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2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Structure
CAS No.
102691-36-1
Chemical Name:
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
Synonyms
P-REAGENT;2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE;3-Bis(diisopropylamino)phosphanyloxypropanenitrile;3-(bis(diisopropylamino)phosphinooxy)propanenitrile;THERAPEUTIC GRADE PHOS REAGENT;BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE;94.0%(GC&phosphordiamidit;Phosphorus reagent B;Phosphorous reagent A
CBNumber:
CB1231672
Molecular Formula:
C15H32N3OP
Molecular Weight:
301.41
MOL File:
102691-36-1.mol
MSDS File:
SDS
Modify Date:
2024/6/13 17:03:25

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Properties

Boiling point 100 °C0.5 mm Hg(lit.)
Density 0.949 g/mL at 25 °C(lit.)
refractive index n20/D 1.470(lit.)
Flash point 141 °F
storage temp. -20°C
solubility Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly)
form liquid
pka 6.78±0.70(Predicted)
color colorless
Sensitive moisture sensitive, store cold
BRN 3590103
Stability Explodes When Heated
InChIKey RKVHNYJPIXOHRW-UHFFFAOYSA-N
LogP 4.04 at 20℃
CAS DataBase Reference 102691-36-1(CAS DataBase Reference)
EPA Substance Registry System Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS07
Signal word  Warning
Hazard statements  H226-H302-H317-H412
Precautionary statements  P210-P233-P273-P280-P301+P312-P303+P361+P353
Hazard Codes  Xi,Xn
Risk Statements  5-36/37/38-42/43-36/38
Safety Statements  3-26-36-24/25-23-45-36/37
RIDADR  UN 1993 3/PG 3
WGK Germany  3
10-21-34
Hazard Note  Irritant/May Explode on Heating
HazardClass  8
PackingGroup  I
HS Code  29299000
NFPA 704
2
1 0

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 305995 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite 97% 102691-36-1 1G ₹6191.9 2022-06-14 Buy
Sigma-Aldrich(India) 305995 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite 97% 102691-36-1 5G ₹20903.08 2022-06-14 Buy
TCI Chemicals (India) C2228 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite min. 95.0 % 102691-36-1 1G ₹5600 2022-05-26 Buy
TCI Chemicals (India) C2228 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite min. 95.0 % 102691-36-1 5G ₹14700 2022-05-26 Buy
ottokemi B 5244 3-((Bis(diisopropylamino)phosphino)oxy) 97% 102691-36-1 1gm ₹5589 2022-05-26 Buy
Product number Packaging Price Buy
305995 1G ₹6191.9 Buy
305995 5G ₹20903.08 Buy
C2228 1G ₹5600 Buy
C2228 5G ₹14700 Buy
B 5244 1gm ₹5589 Buy

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemical Properties,Uses,Production

Description

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is a colorless viscous liquid, which is soluble in most organic solvents. It is a widely used phosphitylating reagent for the preparation of various phosphorylated biomolecules, such as nucleoside carbohydrate conjugates, phospholipids and glycopeptides. In particular, this reagent is highly effective for automated solid-phase DNA/RNA oligonucleotide synthesis. It has shown great utility in the coupling of nucleobases or carbohydrates via their phosphotriesters in the presence of activators such as 1H-tetrazole, in moderate yields under mild conditions.This compound is cheaper and more stable than 2-cyanoethyl N,N-diisopropylchlorophosphorodiamidite (the other commonly used phosphinylating reagent)[1].

Chemical Properties

Clear to Cloudy Colourless Liquid

Uses

Reagent for synthesizing phosphitylated nucleotides.1

Application

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is an important organic reagent widely used in the preparation of modified and unmodified nucleoside phosphoramidites. Nucleoside phosphoramidites are ideal reagents for polymer-supported synthesis of oligonucleotides. The diisopropylamino leaving group is readily cleaved upon contact with the azole catalyst, resulting in an efficient coupling reaction with the free hydroxyl group on the protected nucleoside.

Synthesis

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
3-((dichlorophosphaneyl)oxy)propanenitrile could synthesize 2-Cyanoethyl N, N, N', N'-tetraisopropylphosphorodiamidite with diisopropylamine. This method is inexpensive manner using a two-step, one-pot procedure and purified by vacuum distillation[2]. 

References

[1] Hada N, et al. Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. Carbohydrate Research, 2008; 343: 343, 2221.
[2] Ching S, et al. Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase. Bioorganic & Medicinal Chemistry, 2010; 18: 6657-6665.

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2-Cyanoethoxybis(N,N-diisopropylaMino)phosphine Bis(diisopropylaMino)(2-cyano N,N,N',N'-Tetrakis(1-Methylethyl)phosphorodiaMidous Acid 2-Cyanoethyl Ester 2-Cyanoethyl N,N,N',N'-tetra(prop-2-yl)phosphorodiamidoite 2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodiaMidite 2-CYANOETHYLTETRAISOPROPYLPHOSPHORO-DIA 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 97% 2-Cyanoethyl N,N,N',N'-tetra(i-propyl)phosphorodiamidite CTPPA 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodia Bis(diisopropylamino)(2-cyanoethoxy)phosphine P-Reagent 2-Cyanoethyl-N,N',N'-Tetraisopropylphosphordiamidite 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORAMIDITE 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORDIAMIDITE 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester 2-CYANOETHYL-N,N,N'',N''-TETRAISO-PROPYLPHOSPHORAMIDITE(P-REAGENT) b-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite TETRAISOPROPYLPHOSPHORODIAMIDITE 5) 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite PHOSPHORODIAMIDOUS ACID, N,N,N'',N''-TETRAKIS(1-METHYLETHYL)-, 2-CYANOETHYL ESTER 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite 98% 2-Cyanoethyl N,N,N',N'-tetra(i-propyl)phosphorodiamidite, min. 98% 2-Cyanoethyl-N,N,Nzzhlxy,Nzzhlxy-tetraisopropylphosphordiamidite (P-Reagent) 2-O-cyanoethyl-N,N,N’,N’-tetraisopropylphosphordiamidite 3-({bis[bis(propan-2-yl)amino]phosphanyl}oxy)propanenitrile 3-((Bis(diisopropylamino)phosphino)oxy), 97% Phosphorous reagent A Phosphorus reagent B 2-CYANOETHYL TETRAISOPROPYLPHOSPHOR 2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite 95+% 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(CTPPA) 94.0%(GC& 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite > N,N,N',N'-tetraisopropyL phosphordiamidit β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodiamidite P-REAGENT THERAPEUTIC GRADE PHOS REAGENT BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE 2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE 3-(bis(diisopropylamino)phosphinooxy)propanenitrile 3-Bis(diisopropylamino)phosphanyloxypropanenitrile bis(2-cyano-1,1-dimethylethyl)-N,N-diisopropylphosphoramidite 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite CTPPA2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 102691-36-1 102691-30-1 916966-01-5 CH32CH2N2POCH2CH2CN C15H38N3OP C15H32N3OP C15H32N3P C15H32N3PO Phosphoramidites Phosphorus Compounds