CAS: 827-01-0; 5-Chloroindole-3-Carboxaldehyde

该化合物是一种多用途的七环化合物,其特点是在三点位置上有一个有气态组的化氯替代蛋白核心,这种结构使它成为有机合成中的宝贵中间体,特别是用于制备药品,农用化学品和功能材料.这种替代物增强了交叉反应的回动性,而甲醛组则作为进一步衍生(例如凝聚或减少)的关键功能处理器.在标准条件下,它的高纯度和稳定性确保研究和工业应用的可靠性能.由于具有明确的再反应特征,该复合物通常用于生物活性分子的合成,包括潜在的治疗剂.

英文名称5-Chloroindole-3-Carboxaldehyde
中文名称5-氯吲哚-3-甲醛
IUPAC名称5-chloro-1H-indole-3-carbaldehyde
其它别名5-氯-3-吲哚甲醛; 5-Chloro-3-Formylindole
CAS编号827-01-0
MFCD编号:MFCD00175291
EINECS号:627-809-7
分子式:C9H6ClNO
分子量:179.6
产品CID: 1817110
产品分类有机原料→分子砌块→芳杂环类化合物→吲哚类化合物

相似结构搜索
产品信息参考;
InChIKey: YXEXOIGXNYITQH-UHFFFAOYSA-N
InChI=1S/C9H6ClNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H…
计算化学: 氢键受体数1.0氢键供体数1.0可旋转键数1.0

物理性质

熔点213-216°C
沸点373.4±22.0 °C at 760 mmHg
闪点179.6±22.3 °C
密度1.4±0.1 g/cm3
pKa:14.59±0.30(预测)
PSA:32.86
LogP:2.6338
折射率1.732
蒸汽压0.0±0.8 mmHg at 25°C
敏感性空气敏感
外观形态浅橙色粉末
储存条件置于阴暗处,密封, 常温干燥保存
产品应用该化合物用于编制: 5-九硝酸酯-3-氨二甲二甲苯丁氨基乙酰氨氨基氨基磺酰胺-2-[(5-5-氯-1H-因多醇-3-3-3-1-氟基甲基乙烯基)-2-(1-H-1-因多尔醇-3-1-3-基)乙酰二氯二烯-1-(2-2-二二氟基溴基氟乙烯基-1-(2-三甲基新甲基新甲苯基甲基甲基甲基基甲基)酯

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2
严重眼刺激类别2A
警示词Warning(警告)
危险描述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-P271-P280-P302+P352-P304+P340-P362-P405-P501
危险等级IRRITANT
UN编号NONH for all modes of transport
危险品标志Xi,Xn
安全声明26-36-36/37/39-22
危险类别码36/37/38-20/21/22
WGK Germany3

欧盟法规

ECHA物质C&L通报

上下游产品

合成工艺路线路线简述

合成目标产物 5-Chloroindole-3-Carboxaldehyde 主要起始原料 Hexamethylenetetramine And 5-Chloroindole
877-03-2 = 827-01-0
反应条件:1.1 Reagents: Cuprous Chloride Solvents: N-Methyl-2-Pyrrolidone; Rt -> 210 °C; 15 H,205 - 210 °C
标题:Highly Convenient And Large Scale Synthesis Of 5-Chloroindole And Its 3-Substituted Analogues
作者:Keetha,Laxminarayana; Et Al
参考文献:Journal Of The Korean Chemical Society 日期:2011 卷标:55(2) 页码:240-242]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Potassium Iodide,Water Catalysts: Red 21 Solvents: Acetonitrile; 48 H,Rt
标题:Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y As A Photoredox Catalyst
作者:Zhao,Yin; Et Al
参考文献:Synlett 日期:2022 卷标:33(7) 页码:659-663]

17422-32-1 + 298-12-4 = 827-01-0
反应条件:1.1 Reagents: Ammonium Persulfate Solvents: Dimethyl Sulfoxide,Water; 2 H,Rt1.2 Reagents: Water; Rt
标题:(Nh4)2S2O8-Mediated Metal-Free Decarboxylative Formylation/acylation Of α-Oxo/ketoacids And Its Application To The Synthesis Of Indole Alkaloids
作者:Dinesh,Votarikari; Et Al
参考文献:Journal Of Organic Chemistry 日期:2022 卷标:87(15) 页码:10359-10365]

17422-32-1 + 298-12-4 = 827-01-0
反应条件:1.1 Solvents: Acetonitrile,Water; 6 H,Rt1.2 Reagents: Water
标题:Photochemical Decarboxylative Formylation Of Indoles With Aqueous Glyoxylic Acid
作者:Dinesh,Votarikari; Et Al
参考文献:Synlett 日期:2023 卷标:34(7) 页码:855-857]

1242737-14-9 = 827-01-0
反应条件:1.1 Reagents: Sodium Carbonate,Boronic Acid Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: 1,4-Dioxane; Reflux1.2 Reagents: Phosphorus Oxychloride; 0 - 23 °C
标题:Novel Benzofuran-3-One Indole Inhibitors Of Pi3 Kinase-α And The Mammalian Target Of Rapamycin: Hit To Lead Studies
作者:Bursavich,Matthew G.; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2010 卷标:20(8) 页码:2586-2590]

224156-28-9 = 827-01-0
反应条件:1.1 -2.1 Reagents: Phosphorus Oxychloride
标题:The Vilsmeier Reaction Of Fully Conjugated Carbocycles And Heterocycles
作者:Jones,Gurnos; Et Al
参考文献:Organic Reactions (Hoboken 日期:1997 卷标:49]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Dimethylformamide; 30 Min,Cooled1.2 Solvents: Dimethylformamide; 1 H,40 °C1.3 Reagents: Sodium Hydroxide Solvents: Water; Ph 8,Cooled
标题:Synthesis And Antiproliferative Activity Of New N-Acylhydrazone Derivatives Containing Benzothiazole And Indole Based Moiety
作者:Liu,Kai; Et Al
参考文献:Pharmaceutical Chemistry Journal 日期:2020 卷标:54(4) 页码:345-352]

17422-32-1 + 1535-67-7 = 827-01-0
反应条件:1.1 Catalysts: Bismuth Triflate Solvents: 1,1,1,3,3,3-Hexafluoro-2-Propanol; 5 Min,Rt1.2 Solvents: 1,1,1,3,3,3-Hexafluoro-2-Propanol; 12 H,Rt1.3 Reagents: 2-Iodoxybenzoic Acid Solvents: Dimethyl Sulfoxide,Water; 1 H,Rt1.4 Reagents: Sodium Sulfite Solvents: Water; Rt1.5 Reagents: Sodium Bicarbonate Solvents: Water; Basified,Rt
标题:Bi(Otf)3 Enabled C-F Bond Cleavage In Hfip: Electrophilic Aromatic Formylation With Difluoro(Phenylsulfanyl)Methane
作者:Betterley,Nolan M.; Et Al
参考文献:Asian Journal Of Organic Chemistry 日期:2018 卷标:7(8) 页码:1642-1647]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide,Pivalic Acid Catalysts: Ruthenium Trichloride Solvents: N-Methylacetamide; 0 °C; 24 H,25 °C
标题:Mild And Selective Ru-Catalyzed Formylation And Fe-Catalyzed Acylation Of Free (N-H) Indoles Using Anilines As The Carbonyl Source
作者:Wu,Wenliang; Et Al
参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(31) 页码:11924-11927]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Pivalic Acid,Tert-Butyl Peroxybenzoate Catalysts: Tetrabutylammonium Iodide Solvents: Dimethyl Sulfoxide; 8 H,80 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water
标题:Nbu4Ni-Catalyzed C3-Formylation Of Indoles With N-Methylaniline
作者:Li,Lan-Tao; Et Al
参考文献:Chemical Communications (Cambridge 日期:2012 卷标:48(42) 页码:5187-5189]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Oxygen Catalysts: Iodine Solvents: Dimethylformamide; 12 H,100 °C
标题:Iodine-Catalyzed C3-Formylation Of Indoles Via C-N Bond Cleavage Of Tertiary Amines Under Aerobic Conditions
作者:Lu,Lin; Et Al
参考文献:Tetrahedron 日期:2015 卷标:71(22) 页码:3637-3641]

17422-32-1 + 298-12-4 = 827-01-0
反应条件:1.1 Reagents: Sodium Perchlorate Catalysts: Aniline,Platinum Solvents: Dimethyl Sulfoxide,Water; 7 H,Rt
标题:Synthesis Of 3-Formylindoles Via Electrochemical Decarboxylation Of Glyoxylic Acid With An Amine As A Dual Function Organocatalyst
作者:Lin,Dian-Zhao; Et Al
参考文献:Organic Letters 日期:2019 卷标:21(15) 页码:5862-5866]

17422-32-1 = 827-01-0
反应条件:1.1 Reagents: Ammonia,Oxygen Catalysts: Iron Chloride (Fecl3) Solvents: Dimethylformamide,Water; 6 H,130 °C
标题:Iron-Catalyzed C3-Formylation Of Indoles With Formaldehyde And Aqueous Ammonia Under Air
作者:Wang,Qing-Dong; Et Al
参考文献:Synlett 日期:2017 卷标:28(19) 页码:2670-2674]

63665-97-4 = 827-01-0
反应条件:1.1 -2.1 Reagents: Phosphorus Oxychloride
标题:The Vilsmeier Reaction Of Fully Conjugated Carbocycles And Heterocycles
作者:Jones,Gurnos; Et Al
参考文献:Organic Reactions (Hoboken 日期:1997 卷标:49]

44205-36-9 = 827-01-0
反应条件:1.1 -2.1 -3.1 Reagents: Phosphorus Oxychloride
标题:The Vilsmeier Reaction Of Fully Conjugated Carbocycles And Heterocycles
作者:Jones,Gurnos; Et Al
参考文献:Organic Reactions (Hoboken 日期:1997 卷标:49

5-溴吲哚-3-甲醛置于copper(L) Chloride体系中,用 N-甲基吡咯烷酮作为反应溶剂,化学反应 15.0H,以83%的收率获得产物5-氯吲哚-3-甲醛
参考文献:Highly Convenient And Large Scale Synthesis Of 5-Chloroindole And Its 3-Substituted Analogues
标题:Highly Convenient And Large Scale Synthesis Of 5-Chloroindole And Its 3-Substituted Analogues
摘要:我们开发了一种利用cucl和n-Methyl-2-Pyrrolidone通过卤素-卤素交换反应从5-Bromoindole及其衍生物合成5-Chloroindole及其3取代类似物的一锅法大规模合成方法,获得了非常好的产率.
DOI:10.5012/jkcs.2011.55.2.240

海关参考信息

2903919090-氯苯
2912110000-甲醛
💡 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-8178559-B2
优先权日:2004-12-30
标题:Organic compounds
发明人：BREITENSTEIN WERNER; EHARA TAKERU; EHRHARDT CLAUS; GROSCHE PHILIPP; HITOMI YUKO; IWAKI YUKI; KANAZAWA TAKANORI; KONISHI KAZUHIDE; MAIBAUM JUERGEN KLAUS; MASUYA KEIICHI; IWASAKI ATSUKO; OSTERMANN NILS; SUZUKI MASAKI; TOYAO ATSUSHI; YOKOKAWA FUMIAKI
权利人:BREITENSTEIN WERNER; EHARA TAKERU; EHRHARDT CLAUS; GROSCHE PHILIPP; HITOMI YUKO; IWAKI YUKI; KANAZAWA TAKANORI; KONISHI KAZUHIDE; MAIBAUM JUERGEN KLAUS; MASUYA KEIICHI; IWASAKI ATSUKO; OSTERMANN NILS; SUZUKI MASAKI; TOYAO ATSUSHI; YOKOKAWA FUMIAKI; NOVARTIS AG
摘要:3,4-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,4-substituted piperidine compound, and/or a method of treatment comprising administering a 3,4substituted piperidine compound, a method for the manufacture of a 3,4-substituted piperidine compound, and novel intermediates and partial steps for their synthesis are disclosed. The 3,4-disubstituted piperidine compounds have the formula (I), wherein the symbols have the meanings defined in the specification.