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Thermo Scientific Chemicals
2-Cyanoethyl diisopropylchlorophosphoramidite, 95%
CAS: 89992-70-1 | C9H18ClN2OP | 236.68 g/mol
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Chemical Identifiers
CAS89992-70-1
IUPAC Name3-({[bis(propan-2-yl)amino](chloro)phosphanyl}oxy)propanenitrile
Molecular FormulaC9H18ClN2OP
InChI KeyQWTBDIBOOIAZEF-UHFFFAOYNA-N
SMILESCC(C)N(C(C)C)P(Cl)OCCC#N
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Specifications
Specification Sheet
Specification SheetFormLiquid
Appearance (Color)Clear to turbid or hazy colorless to yellow
Assay from Supplier's CofA≥94.0%
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Miscible with chloroform and dichloromethane.
Notes
Reacts violently with water. Incompatible with alcohols and strong bases.
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.
Solubility
Miscible with chloroform and dichloromethane.
Notes
Reacts violently with water. Incompatible with alcohols and strong bases.
RUO – Research Use Only
General References:
- 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.