CAS: 90-90-4; (4-Bromophenyl)(Phenyl)Methanone

该化合物是一种溴化芳香酮,广泛用作有机合成和制药生产中的关键中间体,其独特结构以苯环上的溴替代物为特征,增强了交叉反应的回动性,如铃木和乌伦联结,有利于构建复杂的分子框架.复合物具有很高的纯度和稳定性,适合材料科学,农用化学品和光化剂的应用.其晶体形式确保易于处理和精确测量实验室环境.4-Bromobenzophenone因其在电子哲学替代和高级功能材料的前体方面的一贯性能而受到重视.

英文名称(4-Bromophenyl)(Phenyl)Methanone
中文名称4-溴二苯甲酮
IUPAC名称(4-bromophenyl)(phenyl)methanone
其它别名4-溴苯并苯基酮 10G; 4溴二苯甲酮; P-Benzoylbromobenzene
CAS编号90-90-4
MFCD编号:MFCD00000103
EINECS号:202-024-9
FDA UNII编号:XJ7EB9BC7F
分子式:C13H9BrO
分子量:261.11
产品CID: 1942950
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: KEOLYBMGRQYQTN-UHFFFAOYSA-N
InChI=1S/C13H9BrO/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9H…
计算化学: 氢键受体数1.0氢键供体数0.0可旋转键数2.0

物理性质

熔点78-82°C
沸点346.8°C at 760 mmHg
闪点81.3°C
密度1.4±0.1 g/cm3
PSA:17.07
LogP:3.6801
折射率1.610
蒸汽压0.0±0.8 mmHg at 25°C
溶解性Insoluble In Water But Slightly Soluble In Other Solvents Such As Ethanol, Ether And Benzene.
外观形态白色至浅米色结晶粉末
储存条件密封, 常温干燥保存
产品应用该化合物用于化学试剂和药剂中间体.

MSDS等安全信息

GHS象形图
GHS符号GHS08 & GHS09;
注释: Health hazard & Environment
危险类别特定目标器官毒性-重复接触类别2
水生慢性毒性类别2
特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
严重眼刺激类别2
警示词Warning(警告)
危险描述H373 |长期或反复接触可能损害器官.
H411 |对水生生物有毒并具有长期持续影响.
H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
UN编号NONH for all modes of transport
危险品标志Xi
安全声明37/39-26
危险类别码36/37/38
WGK Germany3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

合成目标产物 4-Bromobenzophenone 主要起始原料 4-Bromophenylboronic Acid And Benzoyl Chloride
29334-16-5 = 90-90-4
反应条件:1.1 Catalysts: Cesium,(Tribromoplumbyl)- Solvents: 1,2-Dichloroethane; 4.2 H,Rt
标题:Visible-Light Photocatalytic Highly Selective Oxidation Of Alcohols Into Carbonyl Compounds By Cspbbr3 Perovskite
作者:Fan,Qiangwen; Liu,Dawei; Xie,Zongbo; Le,Zhanggao; Zhu,Haibo; Et Al
参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(20) 页码:14559-14570]

192436-83-2 + 591-51-5 = 90-90-4
反应条件:1.1 Solvents: Diethyl Ether,Butyl Ether; 2.5 H,-30 °C
标题:Discovery Of 1,1'-Biphenyl-4-Sulfonamides As A New Class Of Potent And Selective Carbonic Anhydrase Xiv Inhibitors
作者:La Regina,Giuseppe; Coluccia,Antonio; Famiglini,Valeria; Pelliccia,Sveva; Monti,Ludovica; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2015 卷标:58(21) 页码:8564-8572]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Hydrogen Peroxide Catalysts: 1450802-38-6 Solvents: Water; Rt; 65 Min,Rt
标题:Application Of Copper(Ii) Schiff Base Complex Grafted In The Silica Network As Efficient Nanocatalyst In Oxidation Of Alcohols
作者:Eshtiagh-Hosseini,Hossein; Tabari,Taymaz; Eshghi,Hossein
参考文献:Asian Journal Of Chemistry 日期:2013 卷标:25(6) 页码:3307-3312]

2116-36-1 = 90-90-4
反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide Catalysts: Pyridine,Iodine Solvents: Water; Rt; Overnight,80 °C
标题:A Metal-Free Catalytic System For The Oxidation Of Benzylic Methylenes And Primary Amines Under Solvent-Free Conditions
作者:Zhang,Jintang; Wang,Zhentao; Wang,Ye; Wan,Changfeng; Zheng,Xiaoqi; Et Al
参考文献:Green Chemistry 日期:2009 卷标:11(12) 页码:1973-1978]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Oxygen Solvents: Acetone; Rt
标题:External Catalyst- And Additive-Free Photo-Oxidation Of Aromatic Alcohols To Carboxylic Acids Or Ketones Using Air/o2
作者:Xu,Meng; Ou,Jinhua; Luo,Kejun; Liang,Rongtao; Liu,Jian; Et Al
参考文献:Molecules 日期:2023 卷标:28(7)]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide Catalysts: Cobalt Iron Oxide (Cofe2O4) Solvents: Dimethyl Sulfoxide,Water; 4.5 H,90 °C
标题:Magnetically Retrievable Mfe2O4 Spinel (M = Mn,Co,Cu,Ni,Zn) Catalysts For Oxidation Of Benzylic Alcohols To Carbonyls
作者:Burange,Anand S.; Kale,Sandip R.; Zboril,Radek; Gawande,Manoj B.; Jayaram,Radha V.
参考文献:Rsc Advances 日期:2014 卷标:4(13) 页码:6597-6601]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide Catalysts: Cerium Chromium Oxide (Cecro3) Solvents: Dimethyl Sulfoxide,Water; 5 Min; 5 H,90 °C
标题:Oxidation Of Benzylic Alcohols To Carbonyls Using Tert-Butyl Hydroperoxide Over Pure Phase Nanocrystalline Cecro3
作者:Burange,Anand S.; Jayaram,Radha V.; Shukla,Rakesh; Tyagi,Avesh K.
参考文献:Catalysis Communications 日期:2013 卷标:40 页码:27-31]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Tetrabutylammonium Bromide,Sodium Nitrite,Oxygen Catalysts: Tempo (Sba-15-Supported) Solvents: Acetic Acid; 4.5 H,60 °C
标题:Green,Transition-Metal-Free Aerobic Oxidation Of Alcohols Using A Highly Durable Supported Organocatalyst
作者:Karimi,Babak; Biglari,Abbass; Clark,James H.; Budarin,Vitaly
参考文献:Angewandte Chemie 日期:2007 卷标:46(38) 页码:7210-7213]

586-75-4 + 934-56-5 = 90-90-4
反应条件:1.1 Catalysts: 2623973-37-3 Solvents: Benzene-D6; Rt -> 75 °C; 4 H,75 °C
标题:Phosphine-Borane Ligands Induce Chemoselective Activation And Catalytic Coupling Of Acyl Chlorides At Palladium
作者:Boudjelel,Maxime; Sadek,Omar; Mallet-Ladeira,Sonia; Garcia-Rodeja,Yago; Sosa Carrizo,E. Daiann; Et Al
参考文献:Acs Catalysis 日期:2021 卷标:11(7) 页码:3822-3829]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: N-Bromosuccinimide,Alumina; 10 Min,Rt; 4 Min,Heated
标题:Microwave-Assisted Solvent-Free Oxidation Of Hydrobenzoins,Benzoins,And Alcohols With Nbs-Al2O3
作者:Khurana,Jitender M.; Arora,Reema
参考文献:Arkivoc (Gainesville 日期:2008 卷标:(14) 页码:211-215]

14874-70-5 + 32785-41-4 = 90-90-4
反应条件:1.1 Reagents: Potassium Bromide,Tetrabutylammonium Tribromide Catalysts: P-Toluenesulfonic Acid Solvents: Methanol; 1.5 H,15 °C
标题:Photochemical Sandmeyer-Type Halogenation Of Arenediazonium Salts
作者:Sivendran,Nardana; Belitz,Florian; Sowa Prendes,Daniel; Manu Martinez,Angel; Schmid,Rochus; Et Al
参考文献:Chemistry - A European Journal 日期:2022 卷标:28(9)]

2116-36-1 = 90-90-4
反应条件:1.1 Reagents: N-Bromosuccinimide,Water Solvents: Chloroform; 3 H,Reflux1.2 Reagents: Sodium Thiosulfate Solvents: Water
标题:Synthesis Of Structurally Diverse Diarylketones Through The Diarylmethyl Sp3 C-H Oxidation
作者:He,Chao; Zhang,Xiaohui; Huang,Ruofeng; Pan,Jing; Li,Jiaqiang; Et Al
参考文献:Tetrahedron Letters 日期:2014 卷标:55(32) 页码:4458-4462]

586-75-4 + 143-66-8 = 90-90-4
反应条件:1.1 Reagents: Potassium Fluoride Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Acetone
标题:Microwave Promoted Palladium-Catalyzed Phenylation Of Aroyl Chlorides With Sodium Tetraphenylborate
作者:Wang,Jin-Xian; Wei,Bangguo; Hu,Yulai; Liu,Zhanxiang; Yang,Yihua
参考文献:Synthetic Communications 日期:2001 卷标:31(24) 页码:3885-3890]

4333-76-0 = 90-90-4
反应条件:1.1 Reagents: Potassium Sulfide,Oxygen Catalysts: Iron Chloride (Fecl3) Solvents: Dimethylformamide; 14 H,1 Atm,80 °C
标题:Fe-S Catalyst Generated In Situ From Fe(Iii)- And S3.--Promoted Aerobic Oxidation Of Terminal Alkenes
作者:Ai,Jing-Jing; Liu,Bei-Bei; Li,Jian; Wang,Fei; Huang,Cheng-Mi; Et Al
参考文献:Organic Letters 日期:2021 卷标:23(12) 页码:4705-4709]

29334-16-5 = 90-90-4
反应条件:1.1 Reagents: Diisopropylcarbodiimide Catalysts: Bis(Dichloro(η6-P-Cymene)Ruthenium) Solvents: Toluene; 24 H,120 °C
标题:Ruthenium-Catalyzed Dehydrogenation Of Alcohols With Carbodiimide Via A Hydrogen Transfer Mechanism
作者:Sueki,Shunsuke; Matsuyama,Mizuki; Watanabe,Azumi; Kanemaki,Arata; Katakawa,Kazuaki; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2020 卷标:2020(31) 页码:4878-4885]

33268-46-1 = 90-90-4
反应条件:1.1 Reagents: Tripotassium Phosphate,Oxygen Catalysts: Tetrabutylammonium Bromide Solvents: Acetone; 45 Min,Rt
标题:Oxidative Coupling Of α-Bromoarylacetonitriles And Oxidative Decyanation Of Diarylacetonitriles Catalyzed By Solid-Liquid Phase Transfer
作者:Zhang,Xin; Hou,Xueling; Han,Fangbin; Ge,Zemei; Cheng,Tieming; Et Al
参考文献:Journal Of Chinese Pharmaceutical Sciences 日期:2012 卷标:21(5) 页码:409-415]

29334-16-5 = 90-90-4
反应条件:1.1 Solvents: 1,2-Dichloroethane; 2.5 H,Rt
标题:Photocatalyst-Free Light-Driven Dehydrogenation Of Alcohols Into Carbonyl Compounds Under Mild Conditions
作者:Fan,Qiangwen; Zhang,Honglei; Ren,Huijun; He,Yanling; Gu,Yuhang; Et Al
参考文献:Chemistry - An Asian Journal 日期:2022 卷标:17(17)]

2996-92-1 + 97839-40-2 = 90-90-4
反应条件:1.1 Catalysts: Cuprous Iodide,Tetrakis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 1 - 2 Min,Rt1.2 Reagents: Tetrabutylammonium Fluoride; Rt; Rt -> 65 °C; 6 H,65 °C
标题:Palladium-Catalyzed Desulfitative C-C Cross-Coupling Reaction Of (Hetero)Aryl Thioesters And Thioethers With Arylsiloxanes
作者:Mehta,Vaibhav Pravinchandra; Sharma,Anuj; Van Der Eycken,Erik
参考文献:Advanced Synthesis & Catalysis 日期:2008 卷标:350 页码:2174-2178]

586-75-4 + 143-66-8 = 90-90-4
反应条件:1.1 Reagents: Alumina,Potassium Fluoride Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Acetone
标题:Microwave-Assisted Cross-Coupling Reaction Of Sodium Tetraphenylborate With Aroyl Chlorides On Palladium-Doped Kf/al2O3
作者:Wang,Jin-Xian; Yang,Yihua; Wei,Bangguo; Hu,Yulai; Fu,Ying
参考文献:Bulletin Of The Chemical Society Of Japan 日期:2002 卷标:75(6) 页码:1381-1382]

589-87-7 + 780-69-8 = 90-90-4
反应条件:1.1 Reagents: Cesium Fluoride Catalysts: Palladium,Bis(Acetonitrile)Dichloro- Solvents: N-Methyl-2-Pyrrolidone; 6 H,1 Atm,80 °C
标题:Carbonylative Hiyama Coupling Of Aryl Halides With Arylsilanes Under Balloon Pressure Of Co
作者:Chang,Sheng; Jin,Ying; Zhang,Xiu Rong; Sun,Yong Bing
参考文献:Tetrahedron Letters 日期:2016 卷标:57(19) 页码:2017-2020

1-溴-4-(苯基乙炔基)苯置于氧气,Copper Diacetate,Potassium Carbonate,苯胺体系中,用二甲基亚砜作为反应溶剂,以58%的收率获得产物4-溴苯甲酰苯
参考文献:铜通过炔烃三价键的裂解从需氧炔烃中合成双芳基酮†
标题:铜通过炔烃三价键的裂解从需氧炔烃中合成双芳基酮†
摘要:据报道,一种新型的铜催化需氧化合物可通过c-C三键的裂解从1,2-二芳基炔烃中合成双芳基酮.该反应是1,2-二芳基炔烃向双芳基酮的新转化.
DOI:10.1039/c4Ra06460G

海关参考信息

2912110000-甲醛
2912210000-苯甲醛
2914190090-其他无环酮
2914399090-其他芳香酮
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-10865390-B2
优先权日:2018-02-12
标题 :Alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols
发明人：NI YE; ZHOU JIEYU; XU GUOCHAO; WANG YUE
权利人:UNIV JIANGNAN
摘要:The present disclosure discloses an alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols, and belongs to the technical field of bioengineering. The alcohol dehydrogenase mutant of the present disclosure has excellent catalytic activity and stereoselectivity, and may efficiently catalyze the preparation of a series of chiral diaryl alcohols in R- and S-configurations. By coupling alcohol dehydrogenase of the present disclosure to glucose dehydrogenase or formate dehydrogenase, the synthesis of chiral diaryl alcohol intermediates of various antihistamines may be achieved. Compared with the prior art, a method for preparing diaryl chiral alcohols through asymmetric catalytic reduction using the alcohol dehydrogenase of the present disclosure has the advantages of simple and convenient operation, high substrate concentration, complete reaction and high product purity, and has great industrial application prospects.

专利号:US-10822593-B2
优先权日:2018-02-12
标题:Alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols
发明人：NI YE; ZHOU JIEYU; XU GUOCHAO; WANG YUE
权利人:UNIV JIANGNAN
摘要:The present disclosure discloses an alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols, and belongs to the technical field of bioengineering. The alcohol dehydrogenase mutant of the present disclosure has excellent catalytic activity and stereoselectivity, and may efficiently catalyze the preparation of a series of chiral diaryl alcohols in R- and S-configurations. By coupling alcohol dehydrogenase of the present disclosure to glucose dehydrogenase or formate dehydrogenase, the synthesis of chiral diaryl alcohol intermediates of various antihistamines may be achieved. Compared with the prior art, a method for preparing diaryl chiral alcohols through asymmetric catalytic reduction using the alcohol dehydrogenase of the present disclosure has the advantages of simple and convenient operation, high substrate concentration, complete reaction and high product purity, and has great industrial application prospects.

专利号:US-11078465-B2
优先权日:2018-02-12
标题:Alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols
发明人：NI YE; WANG YUE; DAI WEI; XU GUOCHAO; ZHOU JIEYU
权利人:UNIV JIANGNAN
摘要:The present disclosure discloses an alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols, and belongs to the technical field of bioengineering. The alcohol dehydrogenase mutant of the present disclosure has excellent catalytic activity and stereoselectivity, and may efficiently catalyze the preparation of a series of chiral diaryl alcohols in R- and S-configurations. By coupling alcohol dehydrogenase of the present disclosure to glucose dehydrogenase or formate dehydrogenase, the synthesis of chiral diaryl alcohol intermediates of various antihistamines may be achieved. Compared with the prior art, a method for preparing diaryl chiral alcohols through asymmetric catalytic reduction using the alcohol dehydrogenase of the present disclosure has the advantages of simple and convenient operation, high substrate concentration, complete reaction and high product purity, and has great industrial application prospects.

专利号:US-5569447-A
优先权日:1994-04-19
标题:Stannylated 3-quinuclidinyl benzilates and methods of preparing radiohalogenated derivatives
发明人：LEE KAN S; HE XIAO-SHU; WEINBERGER DANIEL R
权利人:US HEALTH
摘要:The present invention provides stannylated 3-quinuclidinyl benzilate compounds and a method of synthesizing *AQNB by iodinating such stannylated 3-quinuclidinyl benzilate compounds. The iodination of these stannylated 3-quinuclidinyl benzilates proceeds in as little as five minutes; thus, the stannylated 3-quinuclidinyl benzilates may be converted to *AQNB in situ for immediate use. Using this method, radiolabelling yields as high as 80% have been observed. The present invention also is directed towards a method of synthesis of the stannylated 3-quinuclidinyl benzilate compounds. The method comprises providing a 4'-halo-3-quinuclidinyl benzilate and reacting the 4'-halo-3-quinuclidinyl benzilate with a compound having the formula (SnR 3 ) 2 , wherein R is an alkyl.

专利号:US-2005080260-A1
优先权日:2003-04-22
标题 :Preparation of prodrugs for selective drug delivery
发明人：MILLS RANDELL L; WU GUO-ZHANG
摘要:Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

专利号:US-4453012-A
优先权日:1982-04-22
标题 :Process for the preparation of phenyl ketones
发明人：DESBOIS MICHEL
权利人:RHONE POULENC SPEC CHIM
摘要:A process for the preparation of phenyl ketones, characterized in that, in a first stage, a halo- or trihalomethylbenzene is reacted with a trihalomethylated aliphatic or aromatic compound in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent, and in that, in a second stage, the resultant product is hydrolyzed. The products are used as intermediates in the synthesis of compounds having a pharmaceutical or phytosanitary (e.g., herbicidal) activity.

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[参考文献]: Qingkai Qi, Et Al. Reversible Multistimuli-Response Fluorescent Switch Based On Tetraphenylethene-Spiropyran Molecules. Chemistry. 2015 Jan 12;21(3):1149-55.

合成参考文献

摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2010) 47, 258.
摘要:Griesbeck, A. G.; Soldevilla, A., Science of Synthesis, (2008) 43, 363.
摘要:Wicha, J., Science of Synthesis, (2009) 48, 110.
摘要:de Haro, T.; Garayalde, D.; Nevado, C., Science of Synthesis Knowledge Updates, (2012) 2, 220.
摘要:Delvos, L. B.; Oestreich, M., Science of Synthesis Knowledge Updates, (2017) 1, 155.

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CAS: 90-90-4; (4-Bromophenyl)(Phenyl)Methanone

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