1034-39-5

Basic information

• Product Name: TRIPHENYLPHOSPHINE DIBROMIDE
• Synonyms: TRIPHENYLPHOSPHINE DIBROMIDE;DIBROMO TRIPHENYL PHOSPHINE;DIBROMOTRIPHENYLPHOSPHORANE;BROMOTRIPHENYLPHOSPHONIUM BROMIDE;dibromotriphenyl-phosphoran;Triphenylphosphine dibromide, ca. 33% bromine;Dibromotriphenylphosphorane,98%;Phosphorane, dibromotriphenyl-
• CAS NO: 1034-39-5
• Molecular Formula: C₁₈H₁₅Br₂P
• Molecular Weight: 422.09
• EINECS: 213-855-1
• Product Categories: organophosphorus compound
• Mol File: 1034-39-5.mol
• Article Data: 46

Chemical Properties

• Melting Point: 235 °C (dec.)(lit.)
• Appearance: Light yellow to light pink/Crystalline Powder
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water, dichloromethane, acetonitrile, phenyl cyanide, dimethyl formamide, ether, chloroform, alcohol, carbon tetrachl
• Sensitive: Moisture Sensitive
• BRN: 917652
• CAS DataBase Reference: TRIPHENYLPHOSPHINE DIBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLPHOSPHINE DIBROMIDE(1034-39-5)
• EPA Substance Registry System: TRIPHENYLPHOSPHINE DIBROMIDE(1034-39-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 3-10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1034-39-5(Hazardous Substances Data)

Usage

Description

Triphenylphosphine dibromide is a light yellow to light pink crystalline powder that is widely utilized in various chemical reactions due to its unique properties. It is an essential reagent in the field of organic chemistry, particularly for the conversion of aldoximes into nitriles, cleavage of acetals, and the preparation of alkyl and aryl bromides from alcohols and phenols without rearrangement. Additionally, it reacts with amines to form iminophosphoranes, further expanding its applications in chemical synthesis.

Uses

Used in Chemical Synthesis:
Triphenylphosphine dibromide is used as a reagent for the conversion of aldoximes into nitriles, which are essential building blocks in the synthesis of various organic compounds. This conversion is crucial for the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Cleavage of Acetals:
In the field of organic chemistry, TRIPHENYLPHOSPHINE DIBROMIDE is used as a reagent for the cleavage of acetals. This process is vital for the synthesis of various organic compounds, as it allows for the selective removal of protecting groups in multi-step reactions.
Used in the Formation of Iminophosphoranes:
Triphenylphosphine dibromide reacts with amines to give iminophosphoranes, which are valuable intermediates in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in the Preparation of Alkyl and Aryl Bromides:
In the chemical industry, TRIPHENYLPHOSPHINE DIBROMIDE is used as a reagent for the preparation of alkyl and aryl bromides from alcohols and phenols without rearrangement. These bromides are essential intermediates in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.

Purification Methods

It recrystallises from MeCN/Et2O. Although it has been recrystallised from EtOH, this is not recommended as it converts alcohols to alkyl bromides. It deteriorates on keeping, and it is best to prepare it afresh. [Anderson & Freenor J Am Chem Soc 86 5037 1964, Horner et al. Justus Liebigs Ann Chem 626 26 1959, Beilstein 16 III 864.]

InChI:InChI=1/C18H15BrP.BrH/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1

Upstream product

• 2588-88-7 pentaphenylphosphorane 
• 603-35-0 triphenylphosphine 
• 98-03-3 thiophene-2-carbaldehyde 
• 558-13-4 carbon tetrabromide 
• 104-87-0 4-methyl-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 623-27-8 terephthalaldehyde, 
• 66-77-3 1-naphthaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 2065-67-0 tetraphenylphosphonium iodide 
• 7726-95-6 bromine 

Downstream Products

• 23574-81-4 N-(triphenylphosphoranylidene)pyridin-2-amine 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 33341-95-6 4-phenylazo-N-triphenylphosphoranyliden-aniline 
• 57519-72-9 1-methyl-4-[7-methyl-6-oxo-5,5-diphenyl-4-(triphenyl-λ⁵-phosphanylideneamino)-6,7-dihydro-5H-pyrrolo[3,2-e][1,3]oxazin-2-ylidene]-3,3-diphenyl-pyrrolidine-2,5-dione 
• 900-92-5 triphenyl[(isopropyl)amino]phosphanium bromide 
• 69982-03-2 2-(triphenylphosphoranylideneamino)benzimidazole 
• 80232-66-2 C₂₆H₁₉N₂O₂P 
• 76826-09-0 (2-Hydroxy-4-methylphenylimino)triphenylphosphoran 
• 52826-42-3 bromure de triphenyl N-benzylaminophosphonium 
• 159428-10-1 C₅₀H₄₂N₂P₂ 
• 159428-07-6 C₄₉H₄₀N₂P₂ 
• 159428-16-7 O(C₆H₄NP(C₆H₅)3)2 
• 164408-46-2 2-methylthio-N-triphenylphosphoranylideneaniline 
• 159683-25-7 (C₆H₅)3P(OCH₂CF₂Cl)2 

Relevant articles and documents

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Chemistry of iminofurans: X. Synthesis and hydrolysis of 5-aryl(hetaryl)-2-[(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)imino]furan-3(2H)-ones

5-Aryl(hetaryl)furan-2,3-diones reacted with N-(triphenyl-λ5-phosphanylidene)-4,5,6,7-tetrahydro-1-benzothiophen-2-amines to give 5-aryl(hetaryl)-2-[(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)imino]furan-3(2H)-ones whose acid hydrolysis afforded 4-aryl(hetaryl)-2-hydroxy-4-oxo-N-(4,5,6,7-tetrahydro-1-benzothiophen- 2-yl)but-2-enamides.

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Synthesis and 17O NMR spectroscopy of a series of 17O labeled triarylphosphine oxides

A series of nine 17O labeled triarylphosphine oxides [(p-R-C6H4)3PO] was synthesized, 17O NMR spectroscopic studies were carried out (toluene solvent/95 °C and CDCl3/60 °C) and the spectrum was fit with two Lorentzian peaks. The chemical shifts range from δ 51.8 to 55.7 in toluene and δ 44.8 to 48.9 in CDCl3, while 1JPO varies from 159.6 to 168.6 Hz in toluene. The data were fit to the Taft DSP and Hammett equations and related to other NMR parameters for this system and the analogous λ5-phosphazenes [(p-R-C6H4)3PNPh]. Using the Taft DSP equation the 17O substituent chemical shifts gave ρI and ρR with opposite signs which is different from what is observed with the λ5-phosphazenes. 1JPO, on the other hand correlates best with the Hammett σ+p constants. The data are consistent with a triple bond contribution to the PO bonding.

CRYSTALLINE FORMS OF 4-(1-(1,1-DI(PYRIDIN-2-YL)ETHYL)-6-(3,5-DIMETHYLISOXAZOL-4-YL)-1H- PYRROLO[3,2-B]PYRIDIN-3-YL)BENZOIC ACID THAT INHIBITS BROMODOMAIN

Forms of 4-(1-(1,1-di(pyridin-2-yl)ethyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-3-yl)benzoic acid were prepared and characterized in the solid state: Compound I. Also provided are processes of manufacture and methods of using the forms of Compound I.

Structure-property relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: The effect of branching topology and chirality

Three novel diglycerol tetraether lipids with one membrane-spanning chain have been synthesized. These lipids contain only two or four racemic methyl branches at selected positions of the hydrophobic chains in contrast to natural lipids from archaebacterial membranes with an isoprenoid substitution pattern. The insertion of the methyl moieties was realized starting from either (RS)-citronellyl bromide or the inexpensive methyl malonic acid ethyl ester. For chain elongation the Cu-catalysed Grignard coupling reaction was used. The preparation of diglycerol tetraethers was either performed by condensing suitable blocked monoglycerol diethers by Grubbs metathesis or by reaction of the transmembrane C32-chain with blocked glycerols followed by further alkylation steps. Finally, we could show that the resulting lipids can form closed lipid vesicles comparable to the optically pure counterparts. Therefore, these much simpler lipids compared to the natural lipids from archaebacterial membranes are also suitable for preparation of stable tailored liposomes. This journal is the Partner Organisations 2014.