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

Bezeichnung:2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

CAS-Nr102691-36-1

Englisch Name:2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

CBNumberCB1231672

SummenformelC15H32N3OP

Molgewicht301.41

MOL-Datei102691-36-1.mol

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite physikalisch-chemischer Eigenschaften

Siedepunkt	100 °C0.5 mm Hg(lit.)
Dichte	0.949 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.470(lit.)
Flammpunkt	141 °F
storage temp.	-20°C
Löslichkeit	Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly)
pka	6.78±0.70(Predicted)
Aggregatzustand	liquid
Farbe	colorless
Sensitive	moisture sensitive, store cold
BRN	3590103
Stabilität	Explodes When Heated
InChIKey	RKVHNYJPIXOHRW-UHFFFAOYSA-N
LogP	4.04 at 20℃
CAS Datenbank	102691-36-1(CAS DataBase Reference)
EPA chemische Informationen	Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	5-36/37/38-42/43-36/38
S-Sätze:	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

Gefahreninformationscode (GHS)

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R5:Beim Erwärmen explosionsfähig.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S3:Kühl aufbewahren.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
Beschreibung
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].
Chemische Eigenschaften
Clear to Cloudy Colourless Liquid
Verwenden
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
Verwenden
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.
Synthese

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].
Einzelnachweise
[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.

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Upstream-Materialien And Downstream Produkte

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