2-Iodoaniline
(Synonyms: 2-Iodophenylamine) 目录号 : GC681942-Iodoaniline (2-Iodophenylamine) 是一种苯胺衍生物，具有潜在的肝毒性和肾毒性活性。
Cas No.:615-43-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Iodoaniline (2-Iodophenylamine) is an aniline derivative, and has potential hepatotoxic and nephrotoxic activity[1].
2-Iodoaniline (1.0 mM/kg, 1.25 mM/kg for 2.5 mL; i.p.; single dose) exhibits hepatotoxic and nephrotoxic potential in Male Fischer 344 rats[1].
| Animal Model: | Male Fischer 344 rats (185-260 g)[1] |
| Dosage: | 1.0 mM/kg, 1.25 mM/kg for 2.5 mL |
| Administration: | Intraperitoneal injection; single dose; monitored renal and hepatic function 24 h after treatment |
| Result: | Induced oliguria, diminished kidney weight, tubular casts and decreased renal cortical slice accumulation of organic anions. Elevated plasma ALT/GPT activity and altered morphology in the centrilobular region. |
[1]. Valentovic MA, et al. Acute renal and hepatic toxicity of 2-haloanilines in Fischer 344 rats. Toxicology. 1992 Nov 1;75(2):121-31.
| Cas No. | 615-43-0 | SDF | Download SDF |
| 别名 | 2-Iodophenylamine | ||
| 分子式 | C6H6IN | 分子量 | 219.02 |
| 溶解度 | DMSO : 100 mg/mL (456.58 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.5658 mL | 22.829 mL | 45.6579 mL |
| 5 mM | 0.9132 mL | 4.5658 mL | 9.1316 mL |
| 10 mM | 0.4566 mL | 2.2829 mL | 4.5658 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(ii) cascade catalysis of 2-Iodoaniline/phenols
Chem Commun (Camb) 2016 Jul 5;52(56):8703-6.PMID:27331350DOI:10.1039/c6cc04554e.
A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(i)/Pd(0)/Cu(ii) catalysis. 2-Iodoanilines and phenols undergo a Cu(i)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(ii)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
Syntheses and Structures of the Complexes cis-[M(C(6)F(5))(2)(N&arcraise;X)] (M = Pd, Pt; N&arcraise;X = 2-Iodoaniline, 2-Benzoylpyridine) Containing N&arcraise;X Acting as a Didentate Chelating Ligand and Displaying I-->M or O-->M Interactions
Inorg Chem 1996 Jan 3;35(1):56-62.PMID:11666164DOI:10.1021/ic950283+.
Complexes cis-[M(C(6)F(5))(2)(THF)(2)] (M = Pd, Pt) are weak Lewis acids and react with the halocarbon ligand 2-Iodoaniline (R-I) yielding the corresponding cis-[M(C(6)F(5))(2)(R-I)] [M = Pd (1), Pt (2)]. In these complexes a (C-)I-M bond is present. The use of other 2-haloanilines (halogen = F, Cl, Br) does not yield the analogous complexes because of the lesser nucleophilic character of the halogen involved. The presence of the (C-)I-Pt bond in 2 has been confirmed by an X-ray structure determination, which also reveals an N-H.M hydrogen bond between two neutral molecules. Complex 2 crystallizes in the space group P&onemacr;: Z = 4; a = 11.797(4) Å; b = 13.735(4) Å; c = 14.107(4) Å; alpha = 97.24(2) degrees; beta = 90.91(2) degrees; gamma = 99.44(2) degrees; V = 2235(2) Å(3). Similarly, complexes cis-[M(C(6)X(5))(2)(THF)(2)] (M = Pd, Pt; X = F, Cl) react with the ligand 2-benzoylpyridine {R-C(O)Ph}, in which the oxygen atom of the ketonic group can behave as a nucleophilic center, yielding the complexes cis-[M(C(6)X(5))(2){R-C(O)Ph}] [M = Pd, X = F (3); M = Pt, X = F (4), Cl (5)]. Complex 3 crystallizes in the space group C2/c: Z = 16; a = 26.284(3) Å; b = 10.623(1) Å; c = 31.423(4) Å; beta = 93.15(1) degrees; V = 8760(2) Å(3). The I-M or O-M bonds in complexes 1-5 are weak and can be easily broken by the addition of neutral (CO, PPh(3), and CH(3)CN) or anionic (Br(-)) ligands.
Synthesis of 2-aryl-3-trifluoromethylquinolines using (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane
J Org Chem 2013 Jun 21;78(12):6196-201.PMID:23705690DOI:10.1021/jo400859s.
The Hiyama cross-coupling reaction of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane (1) with 2-Iodoaniline (2) proceeded without any protection of the amino group. The coordination of copper(II) fluoride to 2,2'-bipyridyl provided the fluoride source required to trigger this reaction, affording (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline (3). In the presence of a stoichiometric amount of [Cu(OTf)]2·C6H6, the treatment of 3 with an aryl aldehyde at 200 °C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.
Formation of Protonated ortho-Quinonimide from ortho-Iodoaniline in the Gas Phase by a Molecular-Oxygen-Mediated, ortho-Isomer-Specific Fragmentation Mechanism
J Am Soc Mass Spectrom 2020 Apr 1;31(4):864-872.PMID:32233379DOI:10.1021/jasms.9b00108.
Upon collisional activation under mass spectrometric conditions, protonated 2-, 3-, and 4-iodoanilines lose an iodine radical to generate primarily dehydroanilinium radical cations (m/z 93), which are the distonic counterparts of the conventional molecular ion of aniline. When briefly accumulated in the Trap region of a Triwave cell in a SYNAPT G2 instrument, before being released for ion-mobility separation, these dehydroanilinium cations react readily with traces of oxygen present in the mobility gas to form peroxyl radical cations. Although all three isomeric dehydroanilinium ions showed avid affinity for O2, their reactivities were distinctly different. For example, the product-ion spectra recorded from mass-selected m/z 93 ion from 3- and 4-iodoanilines showed a peak at m/z 125 for the respective peroxylbenzenaminium ion. In contrast, an analogous peak at m/z 125 was absent in the spectrum of the 2-dehydroanilinium ion generated from 2-Iodoaniline. Evidently, the 2-peroxylbenzenaminium ion generated from the 2-dehydroanilinium ion immediately loses a •OH to form protonated ortho-quinonimide (m/z 108).
Dissecting the Electronic Contribution to the Regioselectivity of the Larock Heteroannulation Reaction in the Oxidative Addition and Carbopalladation Steps
J Org Chem 2022 Jan 21;87(2):1218-1229.PMID:34989564DOI:10.1021/acs.joc.1c02560.
Substituted 2-Iodoaniline derivatives were prepared and utilized as reactants, along with asymmetric diarylacetylenes, to synthesize a series of 6-substituted-2,3-diarylindole derivatives via the Larock heteroannulation reaction. Electron-donating substituents on the 2-Iodoaniline derivatives retarded the reaction, while electron-withdrawing substituents provided a complete conversion to the indole products. In addition, the electronic properties of the substituted 2-Iodoaniline reactants displayed no influence toward regioselectivity. On the contrary, the electronic effect from unsymmetrical diarylacetylenes significantly influenced the regiochemical outcome of the reaction. Density functional theory calculations of the oxidative addition and carbopalladation steps revealed the electronic influences of the substituted 2-Iodoaniline derivatives toward the overall rate of the reaction. In contrast, the electronic properties of the asymmetric diarylacetylene remained the critical product-determining factor of regioselectivity.