Tetrakis(hydroxymethyl)phosphonium chloride synthesis
- Product Name:Tetrakis(hydroxymethyl)phosphonium chloride
- CAS Number:124-64-1
- Molecular formula:C4H12ClO4P
- Molecular Weight:190.56
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124-64-1
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Yield:124-64-1 80%
Reaction Conditions:
Stage #1: formaldehydwith phosphorus;bis(tri-n-butyltin)oxide;1,1'-azobis(1-cyanocyclohexanenitrile) in ethanol at 20; for 16 h;
Stage #2: with hydrogenchloride in 1,4-dioxane;ethanol at 20; for 4 h;Catalytic behavior;Cooling with liquid nitrogen;Reagent/catalyst;
Steps:
Synthesis and isolation of THPC (17) via hydrostannylation starting from (Bu3Sn)2O, with recycling of Bu3SnCl (20) (5 mmol scale).
To a 500-ml round-bottomed Schlenk flask were added P4 (620 mg, 5 mmol) and PhMe (250 ml). After stirring to obtain a homogeneous solution, (Bu3Sn)2O (10.2 ml, 20 mmol), PMHS (2.3 ml, 40 mmol) and ACN (244 mg, 1 mmol) were added. The Schlenk flask was immediately and thoroughly wrapped in Al foil to exclude any ambient light, and the stirred reaction mixture was heated to 80 °C for three days. Following removal of volatiles under vacuum, EtOH (250 ml) and paraformaldehyde (7.51 g, 250 mmol) were added, and the resulting suspension was stirred at room temperature for 16 h. The mixture was frozen in a liquid-nitrogen bath and HCl (4.0 M in 1,4-dioxane, 50 ml, 200 mmol) was added. After thawing, the reaction mixture was stirred at room temperature for 4 h. The pale yellow suspension was filtered through a bed of Celite in a glass frit (P4) column, and volatiles were removed under vacuum. The remaining oily solid residue was triturated with Et2O (200 ml) overnight, filtered and washed with further Et2O (2 x 25 ml). The resulting white solid was then again extracted into EtOH (2 x 100 ml). Following filtration and removal of volatiles under vacuum, the desired product was obtained as a white solid (3.05 g, 80%).
References:
Scott, Daniel J.;Cammarata, Jose;Schimpf, Maximilian;Wolf, Robert [Nature Chemistry,2021,vol. 13,# 5,p. 458 - 464]
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7803-51-2
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124-64-1
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2767-80-8
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124-64-1
225 suppliers
$7.00/25g
50-00-0
842 suppliers
$10.00/25g
2767-80-8
69 suppliers
$63.00/250mg
124-64-1
225 suppliers
$7.00/25g