ChemicalBook > CAS DataBase List > 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

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

CAS No.102691-36-1
Chemical Name:2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
CBNumber:CB1231672
Molecular Formula:C15H32N3OP
Formula Weight:301.41
MOL File:102691-36-1.mol

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

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)
pka 6.78±0.70(Predicted)
form liquid
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)
UNSPSC Code 12352100
NACRES NA.22

Safety

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
F :10-21-34
Hazard Note :Irritant/May Explode on Heating
HazardClass :8
PackingGroup :I
HS Code :29299000

NFPA 704:

	2
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H226-H302-H317-H412
Precautionary statements P210-P233-P273-P280-P301+P312-P303+P361+P353

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

Brand: Sigma-Aldrich(India)
Product number: 305995
Product name : 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite
Purity: 97%
Packaging: 1G
Price: ₹6191.9
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 305995
Product name : 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite
Purity: 97%
Packaging: 5G
Price: ₹20903.08
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: C2228
Product name : 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
Purity: min. 95.0 %
Packaging: 1G
Price: ₹5600
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: C2228
Product name : 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
Purity: min. 95.0 %
Packaging: 5G
Price: ₹14700
Updated: 2022/05/26
Buy: Buy

Brand: ottokemi
Product number: B 5244
Product name : 3-((Bis(diisopropylamino)phosphino)oxy)
Purity: 97%
Packaging: 1gm
Price: ₹5589
Updated: 2022/05/26
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2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemical Properties,Usage,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 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
- in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotide
- as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine
- in situ preparation of deoxyribonucleoside phosphoramidites
- in preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymine
- as reagent for synthesizing phosphitylated nucleotides
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
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.