3-溴苯甲醛
化合物
3-溴苯甲醛是一種有機化合物,化學式為C7H5BrO。它在室溫為無色液體。[6]
3-溴苯甲醛 | |
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IUPAC名 3-Bromobenzaldehyde | |
英文名 | 3-Bromobenzaldehyde |
別名 | 間溴苯甲醛 |
識別 | |
CAS號 | 3132-99-8 |
ChemSpider | 21106543 |
SMILES |
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InChI |
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InChIKey | SUISZCALMBHJQX-UHFFFAOYAJ |
性質 | |
化學式 | C7H5BrO |
摩爾質量 | 185.02 g·mol−1 |
外觀 | 無色液體 |
密度 | 1.587 g·cm−3(25 °C)[1] 1.3007 g·cm−3(30 °C)[2] |
熔點 | 18—21 °C(291—294 K)[1] |
沸點 | 233—236 °C(506—509 K)[1] 234.5 °C(507.6 K)[3] |
溶解性(水) | 0.043 g(25 °C)[4] |
危險性 | |
警示術語 | R:R22-R36/38[5] |
安全術語 | S:S26-S36/37[5] |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
製備
3-溴苯甲醛可由苯甲醛和溴在氯化鋁催化下、在1,2-二氯乙烷中於40-45°C反應得到;[7]或通過3-溴苯甲醇的催化氧化反應製得。[8][9]
性質
3-溴苯甲醛的C–Br鍵和醛基都可發生反應。例如,它可以和苯硼酸在鈀催化劑和鹼的存在下發生鈴木偶聯反應(C–C偶聯),得到聯苯-3-甲醛:[11][12]
它和活潑亞甲基化合物可以發生克腦文蓋爾縮合反應,例如和氰乙酸乙酯反應,生成3-(3-溴苯基)-2-氰基丙烯酸乙酯[13];和丙二腈反應,生成3-溴亞苄基丙二腈[14]:
它和胺可以發生C–N偶聯反應,如和苄胺反應,得到N-(3-溴亞苄基)苄胺;[15]和4-氨基嗎啉反應,得到N-(3-溴亞苄基)氨基嗎啉。[16]
其醛基也可以發生氧化還原反應,如它可以被硼氫化鈉還原為3-溴苯甲醇[17];在鈀催化下被氫氣還原為3-溴甲苯[18];或者被氧氣[19]、過氧化叔丁醇[20]等氧化劑氧化為3-溴苯甲酸。
參考文獻
- ^ 1.0 1.1 1.2 3-Bromobenzaldehyde. Sigma-Aldrich. [2021-07-10].
- ^ Bergmann, Ernst D.; Zimkin, E.; Pinchas, S. Reaction products of primary β-hydroxy amines with carbonyl compounds. II. Molecular refraction and infrared spectra. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1952. 71: 168-191. ISSN: 0370-7539. CODEN: RTCPB4.
- ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-10].
- ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2021 ACD/Labs). Retrieved from SciFinder. [2021-07-10].
- ^ 5.0 5.1 A11941: 3-Bromobenzaldehyde, 97%. Alfa Aesar. [11 October 2013]. (原始內容存檔於2015年6月10日).
- ^ 间溴苯甲醛. ChemicalBook. [2021-05-10]. (原始內容存檔於2021-05-10).
- ^ 趙昊昱,吳朝華. 間溴苯甲醛. 醫藥中間體及其化工原料, 2004. 4: 31
- ^ Lagerblom, Kalle; Wrigstedt, Pauli; Keskiväli, Juha; Parviainen, Arno; Repo, Timo. Iron-Catalysed Selective Aerobic Oxidation of Alcohols to Carbonyl and Carboxylic Compounds. ChemPlusChem. 2016, 81 (11): 1160–1165. ISSN 2192-6506. doi:10.1002/cplu.201600240.
- ^ Wang, Lianyue; Bie, Zhixing; Shang, Sensen; Lv, Ying; Li, Guosong; Niu, Jingyang; Gao, Shuang. Bioinspired aerobic oxidation of alcohols with a bifunctional ligand based on bipyridine and TEMPO. RSC Advances. 2016, 6 (41): 35008–35013. ISSN 2046-2069. doi:10.1039/C6RA05536B.
- ^ Balicki, Roman; Kaczmarek, Lukasz. Mild Reductive Deoximation with TiCl4/NaI Reagent System. Synthetic Communications. 1991, 21 (17): 1777–1782. ISSN 0039-7911. doi:10.1080/00397919108021576.
- ^ Li, Hongmiao; Tan, Xin; Zhang, Jianyong. Coordination-Driven Terpyridyl Phosphine Pd(II) Gels. Chinese Journal of Chemistry. 2015, 33 (1): 141–146. ISSN 1001-604X. doi:10.1002/cjoc.201400479.
- ^ Zawartka, Wojciech; Pośpiech, Piotr; Cypryk, Marek; Trzeciak, Anna M. Palladium supported on aminopropyl-functionalized polymethylsiloxane microspheres: Simple and effective catalyst for the Suzuki–Miyaura C–C coupling. Journal of Molecular Catalysis A: Chemical. 2015, 407: 230–235. ISSN 1381-1169. doi:10.1016/j.molcata.2015.07.002.
- ^ Jia, Yueqing; Fang, Yanjun; Zhang, Yingkui; Miras, Haralampos N.; Song, Yu-Fei. Classical Keggin Intercalated into Layered Double Hydroxides: Facile Preparation and Catalytic Efficiency in Knoevenagel Condensation Reactions. Chemistry - A European Journal. 2015, 21 (42): 14862–14870. ISSN 0947-6539. doi:10.1002/chem.201501953.
- ^ Zhao, Shen; Chen, Yang; Song, Yu-Fei. Tri-lacunary polyoxometalates of Na8H[PW9O34] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives. Applied Catalysis A: General. 2014, 475: 140–146. ISSN 0926-860X. doi:10.1016/j.apcata.2014.01.017.
- ^ Ou, Xiaoxu; Labes, Ricardo; Battilocchio, Claudio; Ley, Steven V. Preparation of homoallylic amines via a three-component coupling process. Organic & Biomolecular Chemistry. 2018, 16 (36): 6652–6654. ISSN 1477-0520. doi:10.1039/C8OB01831F.
- ^ Xu, Pan; Wang, Guoqiang; Zhu, Yuchen; Li, Weipeng; Cheng, Yixiang; Li, Shuhua; Zhu, Chengjian. Visible-Light Photoredox-Catalyzed C−H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism. Angewandte Chemie International Edition. 2016, 55 (8): 2939–2943. ISSN 1433-7851. doi:10.1002/anie.201508698.
- ^ Rayati, Saeed; Bohloulbandi, Elaheh; Zakavi, Saeed. Sodium borohydride reduction of aldehydes catalyzed by an oxovanadium(IV) Schiff base complex encapsulated in the nanocavity of zeolite-Y. Inorganic Chemistry Communications. 2015, 54: 38–40. ISSN 1387-7003. doi:10.1016/j.inoche.2015.02.004.
- ^ Wang, Shuguo; Zhou, Peng; Jiang, Liang; Zhang, Zehui; Deng, Kejian; Zhang, Yuhua; Zhao, Yanxi; Li, Jinlin; Bottle, Steven; Zhu, Huaiyong. Selective deoxygenation of carbonyl groups at room temperature and atmospheric hydrogen pressure over nitrogen-doped carbon supported Pd catalyst. Journal of Catalysis. 2018, 368: 207–216. ISSN 0021-9517. doi:10.1016/j.jcat.2018.10.017.
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