540-37-4 Usage
Description
4-Iodoaniline, an iodine-substituted aniline, is a beige to greyish-brown crystalline powder known for its potent methemoglobin-forming properties. It is soluble in alcohol, ether, and chloroform, and slightly soluble in water. 4-Iodoaniline has a wide range of applications across various industries due to its unique chemical properties.
Uses
Used in Chemical Synthesis:
4-Iodoaniline is used as a chemical intermediate for the manufacturing of pesticides, dyes, and drugs. Its iodine substitution makes it a versatile compound in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
4-Iodoaniline is utilized in the development of drugs, taking advantage of its reactivity and potential for chemical modifications. It has been shown to be a more potent nephrotoxicant in vitro than other anilines, which may have implications for drug design and safety assessments.
Used in Dye Manufacturing:
In the dye industry, 4-Iodoaniline is used as a chemical intermediate to produce a variety of dyes with specific color properties. Its unique structure allows for the creation of dyes with desired characteristics.
Used in Pesticide Production:
4-Iodoaniline serves as a key intermediate in the synthesis of certain pesticides, contributing to the development of effective and targeted pest control solutions.
Used in Material Science:
4-Iodoaniline has been used to prepare phenyl-functionalized graphene oxide (I-Ph-GO), which has potential applications in material science, particularly in the development of advanced materials with enhanced properties.
Used in Suzuki Reaction:
The Suzuki reaction, a widely used method for the formation of carbon-carbon bonds, often involves 4-Iodoaniline as a reactant. This reaction is crucial in the synthesis of complex organic molecules and contributes to the development of new compounds with various applications.
Used in the Preparation of Star Polybenzamides:
Palladium-catalyzed carbonylation of 4-Iodoaniline results in the formation of four-armed star polybenzamides, which have potential applications in various fields due to their unique structure and properties.
Preparation
4-Iodoaniline is obtained by the reaction of aniline and iodine in the presence of sodium bicarbonate. Add aniline and sodium bicarbonate to water and slowly add crushed iodine in stages with vigorous stirring. If the reaction solution is yellow, add a little sodium bisulfite to make it discolor, then filter and get the crude product. Then the product is recrystallized by ethanol to obtain 4-Iodoaniline.
Purification Methods
Crystallise it from pet ether (b 60-80o) by refluxing, then cool it in an ice-salt bath freezing mixture. Dry it in air. Alternatively, crystallise it from EtOH and dry it in vacuo for 6hours at 40o [Edidin et al. J Am Chem Soc 109 3945 1987]. The N-acetyl derivative has m 184o (from MeOH). [Beilstein 12 IV 1544.]
Check Digit Verification of cas no
The CAS Registry Mumber 540-37-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 0 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 540-37:
(5*5)+(4*4)+(3*0)+(2*3)+(1*7)=54
54 % 10 = 4
So 540-37-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H6IN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
540-37-4Relevant articles and documents
A facile reduction procedure for nitroarenes with Cp2TiCl2/Sm system
Huang, You,Liao, Puhong,Zhang, Yongmin,Wang, Yulu
, p. 1059 - 1063 (1997)
Nitroarenes can be reduced to the corresponding primary amines in good yields with Cp2TiCl2/Sm system under mild and neutral conditions.
Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water
Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao
, p. 299 - 306 (2021/05/10)
An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]
In situcreation of multi-metallic species inside porous silicate materials with tunable catalytic properties
Liu, Yang-Yang,Wu, Chuan-De,Zhan, Guo-Peng
supporting information, p. 6185 - 6188 (2021/06/30)
Porous metal silicate (PMS) material PMS-11, consisting of uniformly distributed multi-metallic species inside the pores, is synthesized by using a discrete multi-metal coordination complex as the template, demonstrating high catalytic activity and selectivity in hydrogenation of halogenated nitrobenzenes by synergistically activating different reactant moleculesviaNi and Co transition metal centers, while GdIIILewis acid sites play a role in tuning the catalytic properties.