56183-63-2

Basic information

• Product Name: BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE
• Synonyms: BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE;BIS(DI-I-PROPYLAMINO)CHLOROPHOSPHINE;bis(diisopropylamino)chlorophosphane;Bis-(diisopropylamino)-chlorphosphin;Bis(diisopropylamino)phosphanylchloride;Bis(N,N-diisopropylamino)chlorophosphine;Chlorbis(diisopropylamino)phosphan;Chloro(bis(diisopropylamino))phosphane
• CAS NO: 56183-63-2
• Molecular Formula: C₁₂H₂₈ClN₂P
• Molecular Weight: 266.79
• Product Categories: Ligand;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;organophosphine halide;Achiral Phosphine;Alkyl Phosphine;P-Cl
• Mol File: 56183-63-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 100-104 °C(lit.)
• Boiling Point: 291℃
• Flash Point: 130℃
• Appearance: white to off-white/Powder
• PKA: 4.50±0.70(Predicted)
• Sensitive: air sensitive, moisture sensitiv
• CAS DataBase Reference: BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE(56183-63-2)
• EPA Substance Registry System: BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE(56183-63-2)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 1
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 56183-63-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Bis(diisopropylamino)chlorophosphine has been used in the synthesis of tert-butyl tetraisopropylphosphorodiamidite ligand for palladium-catalyzed Buchwald–Hartwig amination reaction.It is also can be used to synthesize:acyclic N-phosphonio imine catalyst for selective epoxidationsboryl-substituted methylenephosphonium derivatives

Upstream product

• 113533-22-5 C--N-nitrilimine 
• 109065-32-9 (chloro)diazomethylenephosphorane 
• 80907-47-7 {NEt₄}{HW(CO)5} 
• 117270-09-4 ({(CH₃)2CH}2N)2PPCl₂ 
• 97135-48-3 (bis(diisopropylamino)phosphanyl)(trimethylsilyl)diazomethane 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 108-18-9 diisopropylamine 

Downstream Products

• 108549-21-9 benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 350038-30-1 bis(dialkylaminophosphanyl)imine 
• 128388-72-7 tetrakis(diisopropylamino)diphosphane 
• 86660-77-7 bis(N,N-diisopropylamino)phosphine 
• 698376-85-1 C₂₀H₃₇N₂O₂P 
• 133728-85-5 C₄₇H₆₄N₇O₇P 
• 408512-17-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine 3'-(N,N,N',N'-tetraisopropyl)phosphorodiamidite 
• 864848-09-9 (1-isopropyl-2-methyl-propyl)-bis(diisopropylamino)phosphanyl-(para-bis(diisopropylamino)phosphanyl-phenyl)-amine 
• 864848-01-1 bis(diisopropylamino)phosphanyl-(para-bis(diisopropylamino)phosphanyl-phenyl)-triisopropylsilanyl-amine 
• 864848-05-5 (para-bis(diisopropylamino)phosphanyl-phenyl)-(1-isopropyl-2-methyl-propyl)-amine 
• 291299-92-8 N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diisopropylamino)-[2-[N-isopropyl-N-(4-methoxybenzoyl)amino]ethoxy]phosphinyl-2'-deoxycytidine 
• 291299-91-7 N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diisopropylamino)-[2-[N-isopropyl-N-(4-methoxybenzoyl)amino]ethoxy]phosphinyl-2'-deoxyadenosine 

Relevant articles and documents

N-Phosphino- and N-Phosphonionitrilimines: From Nucleophilic to Electrophilic 1,3-Dipoles

N-[Bis(diisopropylamino)phosphino]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (1) reacts with electron-poor dipolarophiles such as maleimide, methyl vinyl ketone, and 1,4-naphthoquinone via HOMO(dipole)-controlled [2+3] cycloadditions, while N-[bis(diisopropylamino)(methyl)phosphonio]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (2a) reacts with electron-rich dipolarophiles such as norbornadiene and ethyl trans-pyrrolineacrylate via LUMO(dipole)-controlled [2+3] cycloadditions. Carbon disulfide reacts with 1 via a formal [4+2] cycloaddition leading to phosphazene containing heterocycle 11 in 75% yield. Dipole 1 is cleaved by HCl, giving the corresponding (thioxophosphoranyl)diazomethane 15, while addition of HCl to 2a leads to hydrazonoyl chloride 16, in 70% isolated yield. Hydrazone 17′ (95%) and phosphazine 18 (80%) are obtained by a 1,3-addition of BuLi to 1 and PhOLi to 2a, respectively. Trimethylphosphine reacts with 2a by a phosphine - carbene coupling reaction, giving the ylide 20 which is isolated in 75% yield.

BULKY ALKYLS, AMIDES, AND ARYLOXIDES OF MAIN GROUP 5 ELEMENTS. PART 1. PERSISTENT PHOSPHINYL AND ARSINYL RADICALS MRR' AND THEIR CHLOROPRECURSORS MRR'Cl AND RELATED COMPOUNDS

Interaction of LiR and MCl3 in appropriate stoicheiometry affords the following new compounds: MCl2 or M2Cl (M = P, As, or Sb), MCl2 or M2Cl (M = As or Sb), or Bi3.Reaction of P(NPri2)Cl2 with Li*OEt2, Li, Li, MgButBr, or NHPri2 yields the corresponding new compound P(NPri2)RCl, while Li with P(NMe2)Cl2 affords P(NMe2)Cl.Reduction of the appropriate phosphorus(III) or arsenic(III) monochloride in toluene by photolysis with the olefin gives the persistent (t1/2 = 3 days to > 1 year in PhMe at 300 K) phosphorus(II) or arsenic(II) alkyl or amide: M2 (M = P or As), M2, P(NR2) (R = Pri or SiMe3), P(NPri2),P2, or P(NPri2).Electron spin resonance parameters are discussed.

Self-neutralizing oligonucleotides with enhanced cellular uptake

There is tremendous potential for oligonucleotide (ON) therapeutics, but low cellular penetration due to their polyanionic nature is a major obstacle. We addressed this problem by developing a new approach for ON charge neutralization in which multiple branched charge-neutralizing sleeves (BCNSs) are attached to the internucleoside phosphates of ON by phosphotriester bonds. The BCNSs are terminated with positively charged amino groups, and are optimized to form ion pairs with the neighboring phosphate groups. The new modified ONs can be prepared by standard automated phosphoramidite chemistry in good yield and purity. They possess good solubility and hybridization properties, are not involved in non-standard intramolecular aggregation, have low cytotoxicity, adequate chemical stability, improved serum stability, and above all, display significantly enhanced cellular uptake. Thus, the new ON derivatives exhibit properties that make them promising candidates for the development of novel therapeutics or research tools for modulation of the expression of target genes.

NEW METHOD OF POLYPHOSPHATE SYNTHESIS

The subject of the invention is a new method of the synthesis of polyphosphate analogues, such as nucleosides, oligonucleotides, carbohydrates, peptides and proteins, which are of biological importance and are used in organic chemistry, molecular biology and biotechnology. Polyphosphate analogues, including in particular nucleoside 5'-triphosphates, display high biological activity and are responsible for the provision and storage of energy in live organisms. The method relates to the synthesis of organic polyphosphates of general formula (1), where n has a value of 0 to 2, while X stands for an organic radical, in particular nucleoside, oligonucleotide, peptide-carbohydrate or a protein radical.