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