2-Cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamidite CAS#: 102691-36-1; ChemWhat Code: 38597
Identification
| Product Name | 2-Cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamidite |
| IUPAC Name | 3-bis[di(propan-2-yl)amino]phosphanyloxypropanenitrile |
| Molecular Structure |  |
| CAS Registry Number | 102691-36-1 |
| EINECS Number | 600-337-9 |
| MDL Number | MFCD00012213 |
| Beilstein Registry Number | 3590103 |
| Synonyms | N,N,N’,N’-tetraisopropyl 2-cyanoethylphosphorodiamidite2-Cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamiditebis(diisopropylamino)(2-cyanoethoxy)phosphine2-cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite3-bis(diisopropylamino)phosphanyloxypropanenitrile2-cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamidite3-((bis(diisopropylamino)phosphaneyl)oxy)propanenitrile2-cyanoethyl N,N,N’,N’-tetraisopropylphosphordiamidite2-cyanoethyl N,N,N’,N’-tetraisopropylphosphoramidite2-cyanoethyl N,N,N’,N’-tetraisopropylphosphordiamidite3-((bis(diisopropylamino)phosphino)oxy)propanenitrile2-cyanoethyl-N,N,N’,N’-tetraisopropylphosphoramidite2-cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite2-cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamidite3-((bis(diisopropylamino)phosphino)oxy)propionitrile2-cyanoethoxybis(N,N-diisopropylamino)phosphine2-cyanoethyl tetraisopropylphosphorodiamidite2-cyanoethyl N,N,N‘,N‘-tetraisopropylphosphorodiamidite2-cyanoethyl-N,N,N’,N’-tetraisopropyl phosphate diamine2-cyanoethoxy N,N,N’,N’-tetraisopropylphosphorodiamidite2-cyanoethyl N,N-diisopropylchlorophosphoramiditeCEP[N(iPr)2]2 2-cyanoethyl N,N,N’,N’-tetraisopropylphosphonamideCTPPA |
| Molecular Formula | C15H32N3OP |
| Molecular Weight | 301.41 |
| InChI | InChI=1S/C15H32N3OP/c1-12(2)17(13(3)4)20(19-11-9-10-16)18(14(5)6)15(7)8/h12-15H,9,11H2,1-8H3 |
| InChI Key | RKVHNYJPIXOHRW-UHFFFAOYSA-N |
| Canonical SMILES | CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCCC#N |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN119569802 | Oligonucleotide-modified compound, and preparation method and application thereof | 2025 |
| CN120136742 | Preparation method of SNA phosphoramidite, intermediate of SNA phosphoramidite and preparation method of intermediate | 2025 |
| CN117362336 | Purification method and preparation method of diamine phosphite compound | 2024 |
| WO2022/13393 | PHOSPHORAMIDITE SYNTHESIS ON-DEMAND | 2022 |
Physical Data
| Appearance | Colorless and Clear liquid |
| Solubility | Acetonitrile (dissolve in small amounts), benzene, chloroform (dissolve in small amounts), methanol (dissolve in small amounts) |
| Flash Point | 141 °F |
| Refractive index | n20/D 1.470(lit.) |
| Sensitivity | moisture sensitive, store cold |
| Melting Point, °C | Solvent (Melting Point) |
| 166 – 167.5 |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 110 | 0.562556 |
| 71 | 0.01 |
| 96 – 110 | 0.05 – 0.2 |
| 115 | 0.6 |
| 117 | 0.5 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| Chemical shifts | 31P | |||
| Chemical shifts | 1H | chloroform-d1 | ||
| Chemical shifts | 31P | [(2)H6]acetone | ||
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 1H NMR (600 MHz, CDCl3) δ 3.76 (dd, J=13.7, 6.4 Hz, 2H), 3.58-3.48 (m, 4H), 2.60 (dd, J=9.3, 3.4 Hz, 2H), 1.17 (dd, J=10.0, 6.8 Hz, 24H); | |
| Spectrum, Chemical shifts | 31P | chloroform-d1 | 31P NMR (162 MHz, CDCl3) δ 123.08 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 13C NMR (101 MHz, CDCl3) δ 117.81, 59.30, 59.05, 44.45, 44.32, 24.39, 24.30, 23.72, 23.66, 20.46, 20.37 | |
| Spectrum, Chemical shifts | chloroform-d1 | 400 |
| Description (Mass Spectrometry) |
| spectrum, electrospray ionisation (ESI) |
| spectrum, electrospray ionisation (ESI), high resolution mass spectrometry (HRMS) |
Route of Synthesis (ROS)
| Conditions | Yield |
| With 1-methyl-1H-imidazole; 1H-tetrazole In DMF (N,N-dimethyl-formamide); toluene at 20℃; for 5h; | 95% |
| With 1-methyl-1H-imidazole; 1H-tetrazole In DMF (N,N-dimethyl-formamide) at 20℃; for 5h; | 95% |
| With 1-methyl-1H-imidazole; 1H-tetrazole In N,N-dimethyl-formamide at 20℃; for 5h; | 95% |
Safety and Hazards
| Pictogram(s) |    |
| Signal | Danger |
| GHS Hazard Statements | H226 (97.2%): Flammable liquid and vapor [Warning Flammable liquids] H302 (11.7%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (90.5%): Causes skin irritation [Warning Skin corrosion/irritation] H317 (97.8%): May cause an allergic skin reaction [Warning Sensitization, Skin] H319 (90.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H334 (89.4%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P370+P378, P403, P403+P235, and P501 (click each P-code to see the statement) (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Class 3; Packaging Group: III; UN Number: 1993 |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 301.412 |
| logP | 2.978 |
| HBA | 4 |
| HBD | 0 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 53.09 |
| Rotatable Bond (RotB) | 9 |
| Matching Veber Rules | 2 |
| Use Pattern |
| DNA/RNA Synthesis : Used to prepare nucleoside phosphoramidite monomers, serving as a crucial upstream reagent in solid-phase oligonucleotide synthesis. |
| Modified Oligonucleotides : Used in the synthesis of LNA, modified nucleosides, functionalized DNA/RNA, and antisense oligonucleotides. |
| Nucleic Acid Drugs : Serving the research and development and production of nucleic acid drugs such as siRNA and ASO. |
| Molecular Biology : Used in the synthesis of DNA primers, probes, and other custom oligonucleotides. |
| Phospholipid Synthesis : Can be used for the phosphorylation construction of some phospholipids/glycerophospholipids. |
| Carbohydrates and Glycopeptides : Can be used in the synthesis of phosphorus-containing sugars, glycopeptides, and other phosphorylated biomolecules. |
| Medicinal Chemistry : Used in the synthesis of phosphorus-containing nucleosides, nucleoside analogs, and other phosphorus-containing bioactive molecules. |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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Other Suppliers | |
| Watson International Limited | Visit Watson Official Website |
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