Introduction
Phosphorodiamidites are a unique class of phosphorus-based compounds characterized by one P–O bond and two P–N moieties. 2-Cyanoethyl tetraisopropylphosphorodiamidite plays a crucial role in solid-phase oligonucleotide synthesis. Beyond their application as synthetic precursors for oligonucleotides, phosphorodiamidites have also been reported as valuable starting materials for the synthesis of industrially relevant polymers and flame-resistant materials, including adhesives, coatings, and laminates.
Manufacture
Cyanoethanol is treated with excess PCl₃ to form the corresponding alkoxydichlorophosphine intermediate, which is subsequently reacted with diisopropylamine to yield 2-cyanoethyl tetraisopropylphosphorodiamidite. Alternatively, 3-trimethylsilanyloxypropionitrile can be reacted with PCl₃, followed by treatment with diisopropylamine, to obtain 2-cyanoethyl tetraisopropylphosphorodiamidite in good yields.
| Synonyms | Bis(diisopropylamino)(2-cyanoethoxy)phosphine |
| CAS no. | 102691-36-1 |
| EINECS no. | 600-337-9 |
| Molecular formula | C15H32N3OP |
| Molecular weight | 301.41 |
| Structure |  |
Applications
The main areas of applications of 2-Cyanoethyl tetraisopropylphosphorodiamidite include:
| Solid-phase oligonucleotide synthesis: |
| Widely used as a key phosphitylating reagent inautomated DNA and RNA synthesis, enabling efficient formation of phosphite triester intermediates. |
| Synthesis of modified oligonucleotides: |
| Applied in the preparation of antisense oligonucleotides, siRNA, aptamers, and other therapeutic nucleic acid analogues. |
| Precursor for P-containing intermediates: |
| Serves as an important building block in the synthesis of phosphoramidite and phosphite derivatives used in fine chemicals and specialty reagents.. |
| Polymer and materials chemistry: |
| Reported as a starting material or intermediate for the preparation of phosphorus-containing polymers.. |
| Flame-retardant materials: |
| Utilized in the development of flame-resistant adhesives, coatings, and laminating materials due to the presence of phosphorus functionality.. |
SPECIFICATIONS
| Test | Unit | Specification |
|---|---|---|
| Appearance | – | Clear liquid |
| Identification by NMR | – | Should conform to the structure |
| Impurities between 181.5-178.6 ppm | % | NMT 0.1 |
| Impurities between 151.2-148 ppm | % | NMT 0.1 |
| Impurities between 121.7-100 ppm | % | NMT 0.2 |
| Impurities < 66.0 ppm | % | NMT 2.0 |
| Impurities between 113-114 ppm | % | NMT 0.0040 |
| Sum of Impurities between 120-148 ppm | % | NMT 0.5 |
| Purity (By 31P NMR) | Area% | NLT 98.0 |
STORAGE & PRECAUTION
Keep sealed at room temperature
PACKING
Globally compliant packaging
REACH Status
REACH registered (https://echa.europa.eu/substance-information/-/substanceinfo/100.107.517)
ExSyn offers 2-Cyanoethyl tetraisopropylphosphorodiamidite on commercial scales and welcomes enquiries. Our exceptional quality and service will make ExSyn your supplier of choice! If you need any additional information or SDS, please contact us.
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