브로모나이트로메테인
브로모나이트로메테인 · 255858_ALDRICH · EINECS 209-258-0 · bromonitro-methan · nitrobromomethane · BROMONITROMETHANE · Nitromethyl bromide · Methane, bromonitro-
식별자 및 물리적 특성
| CAS No. | 563-70-2 |
|---|---|
| 분자식 | Br.C.H2.N.O2 |
| 평균 분자량 | 139.94 g/mol |
| 단동위원소 질량 | 138.9268904 g/mol |
| SMILES | O=[N+]([O-])CBr |
| InChIKey | DNPRVXJGNANVCZ-UHFFFAOYSA-N |
| PubChem CID | 68423 |
| ChEMBL | CHEMBL2335229 |
| EC No. | 209-258-0 |
| DTXSID | DTXSID7060338 |
| 현지명 | 브로모나이트로메테인 |
화학 및 물리적 성질
| XLogP | 0.9 |
|---|---|
| 극성 표면적 | 45.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 5 |
| 형식 전하 | 0 |
| 복잡도 | 39.4 |
| SpringerMaterials Properties | Chemical shift |
| 밀도 | 2.007 @25 °C2.007 g/mL at 25 °C (lit.) |
| 녹는점 | -28 °C |
| 끓는 점 | 146-148 °C/750 mmHg (lit.) |
| 굴절률 | 1.485-1.495 |
| 인화점 | 4°C |
| 저장 조건 | Storage temp. 2-8°C |
| 용해도 | Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slig |
| pKa(산도 계수) | 7.22±0.29(Predicted) |
| 물리적 상태 | 액체 |
| 색상 | 맑은 노란색 |
| 안정성 | 감광성, 휘발성 |
| InChI | 1S/CH2BrNO2/c2-1-3(4)5/h1H2 |
| InChIKey | DNPRVXJGNANVCZ-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)CBr |
| EPA | Methane, bromonitro- (563-70-2) |
화학적 성질
Bromonitromethane is a clear yellow liquid, It is a strong oxidizing agent with properties similar to nitromethane. Bromonitromethane has been used: in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesis. in preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reaction. in diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy.
안전 및 규제
| GHS 분류 | DangerH272 (97.6%): May intensify fireoxidizer [Danger Oxidizing liquidsOxidizing solids]P210, P220, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Methane, bromonitro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Ox. Sol. 2 (97.6%) |
| Protective Action Criteria (PAC) | 0.40 [mg/m3]4.4 [mg/m3]26 [mg/m3] |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | PA5360000 |
| 운송 번호(UN) | 3098 |
| 관세 코드 | 29049095 |
| 위험 문구(R) | 8-36/37/38-20/21/22 |
| 위험 표시 | Xn-O,Xi,O |
| 안전 문구(S) | 36/37/39-26-17-36 |
| 포장분류 | III |
| 위험 등급 | 5.1Eye Irrit. 2Ox. Sol. 2Skin Irrit. 2STOT SE 3 |
| 기존화학 물질 | KE-03689 |
| 저장 분류 | 5.1B - Oxidizing hazardous materials |
용도
용도
Bromonitromethane has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates. Bromonitromethane is a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the interesting 3-azabicyclo[ 3.1.0]hexane ring system. it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzothio-phenes, and nitrothiazoles, polyfunctionalized nitrocyclopropanes. It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes. In addition, it could be used as a bromine donor.
제조 및 합성 방법
제조 방법
Bromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. A typical procedure is as following: freshly distilled nitromethane was stirred at 0℃ and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification.