CAS: 83-34-1; 3-Methyl-1H-Indole

• 英文名称3-Methyl-1H-Indole
• 中文名称3-甲基吲哚
• IUPAC名称3-methyl-1H-indole
• 其它别名粪臭素; 3-甲基吲哚; 3甲基吲哚; 3-Methylindole; 3-Methyl-1H-Indole
• CAS编号83-34-1
• MFCD编号:MFCD00005627
• EINECS号:201-471-7
• FDA UNII编号:9W945B5H7R
• 分子式:C9H9N
• 分子量:131.17
• 产品CID: 1822442
• 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
• InChIKey: ZFRKQXVRDFCRJG-UHFFFAOYSA-N
• InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3…
• 计算化学: 氢键受体数0.0氢键供体数1.0可旋转键数0.0

物理性质

• 熔点92-97°C
• 沸点265-266°C at 760 mmHg
• 闪点132°C
• 密度1.1±0.1 g/cm3
• pKa:17.30±0.30(预测)
• PSA:15.79
• LogP:2.47632
• 折射率1.655
• 蒸汽压0.0±0.5 mmHg at 25°C
• 溶解性可溶于氯仿(少许),甲醇(少许)
• 敏感性白色鳞片结晶。具有粪便的动物臭。浓时，令人作呕。稀释后具有茉莉花香。极度稀释后有成熟的水果的香味。天然存在于粪便、灵猫香中。
• 外观形态白色或略棕色片
• 储存条件2-8°C
• 产品应用3-甲基吲哚具有令人不愉快的粪臭味,但经大量稀释后有愉快的香味,特别具有灵猫香基的香韵,在干酪,坚果,葡萄等制品中加入少量就有效果,在海味香精中加入,可具鱼肉味.
• 性质描述白色片状结晶.熔点为95°C,沸点为265-266°C(100.7kPa).溶于乙醇和油中,微溶于水.

MSDS等安全信息

• GHS象形图
• GHS符号GHS07 & GHS09;
  注释: Exclamation mark & Environment
• 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
  水生慢性毒性 类别2
  急性毒性 类别4(吸入)
  急性毒性 类别4(经皮)
  急性毒性 类别4(经口)
  皮肤致敏 类别1
  水生急性毒性 类别1
  特定目标器官毒性-单次接触 类别1
  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.
  H411 |对水生生物有毒并具有长期持续影响.
  H332 |吸入有害.
  H312 |皮肤接触有害.
  H302 |吞咽有害.
  H317 |可能引起皮肤过敏反应.
  H400 |对水生生物毒性极大.
  H370 |损害器官.
• 防范说明P273-P391-P501
• 危险等级9
• UN编号3077.0
• 危险品标志Xi:Irritant
• 包装等级Ⅲ
• 安全声明S26-S36
• 危险类别码R36/37/38
• WGK Germany2

欧盟法规

上下游产品

合成工艺路线路线简述

• 合成目标产物 3-Methylindole 主要起始原料 Indole-3-Carboxaldehyde
• 23543-66-0 = 83-34-1
  反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile
  标题:Dbu,A Highly Efficient Reagent For The Facile Regeneration Of (Hetero)Arylamines From Their Acetamides And Benzamides: Influence Of Solvent,Temperature,And Microwave Irradiation
  作者:Chakrabarty,Manas; Et Al
  参考文献:Synthetic Communications 日期:2002 卷标:32(2) 页码:265-272]
  
  3867-18-3 = 83-34-1
  反应条件:1.1 Reagents: Hydrogen Catalysts: Triphenylphosphine,Dicarbonylrhodium Acetylacetonate Solvents: Toluene; 30 Bar,60 °C
  标题:Interrupted Intramolecular Hydroaminomethylation Of N-Protected-2-Vinyl Anilines: Novel Access To 3-Substitued Indoles Or Indoline-2-Ols
  作者:Hochberger-Roa,Frank; Et Al
  参考文献:Molecules 日期:2022 卷标:27(3)]
  
  52562-19-3 = 83-34-1
  反应条件:1.1 Reagents: Bis(Trifluoroacetoxy)Iodobenzene Solvents: Tetrahydrofuran; 5 Min,Rt
  标题:Synthesis Of Indoles From O-Haloanilines
  作者:Chebieb,Assia; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(14) 页码:10164-10170]
  
  120-72-9 = 83-34-1
  反应条件:1.1 Reagents: Cesium Carbonate Catalysts: 2885997-69-1 Solvents: Methanol; 24 H,110 °C
  标题:α-Methylation Of Ketones And Indoles Catalyzed By A Manganese(I) Pcnhcp Pincer Complex With Methanol As A C1 Source
  作者:Thenarukandiyil,Ranjeesh; Et Al
  参考文献:Organometallics 日期:2023 卷标:42(1) 页码:62-71]
  
  289621-37-0 = 83-34-1
  反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran,Hexane; -78 °C; 2 H,40 - 45 °C; 45 °C -> Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt
  标题:An Efficient Procedure For The Deprotection Of N-Pivaloylindoles,Carbazoles And β-Carbolines With Lda
  作者:Avendano,Carmen; Et Al
  参考文献:Synlett 日期:2005 卷标:(1) 页码:107-110]
  
  4375-15-9 = 83-34-1
  反应条件:1.1 Catalysts: Chloro[2-[1-[(4-Methoxyphenyl)Imino-Kn]Ethyl]-5-[(1-Pyrenylsulfonyl)Oxy]Phenyl-K... (Immobilized On Multiwalled Carbon Nanotubes) Solvents: 2,2,2-Trifluoroethanol,Water; 12 H,100 °C
  标题:Immobilization Of Cyclometalated Iridium Complex Onto Multiwalled Carbon Nanotubes For Dehydrogenation Of Indolines In Aqueous Solution
  作者:Liu,Huan; Et Al
  参考文献:Industrial & Engineering Chemistry Research 日期:2017 卷标:56(40) 页码:11413-11421]
  
  487-89-8 = 83-34-1
  反应条件:1.1 Reagents: Potassium Hydroxide Catalysts: Bis(Dichloro(η6-P-Cymene)Ruthenium) Solvents: Ethanol; 24 H,100 °C
  标题:Ruthenium-Catalyzed Regioselective Synthesis Of C3-Alkylated Indoles Following Transfer Hydrogenation Or Borrowing Hydrogen Strategy
  作者:Chen,Xia; Et Al
  参考文献:Synthesis 日期:2023 卷标:55(9) 页码:1460-1466]
  
  487-89-8 = 83-34-1
  反应条件:1.1 Reagents: Hydrazine Hydrate (1:1) Catalysts: Palladium Solvents: Ethanol,Water; Rt; 24 H,100 °C
  标题:Recyclable Pd/c Catalyzed One-Step Reduction Of Carbonyls To Hydrocarbons Under Simple Conditions Without Extra Base
  作者:Zhou,Xiao-Yu; Et Al
  参考文献:Tetrahedron Letters 日期:2020 卷标:61(5)]
  
  73396-87-9 = 83-34-1
  反应条件:1.1 Reagents: Sodium Carbonate,Tetrabutylammonium Bromide Catalysts: Palladium Diacetate Solvents: Dimethylformamide
  标题:The Intramolecular Heck Reaction
  作者:Link,J. T.
  参考文献:Organic Reactions (Hoboken 日期:2002 卷标:60]
  
  59-88-1 = 83-34-1
  反应条件:1.1 Reagents: Acetic Acid; 30 Min,50 °C1.2 3 H,120 °C
  标题:Visible Light-Induced Benzylic C(Sp3)-C(Sp2) Defluorinative Coupling Between Indole Derivatives And Polyfluoroarenes
  作者:Li,Yan; Et Al
  参考文献:Advanced Synthesis & Catalysis 日期:2023 卷标:365(19) 页码:3284-3289]
  
  36797-43-0 = 83-34-1
  反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylacetamide; Rt; 6 H,60 °C1.2 Reagents: Ammonium Chloride Solvents: Water
  标题:Divergent Synthesis Of 2-Methylthioindole And 2-Unsubstituted Indole Derivatives Mediated By Socl2 And Dimethyl/diethyl Sulfoxides
  作者:Zhang,Jingran; Et Al
  参考文献:Organic & Biomolecular Chemistry 日期:2022 卷标:20(40) 页码:7886-7890]
  
  36797-43-0 = 83-34-1
  反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylacetamide; 2 H,60 °C1.2 Reagents: Ammonium Chloride Solvents: Water
  标题:A Nah-Promoted N-Detosylation Reaction Of Diverse P-Toluenesulfonamides
  作者:Sun,Wanwan; Et Al
  参考文献:Tetrahedron Letters 日期:2020 卷标:61(43)]
  
  700-06-1 = 83-34-1
  反应条件:1.1 Reagents: Potassium Tert-Butoxide,Oxygen Catalysts: Iridium,Di-μ-Chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-Pentamethyl-2,4-Cyclopen... Solvents: Methanol; 17 H,140 °C
  标题:Iridium-Catalyzed Methylation Of Indoles And Pyrroles Using Methanol As Feedstock
  作者:Chen,Shu-Jie; Et Al
  参考文献:Rsc Advances 日期:2015 卷标:5(86) 页码:70329-70332]
  
  = 83-34-1
  反应条件:1.1 Catalysts: Nickel Solvents: Methanol
  标题:Desulfuration Of Some Sterically Hindered Thio Ethers With Raney Nickel
  作者:Pfaender,Peter; Et Al
  参考文献:Justus Liebigs Annalen Der Chemie 日期:1969 卷标:719 页码:119-26]
  
  23543-66-0 = 83-34-1 [标题:Reaction Conditions
  标题:Synthesis Of Mescaline,N-Methyl-,And N,N-Dimethylmescaline
  作者:Banholzer,K.; Et Al
  参考文献:Helvetica Chimica Acta 日期:1952 卷标:35 页码:1577-81]
  
  3867-18-3 = 83-34-1
  反应条件:1.1 Reagents: Hydrogen Catalysts: Rhodium(1+),[(1,2,5,6-η)-1,5-Cyclooctadiene][tetrakis(1-Methylethyl) 2,2′-[1,3-... Solvents: Tetrahydrofuran
  标题:Characterization And Application Of Catalytic Regioselective Hydroformylation With A Cationic Bis(Dioxaphospholane)Rhodium Catalyst Precursor
  作者:Kwok,Thomas J.; Et Al
  参考文献:Organometallics 日期:1993 卷标:12(5) 页码:1954-9]
  
  52562-19-3 = 83-34-1
  反应条件:1.1 Reagents: 1-Fluoro-1,3-Dihydro-3,3-Dimethyl-1,2-Benziodoxole Solvents: Acetonitrile; Rt
  标题:Fluorine As A Traceless Directing Group For The Regiodivergent Synthesis Of Indoles And Tryptophans
  作者:Andries-Ulmer,Anna; Et Al
  参考文献:Journal Of The American Chemical Society 日期:2018 卷标:140(40) 页码:13034-13041]
  
  52562-19-3 = 83-34-1
  反应条件:1.1 Reagents: Oxygen Catalysts: Oxindole,Ferric Bromide Solvents: Dimethylacetamide; 100 °C1.2 Reagents: Water; Cooled
  标题:Iron-Catalyzed Intramolecular C-H Amination For The Synthesis Of N-H Carbazoles And Indoles
  作者:Wang,Zheng-Lin; Et Al
  参考文献:Green Chemistry 日期:2023 卷标:25(11) 页码:4463-4468]
  
  120-72-9 = 83-34-1
  反应条件:1.1 Reagents: Cesium Carbonate Catalysts: Pentacarbonylchlororhenium,1,1′-[2-[(Diphenylphosphino)Methyl]-2-Methyl-1,3-Propanediyl]Bis[1,1-Diphenylpho...; 24 H,140 °C
  标题:Rhenium(I)-Catalyzed C-Methylation Of Ketones,Indoles,And Arylacetonitriles Using Methanol
  作者:Shee,Sujan; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(9) 页码:6943-6951]
  
  120-72-9 = 83-34-1
  反应条件:1.1 Reagents: Potassium Hydroxide Catalysts: (Oc-6-12)-Dichloro[4-[[(S)-Ethylthio-Ks]Methyl]Acridine-Kn](Triphenylphosphine)R... Solvents: Methanol; 18 H,135 °C
  标题:Ruthenium Pincer Complex Catalyzed Selective Synthesis Of C-3 Alkylated Indoles And Bisindolylmethanes Directly From Indoles And Alcohols
  作者:Biswas,Nandita; Et Al
  参考文献:Advanced Synthesis & Catalysis 日期:2020 卷标:362(14) 页码:2902-2910]
  
  289621-37-0 = 83-34-1
  反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 0 °C; 2 H,40 - 45 °C; Cooled1.2 Reagents: Ammonium Chloride Solvents: Water; Rt
  标题:A Systematic Study Of Two Complementary Protocols Allowing The General,Mild And Efficient Deprotection Of N-Pivaloylindoles
  作者:Ruiz,Miriam; Et Al
  参考文献:Tetrahedron 日期:2012 卷标:68(2) 页码:705-710]
  
  289621-37-0 = 83-34-1
  反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; 2 H,40 - 45 °C1.2 Reagents: Water
  标题:Deprotection Of N-Pivaloylindoles,Carbazoles And Beta-Carbolines With A Lithium Base
  作者:Sanchez,J. Domingo; Et Al
  参考文献:International Electronic Conferences On Synthetic Organic Chemistry 日期:2004 卷标:1 页码:1-5]
  
  4375-15-9 = 83-34-1
  反应条件:1.1 Catalysts: Tris(2,2′-Bipyridyl)Ruthenium(Ii) Chloride,Cobalt,Bis[[2,3-Butanedione Di(Oximato-Kn)](1-)]Chloro(Pyridine)-,(Oc-6-42)- Solvents: Ethanol; 24 H,30 °C
  标题:Acceptorless Dehydrogenation Of N-Heterocycles By Merging Visible-Light Photoredox Catalysis And Cobalt Catalysis
  作者:He,Ke-Han; Et Al
  参考文献:Angewandte Chemie 日期:2017 卷标:56(11) 页码:3080-3084]
  
  4375-15-9 = 83-34-1
  反应条件:1.1 Catalysts: 2,2,2-Trifluoroethanol,Chloro[4-Methoxy-2-[1-[(4-Methoxyphenyl)Imino-Kn]Ethyl]Phenyl-Kc][(1,2,3,4,5-η)-...; 20 H,Reflux
  标题:Acceptorless Dehydrogenation Of Nitrogen Heterocycles With A Versatile Iridium Catalyst
  作者:Wu,Jianjun; Et Al
  参考文献:Angewandte Chemie 日期:2013 卷标:52(27) 页码:6983-6987]
  
  73396-87-9 = 83-34-1
  反应条件:1.1 Reagents: Potassium Carbonate Catalysts: Triphenyl Phosphite,Dichlorobis(Tricyclohexylphosphine)Palladium Solvents: Dimethylformamide; 24 H,90 °C
  标题:Palladium-Catalyzed Synthesis Of Indoles Via Intramolecular Heck Reaction
  作者:Yang,Hailong; Et Al
  参考文献:Catalysis Communications 日期:2013 卷标:38 页码:21-25]
  
  73396-87-9 = 83-34-1
  反应条件:1.1 Reagents: Sodium Carbonate Catalysts: Tetrabutylammonium Chloride,Palladium Diacetate Solvents: Dimethylformamide; 24 H,25 °C
  标题:Palladium(Ii) Acetate
  作者:Grennberg,Helena; Et Al
  参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2015 卷标:1 页码:1-35]
  
  850331-85-0 = 83-34-1
  反应条件:1.1 Reagents: Cesium Carbonate,Cesium Formate Catalysts: Butanethiol,3,5-Bis(1,1-Dimethylethyl)[1,1′-Biphenyl]-4-Ol Solvents: Dimethylformamide; 3 H,Rt
  标题:Deprotection Of Benzyl-Derived Groups Via Photochemically Mesolytic Cleavage Of C-N And C-O Bonds
  作者:Liang,Kangjiang; Et Al
  参考文献:Chem 日期:2023 卷标:9(2) 页码:511-522]
  
  19365-61-8 + 551-93-9 = 83-34-1
  反应条件:1.1 Solvents: Dimethyl Sulfoxide,Tetrahydrofuran
  标题:Arsonium Ylides In The Synthesis Of Indoles
  作者:Bravo,Pierfrancesco; Et Al
  参考文献:Tetrahedron Letters 日期:1970 卷标:(52) 页码:4535-8]
  
  = 83-34-1 [标题:Reaction Conditions
  标题:The Transition Metal-Catalyzed N-Heterocyclization. The Rhodium-Catalyzed Synthesis Of Indoles
  作者:Watanabe,Yoshihisa; Et Al
  参考文献:Chemistry Letters 日期:1980 卷标:(5) 页码:603-4]
  
  = 83-34-1
  反应条件:1.1 2 H,40 °C1.2 Reagents: Aluminum Chloride Solvents: Water; Rt; Rt -> 120 °C; 0.5 H,120 °C
  标题:Synthesis Of 3-Methylindole And Its New Purification Method
  作者:Xu,Jianguo; Et Al
  参考文献:Huagong Shengchan Yu Jishu 日期:2005 卷标:12(4) 页码:12-14]
  
  59-88-1 = 83-34-1
  反应条件:1.1 Catalysts: 1H-Imidazolium,1-(4-Sulfobutyl)-3-[3-(Trihydroxysilyl)Propyl]-,4-Methylbenzene... (Silica Supported) Solvents: Ethanol; 4 H,Rt
  标题:Novel And Efficient Heterogeneous 4-Methylbenzenesulfonic Acid-Based Ionic Liquid Supported On Silica Gel For Greener Fischer Indole Synthesis
  作者:Hu,Yu-Lin; Et Al
  参考文献:Catalysis Letters 日期:2016 卷标:146(5) 页码:968-976]
  
  59-88-1 = 83-34-1
  反应条件:1.1 Solvents: Acetic Acid; 50 °C; 3 H,Reflux
  标题:Palladium-Catalyzed Dearomative Allylation Of Indoles With Cyclopropyl Acetylenes: Access To Indolenine Derivatives
  作者:Lu,Chuan-Jun; Et Al
  参考文献:Organic & Biomolecular Chemistry 日期:2021 卷标:19(3) 页码:635-644]
  
  14722-38-4 = 83-34-1
  反应条件:1.1 Reagents: Zinc Solvents: Acetic Acid,Water
  标题:Heterocyclic Compounds Of Nitrogen. Vii. Ring Contraction Of Some Cinnolines And Dihydrocinnolines
  作者:Besford,L. S.; Et Al
  参考文献:Journal Of The Chemical Society 日期:1964 卷标:4037 页码:4037-44]
  
  14722-38-4 = 83-34-1 [标题:Reaction Conditions
  标题:Product Class 13: Indole And Its Derivatives
  作者:Joule,J. A.
  参考文献:Science Of Synthesis 日期:2001 卷标:10 页码:361-652]
  
  36797-43-0 = 83-34-1
  反应条件:1.1 Reagents: Formic Acid,Diisopropylethylamine Catalysts: Iridium(1+),[4,4′-Bis(1,1-Dimethylethyl)-2,2′-Bipyridine-Kn1,Kn1′]Bis[2-(2-Pyri... Solvents: Acetonitrile; 24 H,Rt
  标题:Electron Transfer Photoredox Catalysis: Development Of A Photoactivated Reductive Desulfonylation Of An Aza-Heteroaromatic Ring
  作者:Qiang-Liu; Et Al
  参考文献:Advanced Synthesis & Catalysis 日期:2020 卷标:362(15) 页码:3110-3115]
  
  57502-99-5 = 83-34-1 [标题:Reaction Conditions
  标题:An Efficient Synthesis Of Indole
  作者:Ito,Yoshihiko; Et Al
  参考文献:Journal Of The American Chemical Society 日期:1977 卷标:99(10) 页码:3532-4]
  
  63212-32-8 = 83-34-1
  反应条件:1.1 Reagents: Piperidine,2,2,6,6-Tetramethyl-,Lithium Salt (1:1) Solvents: Diglyme
  标题:Lateral Lithiation Reactions Promoted By Heteroatomic Substituents
  作者:Clark,Robin D.; Et Al
  参考文献:Organic Reactions (Hoboken 日期:1995 卷标:47]
  
  700-06-1 = 83-34-1
  反应条件:1.1 Solvents: Diethyl Ether
  标题:Hydrogenolysis Of 3-(Hydroxymethyl)Indole And Other Indole Derivatives With Lithium Aluminum Hydride
  作者:Leete,Edward; Et Al
  参考文献:Canadian Journal Of Chemistry 日期:1953 卷标:31 页码:775-84

海关参考信息

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