DIBENZYL DIISOPROPYLPHOSPHORAMIDITE CAS 108549-23-1
DIBENZYL DIISOPROPYLPHOSPHORAMIDITE Basic information
| Product Name: | DIBENZYL DIISOPROPYLPHOSPHORAMIDITE |
| Synonyms: | N-[bis(phenylmethoxy)phosphanyl]-N-propan-2-yl-propan-2-amine;N-[bis(phenylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine;Dibenzyl-N,N-disisopropylphosphoramidite;Dibenzyl N,N-diisopropylphosphoramidite, 95+%;Dibenzyl N,N-diisopropylphosphoramidite, tech 90%;DIBENZYL N,N-DIISOPRO;DIBENZYL DIISOPROPYLPHOSPHORAMIDITE;DIBENZYLOXY(DIISOPROPYLAMINO)PHOSPHINE |
| CAS: | 108549-23-1 |
| MF: | C20H28NO2P |
| MW: | 345.42 |
| EINECS: | 629-628-9 |
| Product Categories: | OLED materials,pharm chemical,electronic;Organic Building Blocks;Phosphoramidites;Phosphorus Compounds;Phospholipids - 13C & 2H;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Phosphorylation;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Phosphorylating and Phosphitylating Agents;SiChem;OLED |
| Mol File: | 108549-23-1.mol |
DIBENZYL DIISOPROPYLPHOSPHORAMIDITE Chemical Properties
| Boiling point | 130 °C0.55 mm Hg(lit.) |
| density | 1.028 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 158 °F |
| storage temp. | 2-8°C |
| solubility | Soluble in chloroform. |
| pka | 4.50±0.70(Predicted) |
| form | Oil |
| color | Clear Colourless |
| Water Solubility | THF: soluble(lit.) acetonitrile: soluble(lit.) cold water: insoluble(lit.) dichloromethane: soluble(lit.) |
| Sensitive | Moisture Sensitive |
| BRN | 3616864 |
| InChI | InChI=1S/C20H28NO2P/c1-17(2)21(18(3)4)24(22-15-19-11-7-5-8-12-19)23-16-20-13-9-6-10-14-20/h5-14,17-18H,15-16H2,1-4H3 |
| InChIKey | ANPWLBTUUNFQIO-UHFFFAOYSA-N |
| SMILES | P(N(C(C)C)C(C)C)(OCC1=CC=CC=C1)OCC1=CC=CC=C1 |
| CAS DataBase Reference | 108549-23-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-37/39 |
| WGK Germany | 3 |
| F | 3-10-21 |
| HS Code | 29319090 |
| Storage Class | 10 - Combustible liquids |
| Description | Dibenzyl diisopropylphosphoramidite is a versatile phosphitylating agent. |
| Chemical Properties | Clear Colourless Liquid |
| Uses | A versatile phosphitylating agent |
| Uses | Dibenzyl N,N-diisopropylphosphoramidite may be used for the preparation of phosphopeptides. It is used for the synthesis of a GDP (guanosine diphosphate) analog, SML-8-73-1. It is useful for nucleotide coupling. |
| Synthesis | 921-26-6 100-51-6 108549-23-1 General procedure for the synthesis of diphenyl N,N'-diisopropylphosphoramidite from dichloro-N,N-diisopropylphosphoramidite and benzyl alcohol: 42 g (207.92 mmol) of dichloro-N,N-diisopropylphosphoramidite was placed in a 500 mL round-bottomed flask, and 300 mL of anhydrous tetrahydrofuran was added, and dissolved by stirring. Subsequently 66 mL (455.44 mmol, 46 g) of anhydrous triethylamine was added. The flask was cooled to 0°C in an ice-salt bath and 45 mL (416.67 mmol, 45 g) of anhydrous benzyl alcohol was added slowly and dropwise under nitrogen protection, keeping the reaction temperature close to 0°C. Upon completion of the reaction, the suspension was added dropwise and the formation of a white solid was observed. The reaction mixture was removed from the ice bath, returned to room temperature and stirring was continued for 3 hours. After stopping stirring, it was allowed to stand for 10 minutes for filtration and the solid was washed with tetrahydrofuran. The filtrate was collected and the solvent was removed by rotary evaporation to give the crude product. Without column chromatographic purification, 54.0 g of the oily product was obtained directly in 75.3% yield. |
| References | [1] Tetrahedron, 1991, vol. 47, # 26, p. 4709 - 4722 [2] Patent: CN102977145, 2017, B. Location in patent: Paragraph 0196; 0197 [3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 11, p. 1239 - 1246 [4] Journal of Medicinal Chemistry, 1994, vol. 37, # 23, p. 3918 - 3927 [5] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7719 - 7726 |
DIBENZYL DIISOPROPYLPHOSPHORAMIDITE Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Toluene-->Triethylamine-->Phosphorus trichloride-->Diisopropylamine-->Benzyl alcohol-->DIISOPROPYLPHOSPHORAMIDOUS DICHLORIDE |
| Preparation Products | D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,5,6-tris-O-(phenylmethyl)-, bisbis(phenylmethyl) phosphate-->dibenzyl (2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-yl) phosphate |
