2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite CAS 102691-36-1
Introduction：Basic information about 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite CAS 102691-36-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Basic information
| Product Name: | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite |
| Synonyms: | P-REAGENT;2-Cyanoethoxybis(N,N-diisopropylaMino)phosphine;Bis(diisopropylaMino)(2-cyano;N,N,N',N'-Tetrakis(1-Methylethyl)phosphorodiaMidous Acid 2-Cyanoethyl Ester;THERAPEUTIC GRADE PHOS REAGENT;2-Cyanoethyl N,N,N',N'-tetra(prop-2-yl)phosphorodiamidoite;2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite;2-CYANOETHYLTETRAISOPROPYLPHOSPHORO-DIA |
| CAS: | 102691-36-1 |
| MF: | C15H32N3OP |
| MW: | 301.41 |
| EINECS: | 600-337-9 |
| Product Categories: | OLED materials,pharm chemical,electronic;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphoramidites;Phosphorus Compounds;Phosphorylating and Phosphitylating Agents;Nucleic acids;Regant series;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Other;OLED |
| Mol File: | 102691-36-1.mol |
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemical Properties
| Boiling point | 100 °C0.5 mm Hg(lit.) |
| density | 0.949 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 141 °F |
| storage temp. | -20°C |
| solubility | Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly) |
| pka | 6.78±0.70(Predicted) |
| form | liquid |
| color | colorless |
| Sensitive | moisture sensitive, store cold |
| BRN | 3590103 |
| Stability: | 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 | 4.04 at 20℃ |
| CAS DataBase Reference | 102691-36-1(CAS DataBase Reference) |
| EPA Substance Registry System | Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 5-36/37/38-42/43-36/38 |
| Safety Statements | 3-26-36-24/25-23-45-36/37 |
| RIDADR | UN 1993 3/PG 3 |
| WGK Germany | 3 |
| F | 10-21-34 |
| Hazard Note | Irritant/May Explode on Heating |
| HazardClass | 8 |
| PackingGroup | I |
| HS Code | 29299000 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 3 Flam. Liq. 3 Skin Sens. 1B |
| Description | 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]. |
| Chemical Properties | Clear to Cloudy Colourless Liquid |
| Uses | Reagent for synthesizing phosphitylated nucleotides.1 |
| Uses | 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
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| Application | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is an important organic reagent widely used in the preparation of modified and unmodified nucleoside phosphoramidites. Nucleoside phosphoramidites are ideal reagents for polymer-supported synthesis of oligonucleotides. The diisopropylamino leaving group is readily cleaved upon contact with the azole catalyst, resulting in an efficient coupling reaction with the free hydroxyl group on the protected nucleoside. |
| Synthesis | 3-((dichlorophosphaneyl)oxy)propanenitrile could synthesize 2-Cyanoethyl N, N, N', N'-tetraisopropylphosphorodiamidite with diisopropylamine. This method is inexpensive manner using a two-step, one-pot procedure and purified by vacuum distillation[2]. |
| References | [1] Hada N, et al. Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. Carbohydrate Research, 2008; 343: 343, 2221. [2] Ching S, et al. Synthesis of cyclic di-nucleotidic acids as potential inhibitors targetingdiguanylate cyclase. Bioorganic & Medicinal Chemistry, 2010; 18: 6657-6665. |
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Preparation Products And Raw materials
| Raw materials | 5'-AMINO-5'-DEOXYTHYMIDINE-->BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE-->2-CYANOETHYL PHOSPHORODICHLORIDITE-->Diisopropylamine |
| Preparation Products | Ceftibuten-->anionic starch-->DMT-DCYTIDINE (N6-BENZOYL) CYANOETHYL PHOSPHORAMIDITE)-->DMT-dG(dmf) Phosphoramidite-->Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-(1,7-octadiyn-1-yl)-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]-->Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite], (S)- (9CI)-->DMT-dA(bz) Phosphoramidite-->3'-DA CEP-->5'-DMT-3'-O-TBDMS-N1-Me-Pseudouricdine-CE-Phosphoramidite-->4-THIO-DU CEP-->(2R,3S,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-5-(2,4-DIOXO-5-(3-(2,2,2-TRIFLUOROACETAMIDO)PROP-1-YNYL)-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE-->DMT-2'O-Methyl-rU Phosphoramidite |
