2-Cyanoethyl tetraisopropylphosphorodiamidite
P-REAGENT · 3-Bis(diisopropylamino)phosphanyloxypropanenitrile · 2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE · 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite · BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE · 3-(bis(diisopropylamino)phosphinooxy)propanenitrile · THERAPEUTIC GRADE PHOS REAGENT · TETRAISOPROPYLPHOSPHORODIAMIDITE
Identifikatoren & physikalische Daten
| CAS No. | 102691-36-1 |
|---|---|
| Summenformel | C15H32N3OP |
| Durchschnittliche Molmasse | 301,41 g/mol |
| Monoisotopische Masse | 301,22829927 g/mol |
| SMILES | CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C |
| InChIKey | RKVHNYJPIXOHRW-UHFFFAOYSA-N |
| PubChem CID | 128153 |
| EC No. | 600-337-9 |
| DTXSID | DTXSID8075176 |
Chemische & physikalische Eigenschaften
| XLogP | 3,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 39,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 273 |
| Siedepunkt | 100 °C0.5 mm Hg(lit.) |
| Dichte | 0.949 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.470(lit.) |
| Flammpunkt | 141 °F |
| Lagerbedingungen | -20°C |
| Löslichkeit | Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly) |
| Aggregatzustand | liquid |
| pKa (Säurekonstante) | 6.78±0.70(Predicted) |
| Farbe | colorless |
| BRN | 3590103 |
| Stabilität | Explodes When Heated |
| 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 |
| InChIKey | RKVHNYJPIXOHRW-UHFFFAOYSA-N |
| SMILES | CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C |
| LogP (Verteilungskoeffizient) | 4.04 at 20℃ |
| CAS Datenbank | 102691-36-1(CAS DataBase Reference) |
| EPA chemische Informationen | Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226 (97.2%): Flammable liquid and vapor [Warning Flammable liquids]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)Aggregated GHS information provided per 179 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 01-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25176Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Flam. Liq. 3 (97.2%) |
| F | 10-21-34 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 1993 3/PG 3 |
| Zollcode | 29299000 |
| R-Sätze (R) | 5-36/37/38-42/43-36/38 |
| Gefahrensymbole | Xi,Xn |
| hazard_note | Irritant/May Explode on Heating |
| Sicherheitshinweise (S) | 3-26-36-24/25-23-45-36/37 |
| Gefahrenklasse | 8Acute Tox. 4 OralAquatic Chronic 3Flam. Liq. 3Skin Sens. 1B |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Beschreibung
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].
Verwenden
Reagent for synthesizing phosphitylated nucleotides.1