Abstract
image
[2209891‐87‐0]
C
9
H
4
F
3
IN
2
O
2
(MW 356.04)
InChI =
1S/C9H5F3IN2O2/c10‐9(11,12)8(15‐14)13‐6‐4‐2‐1‐3‐5(6)7(16)17‐13/h1‐4,14H/q+1
InChIKey =
GDZYWAHOHOTWJD‐UHFFFAOYSA‐N
(reagent used to generate trifluoroethylcarbyne)
Physical Data
: mp 146–147 °C, d 2.0201 g cm
−3
.
1
Solubility
: soluble in CH
3
CN, CH
2
Cl
2
, CHCl
3
, DMSO, and ClCH
2
CH
2
Cl.
2
Analysis of Reagent Purity
:
1
H NMR (400 MHz, CD
3
CN) δ 8.20 (dd,
J
= 7.4 and 1.7 Hz, 1
H
), 8.03 (dd,
J
= 8.3 and 0.9 Hz, 1
H
), 7.87 (ddd,
J
= 8.3, 7.2, and 1.7 Hz, 1
H
), and 7.78 (td,
J
= 7.3 and 1.0 Hz, 1
H
) ppm; and singlet in
19
F NMR at δ −54.41 ppm. IR (film, cm
−1
) 3068, 2358, 2094, 1653, 1290, 1263, and 1120.
1,2
Preparative Methods
: addition of trimethylsilyl trifluoromethanesulfonate to 1‐acetoxy‐1,2‐benziodoxol‐3(1
H
)‐one at 24 °C, followed by the addition of pyridine and finally slow addition of a solution of 2,2,2‐trifluorodiazoethane.
1,2
Purification
: recrystallization using a mixture of diethyl ether and dichloromethane in a 5:1 ratio.
1,2
Handling, Storage, and Precautions
: the reagent should be kept tightly closed and stored at −24 °C.
1,2