3469-69-0

Basic information

• Product Name: 4-Iodopyrazole
• Synonyms: 4-IODOPYRAZOLE;4-IODO-1H-PYRAZOLE;1H-PYRAZOLE, 4-IODO-;4-IODOPYRAZOLE 99%;4-Iodopyrazole ,98%;4-Lodophrazole;4-LODO PYRAZOLE;4-Iodopyrazole, 97+%
• CAS NO: 3469-69-0
• Molecular Formula: C₃H₃IN₂
• Molecular Weight: 193.97
• EINECS: 222-434-1
• Product Categories: Azoles;blocks;Iodides;Halides;Pyrazoles & Triazoles;Pyrazoles & Triazoles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks
• Mol File: 3469-69-0.mol

Chemical Properties

• Melting Point: 108-110 °C(lit.)
• Boiling Point: 291.886 °C at 760 mmHg
• Flash Point: 130.328 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 2.336 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 12.99±0.50(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Iodopyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodopyrazole(3469-69-0)
• EPA Substance Registry System: 4-Iodopyrazole(3469-69-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: UQ7145000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3469-69-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Iodopyrazole is used as a key intermediate in the synthesis of (pyrazolyl)oxobenzocycloheptapyridinyl acetamides, which are known to act as inhibitors of c-Met. These inhibitors have potential applications in the treatment of various diseases, including cancer, by targeting the c-Met receptor and modulating its activity.
Used in Organic Synthesis:
4-Iodopyrazole is also used in the indium-mediated synthesis of heterobiaryls, which are valuable building blocks in the preparation of pharmaceuticals, agrochemicals, and other organic compounds. The use of 4-Iodopyrazole in this process allows for the efficient and selective formation of heterobiaryl compounds, contributing to the advancement of organic synthesis and the development of new molecules with potential applications in various industries.

InChI:InChI=1/C3H3IN2/c4-3-1-5-6-2-3/h1-2H,(H,5,6)

Upstream product

• 288-13-1 NH-pyrazole 
• 28466-26-4 4-aminopyrazole 
• 2075-45-8 4-bromo-1H-pyrazole 

Downstream Products

• 98027-52-2 1-(4-iodo-1H-pyrazol-1-yl)ethanone 
• 116228-38-7 1-Benzoyl-4-jodpyrazol 
• 145243-92-1 4-iodo-1-(methoxymethyl)-1H-pyrazole 
• 116228-40-1 4-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole 
• 82099-88-5 4-iodo-1-(2,4,6-trimethylbenzoyl)pyrazole 
• 50877-42-4 1-benzyl-4-iodo-1H-pyrazole 
• 87844-46-0 1-hydroxy-4-iodopyrazole 
• 191980-54-8 4-iodo-1-(triphenylmethyl)-1H-pyrazole 
• 175474-15-4 4-(1H-pyrazol-4-yl)but-3-yn-1-ol 
• 266328-09-0 1-(2-fluoro-4-nitro-phenyl)-4-iodo-1H-pyrazole 
• 609342-49-6 Acetic acid (1S,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-iodo-pyrazol-1-ylmethoxy)-cyclohexyl ester 
• 313350-84-4 1-(4-tert-butyl-benzyl)-4-iodo-1H-pyrazole 
• 406234-86-4 1-(cyclohexylmethyl)-4-iodo-1H-pyrazole 
• 313350-82-2 4-iodo-N-isopropyl-1H-pyrazole 

Relevant articles and documents

4-Phosphopyrazol-2-yl alanine: A non-hydrolysable analogue of phosphohistidine

We report the synthesis of a stable analogue of τ-phosphohistidine: 4-phosphopyrazol-2-yl alanine (pPza). Polyclonal antibodies generated against the mimic show high reactivity and selectivity for τ-phosphohistidine, with minor or no cross-reactivity towards non-phosphorylated histidine or O-phosphoamino acids, including phosphotyrosine.

Improved synthesis of 1H-pyrazole-4-carbaldehyde

A simple and convenient two-step method for the synthesis of the title compound 1 was developed using N-protected 4-pyrazolilmagnesium bromide 9 as a key intermediate. Laborious procedures for purification or isolation of target compound are not required, therefore, up to 20g of 1 could be obtained in a single run.

Cytotoxic Ruthenium(II) Complexes of Pyrazolylbenzimidazole Ligands That Inhibit VEGFR2 Phosphorylation

Eight new ruthenium(II) complexes of N,N-chelating pyrazolylbenzimidazole ligands of the general formula [RuII(p-cym)(L)X]+ [where the ligand L is 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole (L1) substituted at the 4 position of the pyrazole ring by Cl (L2), Br (L3), or I (L4) and X = Cl- and I-] were synthesized and characterized using various analytical techniques. Complexes 1 and 3 were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups P21/n and P21/c, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) p-cymene complexes (2, 4, 6, and 8) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (1, 3, 5, and 7). The halido-substituted 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole ligands, designed as organic-directing molecules, inhibit vascular endothelial growth factor receptor 2 (VEGFR2) phosphorylation. In addition, the ruthenium(II) complexes display a potential to bind to DNA bases. The cytotoxicity profile of the complexes (IC50 ca. 9-12 μM for 4-8) against the triple-negative breast cancer cells (MDA-MB-231) show that most of the complexes are efficient. The lipophilicity and cellular accumulation data of the complexes show a good correlation with the cytotoxicity profile of 1-8. The representative complexes 3 and 7 demonstrate the capability of arresting the cell cycle in the G2/M phase and induce apoptosis. The inhibition of VEGFR2 phosphorylation with the representative ligands L2 and L4 and the corresponding metal complexes 3 and 7 in vitro shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, L2, L4, 3, and 7 inhibit the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) and proto-oncogene tyrosine-protein kinase (Src), capable of acting downstream of VEGFR2 as well as independently. Compounds L2, L4, 3, and 7 have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for L2 and 3 in the Tg(fli1:gfp) zebrafish model and found that L2 is more effective in vivo compared to 3 in inhibiting angiogenesis.

Cui-catalyzed coupling reactions of 4-iodopyrazoles and alcohols: Application toward withasomnine and Homologs

The direct 4-alkoxylation of 4-iodo-1H-pyrazoles with alcohols was achieved by a CuIcatalyzed coupling protocol. The optimal reaction conditions employed excess alcohol and potassium t-butoxide (2 equiv) in the presence of CuI (20 mol%) and 3,4,7,8-tetramethyl-1,10-phenanthroline (20 mol%) at 130 °C for 1 h under microwave irradiation. The present method was efficiently applied to the synthesis of withasomnine and its six- and seven-membered cyclic homologs.

Method for synthesizing 1 - methyl -4 -iodo pyrazole (by machine translation)

The invention relates to the technical field 1 - methyl -4 - iodinol synthesis, in particular to a synthesis method of 1 - methyl -4 - iodo pyrazole. The synthesis method of 1 - methyl -4 - iodinol comprises the following steps: (1) mixing 1 - methylpyrazole with iodine, heating to 40 - 80 °C, dropwise adding an oxidizing agent aqueous solution to carry out iodination reaction, and (2) adding alkali liquor to 5 - 9 DEG C to obtain a light yellow crystal, namely 1 - methyl -4 - iodo pyrazole. To 1 - methyl -4 - iodinol synthesis method, 1 - methylpyrazole raw materials are used as the iodinating agent, and an oxidizing agent, an oxidizing agent and hydrogen iodide are added to generate iodine, so that iodine is fully utilized, the reaction rate and product yield are improved, and the synthesis cost 1 - methyl -4 -iodo pyrazole is greatly reduced. (by machine translation)

PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR

This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.

Deprotonation of 4-ethynylpyrazolium salts

4-Ethynyl-1,2-dimethylpyrazolium salts were prepared by methylation of the corresponding 4-ethynyl-1-methylpyrazoles with trimethyloxonium tetrafluoroborate and were deprotonated to give the corresponding pyrazolium-4acetylenides, which are mesomeric betaines. These can be represented as alkynyl- or mesoionic allenylidene-type resonance forms. Calculations and spectroscopic investigations were performed to determine the contribution of each canonical form to the overall structure. Ylides and N-heterocyclic carbenes are tautomers of the betaines. Their relative stabilities have been compared.

Bivalent carbamates as novel control agents of the malaria mosquito, Anopheles gambiae

Widespread pyrethroid resistance has caused an urgent need to develop new insecticides for control of the malaria mosquito, Anopheles gambiae. Insecticide discovery efforts were directed towards the construction of bivalent inhibitors that occupy both the peripheral and catalytic sites of the mosquito acetylcholinesterase (AChE). It was hypothesized that this approach would yield a selective, high potency inhibitor that would also circumvent known catalytic site mutations (e.g. G119S) causing target site resistance. Accordingly, a series of bivalent phthalimide-pyrazole carbamates were prepared having an alkyl chain linker of varying length, along with other modifications. The most active compound was (1-(3-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-4-yl methylcarbamate, 8a), which has a chain length of three carbons, good mosquito anticholinesterase activity, and ca. 5-fold selectivity compared to human AChE. Moreover, this compound was toxic to mosquitoes by topical application (LD50 = 63 ng/female) with only 6-fold cross resistance in the Akron strain of Anopheles gambiae that showed 50- to 60-fold resistance to conventional carbamate insecticides. However, contact lethality in the WHO paper assay was disappointing. The implications of these results for design of new mosquitocides are discussed.

A 1-alkyl-pyrazol-4-boronic acid frequency method for the synthesis of ester

The invention belongs to the field of organic chemical synthesis and provides a synthetic method of 1-alkylpyrazole-4-boronic acid pinacol ester. The synthetic method comprises the following three steps: 1. reacting pyrazole with iodine and hydrogen peroxide to generate 4-iodopyrazole A; 2. reacting the 4-iodopyrazole with alkyl halide to obtain an intermediate B; 3. preparing a Grignard reagent of the raw material by using 1-alkyl-4-iodopyrazole as a raw material and adopting an isopropyl Grignard reagent exchange method at 0-30 DEG C, with BE001 as a boron reagent, and reacting to obtain the final product. The technological method is accessible in raw materials, simple and convenient to operate and lower in cost and is a proper method for preparing 1-alkylpyrazole-4-boronic acid pinacol ester compounds.

Mild regioselective iodination of pyrazoles using n-butyltriphenylphosphonium peroxodisulfate

A practical, efficient and inexpensive method of synthesis of iodopyrazoles by the reaction of pyrazoles with iodine using n-butyltriphenylphosphonium peroxodisulfate as an oxidant at room temperature is reported. The use of n-butyltriphenylphosphonium peroxodisulfate is feasible due to its easy preparation and handling, high stability and activity.