921-26-6

Basic information

• Product Name: DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE
• Synonyms: (N,N-diisopropylamino)dichlorophosphine;Dichloro(diisopropylamino)phosphine;dichloro-N,N-diisopropylaminophosphine;Diisopropylaminodichlorphosphan;N,N-diisopropyldichlorophosphoramidite;N-diisopropylaminodichlorophosphane;DIISOPROPYLAMINOPHOSPHORDICHLORIDE;DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE
• CAS NO: 921-26-6
• Molecular Formula: C₆H₁₄Cl₂NP
• Molecular Weight: 202.06
• Product Categories: Phospholipids - 13C & 2H;Phosphorylating and Phosphitylating Agents;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors
• Mol File: 921-26-6.mol
• Article Data: 56

Chemical Properties

• Boiling Point: 56-58°C/15mmHg.
• Flash Point: 66 °C
• Appearance: Colourless Oil
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.2mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• PKA: -1.00±0.70(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE(921-26-6)
• EPA Substance Registry System: DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE(921-26-6)

Safety Data

• Hazard Codes: E,C
• Statements: 1-5-14-34
• Safety Statements: 15-26-27-36/37/39-45
• RIDADR: 2846
• WGK Germany: 3
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 921-26-6(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C6H14Cl2NP/c1-5(2)9(6(3)4)10(7)8/h5-6H,1-4H3

Upstream product

• 108-18-9 diisopropylamine 
• 109-78-4 3-Hydroxypropionitrile 
• 7719-12-2 phosphorus trichloride 
• 125455-29-0 1-chloro-2-(diisopropylamino)-3,3-bis(trimethylsilyl)diphosphirane 
• 86660-78-8 tetrakis(diisopropylamino)cyclotetraphosphine 

Downstream Products

• 103457-17-6 3-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-diisopropylamino-6-phenyl-3H-7-oxa-1,3,4,5,8a-pentaaza-8-phospha-cyclopenta[b]naphthalen-9-one 
• 133843-95-5 di(4-fluorobenzyl)N,N-diisopropylphosphoramidite 
• 121373-20-4 N,N-Diisopropyl-bis<2-(trimethylsilyl)ethyl>phosphoramidite 
• 102690-87-9 bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite 
• 151239-26-8 4-{[({[4-(acetyloxy)phenyl]methoxy}[bis(propan-2-yl)amino]phosphanyl)oxy]methyl}phenyl acetate 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 145471-95-0 (benzyloxy)<(3-(N-carbobenzoxyamino)propyl)oxy>(diisopropylamino)phosphine 
• 151239-27-9 Bis(4-isobutyryloxybenzyl) N,N-diisopropylphosphoramidite 
• 118818-61-4 trans-N,N-diisopropylamino-N'-<2,4,6-tri(tert-butyl)phenyl>iminophosphine 
• 153413-65-1 O,O'-bis-(4-nitrophenyl) N,N-diisopropylphosphoramidite 
• 120362-98-3 <2-Chlor-2,3,5-tris(diisopropylamino)-4-(triphenylphosporanyliden)-3H-1,2,3-azadiphospholium>-tetraphenylborat 
• 120312-30-3 <2-Chlor-2,3,5-tris(diisopropylamino)-4-(triphenylphosphoranyliden)-3H-1,2,3-azaphosphaarsolium>-tetraphenylborat 
• 120363-02-2 <2-Chlor-5--2,3-bis(diisopropylamino)-4-(triphenylphosphoranyliden)-3H-1,2,3-azadiphospholium>-tetraphenylborat 
• 143237-81-4 (1S*,2R*)-1-(N,N-diisopropylamino)-1-oxo-2-benzyl-Δ³-phospholene 

Relevant articles and documents

Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence

Palladium-catalyzed enantioselective dearomative arylalkynylation of N-substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL-based phosphoramidite as the chiral ligand. A wide range of 2,3-disubstituted indolines, bearing vicinal quaternary and tertiary stereocenters, were efficiently constructed in one step with excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (>20:1).

Synthesis and biological evaluation of phospholane and dihydrophosphole analogues of the glutamate receptor agonist AP4

The syntheses and preliminary pharmacological characterisation of two novel cyclic phosphinic acid-containing amino acids designed as conformationally restricted analogues of the metabotropic glutamate receptor agonist AP4 (1) are reported.

Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates

A regioselective Pd-catalyzed allylic amination reaction of dienyl allylic carbonates and aromatic amines has been developed by means of phosphoramidite-palladium catalysis. The regioselectivity could be altered by the counterion of the π-allylpalladium intermediate. As a result, either branched Z-dienyl allylic amines or linear conjugated allylic amines were generated in high levels of regioselectivity from the same substrates by tuning the reaction conditions.

Synthesis of Phospho-Polypeptides via Phosphate-Containing N-Carboxyanhydride: Application in Enzyme-Induced Self-Assembly, and Calcium Carbonate Mineralization

An easy synthetic strategy was developed to synthesize the phosphate-functionalized amino acid N-carboxyanhydride (NCA), using simple primary amine initiators to obtain homo and block phospho-polypeptides with controlled molecular weight and molecular weight distribution. The methodology was extended to the synthesis of the end-functionalized homo polypeptides (15 to 50 repeat unit) and block co-polypeptides with PEG (0.7 K, 2 K, and 5 K) and glycopolypeptide (15-unit mannose glycopolypeptide) as one of the blocks. The deprotected fully water-soluble anionic phosphate-based polypeptides showed pH-dependent helical conformation with a helical content of 20 %, which further changed to β-sheets upon addition of the enzyme alkaline phosphatase (ALP) due to dephosphorylation. The block co-polypeptide containing PEG as one of the blocks led to its self-assembly into colloidal structures, such as vesicles with a hydrodynamic diameter of ～250 nm, due to the formation of amphiphilic block co-polymer upon dephosphorylation. The nature of the colloidal structures formed can be temporally controlled by the extent of dephosphorylation. Finally, the phospho-polypeptides serve as a template for the mineralization of calcium carbonate with varying polymorphs and morphologies.