2-Methoxypyrimidine-5-boronic acid
2-METHOXYL-5-PYRIMIDYLBORIC ACID · 2-Methoxypyrimidine-5-boronicaci · 2-Methoxy PyriMidine boronic acid · 2-Methoxy-5-pyriMidylboronic Acid · 2-METHOXYL-5-PYRIMIDINEBORIC ACID · 2-METHOXY-5-PYRIMIDINEBORONIC ACID · 2-METHOXYPYRIMIDINE-5-BORONIC ACID · 2-MethoxypyriMidine-4-boronic acid
식별자 및 물리적 특성
| CAS No. | 628692-15-9 |
|---|---|
| 분자식 | C5H7BN2O3 |
| 평균 분자량 | 153.93 g/mol |
| 단동위원소 질량 | 154.05497248 g/mol |
| SMILES | COc1ncc(B(O)O)cn1 |
| InChIKey | YPWAJLGHACDYQS-UHFFFAOYSA-N |
| PubChem CID | 2736778 |
| EC No. | 670-240-4 |
| DTXSID | DTXSID70371597 |
화학 및 물리적 성질
| 극성 표면적 | 75.5 |
|---|---|
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 116 |
| 녹는점 | 161°C(lit.) |
| 끓는 점 | 378.3±52.0 °C(Predicted) |
| 밀도 | 1.33±0.1 g/cm3(Predicted) |
| 저장 조건 | Keep in dark place,Sealed in dry,Room Temperature |
| 용해도 | 메탄올에 용해됨 |
| 물리적 상태 | powder to crystal |
| pKa(산도 계수) | 5.59±0.11(Predicted) |
| 색상 | 흰색에서 밝은 노란색 |
| InChI | InChI=1S/C5H7BN2O3/c1-11-5-7-2-4(3-8-5)6(9)10/h2-3,9-10H,1H3 |
| InChIKey | YPWAJLGHACDYQS-UHFFFAOYSA-N |
| SMILES | B(C1=CN=C(OC)N=C1)(O)O |
화학적 성질
Off-white to light yellow solid
안전 및 규제
| GHS 분류 | WarningH302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (89.1%) |
| 수질 위해 등급(WGK) | WGK 3 |
| 관세 코드 | 29349990 |
| 위험 문구(R) | 36-41-36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-39-36/37/39 |
| 위험 등급 | IRRITANTAcute Tox. 4 OralEye Irrit. 2 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
2-Methoxypyrimidine-5-boronic acid serves as a coupling partner in Suzuki–Miyaura reactions to synthesize diverse heterocyclic scaffolds. It reacts with intermediates such as compound 26 or 6-bromo-3-(4-hydroxyphenyl)-coumarin using potassium carbonate and palladium catalysts (e.g., Pd(OAc)₂ or 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride) in solvents including DMF or deep eutectic systems at 85 °C. The reagent also couples with 2-(4-((4-chloro-6-morpholino-1,3,5-triazin-2-yl)amino)phenyl)ethan-1-ol in DME/aqueous sodium carbonate under microwave heating[1][2][3]. The compound participates in Liebeskind–Srögl couplings with thioester or amide intermediates (such as series 18a–18c or 20a–20f) using tetrakis(triphenylphosphine)palladium(0) and copper(I) thiophene-2-carboxylate in THF at 100 °C, yielding target products in ranges of 22–55% or 29–50%[1].
제조 및 합성 방법
생산 방법
5-Bromo-2-methoxypyrimidine could synthesize 2-Methoxypyrimidine-5-boronic acid as the start material.