3-溴苯甲醛

3-溴苯甲醛
	IUPAC名; 3-Bromobenzaldehyde
英文名	3-Bromobenzaldehyde
别名	间溴苯甲醛
识别
CAS号	3132-99-8
ChemSpider	21106543
SMILES	C1=CC(=CC(=C1)Br)C=O;
InChI	1/C7H5BrO/c8-7-3-1-2-6(4-7)5-9/h1-5H;
InChIKey	SUISZCALMBHJQX-UHFFFAOYAJ
性质
化学式	C7H5BrO
摩尔质量	185.02 g·mol−1
外观	无色液体
密度	1.587 g·cm−3（25 °C）; 1.3007 g·cm−3（30 °C）
熔点	18—21 °C（291—294 K）
沸点	233—236 °C（506—509 K）; 234.5 °C（507.6 K）
溶解性（水）	0.043 g（25 °C）
危险性
警示术语	R：R22-R36/38
安全术语	S：S26-S36/37
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

3-溴苯甲醛是一种有机化合物，化学式为C₇H₅BrO。它在室温为无色液体。^[6]

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制备

3-溴苯甲醛可由苯甲醛和溴在氯化铝催化下、在1,2-二氯乙烷中于40-45°C反应得到；^[7]或通过3-溴苯甲醇的催化氧化反应制得。^[8]^[9]

3-溴苯甲醛肟和四氯化钛、碘化钠在乙腈中反应，也能得到3-溴苯甲醛。^[10]

性质

3-溴苯甲醛的C–Br键和醛基都可发生反应。例如，它可以和苯硼酸在钯催化剂和碱的存在下发生铃木偶联反应（C–C偶联），得到联苯-3-甲醛：^[11]^[12]

它和活泼亚甲基化合物可以发生克脑文盖尔缩合反应，例如和氰乙酸乙酯反应，生成3-(3-溴苯基)-2-氰基丙烯酸乙酯^[13]；和丙二腈反应，生成3-溴亚苄基丙二腈^[14]：

它和胺可以发生C–N偶联反应，如和苄胺反应，得到N-(3-溴亚苄基)苄胺；^[15]和4-氨基吗啉反应，得到N-(3-溴亚苄基)氨基吗啉。^[16]

其醛基也可以发生氧化还原反应，如它可以被硼氢化钠还原为3-溴苯甲醇^[17]；在钯催化下被氢气还原为3-溴甲苯^[18]；或者被氧气^[19]、过氧化叔丁醇^[20]等氧化剂氧化为3-溴苯甲酸。

参考文献

[1]
3-Bromobenzaldehyde. Sigma-Aldrich. [2021-07-10].
[2]
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.
[3]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-10].
[4]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2021 ACD/Labs). Retrieved from SciFinder. [2021-07-10].
[5]
A11941: 3-Bromobenzaldehyde, 97%. Alfa Aesar. [11 October 2013]. （原始内容存档于2015年6月10日）.
[6]
间溴苯甲醛. ChemicalBook. [2021-05-10]. （原始内容存档于2021-05-10）.
[7]
赵昊昱,吴朝华. 间溴苯甲醛. 医药中间体及其化工原料, 2004. 4: 31
[8]
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.
[9]
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.
[10]
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.
[11]
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.
[12]
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.
[13]
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.
[14]
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.
[15]
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.
[16]
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.
[17]
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.
[18]
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.
[19]
Mukhopadhyay, Chhanda; Datta, Arup. Bismuth(III) nitrate pentahydrate: a stoichiometric reagent for microwave induced mild and highly efficient aerial oxidation of aromatic aldehydes under solvent-free conditions. Catalysis Communications. 2008, 9 (15): 2588–2592. ISSN 1566-7367. doi:10.1016/j.catcom.2008.07.019.
[20]
Yang, Fan; Qiu, Tian; Chi, Cheng; Liang, Shuang; Deng, Lei; Wang, Xuyang; Wang, Chunxia; Fu, Jingyi; Wang, Ying; Li, Yongfeng. Synergistic effects of nitrogen-doped graphene and Fe2O3 nanocomposites in catalytic oxidization of aldehyde with O2. Chemical Engineering Journal. 2017, 330: 880–889. ISSN 1385-8947. doi:10.1016/j.cej.2017.08.022.

[SA-1] [1]
3-Bromobenzaldehyde. Sigma-Aldrich. [2021-07-10].

[2] [2]
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.

[3] [3]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-10].

[4] [4]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2021 ACD/Labs). Retrieved from SciFinder. [2021-07-10].

[alfa-5] [5]
A11941: 3-Bromobenzaldehyde, 97%. Alfa Aesar. [11 October 2013]. （原始内容存档于2015年6月10日）.

[6] [6]
间溴苯甲醛. ChemicalBook. [2021-05-10]. （原始内容存档于2021-05-10）.

[7] [7]
赵昊昱,吴朝华. 间溴苯甲醛. 医药中间体及其化工原料, 2004. 4: 31

[8] [8]
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.

[9] [9]
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.

[10] [10]
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.

[11] [11]
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.

[12] [12]
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.

[13] [13]
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.

[14] [14]
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.

[15] [15]
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.

[16] [16]
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.

[17] [17]
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.

[18] [18]
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.

[19] [19]
Mukhopadhyay, Chhanda; Datta, Arup. Bismuth(III) nitrate pentahydrate: a stoichiometric reagent for microwave induced mild and highly efficient aerial oxidation of aromatic aldehydes under solvent-free conditions. Catalysis Communications. 2008, 9 (15): 2588–2592. ISSN 1566-7367. doi:10.1016/j.catcom.2008.07.019.

[20] [20]
Yang, Fan; Qiu, Tian; Chi, Cheng; Liang, Shuang; Deng, Lei; Wang, Xuyang; Wang, Chunxia; Fu, Jingyi; Wang, Ying; Li, Yongfeng. Synergistic effects of nitrogen-doped graphene and Fe2O3 nanocomposites in catalytic oxidization of aldehyde with O2. Chemical Engineering Journal. 2017, 330: 880–889. ISSN 1385-8947. doi:10.1016/j.cej.2017.08.022.

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