A-(P-TOLUENESULFONYL)-4-FLUOROBENZYLISONITRILE Chemical Properties

Melting point:

>89°C (dec.)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White to Light Orange

InChI

InChI=1S/C15H12FNO2S/c1-11-3-9-14(10-4-11)20(18,19)15(17-2)12-5-7-13(16)8-6-12/h3-10,15H,1H3

InChIKey

UXCQPEDHCCJBNL-UHFFFAOYSA-N

SMILES

C(C1C=CC(F)=CC=1)([N+]#[C-])S(C1C=CC(C)=CC=1)(=O)=O

Safety Information

Hazard Codes 

Xi

HS Code 

2930909899

A-(P-TOLUENESULFONYL)-4-FLUOROBENZYLISONITRILE Usage And Synthesis

Uses

Alpha-(p-toluenesulfonyl)-4-fluorobenzylisonitrile is a useful reagent for the development of DNA-compatible method for novel functionalized imidazoles.

Synthesis

4-Fluorophenyl-toluenesulfonylmethylformamide (2.01 g, 6.25 mmol) was used as the raw material, which was dissolved in DME (32 mL) and cooled to -10 °C. POCl3 (1.52 mL, 16.3 mmol) and triethylamine (4.6 mL, 32.6 mmol, dissolved in DME 3 mL) were added sequentially while keeping the internal temperature below -5 °C. The reaction mixture was slowly warmed to room temperature over 1 h and subsequently poured into water and extracted with EtOAc. The organic phase was washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated. The residue was ground with petroleum ether and filtered to give α-tosyl(4-fluorobenzyl)isonitrile (1.7 g, 90% yield).1H NMR (CDCl3) δ 7.63 (d, 2H), 7.33 (m, 4H), 7.10 (t, 2H), 5.60 (s, 1H), 2.50 (s, 3H).

References

[1] Patent: US6046208, 2000, A
[2] Patent: US5658903, 1997, A
[3] Patent: US5716955, 1998, A
[4] Patent: US5739143, 1998, A
[5] Patent: US5756499, 1998, A

A-(P-TOLUENESULFONYL)-4-FLUOROBENZYLISONITRILE(165806-95-1)Related Product Information

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