TETRABUTYLAMMONIUM FLUORIDE
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TETRABUTYLAMMONIUM FLUORIDE
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CAS No:
22206-57-1
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Formula:
C16H36FN
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Chemical Name:
TETRABUTYLAMMONIUM FLUORIDE
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Synonyms:
TETRABUTYLAMMONIUM FLUORIDE ON ALUMINA;TETRA-N-BUTYLAMMONIUM FLUORIDE;TETRA-N-BUTYLAMMONIUM FLUORIDE HYDRATE;TETRA-N-BUTYLAMMONIUM FLUORIDE ON SILICA GEL;'FLUORIDE' ON SILICA GEL;Tetrabutylammoniumfluoridehydrate,98%;1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate;TETRABUTYLAMMONIUM FLUOROIDE HYDRATE
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CAS No:
Characteristics
0.00000
2.00760
white crystal
0.953 g/mL at 25ºC
62-63 °C(lit.)
1 °F
n20/D 1.456
2-8°C
Safety Information
Ⅱ
8
UN 2924 3/PG 2
3
34
26-27-36/37/39-45
C
hygroscopic
P280-P305 + P351 + P338-P310
H314
TETRABUTYLAMMONIUM FLUORIDE Use and Manufacturing
The compound 3 (0.2 g, 0.7 mmol) was dissolved in THF (20 mL). The reaction mixture was cooled to '78 C, followed by the addition of NBu4F'3H2O (0.22 g, 0.7 mmol). The temperature of the mixture was raised to 0 C, the mixture was poured into 10percent aqueous HCl (10 mL) and extracted with diethyl ether (2×20 mL).The organic extracts were combined and dried with sodium sulfate, the solvent was evaporated. The product was purified by column chromatography (eluent hexane). The yield was 0.042 g(0.20 mmol, 28percent), a white foam. Found (percent): C, 34.01; H, 6.73.C6H14B10O. Calculated (percent): , 34.27; , 6.71. 1H NMR(CDCl3), : 5.16 (s, 1 H, CHO); 4.39 (d, 1 H, HCHO, J = 8.7 Hz);4.29 (d, 1 H, HCHO, J = 8.8 Hz); 2.78 (d, 1 H, C'CH, J = 2.1 Hz);3.13'1.47 (br.m, 10 H, BH). 13C NMR (CDCl3), : 80.0 (Ccarb);78.5 (Ccarb); 77.7 (C'CH); 76.9 (C'CH); 73.2(CHO); 73.1(CH2O). 11B NMR (CDCl3), : '5.8 (d, 2 B, J =151 Hz); '7.5(d, 1 B, J =154 Hz); '8.2 (d, 2 B, J =163 Hz); '10.1 (d, 1 B, J =180 Hz); '12.4 (d, 2 B, J =170 Hz); '13.1 (d, 2 B, J =154 Hz).After the penultimate step, the resultant 2-trimethylsilanyl-ethyl ester (245 mg, 0.107 mmol, Eq: 1.00) was combined with THF abs, (5 mL) to give a colorless solution. Tetrabutyl-ammonium fluoride trihydrate (168 mg, 0.533 mmol, Eq: 5.00) was added at 0° C. and the reaction was stored in the fridge over night.Pouring onto crushed ice, extraction with ethyl acetate, washing with water, drying over Na2SO4, and evaporation of all solvents yielded a sticky oil.Dissolution in acetonitrile and water and lyophilization afforded eventually 0.120 g of the title compound as white solid, MS (ISP): 112.5 [M+2Na]2+/2.
Reagent for the preparation of terminal olefins from primary alkyl iodides.
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