3348-44-5

Usage

Uses

Used in Chemical Synthesis:
Bis(dimethylamino)chlorophosphine is used as a precursor in the synthesis of organophosphorus compounds for various applications, including the production of pharmaceuticals, pesticides, and other specialty chemicals.
Used in Organic Reactions:
In the field of organic chemistry, Bis(dimethylamino)chlorophosphine is used as a catalyst to facilitate specific reactions, enhancing the efficiency and selectivity of the processes.
Used in Polymer Production:
Bis(dimethylamino)chlorophosphine is utilized in the production of polymers, where it may act as a catalyst or a component in the polymerization process, contributing to the development of materials with desired properties.
Used in Flame Retardant Industry:
In the flame retardant industry, Bis(dimethylamino)chlorophosphine is used to produce flame retardants that are incorporated into materials to reduce their flammability and improve fire safety.
Used in Agrochemicals:
Bis(dimethylamino)chlorophosphine is employed in the production of agrochemicals, such as pesticides and herbicides, where it may serve as an intermediate or a catalyst in the synthesis of active ingredients.

InChI:InChI=1/C4H12ClN2P/c1-6(2)8(5)7(3)4/h1-4H3

Upstream product

• 124-40-3 dimethyl amine 
• 1608-26-0 Hexamethylphosphorous triamide 
• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 18611-22-8 N-diethoxyphosphinoyltrifluoroacetimidoyl chloride 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 1630-79-1 tetrakis(dimethylamido)diborane 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 51-80-9 bis-(dimethylamino)methane 

Downstream Products

• 40535-53-3 1,3-Bis-benzenesulfonyl-N,N,N',N'-tetramethyl-[1,3,2,4]diazadiphosphetidine-2,4-diamine 
• 40535-55-5 1,3-Bis-(4-methoxy-benzenesulfonyl)-N,N,N',N'-tetramethyl-[1,3,2,4]diazadiphosphetidine-2,4-diamine 
• 55590-38-0 (10-TB-5-12)-tetra-N-methyl-2,3-diphenyl-10λ⁵-benzo[d][1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole-10,10-diamine 
• 72170-53-7 C₁₆H₂₂N₂OP₂ 
• 14937-39-4 methyl-bis(dimethylamino)phosphine 
• 47071-60-3 p-C₆H₄(P(N(CH₃)2)2)2 
• 65149-56-6 tetra-N-methyl-2,3-diphenyl-11λ⁵-[1,3,2]oxazaphospholo[3',2':2,3][1,2,4,3]triazaphospholo[4,5-a]pyridine-11,11-diamine 
• 66442-09-9 1-cyclohexen-1-yl tetramethylphosphorodiamidite 
• 6143-71-1 bis(dimethylamino)phenyl phosphine 
• 19946-85-1 N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidic chloride 
• 66442-10-2 C₁₀H₂₀ClN₂OP 
• 66393-56-4 bis(dimethylamino)-4-methoxyphenyl phosphine 
• 88127-59-7 Phosphorigsaeurebis(dimethylamid)-o-chlorphenylester 
• 88127-60-0 Phosphorigsaeurebis(dimethylamid)-o-bromphenylester 

Relevant academic research and scientific papers

Bis-carbaborane-bridged bis-glycophosphonates as boron-rich delivery agents for BNCT

The synthesis and properties of boron-rich bis(meta-carbaborane) derivatives containing glycophosphonate and glycophosphonothioate moieties are reported. All compounds are water-soluble; however, the tetragalactosylated compounds show lower solubility tha

Immobilization of a N-substituted azaphosphatrane in nanopores of SBA-15 silica for the production of cyclic carbonates

A novel N-substituted azaphosphatrane molecular precursor bearing an alkyne tether was synthesized using a multi-step strategy and covalently immobilized onto SBA-15 type silica through triazole linkages by means of the well-known click chemistry. The resulting hybrid material, [7]@SBA-15, was characterized well by methods appropriate to molecular species (e.g. solid state 13C, 31P and 29Si NMR, infrared spectroscopy and elemental analysis) as well as techniques more commonly associated with the characterization of mesoporous solids (nitrogen sorption isotherms, powder X-ray diffraction, TGA analysis). The catalytic activity of [7]@SBA-15 was then evaluated in the coupling of CO2 with two epoxides (styrene oxide and epichlorohydrin) and compared to its monotriazole modified AZAP molecular analog, 8. This work represents the first example of silica modified N-substituted azaphosphatrane for the production of cyclic carbonates. This journal is the Partner Organisations 2014.

The enthalpies of formation of (dimethylamino)dichlorophosphine, bis(dimethylamino)chlorophosphine, and tris(dimethylamino)phosphine

The standard molar enthalpies of formation at the temperature 298.15 K of (CH3)2NPCl2 (l), 2PCl(l), and 3P(l) have been determined by reaction calorimetry as -(286.3 +/- 2.4) kJ*mol-1, -(220.1 +/- 2.3) kJ*mol-1, and -(112.8 +/- 2.3) kJ*mol-1, respectively.Enthalpies of vaporization have been obtained from vapour-pressure measurements and the corresponding values of ΔfH0m(g) derived as -(245.5 +/- 2.5) kJ*mol-1, -(174.2 +/- 2.6) kJ*mol-1, and -(71.3 +/- 2.4) kJ*mol-1, respectively.The values of the bond enthalpies D(P-Cl) and D(P-N) in substituted phosphines are discussed.

Tris(tetramethylguanidinyl)phosphine: The Simplest Non-ionic Phosphorus Superbase and Strongly Donating Phosphine Ligand

We report the synthesis and properties of the much sought-after tris(1,1,3,3-tetramethylguanidinyl) phosphine P(tmg)3, a crystalline, superbasic phosphine accessible through a short and scalable procedure from the cheap and commercially available bulk chemicals 1,1,3,3-tetramethylguanidine, tris(dimethylamino)-phosphine and phosphorus trichloride. The new phosphine exhibits exceptional electron donor properties and readily forms transition metal complexes with gold(I), palladium(II) and rhodium(I) precursors. The formation of zwitterionic Lewis base adducts with carbon dioxide and sulfur dioxide was explored. In addition, the complete series of phosphine chalcogenides was prepared from the reaction of P(tmg)3 with N2O and the elemental chalcogens.

Encaging the Verkade's superbases: Thermodynamic and kinetic consequences

Proazaphosphatranes, also known as Verkade's superbases, are nonionic species, which exhibit catalytic properties for a wide range of reactions. The properly designed host molecule 3 and its protonated counterpart [3·H]+Cl- were synthesized to study how confinement can modify the stability and the reactivity of a Verkade's superbase. The results show that the encapsulation does not alter the strong basicity of the proazaphosphatrane, but dramatically decreases the rate of proton transfer.

A flexible approach to different families of bidentate P,P ligands as highly efficient ligands for asymmetric catalysis

A novel and versatile approach has led to the synthesis of various classes of mono- and bidentate phospholane and phosphinite ligands based on a benzothiophene scaffold. The ligand functions in the bidentate ligands can be introduced independently and consecutively. A bis-phospolane ligand as well as its rhodium complex have been characterized by crystal-structure determinations. The bis-phospholane ligands were tested in the catalysed asymmetric homogeneous hydrogenation of dehydroamino acid derivatives, enamides and itaconates and gave ee values of up to 98.7 %. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for stille cross-coupling: Coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls

A family of proazaphosphatrane ligands [P(RNCH2CH 2)2N(R′NCH2CH2): R = R′ = i-Bu, 1; R = Bz, R′ = 1-Bu, 3; R = R′ = Bz, 4] for palladium-catalyzed Stille reactions of aryl chlorides is described. Catalysts derived from ligands 1 and 4 efficiently catalyze the coupling of electronically diverse aryl chlorides with an array of organotin reagents. The catalyst system based on the ligand 3 is active for the synthesis of sterically hindered biaryls (di-, tri-, and tetra-ortho substituted). The use of ligand 4 allows room-temperature coupling of aryl bromides and it also permits aryl inflates and vinyl chlorides to participate in Stille coupling.

Solid-phase chemical synthesis of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides

Phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides were prepared via a solid-phase synthesis strategy. Under Reformatsky reaction conditions, novel esterified acetic acid phosphinodiamidites were synthesized and condensed with appropriately protected 5′-O-(4, 4′-dimethoxytrityl)-2′-deoxynucleosides to yield 3′-O-phosphinoamidite reactive monomers. These synthons when activated with tetrazole were used with an automated DNA synthesizer to prepare phosphonoacetic acid modified internucleotide linkages on controlled pore glass. The phosphinoacetate coupling products were quantitatively oxidized at each step with (1S)-(+)-(10-camphorsulfonyl)oxaziridine or 3H-1,2-benzodithiol-3-one-1,1-dioxide to produce mixed sequence phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides with an average per cycle coupling efficiency of greater than 97%. Completely deprotected, modified oligodeoxynucleotides were purified by reverse-phase HPLC and characterized by ion exchange HPLC, 31P NMR, and MALDI/TOF mass spectroscopy. Both analogues were stable toward hydrolysis with snake venom phosphodiesterase and stimulated RNase H1 activity.

Totally diastereoselective synthesis of new P-chirogenic o-trimethylsiloxyaryl diazaphospholidines and o-hydroxyaryl diazaphospholidine-borane complexes

The totally diastereoselective synthesis of several P(III)-chirogenic o-trimethylsiloxyaryl diazaphospholidines 4 was achieved by exchange reactions in refluxing toluene from the key intermediates, o-trimethylsiloxyaryl bis(dimethylamino) phosphines 2, and various chiral diamines 3. In the case of the use of a non-C2-symmetric chiral auxiliary such as (S)-2-anilinomethylpyrrolidine (3a), compounds 4a-g, containing a stereogenic phosphorus atom, were obtained in diastereomerically pure form as the thermodynamic anti-diastereomers. Complexation of the diazaphospholidines 4 by borane-dimethylsulfide and subsequent methanolysis of the siloxy ether function lead to the formation of the desired o-hydroxyaryl diazaphospholidine-borane complexes 5 in good yields, ranging from 71 to 86%.

Phosphonites based on the paracyclophane backbone: New ligands for highly selective rhodium-catalyzed asymmetric hydrogenation

Figure presented The synthesis of new phosphonites with a chiral paracyclophane backbone is described. The rhodium complexes derived from the phosphonites bearing biphenoxy and binaphthoxy substituents are highly active and highly selective catalysts for the asymmetric hydrogenation of dehydroamino acids and esters.