2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite , 97% , 102691-36-1

Synonym(s):
Bis(diisopropylamino)(2-cyanoethoxy)phosphine

CAS NO.：102691-36-1

Empirical Formula: C15H32N3OP

Molecular Weight: 301.41

MDL number: MFCD00012213

EINECS: 600-337-9

PRODUCT 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)
• 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)

Description and Uses

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].

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

Safety

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