브로모시클로프로판
브로모사이클로프로페인 · 브로모시클로프로판 · 사이클로프로필브로민화물 · BROMOCYCLOPROPANE · Cyclopropyl · Cyclopropyl bromine · BromocycL · NSC 89692
식별자 및 물리적 특성
| CAS No. | 4333-56-6 |
|---|---|
| 분자식 | C3H5Br |
| 평균 분자량 | 120.98 g/mol |
| 단동위원소 질량 | 119.95746226 g/mol |
| SMILES | BrC1CC1 |
| InChIKey | LKXYJYDRLBPHRS-UHFFFAOYSA-N |
| PubChem CID | 78037 |
| EC No. | 224-375-7 |
| DTXSID | DTXSID8063418 |
| 현지명 | 브로모시클로프로판 |
화학 및 물리적 성질
| XLogP | 1.5 |
|---|---|
| 극성 표면적 | 0 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 4 |
| 형식 전하 | 0 |
| 복잡도 | 22.5 |
| 물질 분류 | Other Classes -> Halogenated Cyclic Hydrocarbons |
| SpringerMaterials Properties | Schoenflies notation |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| 끓는 점 | 69 °C (lit.) |
| 밀도 | 1.51 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.458(lit.) |
| 인화점 | 20 °F |
| 저장 조건 | 2-8°C |
| 용해도 | 클로로포름(소량으로 용해), 메탄올(약간 용해됨) |
| 물리적 상태 | 액체 |
| 비중 | 1.510 |
| 색상 | 무색의 |
| 용해도 | 섞일 수 없음 |
| BRN | 1900287 |
| InChI | InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2 |
| InChIKey | LKXYJYDRLBPHRS-UHFFFAOYSA-N |
| SMILES | C1(Br)CC1 |
| NIST | Cyclopropyl bromide(4333-56-6) |
| EPA | Cyclopropane, bromo- (4333-56-6) |
화학적 성질
Light yellow to clear colourless liquid, boiling point 67-69°C, refractive index (nD20) 1.4605, density (d420) 1.5120, flash point -6°C.
안전 및 규제
| GHS 분류 | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 54 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Bromocyclopropane: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | A skin and strong eye irritant[Alfa Aesar MSDS] See Iodocyclohexane. See Ethyl bromide. |
| Hazard Classes and Categories | Flam. Liq. 2 (100%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 1993 3/PG 2 |
| 관세 코드 | 29035990 |
| 위험 문구(R) | 11-36/37/38 |
| 위험 표시 | F,Xi |
| 안전 문구(S) | 16-26-36-37/39 |
| 포장분류 | II |
| 위험 등급 | 3Flam. Liq. 2 |
| 기존화학 물질 | KE-09321 |
| F 고인화성물질 | 8-19 |
| 위험 참고 사항 | Irritant |
| 저장 분류 | 3 - Flammable liquids |
용도
개요
Cyclopropyl bromide is also named as Bromocyclopropane. It is used in organic synthesis, for instance, for the formation of a Grignard Reagent, cyclopropyllithium. It is also used as an intermediate in the manufacture of pharmaceutical and agrochemical products.
용도
Bromocyclopropane is primarily used an intermediate in the manufacture of pharmaceutical and agrochemical products. It is also used in the production of cyclopropyl boric acid. It is used as an intermediate in organic synethesis.
제조 및 합성 방법
제조 방법
Bromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at 29° (53% yield) or in tetrachloroethane at 20° to 25° (15–20% yield). Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield. An attempt to prepare the bromide via the von Braun reaction was unsuccessful. Ten percent yields are reported for the photobromination of cyclopropane and the photochemical rearrangement of allyl bromide. Treatment of 1,1,3-tribromopropane with methyllithium prepared from methyl bromide furnishes a 60–65% yield of bromocyclopropane.