CAS: 872-31-1; 3-Bromothiophene

该化合物是一种卤化的杂交循环化合物,广泛用作有机合成的多用途中间体.它以三处位置的硫苯环替代溴,能够通过相互交织的反应,例如铃木或Stille联结,使其高效地发挥作用,从而对建筑复杂的硫苯基结构很有价值.该化合物具有良好的稳定性和再活动性,便于其在制药,农用化学品和材料科学中使用.其高纯度和一贯的质量确保了在要求应用方面的可靠性能. 3-Bromothiophene由于有能力改变光学特性,特别有利于合成聚合物和电子材料的合成. 由于其易燃性和潜在刺激性,建议进行适当的处理.

英文名称3-Bromothiophene
中文名称3-溴噻吩
IUPAC名称3-bromothiophene
其它别名3-Thienyl bromide
CAS编号872-31-1
MFCD编号:MFCD00005464
EINECS号:212-821-3
FDA UNII编号:G818Z74YV0
分子式:C4H3BrS
分子量:163.04
产品CID: 1878294
产品分类医药中间体 → 噻吩类化合物

相似结构搜索
InChIKey: XCMISAPCWHTVNG-UHFFFAOYSA-N
InChI=1S/C4H3BrS/c5-4-1-2-6-3-4/h1-3H…
计算化学: 氢键受体数1.0氢键供体数0.0可旋转键数0.0

物理性质

熔点<-10°C
沸点150 °C (文献)
闪点140 °F
密度1.74 g/mL at 25 °C (文献)
PSA:28.24
LogP:2.5106
折射率n 20/D 1.591(文献)
蒸汽压16.65 mmHg
溶解性Chloroform (Slightly), Methanol (Slightly)
敏感性光敏感/恶臭
外观形态透明无色至微黄色液体
储存条件置于阴暗处,密封干燥,2-8°C
产品应用有机合成及医药中间体
性质描述该品为微黄色液体.沸点150°C.

MSDS等安全信息

GHS象形图
GHS符号GHS02 & GHS06 & GHS09;
注释: Flame & Skull and crossbones & Environment
危险类别易燃液体类别3
急性毒性类别1(吸入)
急性毒性类别2(经皮)
急性毒性类别3(经口)
特定目标器官毒性 - 单次接触类别3
严重眼刺激类别2
皮肤致敏类别1
水生慢性毒性类别2
急性毒性类别2(吸入)
皮肤腐蚀/刺激类别2
急性毒性类别3(吸入)
急性毒性类别3(经皮)
急性毒性类别1(经皮)
严重眼刺激类别2A
警示词Danger(危险)
危险描述H226 |易燃液体和蒸气.
H330 |吸入致命.
H310 |皮肤接触致命.
H301 |吞咽会中毒.
H335 |可能引起呼吸道刺激.
H319 |造成严重眼刺激.
H317 |可能引起皮肤过敏反应.
H411 |对水生生物有毒并具有长期持续影响.
H315 |造成皮肤刺激.
H331 |吸入会中毒.
H311 |皮肤接触会中毒.
防范说明P210-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
危险等级6.1
UN编号UN 2929 6.1/PG 2
危险品标志T,Xi,N,Xn
风险等级Irritant
包装等级II
安全声明26-36/37/39-45-61-38-28A-16-24/25-23-36-36/37-24/35
危险类别码10-25-41-51/53-36/37/38-23/24/25-20/21/22-43-36/37
WGK Germany3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

2,3-dibromothiophen 2,3,5-tribromothiophene n-butyllithium diethyl ether 3-(2-hydroxyethyl)thiophene 3-bromothiophene-2-carboxylic acid 3-Thiophene carboxylic acid 3-(methylthio)thiophene

合成工艺路线路线简述

7311-64-0 = 872-31-1
反应条件:1.1 Catalysts: Acetic Acid,Silver Carbonate Solvents: Dmso-D6; 16 H,120 °C; 120 °C -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water
标题:Silver-Catalyzed Protodecarboxylation Of Heteroaromatic Carboxylic Acids
作者:Lu,Pengfei; Et Al
参考文献:Organic Letters 日期:2009 卷标:11(24) 页码:5710-5713]

3141-24-0 = 872-31-1
反应条件:1.1 Reagents: Zinc Solvents: Acetic Acid
标题:The Photochemistry Of Thiophene S-Oxides
作者:Arima,Kazuya; Et Al
参考文献:Photochemical & Photobiological Sciences 日期:2005 卷标:4(10) 页码:808-816]

1003-09-4 = 872-31-1
反应条件:1.1 Reagents: Sodium Amide,Ammonium Chloride
标题:Reactions Of Halothiophenes With Metal Amides. Convenient Preparation Of β-Bromothiophenes
作者:Reinecke,Manfred G.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1971 卷标:36(18) 页码:2690-2]

= 872-31-1
反应条件:1.1 Reagents: Bromine Solvents: Chloroform; Cooled; 3 H,60 °C1.2 Reagents: Acetic Acid,Zinc Solvents: Water; 9 H,Reflux
标题:Synthesis Of (3-Alkylthio)Thiophenes
作者:Huang,Jin-Bo; Et Al
参考文献:Yingyong Huaxue 日期:2007 卷标:24(1) 页码:105-107]

= 872-31-1
反应条件:1.1 Reagents: Hydrogen Bromide Solvents: Diethyl Ether,Water; 3.5 H,22 °C; 19 H,22 °C1.2 Reagents: Sodium Thiosulfate Solvents: Water1.3 Reagents: Zinc Solvents: Acetic Acid,Water; 30 Min,Rt -> Reflux; Reflux -> Rt1.4 Solvents: Acetic Acid; 3 H,Rt; 4 H,Rt -> Reflux
标题:Synthesis Of Poly(Thiophene-Alt-Pyrrole) From A Difunctionalized Thienylpyrrole By Kumada Polycondensation
作者:He,Lu-Ying; Et Al
参考文献:Tetrahedron 日期:2015 卷标:71(33) 页码:5399-5406]

3140-93-0 = 872-31-1
反应条件:1.1 Reagents: Ethyl Bromide,Hydrochloric Acid Solvents: Diethyl Ether,Water
标题:Nitrothienols And Halogenated Nitrothiophenes
作者:Hurd,Charles D.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1952 卷标:74 页码:2965-70]

3140-93-0 = 872-31-1
反应条件:1.1 Reagents: Ethyl Bromide,Magnesium Catalysts: Iodine Solvents: Diethyl Ether; 6 H,Reflux1.2 Reagents: Water Solvents: Water
标题:Synthesis And Antimicrobial Activity Of Some Halo Derivatives Of Thiophene
作者:Bardia,Rahul; Et Al
参考文献:Asian Journal Of Chemistry 日期:2004 卷标:16(1) 页码:511-512]

73882-41-4 = 872-31-1
反应条件:1.1 Catalysts: Pyridine
标题:On The Reaction Of Methoxide Ion With Bromoiodothiophenes
作者:Gronowitz,Salo; Et Al
参考文献:Journal Of Heterocyclic Chemistry 日期:1980 卷标:17(1) 页码:171-4]

95602-69-0 = 872-31-1
反应条件:1.1 Reagents: Butyllithium,Water
标题:Thiophene As A Structural Element Of Physiologically Active Substances,Xii. Thiophene Analogs Of Antiviral Chalcones
作者:Binder,Dieter; Et Al
参考文献:Archiv Der Pharmazie (Weinheim 日期:1985 卷标:318(1) 页码:48-59]

95602-70-3 = 872-31-1
反应条件:1.1 Reagents: Butyllithium,Water
标题:Thiophene As A Structural Element Of Physiologically Active Substances,Xii. Thiophene Analogs Of Antiviral Chalcones
作者:Binder,Dieter; Et Al
参考文献:Archiv Der Pharmazie (Weinheim 日期:1985 卷标:318(1) 页码:48-59]

3140-92-9 = 872-31-1
反应条件:1.1 Catalysts: Copper Oxide (Cuo),Sodium Iodide Solvents: Ethanol,1,4-Dioxane2.1 Reagents: Butyllithium,Water
标题:Thiophene As A Structural Element Of Physiologically Active Substances,Xii. Thiophene Analogs Of Antiviral Chalcones
作者:Binder,Dieter; Et Al
参考文献:Archiv Der Pharmazie (Weinheim 日期:1985 卷标:318(1) 页码:48-59]

994-28-5 = 872-31-1
反应条件:1.1 Reagents: Chloro(1-Methylethyl)Magnesium Solvents: Tetrahydrofuran1.2 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: N-Bromosuccinimide,Oxygen Solvents: Dimethylformamide; 4 H,Rt2.2 Reagents: Sodium Thiosulfate Solvents: Water; Rt
标题:Orthogonal Stability And Reactivity Of Aryl Germanes Enables Rapid And Selective (Multi)Halogenations
作者:Fricke,Christoph; Et Al
参考文献:Angewandte Chemie 日期:2020 卷标:59(42) 页码:18717-18722]

3141-24-0 = 872-31-1
反应条件:1.1 Reagents: Zinc Solvents: Acetic Acid,Thiophene; 3 H,Reflux
标题:Enantioselective Chalcogeno-Baylis-Hillman Reaction Of Arylaldehydes With Mvk And Acrylates Catalyzed By Chiral Thiepin-Ticl4 Complex
作者:Yin,Yan; Et Al
参考文献:Chinese Journal Of Chemistry 日期:2014 卷标:32(4) 页码:365-369]

3141-24-0 = 872-31-1
反应条件:1.1 Reagents: Acetic Acid,Zinc Solvents: Water; Heated
标题:Zinc
作者:Knochel,Paul; Et Al
参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2006 卷标:1 页码:1-17]

3958-03-0 = 872-31-1
反应条件:1.1 Reagents: Trioctylmethylammonium Chloride,(T-4)-Bis(Acetato-Ko,Ko′)Lead Solvents: Dichloromethane
标题:Selective Debromination Of Thiophene Derivatives By Electrochemical Reduction
作者:Dapperheld,S.; Et Al
参考文献:Synthesis 日期:1990 卷标:(5) 页码:403-5]

= 872-31-1
反应条件:1.1 Reagents: Bromine Solvents: Chloroform; Rt -> 0 °C; 4.5 H,0 °C; 3.5 H,Reflux1.2 Reagents: Sodium Hydroxide Solvents: Water; 0.5 H,Rt1.3 Reagents: Acetic Acid,Zinc Solvents: Water; 8 H,Reflux
标题:Design,Synthesis,And Fungicidal Activity Of Novel Analogues Of Pyrrolnitrin
作者:Wang,Ming-Zhong; Et Al
参考文献:Journal Of Agricultural And Food Chemistry 日期:2009 卷标:57(17) 页码:7912-7918]

192863-37-9 = 872-31-1
反应条件:1.1 Reagents: Chloramine-T,Sodium Bromide Solvents: Tetrahydrofuran,Water; 10 Min,Rt
标题:Synthesis Of Organic Bromides Via Organotrifluoroborates
作者:Kabalka,George W.; Et Al
参考文献:Organometallics 日期:2004 卷标:23(19) 页码:4519-4521]

2382987-00-8 = 872-31-1
反应条件:1.1 Reagents: N-Bromosuccinimide,Oxygen Solvents: Dimethylformamide; 4 H,Rt1.2 Reagents: Sodium Thiosulfate Solvents: Water; Rt
标题:Orthogonal Stability And Reactivity Of Aryl Germanes Enables Rapid And Selective (Multi)Halogenations
作者:Fricke,Christoph; Et Al
参考文献:Angewandte Chemie 日期:2020 卷标:59(42) 页码:18717-18722]

60404-24-2 = 872-31-1
反应条件:1.1 Catalysts: Methanol
标题:On The Reaction Of Methoxide Ion With Bromoiodothiophenes
作者:Gronowitz,Salo; Et Al
参考文献:Journal Of Heterocyclic Chemistry 日期:1980 卷标:17(1) 页码:171-4]

62601-06-3 = 872-31-1 [标题:Reaction Conditions
标题:A Process For The Preparation Of 3-Bromothiophene Derivatives As Intermediates For Agrochemicals And Pharmaceuticals
参考文献:Japan]

73882-40-3 = 872-31-1
反应条件:1.1 Catalysts: Sodium Methoxide
标题:On The Reaction Of Methoxide Ion With Bromoiodothiophenes
作者:Gronowitz,Salo; Et Al
参考文献:Journal Of Heterocyclic Chemistry 日期:1980 卷标:17(1) 页码:171-4]

3140-92-9 = 872-31-1
反应条件:1.1 Reagents: Iodine Catalysts: Butyllithium2.1 Catalysts: Sodium Methoxide
标题:On The Reaction Of Methoxide Ion With Bromoiodothiophenes
作者:Gronowitz,Salo; Et Al
参考文献:Journal Of Heterocyclic Chemistry 日期:1980 卷标:17(1) 页码:171-4]

3141-26-2 = 872-31-1
反应条件:1.1 Reagents: Iodine Catalysts: Butyllithium2.1 Catalysts: Pyridine
标题:On The Reaction Of Methoxide Ion With Bromoiodothiophenes
作者:Gronowitz,Salo; Et Al
参考文献:Journal Of Heterocyclic Chemistry 日期:1980 卷标:17(1) 页码:171-4]

6324-10-3 = 872-31-1
反应条件:1.1 Reagents: Mercuric Acetate Solvents: Acetic Acid; 4 H,Reflux1.2 Reagents: Sodium Chloride Solvents: Water; 1 H,Reflux1.3 Reagents: Hydrochloric Acid Solvents: Water2.1 Reagents: Ethyl Bromide,Magnesium Catalysts: Iodine Solvents: Diethyl Ether; 6 H,Reflux2.2 Reagents: Water Solvents: Water
标题:Synthesis And Antimicrobial Activity Of Some Halo Derivatives Of Thiophene
作者:Bardia,Rahul; Et Al
参考文献:Asian Journal Of Chemistry 日期:2004 卷标:16(1) 页码:511-512

噻吩置于溴,Sodium Hydroxide,溶剂黄146,锌体系中,用氯仿,水作为反应溶剂,化学反应 8.0H,以80.8%的收率获得产物3-溴噻吩
参考文献:新型吡咯硝酮类似物的设计,合成和杀真菌活性
标题:新型吡咯硝酮类似物的设计,合成和杀真菌活性
摘要:通过简便的方法设计和合成了一系列含有噻吩部分的吡咯硝酮新类似物,并通过1 H核磁共振(NMR)和高分辨率质谱对它们的结构进行了表征.分离了异构体iv-H和vh,并通过2D NMR鉴定了其结构,包括异核多量子相干(hmqc),异核多键相关(hmbc)和核overhauser效应光谱(noesy)光谱.评估了它们对5种真菌的杀真菌活性,结果表明,某些标题化合物在体外对solternaria Solani表现出优异的杀真菌活性,玉蜀黍赤霉,轮纹轮纹病菌,镰孢属omysporum,和尾孢花生在50微克毫升的剂量-1.一些化合物在低剂量下显示中等活性.化合物vh可被认为是进一步设计农业杀菌剂的主要结构.
DOI:10.1021/jf902320E

专利信息

专利号:US-6995289-B2
优先权日:2000-08-02
标题 :Process for synthesis of alpha, beta-unsaturated ketones
发明人：PATEL IAN; HOPES PHILIP
权利人:ASTRAZENECA AB
摘要:A method for the synthesis of an Î±,Î²-unsaturated ketone useful for making substituted 1,4-dihydropyridines is described by reacting an aldehyde with pyrrolidine and then adding a ketone followed by trifluoroacetic acid at low temperature. The synthesis is used in a process for making substituted 1,4-dihydropyridines wherein a vinylogous amide is prepared by reacting a 1,3-cyclohexanedione with a phenylethylamine. The Î±,Î²-unsaturated ketone can be reacted with a vinylogous amide to form a 1,5-diketone which can be converted to a substituted 1,4-dihydropyridine.

专利号:US-6906214-B2
优先权日:2001-07-04
标题:Preparation of aromatic organozinc compounds and composition therefore
发明人：PERICHON JACQUES; GOSMINI CORINNE; FILLON HYACINTHE
权利人:RHODIA CHIMIE SA
摘要:The invention relates to a technique for preparing aromatic organozinc compounds and to a composition therefore. This composition constitutes a reactant that can be used to carry out the synthesis of organozinc compounds, and comprises a cobalt salt, a zinc salt, a polar aprotic solvent and elemental zinc in divided form, the elemental zinc being in solid form, the other elements being in a form dissolved in the solvent. Application to organic synthesis.

专利号:US-2008280855-A1
优先权日:2005-06-22
标题 :Process For the Production of Intermediates For the Preparation of Tricyclic Benzimidazoles
发明人：CHIESA MARIA VITTORIA; PALMER ANDREAS; BUHR WILM; ZIMMERMANN PETER JAN; BREHM CHRISTOF; SIMON WOLFGANG-ALEXANDER; POSTIUS STEFAN; KROMER WOLFGANG; ZANOTTI-GEROSA ANTONIO
权利人:NYCOMED GMBH
摘要:The invention relates to a process for the synthesis of compounds of the formula 1-a and compounds of the formula 1-b. n n n n n n n n n n The compounds of the formula 1-a and the compounds of the formula 1-b, in which the substituents R1, R2, R3, and Ar have the meanings indicated in the description, are valuable intermediates for the preparation of pharmaceutically active compounds.

专利号:EP-4198027-A1
优先权日:2021-12-14
标题:Sustainable process for the synthesis of molecules with antihistamine activity in unconventional biodegradable solvents (deep eutectic solvents)
发明人：QUIVELLI ANDREA FRANCESCA; CAPRIATI VITO; PERNA FILIPPO MARIA; VITALE PAOLA; ROSSI FEDERICO VITTORIO; GARCÃ?A - Ã?LVAREZ JOAQUÃ?N
权利人:UNIV DEGLI STUDI DI BARI; UNIV OVIEDO
摘要:The present invention relates to a sustainable synthetic process for obtaining ethylenediamines molecules with antihistamine activity whose production costs are considerably reduced by employing unconventional biodegradable solvents, such as the Deep Eutectic Solvents, with considerable advantages from a point of view both of the environmental and economic impact.

专利号:WO-2024165749-A1
优先权日:2023-02-10
标题:Synthesis of a water-based p-type donor polymer
发明人：FABIANO SIMONE; YANG CHI-YUAN; LIU TIEFENG; KROON RENEE; HEIMONEN JOHANNA
权利人:N INK AB
摘要:The present invention relates to a method for synthesizing a polymer comprising at least one repeating unit comprising at least one diaromatic moiety, at least one glycol side chain functionalized with a terminal carboxylate and/or sulfonate group, the method comprising the steps of: a) providing a glycol having general formula: H-(O-CH2-(CH2)m)n-OH wherein n is an integer from 1 to 50; and wherein m is an integer from 0 to 10; b) allowing the glycol to react with an aryl halide in presence of a copper halide catalyst, thus forming a first intermediate comprising a first aromatic moiety; c) allowing the first intermediate to undergo oxa-Michael addition to a Michael acceptor comprising a carboxylate and/or sulfonate precursor thus forming a second intermediate comprising the first aromatic moiety and one of the carboxylate and/or sulfonate precursor; d) brominating the first aromatic moiety of the second intermediate, thus forming a third intermediate comprising a brominated first aromatic moiety; e) allowing the brominated first aromatic moiety of the third intermediate to undergo a coupling reaction with a compound comprising a second aromatic moiety, thus forming a polymeric compound comprising at least one repeating unit comprising at least one diaromatic moiety, at least one glycol moiety with a terminal end comprising carboxylate and/or sulfonate precursor; f) deprotecting the carboxylate and/or sulfonate precursor thus forming a polymer comprising at least one repeating unit comprising at least one diaromatic moiety and at least one glycol side chain functionalized with a terminal carboxylate and/or sulfonate group.

专利号:WO-2007141253-A1
优先权日:2006-06-07
标题 :Process for the production of intermediates for the preparation of tricyclic imidazopyridines
发明人：PALMER ANDREAS; BUHR WILM; ZIMMERMANN PETER JAN; BREHM CHRISTOF; CHIESA MARIA VITTORIA; ZANOTTI-GEROSA ANTONIO
权利人:NYCOMED GMBH; PALMER ANDREAS; BUHR WILM; ZIMMERMANN PETER JAN; BREHM CHRISTOF; CHIESA MARIA VITTORIA; ZANOTTI-GEROSA ANTONIO
摘要:The invention relates to a process for the synthesis of compounds of the formula (1-a) and compounds of the formula (1-b). The compounds of the formula 1-a and the compounds of the formula 1-b, in which the substituents R1, R2, R3, and Arom have the meanings indicated in the description, are valuable intermediates for the preparation of pharmaceutically active compounds.

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合成参考文献

摘要:Li, Y.; Xie, W.; Jiang, X., Science of Synthesis Knowledge Updates, (2016) 2, 8.
摘要:Weibel, J.-M.; Blanc, A.; Pale, P., Science of Synthesis Knowledge Updates, (2018) 1, 66.
摘要:Davies, G. H. M.; Wisniewski, S. R., Science of Synthesis Knowledge Updates, (2021) 2, 130.
摘要:Krause, N.; Arisetti, N., Science of Synthesis Knowledge Updates, (2020) 3, 89.
摘要:Schatz, J.; Seler, M., Science of Synthesis Knowledge Updates, (2011) 2, 408.