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

A11552 Triphenylphosphine dibromide, 96%

Codice CAS
1034-39-5
Sinonimi
Dibromotriphenylphosphorane

Dimensioni Prezzo ($) Quantità Disponibilità
10g 37,50
50g 159,00
250g 659,00
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Triphenylphosphine dibromide, 96%

MDL
MFCD00000054
EINECS
213-855-1

Proprietà chimiche

Formula
(C6H5)3PBr2
Peso formula
422.10
Punto di fusione
ca 260° dec.
Sensibilità
Moisture Sensitive
Solubilità
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.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318

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

Dichiarazioni precauzionali: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
917652
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.39
TSCA
Yes

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