155906-13-1

Basic information

• Product Name: 2,5-Difluoro-4-iodoaniline
• Synonyms: 2,5-Difluoro-4-iodoaniline;2,5-Difluoro-4-iodo-phenylamine
• CAS NO: 155906-13-1
• Molecular Formula: C₆H₄F₂IN
• Molecular Weight: 255.0039364
• Mol File: 155906-13-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2,5-Difluoro-4-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Difluoro-4-iodoaniline(155906-13-1)
• EPA Substance Registry System: 2,5-Difluoro-4-iodoaniline(155906-13-1)

Safety Data

• Hazardous Substances Data: 155906-13-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Difluoro-4-iodoaniline is used as a building block for the preparation of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with improved properties and therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2,5-Difluoro-4-iodoaniline serves as a key intermediate in the synthesis of various agrochemicals. Its presence in these compounds can enhance their effectiveness in pest control and crop protection.
Used in Dye and Pigment Manufacturing:
2,5-Difluoro-4-iodoaniline is utilized as an intermediate in the manufacture of dyes and pigments. Its distinctive molecular structure imparts specific color characteristics and properties to the final products, making it a valuable component in this industry.
Organic Synthesis:
2,5-Difluoro-4-iodoaniline is widely used in organic synthesis for the preparation of a range of chemical compounds. Its versatility and reactivity make it a preferred choice for chemists working on the development of new organic molecules with diverse applications.

Upstream product

• 367-30-6 2,5-difluoroaniline 
• 112279-60-4 4-bromo-2,5-difluoroaniline 

Downstream Products

• 910487-20-6 N-(2,5-difluoro-4-iodophenyl)methanesulfonamide 
• 1415730-99-2 8-(3-phenyl[1,2,4]oxadiazol-5-yl)-1-oxa-2,8-diazaspiro[4.5]-dec-2-ene-3-carboxylic acid (2,5-difluoro-4-methylsulfanylphenyl)amide 
• 1415731-00-8 C₂₃H₂₁F₂N₅O₄S 
• 1415731-01-9 2,5-difluoro-4-(methylsulfanyl)phenylamine 
• 307306-10-1 2,5-difluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline 
• 320592-23-2 4-[5-(((p-chlorobenzoyl)oxy)methyl)-4-(benzyloxy)-2,5-dihydro-β-L-furan-2-yl]-2,5-difluoroaniline 

Relevant articles and documents

P -Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles

A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent yields is reported. The heart of the proposed method consists of conversion of a Me 3 Si-C≡C- moiety into a MeC(=O)- group in the presence of p -tolu ene sulfonic acid (p -TSA) passing a stage of ethynylaniline formation. The reaction is metal-free, proceeds under mild conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity.

General and efficient synthesis of polyfluorinated 2-aminotolans and 2-arylindoles

It was established here that cross-coupling of polyfluorinated 2-iodoanilines with arylacetylenes in MeCN in the presence catalytic amounts of Pd(PPh3)2Cl2, CuI and Et3N produces the corresponding 2-aminotolans although their yields are decreased from 98% to 40% with increasing fluorination of the substrates. It was shown that the 2-aminotolans with six or fewer fluorine atoms in their rings can be heterocyclised by heating in ethanol containing p-TSA to produce the corresponding polyfluorinated indoles. Cyclisation of tolans containing larger numbers of fluorine atoms in their rings proceeds most efficiently in the presence of KOH, resulting in 2-phenylindoles containing the current maximum of eight fluorine atoms.

Identification of new potent GPR119 agonists by combining virtual screening and combinatorial chemistry

Virtual screening in a huge collection of virtual combinatorial libraries has led to the identification of two new structural classes of GPR119 agonists with submicromolar in vitro potencies. Herein, we describe the virtual screening process involving feature trees fragment space searches followed by a 3D postprocessing step. The in silico findings were then filtered and prioritized, and finally, combinatorial libraries of target molecules were synthesized. Furthermore the so-called activity-anchor principle is introduced as an element to increase the chance to generate true hits. An activity anchor is a structural element expected to provide key contributions to a certain biological activity. Application of this technique has led to the discovery of two new GPR119-agonist hit series, one of which was further optimized to progress as a novel lead class.

Syntheses of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: 'Cytosine replacement' analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents

A group of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)2 and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)3H afforded the target 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.

Tolane derivatives, liquid crystal compositions containing the derivatives and liquid crystal display devices using the compositions

A tolane derivative, a liquid crystal composition containing the derivative, and a liquid crystal display device including the composition, in which the tolane derivative is represented by the following general formula: STR1 wherein R represents a straigh