crystal
color 
Light yellow to Brown
InChI
InChI=1S/C14H16BrNO2/c1-3-16(4-2)11-5-6-12-10(9-15)7-14(17)18-13(12)8-11/h5-8H,3-4,9H2,1-2H3
InChIKey
JPBOBQNHSXLIBI-UHFFFAOYSA-N
SMILES
C1(=O)OC2=CC(N(CC)CC)=CC=C2C(CBr)=C1
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Safety Information

HS Code 
2932.20.0500
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4-(Bromomethyl)-7-(diethylamino)coumarin Usage And Synthesis

Research

7-Diethylamino-4-methyl coumarin (DEACM) derivatives are widely used as photolabile protecting groups. The photolysis of 4-(Bromomethyl)-7-(diethylamino)coumarin (DEACM-Br) with Br as the leaving group was investigated by Takanoet al. The main reaction path was found to be the generation of radical D via homolytic C–Br bond cleavage. Interestingly, products derived from C-T, the triplet state of the carbocation intermediate (i.e., 7-(diethylamino)-4-methyl cation (C)), were identified, thereby confirming the existence of C-T for the first time[1].

References

[1] Ma-aya Takano."Photoreaction of 4-(Bromomethyl)-7-(diethylamino)coumarin: Generation of a Radical and Cation TripletDiradical during the C-Br Bond Cleavage." Organic Letters (2022).

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