Triethylphosphine

Colorless liquid odor of hyacinths bp, 121 128°C.1 Isopropyl alcohol solution (67% by weight) has strong odor.2 

Pyrophoric.2 Ignites spontaneously on contact with oxidizable material.3 

Practically insoluble in water miscible with alcohol and ether.1 

Oxygen. Action of oxygen at low temperature on triethylphosphine produces an explosive product.4 

Wear eye protection, laboratory coat, and nitrile rubber gloves. Cover liquid with a 1 1 1 mixture by weight of sodium carbonate, clay cat litter (bentonite), and sand. Scoop the solid into a container and transport to the fume hood. Slowly add the solid to laundry bleach (contains about 5% sodium hypochlorite 75 mL per 1 g of triethylphosphine). Maintain a temperature of 45-50°C during addition, and then stir for another 2 hours. Decant the liquid into the drain. Package the solid for disposal by burning.5,6 

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Donor strengths, taken from ref. 207b, based upon the solvent effect on the symmetric stretching frequency of the soft Lewis acid HgBr2. Gutmann s donor number taken from ref 207b, based upon AHr for the process of coordination of an isolated solvent molecule to the moderately hard SbCL molecule in dichioroethane. ° Bulk donor number calculated as described in ref 209 from the solvent effect on the adsorption spectrum of VO(acac)2. Taken from ref 58, based on the NMR chemical shift of triethylphosphine oxide in the respective pure solvent. Taken from ref 61, based on the solvatochromic shift of a pyridinium-A-phenoxide betaine dye. 

Tetra-O-acetyl-l-thio-beta-d-glucopyranosato-S )-(triethylphosphine)gold [34031-32-8]... 

Triethylphosphine [554-70-1] M 118.2, b 100"/7mm, 127-128"/744mm, (I4 0.812, n D 1.457, pK 8.69 (also available as a l.OM sola in THF). All operations should be carried out in an efficient fume cupboard because it is flammable, toxic and has a foul odour. Purified by fractional distn at atm pressure in a stream of dry N2, as it is oxidised by air to the oxide. In 300% excess of CS2 it forms Et3PCS2 (m 118-120" cryst from MeOH) which decomposes in CCI4 to give Et3PS as a white solid m 94" when recryst from EtOH. [Sorettas and Isbell 7 Org Chem 27 273 1962 J Am Chem Soc S2 5791 I960, pK Henderson and Streuli 7 Am Chem Soc S2 5791 I960, see also trimethylphosphine.] Store in a sealed vial under N2. 

Croups Dodecacarbonyidi vanadium (Ammonium sulphide) Triethylphosphine... 

A) Triethylphosphinegoldchloride A solution of 10.0 g (O.OB mol) of thiodiglycol in 25 ml of ethanol is mixed with a solution of 15.76 g (0.04 mol) of gold acid chloride trihydrata-in 75 ml of distilled water. When the bright orange-yellow solution is almost colorless, it is cooled to -5°C and an equally cold solution of 5.0 g (0.0425 mol) of triethylphosphine in... 

Despite several attractive features in this method of direct halogen introduction and the obvious applications in the synthesis of deoxy sugars, its uses have not been further exploited by other groups of workers. Some new related methods have become available which reportedly eliminate the difficulties previously encountered such as rearrangement, unreactivity due to steric hindrance, and phosphonate ester formation. The reaction is based on the observation (28) that triethylphosphine reacts with ethanol and carbon tetrachloride to give ethyl chloride, chloroform, and triethylphosphite. In a new adaptation (76, 77) of this... 

Figure 2.57 Interconversion between rhodium triethylphosphine complexes.

Figure 2.59 Interconversion between dimeric triethylphosphine complexes.

Cobalt, tetraamminepyrophosphato-structures, 1, 202, 203 Cobalt, tetraammine(sarcosine)-chirality, 1,198 Cobalt, triammine-structure, 1, 8—10 Cobalt, tricarbonato-reactions, 1,22 Cobalt, tricarbonylnitroso-exchange reactions, 1, 290 Cobalt, trichloro-equilibrium constant, 1, 517 Cobalt, trichlorobis(triethylphosphine)-structure, 1, 45... 

Treatment of the bis(amidine) derivatives with a strong base such as Bu Li leads to conversion to the corresponding amidinato(amidine) complexes which on further reaction with triethylphosphine loose the coordinated free amidine as illustrated in Scheme 125. ... 

CN (2,3,4,6-tetra-O-acetyl-1 -thio-P-D-glucopyranosato-S)(triethylphosphine)gold... 

In the synthesis of l,3-dithiolan-2-ones from spirocyclic intermediates, via episulfides, substituted tetrathiacyclododecane and the related pentathiacyclopentadecane were isolated in good yields <96JCS(P1)289>. Preparation and molecular dynamics studies of 2,5,8,17,20,23-hexathia[9.9]-p-cyclophane have been reported <96P4203>. The syntheses and properties of thiocrowned l,3-dithiole-2-thiones and their conversion to tetrathiafiilvenes via treatment with triethylphosphine have been described <96LA551>. 

N.m.r. studies are reported on the triethylphosphine and trisdi-methylaminophosphine complexes with boron halides, and triethylphos-phine complexes with aluminium chloride. A correlation of Sp with the number of phosphorus ligands in metal carbonyl complexes has led to a qualitative rationalization of 8p in terms of a- and 7r-bonding. ... 

The hydrogen-bonding ability of triethylphosphine with pyrrole, [see... 

Not surprisingly, the dipole moments of 1 1-complexes of phosphines and aluminium chloride are very large. Triethylphosphine also forms a 2 1 complex whose very low dipole moment suggests a symmetrical structure such as (139). ... 

Uson, R., Laguna, A. and Vicente, J. (1976) Dihaloperhalophenyl(triethylphosphine) gold(III) complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 6(4), 293—305. 

Tetra-0-acetyl-l-thio-(5-D-pyranosato- S-(triethylphosphine)gold(I) Auranofin EtjPAuSAtg... 

Coates, G.E., Kowala, C. and Swan, J.M. (1966) Coordination compounds of Group IB metals. I. Triethylphosphine complexes of Au(I) mercaptides. Australian Journal of Chemistry, 19, 539-545. 

Hill, D.T. and Sutton, B.M. (1980) (2,3,4,6-Tetra-O-acetyl-l-thio-p -d-glucopyranosato-S) (triethylphosphine) gold, C20H34AUO9PS. Acta Crystallographica Section C Crystal Structure Communications, 9, 679-686. 

Ecker, D.J., Hempel, J.C., Sutton, B.M., Kirsch, R. and Crooke, S.T. (1986) Reactions of the metallodrug auranofin [(1-thio-p-D-glucopyranose-2,3,4,6-tetraacetato- S) (triethylphosphine) gold] with biological ligands studied... 

Isab, A.A., Shaw, C.E. Ill and Locke, J. (1988) GC-MS and oxygen-17 NMR tracer studies of triethylphosphine oxide formation from auranofin and water- O in the presence of bovine serum albumin an in vitro model for auranofin metabolism. Inorganic Chemistry, 27, 3406-3409. 

In the presence of air, trimethyl, triethyl, and tributylphosphine combust spontaneously. In the presence of pure oxygen, even though it was at a low temperature, triethylphosphine detonated. In the same conditions, triphenyl-phosphine does not seem to be dangerous. Trimethylphosphine can be stored safely in the air in the form of a complex with silver iodide. 

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