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1034-39-5 - Triphenylphosphine dibromide, 96% - Dibromotriphenylphosphorane - A11552 - Alfa Aesar

A11552 Triphenylphosphine dibromide, 96%

CAS Number
1034-39-5
Synonyms
Dibromotriphenylphosphorane

Size Price ($) Quantity Availability
10g 37.90
50g 160.68
250g 665.38
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Triphenylphosphine dibromide, 96%

MDL
MFCD00000054
EINECS
213-855-1

Chemical Properties

Formula
(C6H5)3PBr2
Formula Weight
422.10
Melting point
ca 260° dec.
Sensitivity
Moisture Sensitive
Solubility
Soluble in water, dichloromethane, acetonitrile, phenyl cyanide, dimethyl formamide, ether, chloroform, alcohol, carbon tetrachloride, acetic acid and carbon disulfide. Sparingly soluble in phenyl chloride, triphenylphosphine and phenyl hydride. Insoluble in aqueous bromine.

Applications

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.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong bases, strong oxidizing agents, bases and active metals.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
917652
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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