테트라벤질피로포스페이트
테트라벤질피로포스페이트 · TETRABENZYL DIPHOSPHATE · PYROPHOSPHORIC ACID TETRABENZYL ESTER · C2gH2gO7P2 · TetrabenzyL · Bis(phenylmethox · Benzyl Pyrophosphate · Tetracyl pyrophosphate
식별자 및 물리적 특성
| CAS No. | 990-91-0 |
|---|---|
| 분자식 | C28H28O7P2 |
| 평균 분자량 | 538.5 g/mol |
| 단동위원소 질량 | 538.13102722 g/mol |
| SMILES | O=P(OCc1ccccc1)(OCc1ccccc1)OP(=O)(OCc1ccccc1)OCc1ccccc1 |
| InChIKey | NSBNXCZCLRBQTA-UHFFFAOYSA-N |
| PubChem CID | 563183 |
| EC No. | 628-817-3 |
| DTXSID | DTXSID00340276 |
| 현지명 | 테트라벤질피로포스페이트 |
화학 및 물리적 성질
| XLogP | 4.9 |
|---|---|
| 극성 표면적 | 80.3 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 7 |
| 회전 가능 결합 수 | 14 |
| 무거운 원자 수 | 37 |
| 형식 전하 | 0 |
| 복잡도 | 612 |
| 녹는점 | 63-66 °C (lit.) |
| 끓는 점 | 601.6±55.0 °C(Predicted) |
| 밀도 | 1.289±0.06 g/cm3(Predicted) |
| 증기압 | 0.001Pa at 140℃ |
| 저장 조건 | -20°C |
| 용해도 | 클로로포름(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 분말 또는 결정성 분말 |
| 색상 | 흰색에서 황백색까지 |
| 용해도 | 물에 약간 용해됩니다. |
| BRN | 2068292 |
| InChI | InChI=1S/C28H28O7P2/c29-36(31-21-25-13-5-1-6-14-25,32-22-26-15-7-2-8-16-26)35-37(30,33-23-27-17-9-3-10-18-27)34-24-28-19-11-4-12-20-28/h1-20H,21-24H2 |
| InChIKey | NSBNXCZCLRBQTA-UHFFFAOYSA-N |
| SMILES | P(=O)(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)OP(=O)(OCC1C=CC=CC=1)OCC1C=CC=CC=1 |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | DangerH314 (96.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 5 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 규제 정보 | Status: Active Update: 28-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19753Status: Active Update: 03-02-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18954 |
| Hazard Classes and Categories | Skin Corr. 1B (96.2%) |
| 수질 위해 등급(WGK) | 3 |
| 운송 번호(UN) | UN 3261 8/PG 2 |
| 관세 코드 | 29209090 |
| 위험 문구(R) | 34 |
| 위험 표시 | C |
| 안전 문구(S) | 26-36/37/39-45 |
| 포장분류 | II |
| 위험 등급 | 8 |
| F 고인화성물질 | 10-21 |
용도
용도
Tetrabenzyl pyrophosphate is used in the preparation of phosphoryl derivatives of shikimic acid in the presence of LDA. It is used in the preparation of dibenzyl phosphoro fluoridate in the presence of cesium fluoride as a catalyst. It is also used as a precursor in pharmaceuticals and involved in the phosphorylation of inositol derivatives.
제조 및 합성 방법
제조 방법
The production of tetrabenzyl pyrophosphate by the action of acyl chlorides on dibenzyl hydrogen phosphate, and a novel reaction of tetraphenyl pyrophosphate.Preparation of Tetrabenzyl Pyrophosphate: A flask fitted with a nitrogen inlet, overhead stirrer, teflon-coated thermocouple probe, and pressure-equalizing addition funnel was charged with 350 milliliters of dry (water content ≦50 μg/mL), peroxide-free tetrahydrofuran, followed by 50.0 grams (174 millimoles) of dibenzylphosphoric acid (DBP), and the resulting mixture was stirred until the solid dissolved (about 10-15 minutes). A solution of 18.9 grams (91.6 millimoles) of dicyclohexylcarbodiimide (DCC) in 215 milliliters of THF was added from the addition funnel to a stirred, cooled (water-bath) solution of DBP at a rate to maintain the temperature at about 20°-25° C. The reaction is slightly exothermic and the addition took about 30 minutes. Within minutes, a precipitate of dicyclohexylurea formed in the mixture. Stirring was continued for about 2 hours at 20°-25° C. The reaction was monitored by HPLC assay using VYDAC C-18 (300A, 4.6×250 mm) column with water (0.02M KH2PO4) acetonitrile as eluent. The reaction was complete in about 1 hour (assay showing <2 percent unreacted DBP). The mixture was then filtered while excluding moisture to remove dicyclohexylurea. The filter cake was washed with two 25 milliliter portions of THF. The solution when assayed by HPLC showed 45.9 grams (98 percent) yield of tetrabenzyl pyrophosphate (TBPP) in 620 milliliters of THF (0.137M). The filtrate was then stored at 0° C. with exclusion of moisture until the next step.