13685-24-0

Basic information

• Product Name: BIS(4-TRIFLUOROMETHYLPHENYL)CHLOROPHOSPHINE
• Synonyms: Chlorobis[4-(trifluoromethyl)phenyl]phosphine, 97%;BIS(4-TRIFLUOROMETHYLPHENYL)CHLOROPHOSPHINE;Bis(4-trifluoromethylphenyl)chlorophosphine,98%;Chlorobis(p-trifluoromethylphenyl)phosphine
• CAS NO: 13685-24-0
• Molecular Formula: C₁₄H₈ClF₆P
• Molecular Weight: 356.63
• Mol File: 13685-24-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 110°C/0.4mm
• Flash Point: 110°C/0.4mm
• Appearance: /
• Density: 1.42g/ml
• Vapor Pressure: 0.00031mmHg at 25°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: BIS(4-TRIFLUOROMETHYLPHENYL)CHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-TRIFLUOROMETHYLPHENYL)CHLOROPHOSPHINE(13685-24-0)
• EPA Substance Registry System: BIS(4-TRIFLUOROMETHYLPHENYL)CHLOROPHOSPHINE(13685-24-0)

Safety Data

• RIDADR: UN3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13685-24-0(Hazardous Substances Data)

Usage

Description

Bis(4-trifluoromethylphenyl)chlorophosphine, also known as Chlorobis[4-(trifluoromethyl)phenyl]phosphine, is an organophosphorus compound characterized by its trifluoromethylphenyl groups and a central phosphorus atom bonded to a chlorine atom. It is a versatile reagent in the field of organic synthesis and material science due to its unique structural properties and reactivity.

Uses

Used in Organic Synthesis:
Bis(4-trifluoromethylphenyl)chlorophosphine is used as a reagent in the synthesis of various organic compounds, particularly those involving phosphorus-carbon bond formation. Its unique structure and reactivity make it a valuable building block for the development of complex organic molecules.
Used in Material Science:
In the field of material science, Bis(4-trifluoromethylphenyl)chlorophosphine is used as a precursor for the development of novel materials with specific properties. Its incorporation into the molecular structure can lead to materials with enhanced stability, reactivity, or other desired characteristics.
Used in the Production of Green Phosphorescent OLEDs:
Bis(4-trifluoromethylphenyl)chlorophosphine is used as a reactant in the synthesis of green phosphorescent OLEDs (Organic Light-Emitting Diodes) based on a novel iridium complex. Its role in the production process is crucial for achieving the desired optical and electronic properties of these advanced display technologies.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, Bis(4-trifluoromethylphenyl)chlorophosphine could potentially be used in the pharmaceutical industry as a building block for the development of new drugs, particularly those targeting the central nervous system or requiring specific pharmacological properties conferred by the presence of phosphorus.

InChI:InChI=1/C14H8ClF6P/c15-22(11-5-1-9(2-6-11)13(16,17)18)12-7-3-10(4-8-12)14(19,20)21/h1-8H

Upstream product

• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 1069-08-5 diethylphosphoramidous dichloride 
• 15929-43-8 bis(4-(trifluoromethyl)phenyl)phosphine oxide 
• 13685-91-1 (diethylamino)bis(4-trifluoromethylphenyl)phosphane 

Downstream Products

• 820253-15-4 2,2'-bis-[bis-(4-trifluoromethyl-phenyl)-phosphinoyl]-[1,1']binaphthalenyl 
• 1398414-41-9 2-((bis(4-(trifluoromethyl)phenyl)phosphino)methyl)-1-methyl-1H-imidazole 
• 1000278-96-5 (2-bromophenyl)-di-(4-trifluoromethylphenyl)phosphane 
• 1449568-79-9 bis[2-bis(4-trifluoromethylphenyl)phosphinophenyl](methyl)silane 
• 1449568-83-5 C₄₁H₂₇ClF₁₂P₂PdSi 
• 944836-22-0 (S)-2-(2-(bis(4-trifluoromethyl-phenyl)-phosphino))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole 
• 1255528-30-3 4-(bis-p-trifluoromethylphenylphosphino)-2,7-di-tert-butyl-9,9-dimethylxanthene 
• 1258840-82-2 (R)-N-benzyl-N-(bis(4-(trifluoromethyl)phenyl)phosphino)-2-methyl-2-propanesulfinamide 
• 503274-08-6 bis(4-trifluoromethylphenyl)phosphine-borane complex 
• 1231209-33-8 N-methyl-N-[bis(4-trifluoromethylphenyl)phosphino]-(S)-1-[2-(diphenylphosphino)phenyl]ethylamine 
• 1231209-28-1 N-[bis(4-trifluoromethylphenyl)phosphino]-(S)-1-[2-(diphenylphosphino)phenyl]ethylamine 
• 1184204-25-8 C₂₅H₁₅F₆N₄PSe 
• 1184204-10-1 3-(6'-(di(p-trifluoromethylphenyl)phosphino)pyridin-2'-yl)-[1,2,3]triazolo[1,5-a]pyridine 
• 1184204-07-6 7-(di(p-fluorophenyl)phosphino)-3-(pyridin-2'-yl)-[1,2,3]triazolo[1,5-a]pyridine 

Relevant articles and documents

Twofold C?H Activation-Based Enantio- and Diastereoselective C?H Arylation Using Diarylacetylenes as Rare Arylating Reagents

C?H bond activation has been established as an attractive strategy to access axially chiral biaryls, and the most straightforward method is direct C?H arylation of arenes. However, the arylating source has been limited to several classes of reactive and bulky reagents. Reported herein is rhodium-catalyzed 1:2 coupling of diarylphosphinic amides and diarylacetylenes for enantio- and diastereoselective construction of biaryls with both central and axial chirality. This twofold C?H activation reaction stays contrast to the previously explored Miura–Satoh type 1:2 coupling of arenes and alkynes in terms of chemoselectivity and proceeded under mild conditions with the alkyne acting as a rare arylating reagent. Both C?H activation events are stereo-determining and are under catalyst control, with the 2nd C?H activation being diastereo-determining in a remote fashion. Analysis of the stereochemistry of the major and side products suggests moderate enantioselectivity of the initial C?H activation–desymmetrization process. However, the minor (R) rhodium vinyl intermediate is consumed more readily in undesired protonolysis, eventually resulting in high enantio- and diastereoselectivity of the major product.

Facial conversion of secondary phosphine oxides R1R2P(O)H to chlorophosphines R1R2PCl by acetyl chloride

A practically useful protocol for the reductive transformation of secondary phosphine oxides R1R2P(O)H to chlorophosphines R1R2PCl using acetyl chloride was disclosed. Various secondary phosphine oxides could be readily reduced to the corresponding chlorophosphines in high yields under mild conditions.

Evidence of Phosphonium-Carbenium Dication Formation in a Superacid: Precursor to Fluorinated Phosphine Oxides

Unambiguously confirmed by low-temperature in situ NMR experiments, X-ray diffraction and vibrational spectroscopy, phosphonium-carbenium superelectrophiles are shown to be generated in strong acidic conditions. Representing crucial intermediates, their exploitation allows for the synthesis of unprecedented fluorinated (cyclic) phosphine oxides.