4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzoic Acid is a photoreactive aromatic diazirine.
A highly photolabile label fixable to biochemical agents.
A highly sensitive photocross-linker.activated at 300 nm for the preparation of photoactivatable biological probes [1].
reaction type: Photoclick reactions
Conversion of the bromo benzene derivative (I) to its Grignard compound and subsequent addition of N-trifluoroacetylpiperidine (II) gives the trifluoroacetophenone (III) which is converted to its oxime tosylate (V). This reacts with liquid ammonia to give the diaziridine ( VI). Further hypochlorite oxidation and cleavage of the oxazoline ring finally yields the desired acid (4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzoic acid, VIII) mentioned in the title.
[1]
[1] Y. HATANAKA Y. K H Nakayama. An improved synthesis of 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic acid for photoaffinity labeling[J]. Heterocycles, 1993, 35 1: 997-1004. DOI:10.3987/COM-92-S(T)93.
