CAS RN: 38078-09-0 | Product Number: D1868
(Diethylamino)sulfur Trifluoride [Fluorinating Reagent]
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This product is extremely corrosive to body tissues such as skin, eyes, mucous membranes and lungs. This reacts violently with water or moisture to produce HF gas, and may decompose violently at over 50 deg C. Please handle very carefully in a fume hood with personal protective equipment such as gloves and safety goggles. Experimental tools should be sufficiently dried.
|Purity / Analysis Method||>90.0%(T)|
|Molecular Formula / Molecular Weight||C__4H__1__0F__3NS = 161.19|
|Physical State (20 deg.C)||Liquid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Moisture Sensitive,Heat Sensitive|
|Reaxys Registry Number||1849066|
|PubChem Substance ID||87568332|
|Merck Index (14)||3113|
|Appearance||Colorless to Yellow to Orange clear liquid|
|Purity(Neutralization titration)||min. 90.0 %|
|Boiling Point||32 °C/10 mmHg|
|Flash point||23 °C|
|Specific Gravity (20/20)||1.23|
|Hazard Statements||H314 : Causes severe skin burns and eye damage.
H226 : Flammable liquid and vapour.
|Precautionary Statements||P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
|Class||8 / 3|
To a solution of 4-nitrobenzyl alcohol (153 mg, 1.0 mmol) in dichloromethane (2.8 mL, 0.36 mol/L) was added DAST (144 µL, 1.1 mmol) dropwise and the mixture was stirred at room temperature for 1 hour. Ice water (3 mL) and dichloromethane (10 mL) was added to the reaction mixture. The reaction mixture was extracted with dichloromethane (5 mL x 3) and the organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 1:99 - 20:80 on silica gel) twice, then was further purified by column chromatography (dichloromethane:hexane = 1:99 - 20:80 on silica gel) to give 4-nitrobenzyl fluoride as a pale yellow solid (111 mg, 72%).
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:4, Rf = 0.50).
Toxic HF would be produced from DAST with moisture in the air, so appropriate protective equipment was used and the work was done in a fume hood.
1H NMR (270 MHz, CDCl3); δ 8.27 (d, J = 7.8 Hz, 1H), 7.54 (d, J = 7.6 Hz, 1H), 5.51 (d, J = 46.7 Hz, 1H).
- 4-NITROBENZYL FLUORIDE
- L. N. Markovski, V. E. Pashinnik, A. V. Kirsanov Synthesis 1973, 787.
- W. J. Middleton, J. Org. Chem. 1975, 40, 574.
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