Bis(diisopropylamino)chlorophosphine

Base Information

• Chemical Name: Bis(diisopropylamino)chlorophosphine
• CAS No.: 56183-63-2
• Molecular Formula: C12H28ClN2P
• Molecular Weight: 266.794
• Hs Code.: 29310099
• European Community (EC) Number: 628-718-5
• DSSTox Substance ID: DTXSID00369907
• Nikkaji Number: J1.175.515A
• Wikidata: Q72445044
• Mol file: 56183-63-2.mol

Synonyms:Phosphorodiamidouschloride, tetrakis(1-methylethyl)- (9CI);Bis(diisopropylamino)chlorophosphine;Chlorobis(N,N-diisopropyl)phosphoramidite;Chlorobis(N,N-diisopropylamino)phosphine;Chlorobis(diisopropylamino)phosphine;Tetraisopropylphosphorodiamidous chloride;

Chemical Property of Bis(diisopropylamino)chlorophosphine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Melting Point: 100-104 °C(lit.)
• Boiling Point: 290.9 °C at 760 mmHg
• PKA: 4.50±0.70(Predicted)
• Flash Point: 129.8 °C
• PSA: 20.07000
• LogP: 4.68970
• Sensitive.: air sensitive, moisture sensitiv
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 266.1678636
• Heavy Atom Count: 16
• Complexity: 160

Purity/Quality:

97% ^*data from raw suppliers

Bis(diisopropylamino)chlorophosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(N(C(C)C)C(C)C)Cl
• 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

Technology Process of Bis(diisopropylamino)chlorophosphine

There total 7 articles about Bis(diisopropylamino)chlorophosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C--N-nitrilimine (113533-22-5) → bis(diisopropylamino)chlorophosphine (56183-63-2) + diazomethane (113597-81-2)

Guidance literature:

With hydrogenchloride; In diethyl ether; dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/jo961443h

Reference yield: 74.0%

diisopropylamine (108-18-9) → bis(diisopropylamino)chlorophosphine (56183-63-2)

Guidance literature:

With phosphorus trichloride; In acetonitrile;

DOI:10.1021/ja027983f

Reference yield: 40.0%

N,N-diisopropylphosphoramide dichloride (921-26-6) + diisopropylamine (108-18-9) → bis(diisopropylamino)chlorophosphine (56183-63-2)

Guidance literature:

In diethyl ether;

DOI:10.1039/DT9800002428

upstream raw materials:

diisopropylamine

N,N-diisopropylphosphoramide dichloride

C--N-nitrilimine

(chloro)diazomethylenephosphorane

Downstream raw materials:

S-(4-chlorobenzyl) N,N,N',N'-tetraisopropylphosphorothiodiamidite

bis(dialkylaminophosphanyl)imine

(bis(diisopropylamino)phosphanyl)(1H-pyrrol-2-ylmethylene)phenylamine

5'-O-(4,4'-dimethoxytrityl)-3'-O-(2-methylthioethoxy)-(N,N-diisopropylamino)phosphinyl-2'-deoxythymidine

Refernces

• 1、 Domanska-Babul, Wioleta,Baranowska, Katarzyna,Pikies, Jerzy. "Synthesis and properties of di-isopropylamino derivatives of diphosphanes and triphosphanes: The x-ray structure of (ipr2n) 2p-p(sime3)2". . p. 936 - 941. Retrieved 2009.
• 2、 Keith, D. Jamin,Townsend, Steven D.. "Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit". supporting information. p. 12939 - 12945. Retrieved 2019/08/22.
• 3、 Kaczyński, Tomasz P.,Manszewski, Tomasz,Chmielewski, Marcin K.. "Stereoselective P-Cyclisation and Diastereoisomeric Purification of 5-Phenyl-3-(pyridin-2-yl)-1,3,2-oxazaphospholidine Formed from a Thermolabile Protecting Group". . p. 2522 - 2527. Retrieved 2016/06/01.