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

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

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

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

Downstream Products

• 503274-08-6 bis(4-trifluoromethylphenyl)phosphine-borane complex 
• 1258840-82-2 (R)-N-benzyl-N-(bis(4-(trifluoromethyl)phenyl)phosphino)-2-methyl-2-propanesulfinamide 
• 820253-15-4 2,2'-bis-[bis-(4-trifluoromethyl-phenyl)-phosphinoyl]-[1,1']binaphthalenyl 
• 919765-85-8 (4-methoxyphenyl){bis[4-(trifluoromethyl)phenyl]}phosphane 

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.

Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.

Synthetic method of RRPCl

The invention provides a synthetic method of RRPCl, and belongs to the field of organic matter synthesis. The synthetic method of RRPCl solves the problems of low reaction yield and the like in the existing RRPCl synthesis, and is characterized in that RRP(O)H is dissolved in an organic solvent and then reacts with acetyl chloride to obtain the RRPCl, and the chemicalreaction formula of the RRPCl is shown as a formula (I), wherein R1 and R2 are aryl and alkyl. The synthetic method has the advantages of the high yield and the like.

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.

Rhodium-catalyzed dehydrocoupling of fluorinated phosphine-borane adducts: Synthesis, characterization, and properties of cyclic and polymeric phosphinoboranes with electron-withdrawing substituents at phosphorus

The dehydrocoupling of the fluorinated secondary phosphine-borane adduct R2PH·BH3 (R = p-CF3C6H 4) at 60°C is catalyzed by the rhodium complex [{Rh(μ-Cl)(1,5-cod)}2] to give the four-membered chain R

Chiral diphosphorus compounds and their transition metal complexes

The present invention relates to chiral diphosphorus compounds and their transition metal complexes, to a process for preparing chiral diphosphorus compounds and their transition metal complexes and also to their use in asymmetric syntheses.

Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor

(Chemical Equation Presented) A new protocol for deoxygenation of various phosphine oxides with retention of configuration is described. The advantage of the new method includes milder conditions and considerably shortened reaction times. Mechanistic studies about the oxygen transfer between the starting phosphine oxide and the sacrificial triphenylphosphine are also presented.

Chiral diphosphorus compounds and transition metal complexes thereof

Tetrahydrofuran bisphosphines of formula (I), are new. Tetrahydrofuran bisphosphines of formula (I): X1, X2 = bonds or O; R1, R2 = H, 1-20C alkyl, 1-20C fluoroalkyl, 2-20C alkenyl, 4-24C aryl, 5-25C aralkyl, 6-26C aralkenyl, NR7R8, OR8, AOR8, ANR7R8 or OC

Asymmetric hydrogenation reactions mediated by a new class of bicyclic bisphosphinites

The bicyclic alcohol (-)-4 was prepared from (-)-bicyclo[3.2.0]hept-2- en-6-one (-)-1 in 50% yield. The diol (-)-4 was coupled to selected chlorophosphines 6-12 to produce a series of bisphosphinites 13-19 in 89-95% yield. From these bisphosphinites were prepared the rhodium complexes 20-26 which were characterised by 31P NMR and used in situ for the asymmetric hydrogenation of α-enamides 27-29. Complexes 21, 23-25 proved to be the superior catalysts for the production of (R)-N-acetylphenylalanine (91, 84, 90 and 87.5% ee) from 27 and (S)-N-acetylalanine methyl ester (70, 72, 68 and 71% ee) from 28.