기본 정보
- 표준 SMILES
O=[N+]([O-])CBr- InChIKey
DNPRVXJGNANVCZ-UHFFFAOYSA-N- 분자식
- Br.C.H2.N.O2
- 평균 분자량
- 139.94 g/mol
- 단동위원소 질량
- 138.9268904
개요
structure in first source
이름 및 식별자
- 우선 이름
- Bromonitromethane
- IUPAC
- bromo(nitro)methane
- 현지명
- 브로모나이트로메테인
- 영어명
- Bromonitromethane
- 분자식
- CH2BrNO2
- 분자량
- 139.94
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
563-70-2- PubChem CID
- 68423
- DTXSID
DTXSID7060338- ChEMBL
CHEMBL2335229- UNII
- EG63P9EUR0
- EC Number
- 209-258-0
- Nikkaji
- J435I
물성
구조 계산 물성
- XLogP
- 0.9
- 극성 표면적
- 45.8 Ų
- 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
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- -28 °C · -28 °C
- 끓는 점
- 146 · 146-148 °C/750 mmHg (lit.)
- 밀도
- 2.007 g/mL · 2.007 g/mL at 25 °C (lit.)
- 굴절률
- 1.485 · 1.485-1.495
- 인화점
- 4 °C · 4°C
- 저장 조건
- 2 · Storage temp. 2-8°C
- 용해도
- Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slig
- 산도 계수 (pKa)
- 7.22 · 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
GHS Classification
Danger
H272 (97.6%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing 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.
유해성 정보
Regulatory Information
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.
안전 및 보호
Protective Action Criteria (PAC)
0.40 [mg/m3]
4.4 [mg/m3]
26 [mg/m3]
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- PA5360000
- ridadr
- 3098
- HS 번호
- 29049095
- risk_code
- 8-36/37/38-20/21/22
- hazard_code
- Xn-O,Xi,O
- safety_code
- 36/37/39-26-17-36
- 포장분류
- III
- 위험 등급
- 5.1
- 기존화학 물질
- KE-03689
- Hazard Classifications
- Eye Irrit. 2Ox. Sol. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 5.1B - Oxidizing hazardous materials
화학 및 산업
용도 및 제조
응용 분야
용도Bromonitromethane 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 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.
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