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Triphenylphosphine dibromide is used as a reagent for conversion of aldoximes into nitriles. It acts as a reagent for cleavage of acetals. It reacts with amines to give iminophosphoranes. Further, it serves as a reagent in the preparation of alkyl and aryl bromides from alcohols and phenols without rearrangement.
Reagent for the conversion of alcohols and phenols to bromides in good yields: J. Org. Chem., 37, 626 (1972). Particularly useful for alcohols where sensitive functionality is present: J. Org. Chem., 49, 431 (1984); Synth. Commun., 22, 2945 (1992). Cleaves dialkyl ethers to the two alkyl bromides: J. Am. Chem. Soc., 86, 5037 (1964); J. Org. Chem., 37, 626 (1972).
Reaction with amines gives iminophosphoranes, which have been used as a means of blocking an amino group to permit monoalkylation: Synthesis, 295 (1980). Iminophosphoranes also undergo a Wittig-like condensation with CO2 or CS2 to give the isocyanates or isothiocyanates respectively: Synthesis, 596 (1982):
Ureas are dehydrated to carbodiimides: Liebigs Ann. Chem., 718, 24 (1968); Synthesis, 373 (1981).
The reagent formed with DMSO at low temperatures provides an alternative to the Swern oxidation for selective conversion of alcohols to carbonyl compounds: Tetrahedron Lett., 43, 8355 (2002).
Wang, R.; Zhao, Y.; Zhu, C.; Huang, X. New Synthesis of 3, 6-Dibromophthalonitrile and Phthalocyanine Having Eight Thienyl Substituents at Peripheral alpha-Positions. J. Heterocycl. Chem. 2015, 52 (4), 1230-1233.
Koshizawa, T.; Yamazaki, Y.; Ohgiya, T.; Shibuya, K. A facile method for converting alcohol to thioether and its application in the synthesis of a novel GPR119 agonist. Tetrahedron 2015, 71 (21), 3231-3236.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378q-P370+P380-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. 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 or doctor/physician. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Evacuate area. Dispose of contents/ container to an approved waste disposal plant