CAS: 87-51-4; 3-Indoleacetic Acid

• 英文名称3-Indoleacetic Acid
• 中文名称3-吲哚乙酸(IAA)
• IUPAC名称indole-3-acetic acid
• 其它别名1H-Indole-3-acetic acid; Heteroauxin; 3-Indolylacetic acid
• CAS编号87-51-4
• MFCD编号:MFCD00005636
• EINECS号:201-748-2
• FDA UNII编号:6U1S09C61L
• 分子式:C10H9NO2
• 分子量:175.1836
• 产品CID: 1882854
• 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: SEOVTRFCIGRIMH-UHFFFAOYSA-N
• InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)…
• 计算化学: 氢键受体数1.0氢键供体数2.0可旋转键数2.0

物理性质

• 熔点165-169°C
• 沸点415°C at 760 mmHg
• 闪点171°C
• 密度620kg/m3
• pKa:4.75(at 25°C)
• PSA:53.09
• LogP:1.795
• 折射率1.5460 (估算)
• 蒸汽压1.24E-07 mmHg at 25 °C
• 溶解性DMSO:30.0(Max Conc. mg/mL);171.25(Max Conc. Mm)
• 敏感性光敏感
• 外观形态类白色至棕褐色结晶
• 储存条件-20°C
• 产品应用用作植物生长刺激素及分析试剂.3-吲哚乙酸以及3-吲哚乙醛,3-吲哚乙腈,抗坏血酸等茁长素类物质在自然界天然存在,3-吲哚乙酸在植物体内生物合成的前体是色氨酸.茁长素的基本作用在于调节植物的生长,不仅能促进生长,而且具有抑制生长和器官建成的作用.茁长素在植物细胞内不仅以游离状态存在,还可以与生物高分子等牢固结合的束缚型茁长素存在,也有与特殊物质形成结合物的茁长素,例如吲哚乙酰基天门冬酰胺,吲哚乙酸阿戊糖和吲哚乙酰葡萄糖等.这可能是茁长素在细胞内的一种贮藏方式,也是解除过剩茁长素毒害的解毒方式.
• 性质描述白色结晶性粉末.易溶于丙酮和乙醚,微溶于氯仿,不溶于水.

MSDS等安全信息

• GHS象形图
• GHS符号GHS07;
  注释: Exclamation mark
• 危险类别急性毒性 类别4(经口)
  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H302 |吞咽有害.
  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.
  H336 |可能引起嗜睡或头晕.
• 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
• 风险等级Irritant
• 安全声明22-24/25
• 危险类别码36/37/38
• WGK Germany3.0

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 Indole-3-Acetic Acid 主要起始原料 Tryptophol
• 54-12-6 = 87-51-4 + 879-37-8
  反应条件:1.1 Reagents: Sulfur Solvents: Pyridine
  标题:Oxidative Degradation Of A-Substituted Carboxylic Acids
  作者:Feichtinger,Hans
  参考文献:Chemische Berichte 日期:1962 卷标:95 页码:2238-42]
  
  1912-33-0 = 87-51-4
  反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
  标题:Efficient Synthesis Of The Peptide Fragment Of The Natural Depsipeptides Jaspamide And Chondramide
  作者:Zarezin,Danil P.; Et Al
  参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(34) 页码:4716-4722]
  
  879-37-8 = 87-51-4
  反应条件:1.1 Solvents: Water
  标题:Preparation Of 3-Indoleacetic Acid; New Synthesis Of Tryptophol
  作者:Snyder,H. R.; Et Al
  参考文献:Journal Of The American Chemical Society 日期:1948 卷标:70 页码:3770-1]
  
  879-37-8 = 87-51-4
  反应条件:1.1 Reagents: L-Tryptophan Catalysts: Indole-3-Acetic Acid Synthetase Solvents: Water; 6 H,Ph 8,37 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
  标题:Tryptophan-Dependent Indole-3-Acetic Acid Biosynthesis By 'Iaa-Synthase' Proceeds Via Indole-3-Acetamide
  作者:Pollmann,Stephan; Et Al
  参考文献:Phytochemistry (Elsevier) 日期:2009 卷标:70(4) 页码:523-531]
  
  120-72-9 + 79-14-1 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide,Hydrochloric Acid Solvents: Water
  标题:Indole-3-Acetic Acid
  作者:Johnson,Herbert E.; Et Al
  参考文献:Organic Syntheses 日期:1964 卷标:44 页码:64-6]
  
  120-72-9 + 79-14-1 = 87-51-4
  反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water
  标题:3-Indoleacetic Acid
  作者:Johnson,Herbert E.; Et Al
  参考文献:Journal Of Organic Chemistry 日期:1963 卷标:28 页码:1246-8]
  
  526-55-6 = 87-51-4
  反应条件:1.1 Reagents: Sodium Tert-Butoxide,1-Hydroxycyclohexyl Phenyl Ketone Solvents: Dichloromethane,Water; Rt1.2 Solvents: Water; Acidified,Rt
  标题:Oxidation Of Primary Alcohols And Aldehydes To Carboxylic Acids With 1-Hydroxycyclohexyl Phenyl Ketone
  作者:Lu,Yi; Et Al
  参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(13) 页码:8114-8122]
  
  526-55-6 = 87-51-4
  反应条件:1.1 Reagents: 1-Hydroxycyclohexyl Phenyl Ketone,Sodium Hydroxide Solvents: 1,2-Dimethoxyethane; 80 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Neutralized
  标题:Oxidation Of Primary Alcohols And Aldehydes To Carboxylic Acids Via Hydrogen Atom Transfer
  作者:Tan,Wen-Yun; Et Al
  参考文献:Organic Letters 日期:2021 卷标:23(17) 页码:6648-6653]
  
  2591-98-2 = 87-51-4
  反应条件:1.1 Catalysts: Aldehyde Dehydrogenase
  标题:Isolation And Total Synthesis Of Stolonines A-C,Unique Taurine Amides From The Australian Marine Tunicate Cnemidocarpa Stolonifera
  作者:Tran,Trong D.; Et Al
  参考文献:Marine Drugs 日期:2015 卷标:13(7) 页码:4556-4575]
  
  62485-98-7 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 18 H,90 °C; 90 °C -> 0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 1
  标题:Regioselective Hydroarylation Reactions Of C3 Electrophilic N-Acetylindoles Activated By Fecl3. An Entry To 3-(Hetero)Arylindolines
  作者:Beaud,Rodolphe; Et Al
  参考文献:Chemistry - A European Journal 日期:2014 卷标:20(24) 页码:7492-7500]
  
  771-51-7 = 87-51-4 [标题:Reaction Conditions
  标题:The Preparation Of Heteroauxin And Tryptamine
  作者:Thesing,Jan; Et Al
  参考文献:Chemische Berichte 日期:1952 卷标:85 页码:324-7]
  
  392-12-1 = 87-51-4
  反应条件:1.1 Reagents: Sodium Peroxoborate Solvents: Water
  标题:Oxidative Decarbonylation Of β-Arylpyruvic Acids Using Sodium Perborate
  作者:Morrow,Nicholas; Et Al
  参考文献:Tetrahedron 日期:1998 卷标:54(33) 页码:9603-9612]
  
  392-12-1 = 87-51-4 [标题:Reaction Conditions
  标题:Cell Kinetics Of Auxin Transport And Activity In Arabidopsis Root Growth And Skewing
  作者:Hu,Yangjie; Et Al
  参考文献:Nature Communications 日期:2021 卷标:12(1)]
  
  31529-27-8 = 87-51-4 [标题:Reaction Conditions
  标题:Action Of Aromatic Diazo Compounds On Compounds Of The Type Of Alkylacetoacetic Esters As A Method Of Preparation Of Arylhydrazones Of α-Keto Acids,α-Amino Acids,And Nitrogenous Heterocyclic Compounds. Xiv. Synthesis Of (2-Carboxy-3-Indolyl)Acetic Acids Substituted In The Benzene Ring And Of The Corresponding 3-Indolylacetic Acids
  作者:Feofilaktov,V. V.; Et Al
  参考文献:Zhurnal Obshchei Khimii 日期:1953 卷标:23 页码:644-56]
  
  73-22-3 = 87-51-4 + 120-72-9 + 771-50-6 + 771-51-7 + 487-89-8 + 879-37-8 + 75833-70-4 + 103986-22-7
  反应条件:1.1 Reagents: Oxygen Solvents: Water; 20 Min,Ph 7.8,37 °C1.2 Reagents: Hydrochloric Acid Solvents: Water
  标题:Production Of Indole-3-Acetic Acid And Related Indole Derivatives From L-Tryptophan By Rubrivivax Benzoatilyticus Ja2
  作者:Mujahid,Md.; Et Al
  参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:89(4) 页码:1001-1008]
  
  157496-76-9 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol,Water
  标题:An Expedient Route To Indole-3-Acetic Acid Derivatives
  作者:Samizu,Kiyohiro; Et Al
  参考文献:Synlett 日期:1994 卷标:(7) 页码:499-500]
  
  879-37-8 = 87-51-4
  反应条件:1.1 Catalysts: Indole-3-Acetamide Hydrolase
  标题:Versatile And Facile One-Pot Biosynthesis For Amides And Carboxylic Acids In E. Coli By Engineering Auxin Pathways Of Plant Microbiomes
  作者:Menon,Navya; Et Al
  参考文献:Acs Catalysis 日期:2022 卷标:12(4) 页码:2309-2319]
  
  120-72-9 + 79-14-1 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Water; 8 H,250 - 275 °C1.2 Solvents: Water; Cooled1.3 Reagents: Hydrochloric Acid Solvents: Water; 28 H,20 °C -> 5 °C
  标题:3-Indolealkanoic Acids
  参考文献:United States]
  
  2591-98-2 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide,Silver Nitrate Solvents: Water; 5 Min,Rt1.2 1 H,60 °C; 60 °C -> Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Acidified
  标题:Synthesis,Structural Characterization,And Antimicrobial Activity Of Novel Ferrocene-N-Acyl Hydrazones Designed By Means Of Molecular Simplification Strategy Celebrating The 100Th Anniversary Of The Birth Of Professor Paulo Freire
  作者:Dos Santos Filho,Jose Mauricio; Et Al
  参考文献:Journal Of Organometallic Chemistry 日期:2022 卷标:979]
  
  62485-98-7 = 87-51-4
  反应条件:1.1 Solvents: Water
  标题:Syntheses Of Heteroauxin,Tryptamine,And Serotonin
  作者:Nenitzescu,Costin D.; Et Al
  参考文献:Chemische Berichte 日期:1958 卷标:91 页码:1141-5]
  
  120-72-9 + 132035-18-8 = 87-51-4
  反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Tetralin
  标题:Solid-Liquid Phase Transfer Catalytic Carboxymethylation - Synthesis Of 3-Indoleacetic Acid (Iaa)
  作者:Cai,Yuzhen; Et Al
  参考文献:Jinan Daxue Xuebao 日期:1990 卷标:11(1) 页码:52-5]
  
  771-51-7 = 87-51-4
  反应条件:1.1 Solvents: Water
  标题:Syntheses With Mannich Bases Of Indole
  作者:Thesing,Jan; Et Al
  参考文献:Chemische Berichte 日期:1955 卷标:88 页码:1295-1306]
  
  771-51-7 = 87-51-4 [标题:Reaction Conditions
  标题:Tetraethylene Glycol Promoted Two-Step,One-Pot Rapid Synthesis Of Indole-3-[1-11C]Acetic Acid
  作者:Lee,Sojeong; Et Al
  参考文献:Tetrahedron Letters 日期:2015 卷标:56(3) 页码:517-520]
  
  1477-49-2 = 87-51-4
  反应条件:1.1 Reagents: Tosylhydrazine Solvents: Methanol1.2 Reagents: Sodium Borohydride Solvents: Tetrahydrofuran
  标题:A Convenient Method For The Synthesis Of Indole-3-Acetic Acids
  作者:Guan,Xiangming; Et Al
  参考文献:Tetrahedron Letters 日期:1994 卷标:35(19) 页码:3013-16

海关参考信息

• 2902200000-苯
  2912110000-甲醛
  2912120000-乙醛
  2915110000-甲酸
• 💡 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

其他信息查阅

• ➥ 象形图和危险代码
• ➥ 防范代码详解
• ➥ 危险代码说明
• ➥ Globally Harmonized System
• ➥ REACH监管