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C8406-10 Cyanoethyl N,N-Diisopropyl Phosphoamidochloridite (2-Cyanoethyl n,n-Diisopropylchlorophosphoramidite) CAS: 89992-70-1

Specifications
References
CAS Number
89992-70-1
Grade
Highly Purified
MDL Number
MFCD00011544
Molecular Formula
C₉H₁₈ClN₂OP
Molecular Weight
236.68
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
2-Cyanoethyl n,n-Diisopropylchlorophosphoramidite; Chloro(diisopropylamino)-β-cyanoethoxyphosphine

2-Cyanoethyl diisopropylchlorophosphoramidite is a useful intermediate in organic synthesis. It acts as a protecting reagent in DNA synthesis. It is involved in the selective monophosphorylation of carbohydrates and nucleosides. It plays an essential role in the conversion of protected ribonucleosides to phosphoramidites. It is also utilized as phosphitylating reagent for 3'-hydroxyl groups in the synthesis of oligodeoxyribonucleotides.

Synonyms
2-Cyanoethyl n,n-Diisopropylchlorophosphoramidite; Chloro(diisopropylamino)-β-cyanoethoxyphosphine
CAS No
89992-70-1
Molecular Formula
C₉H₁₈ClN₂OP
Molecular Weight
236.68
Appearance
Hazy, colorless to yellow oil.
Purity
≥95%
Proton NMR Spectroscopic Analysis
Conforms to reference
Boiling Point
103-105°/0.08mm
Flash Point
>110°(230°F)
Refractive Index
1.4780
Density
1.061g/mL at 25°C (lit.)
Solubility
Benzene, Dichloromethane (Slightly), Chloroform
Stability
Hydrolyzes, Very unstable
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap. Hygroscopic, Store under Inert atmosphere. Reacts violently with water. Incompatible with alcohols and strong bases.
References
Tetrahedron Lett., 24, 5843 (1983), Tetrahedron Lett., 27, 1211 (1986)|Phosphitylating agent for use in oligonucleotide synthesis by the phosphite triester method: Tetrahedron Lett., 24, 5843 (1983); 27, 1211 (1986).|Zhou, Y.; Chladek, S.; Romano, L. J. Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N, N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group. J. Org. Chem. 1994, 59 (3), 556-563.|Balaz, M.; Holmes, A. E.; Benedetti, M.; Proni, G.; Berova, N. Porphyrin substituted phosphoramidites: new building blocks for porphyrin-oligonucleotide syntheses. Bioorg. Med. Chem. 2005, 13 (7), 2413-2421.
USBio References
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