121669-70-3

Basic information

• Product Name: tert-Butyl 4-iodopyrazole-1-carboxylate
• Synonyms: T-BUTYL 4-IODO-1H-PYRAZOLE-1-CARBOXYLATE;TERT-BUTYL 4-IODOPYRAZOLE-1-CARBOXYLATE;4-IODO-PYRAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-BOC-4-IODOPYRAZOLE;tert-Butyl-4-iodo-1H-pyrazole-1-carboxylate;t-Butyl4-iodopyrazole-1-carboxylate;3-tert-butyl-4-iodo-1H-pyrazole-1-carboxylate;1-Boc-3-Methyl-4-iodo-1H-pyrazole 1H-Pyrazole-1-carboxylic acid, 4-iodo-, 1,1-dimethylethyl ester
• CAS NO: 121669-70-3
• Molecular Formula: C₈H₁₁IN₂O₂
• Molecular Weight: 294.09
• Product Categories: Building Blocks;C7 to C8;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles
• Mol File: 121669-70-3.mol

Chemical Properties

• Melting Point: 67-70°C
• Boiling Point: 311.991 °C at 760 mmHg
• Flash Point: 142.488 °C
• Appearance: /
• Density: 1.705 g/cm³
• Vapor Pressure: 0.000544mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C(protect from light)
• PKA: -3.01±0.12(Predicted)
• CAS DataBase Reference: tert-Butyl 4-iodopyrazole-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl 4-iodopyrazole-1-carboxylate(121669-70-3)
• EPA Substance Registry System: tert-Butyl 4-iodopyrazole-1-carboxylate(121669-70-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 121669-70-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-Butyl 4-iodopyrazole-1-carboxylate is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Development:
In the agrochemical industry, tert-Butyl 4-iodopyrazole-1-carboxylate is utilized as a building block for the creation of compounds that can be applied in crop protection and other agricultural applications, leveraging its structural and reactive features to enhance product efficacy.
Used in Materials Science:
Tert-Butyl 4-iodopyrazole-1-carboxylate is employed as a component in the development of new materials, where its unique structure can influence the properties of the resulting materials, such as stability, reactivity, or other specific characteristics desired in various applications.
Used in Medicinal Chemistry for Drug Discovery and Development:
As a versatile intermediate, tert-Butyl 4-iodopyrazole-1-carboxylate is used in medicinal chemistry for the exploration and development of new drugs, taking advantage of its reactivity and structural attributes to create novel therapeutic agents.

InChI:InChI=1/C8H11IN2O2/c1-8(2,3)13-7(12)11-5-6(9)4-10-11/h4-5H,1-3H3

Upstream product

• 3469-69-0 4-iodopyrazole 
• 121-44-8 triethylamine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1093193-29-3 4-ethynyl-1H-pyrazole-1-carboxylate tert-butyl ester 
• 1316228-38-2 C₁₇H₁₉N₅O₂ 
• 1400287-02-6 tert-butyl 4-(6-(4-fluorophenylamino)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate 
• 1400287-04-8 tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate 
• 1400286-84-1 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(4-methoxyphenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-92-1 tert-butyl-2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(3,4-dimethoxyphenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-96-5 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(4-(N,N-dimethylsulfamoyl)phenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-85-2 tert-butyl 6-(4-((1H-pyrazol-1-yl)methyl)phenylamino)-2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-87-4 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(4-(2-morpholinoethoxy)phenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-89-6 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(2-methoxyphenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-95-4 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(2-ethoxyphenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 1400286-93-2 tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-(2-chloro-4-methoxyphenylamino)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 269410-08-4 pyrazole-4-boronic acid pinacol ester 
• 552846-17-0 tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate 

Relevant articles and documents

Flexible side arms of ditopic linker as effective tools to boost proton conductivity of Ni8-pyrazolate metal-organic framework

Two primitive metal-organic frameworks (MOFs), NiL1 and NiL2, based on Ni8O6-cluster and ditopic pyrazolate linkers, L1 (with rigid alkyne arms) and L2 (with flexible alkyne chains), were prepared. The proton conductivities of these MOFs in pristine form and imidazole-encapsulated forms, Im@NiL1 and Im@NiL2, were measured and compared. Upon introduction of imidazole molecules, the proton conductivity could be increased by 3 to 5 orders of magnitude and reached as high as 1.72 × 10?2 S/cm (at 98% RH and 80 °C). Also, whether imidazole molecules were introduced or not, Ni8O6-based MOFs with L2 in general gave better proton conductivity than those with L1 signifying that flexible side arms indeed assist proton conduction probably via establishment of efficient proton-conducting channels along with formation of highly ordered domains of water/imidazole molecules within the network cavities. Beyond the active Ni8O6-cluster, tuning flexibility of linker pendants serves as an alternative approach to regulate/modulate the proton conductivity of MOFs.

Linker Deficiency, Aromatic Ring Fusion, and Electrocatalysis in a Porous Ni8-Pyrazolate Network

The cruciform linker molecule here features two designer functions: the pyrazole donors for framework construction, and the vicinal alkynyl units for benzannulation to form nanographene units into the Ni8-pyrazolate scaffold. Unlike the full 12 connections of the Ni8(OH)4(H2O)2 clusters in other Ni8-pyrazolate networks, significant linker deficiency was observed here, leaving about half of the Ni(II) sites capped by acetate ligands, which can be potentially removed to open the metal sites for reactivity. The crystalline Ni8-pyrazolate scaffold also retains the crystalline order even after thermal treatments (up to 300 °C) that served to partially graphitize the neighboring alkyne units. The resultant nanographene components enhance the electroactive properties of the porous hosts, achieving hydrogen evolution reaction (HER) activity that rivals that of topical nickel/palladium-enabled materials.

Alkynyl-rich compound, preparation method thereof and metal organic framework material

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The invention discloses a synthesis method of pyrazol-4-boronic acid pinacol ester. The method consists of: reacting 4-halogenopyrazole with BOC2O to obtain N-BOC-4-halogenopyrazole, then carrying out reaction with alkyl magnesium lithium, adding aminopinacol borate, conducting acid quenching deprotection, then carrying out rotary evaporation filtering to obtain a solid, and adding organic alkali to conduct dissociation so as to obtain a product. The synthesis method has the advantages of simple operation, good reproducibility and high product purity, and is suitable for large-scale production.

Synthesis of substituted-3-iodo-1H-pyrazole derivatives and their further modification under Sonogashira cross-coupling reaction conditions

A convenient synthetic route for preparation of valuable synthetic intermediates - 1-(1-ethoxyethyl)-3-iodo-1H-pyrazole derivatives has been developed. During this work protection reaction of N-H bond in substituted 3-iodo-1H-pyrazole derivatives with ethyl vinyl ether and migration of ethoxyethyl protecting group was investigated. Synthetic possibilities of Sonogashira cross-coupling reactions of substituted 1-(1-ethoxyethyl)-3-iodo-1H-pyrazole derivatives with phenylacetylene were studied and evaluated.

Highly hydrophobic isoreticular porous metal-organic frameworks for the capture of harmful volatile organic compounds

Tunable hydrophobicity: Efficient air filters for the protection against chemical warfare agents might be achieved by surface functionalization of the pores in robust metal-organic frameworks (MOFs) with fluoroalkyl residues and the precise control of their pore size (see picture). These MOFs capture harmful volatile organic compounds even under extremely moist conditions (80 % relative humidity). Copyright

Structure-based design of orally bioavailable 1 h -Pyrrolo[3,2- C ]pyridine inhibitors of mitotic kinase monopolar spindle 1 (MPS1)

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The present invention relates to the use of certain pyrrolopyridineamino derivatives (hereinafter referred to as “PPA derivatives”), particularly 1H-pyrrolo[3,2-c]pyridine-6-amino derivatives, to inhibit the spindle checkpoint function of Monospindle 1 (Mps1—also known as TTK) kinases either directly or indirectly via interaction with the Mps kinase itself. In particular, the present invention relates to PPA derivatives for use as therapeutic agents for the treatment and/or prevention of proliferative diseases, such as cancer. The present invention also relates to processes for the preparation of the PPA derivatives, and pharmaceutical compositions comprising them. Formula (I)

PYRROLOPYRIDINEAMINO DERIVATIVES AS MPS1 INHIBITORS

The present invention relates to the use of certain pyrrolopyridineamino derivatives (hereinafter referred to as "PPA derivatives"), particularly 1H-pyrrolo[3,2-c]pyridine-6- amino derivatives, to inhibit the spindle checkpoint function of Monospindle 1 (Mps1 – also known as TTK) kinases either directly or indirectly via interaction with the Mps kinase itself. In particular, the present invention relates to PPA derivatives for use as therapeutic agents for the treatment and/or prevention of proliferative diseases, such as cancer. The present invention also relates to processes for the preparation of the PPA derivatives, and pharmaceutical compositions comprising them. Formula (I)