17635-44-8

Basic information

• Product Name: 3,4,5-Tribromopyrazole
• Synonyms: 3,4,5-TRIBROMOPYRAZOLE;3,4,5-TRIBROMO-1H-PYRAZOLE;3,4,5-Tribromopyrazole, 97+%;3,4,5-Tribromopyrazol;3,4,5-TribroMo-1H-pyrazole, 97%, 97%
• CAS NO: 17635-44-8
• Molecular Formula: C₃HBr₃N₂
• Molecular Weight: 304.77
• Product Categories: Heterocyclic Compounds;Heterocycles;Piperidines
• Mol File: 17635-44-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 190-192°C
• Boiling Point: 381.5 °C at 760 mmHg
• Flash Point: 184.5 °C
• Appearance: Off-white solid
• Density: 2.782 g/cm₃
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Methanol
• PKA: 6.47±0.50(Predicted)
• Water Solubility: Insoluble in water. Soluble in Chloroform.
• BRN: 113501
• CAS DataBase Reference: 3,4,5-Tribromopyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Tribromopyrazole(17635-44-8)
• EPA Substance Registry System: 3,4,5-Tribromopyrazole(17635-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 17635-44-8(Hazardous Substances Data)

Usage

Description

3,4,5-Tribromopyrazole is an off-white solid with unique chemical properties that make it a valuable compound in various industries. It is characterized by its tribromine substitutions at the 3, 4, and 5 positions of the pyrazole ring, which contribute to its reactivity and potential applications.

Uses

Used in Pharmaceutical Industry:
3,4,5-Tribromopyrazole is used as a key intermediate for the preparation of 1-aryl-4-substituted piperazine CCR1 antagonists. These antagonists are crucial in the treatment of inflammation and immune disorders, as they help regulate the immune response and reduce inflammation in the body.
Used in Organic Synthesis:
3,4,5-Tribromopyrazole serves as an important raw material and intermediate in organic synthesis. Its unique chemical structure allows for further functionalization and modification, making it a versatile building block for the development of new compounds with various applications.
Used in Pharmaceutical, Agrochemicals, and Dyestuff Industries:
The condensation of 2,4,5-Tribromoimidazole (2,4,5-TBI) with sugar precursors yields 2,4,5-TBI nucleosides, which are significant intermediates in the synthesis of various compounds. These nucleosides find applications in the pharmaceutical industry for the development of new drugs, in agrochemicals for the creation of novel pesticides, and in the dyestuff industry for the production of dyes with specific properties.

InChI:InChI=1/C3HBr3N2/c4-1-2(5)7-8-3(1)6/h(H,7,8)

Upstream product

• 5932-18-3 3,4-dibromo-1H-pyrazole 
• 288-13-1 NH-pyrazole 
• 104599-40-8 1-nitro-3,4,5-tribromo-1H-pyrazole 
• 71-43-2 benzene 
• 923035-87-4 1-vinyl-3,4,5-tribromo-1H-pyrazole 
• 1621-91-6 1H-pyrazole-3-carboxylic acid 

Downstream Products

• 98136-32-4 1-acetyl-3,4,5-tribromo-1H-pyrazole 
• 104599-40-8 1-nitro-3,4,5-tribromo-1H-pyrazole 
• 34157-45-4 2-(3,4,5-tribromo-pyrazol-1-yl)-propionic acid 
• 104599-36-2 3,5-dibromo-4-nitro-1H-pyrazole 
• 90767-31-0 1-benzyl-3,4,5-tribromo-1H-pyrazole 
• 1262050-70-3 2-(3,4,5-tribromo-1H-1-pyrazolylmethyl)phenol 
• 1262050-71-4 4-bromo-2-(3,4,5-tribromo-1H-1-pyrazolylmethyl)phenol 
• 1347628-00-5 8,9-dibromo-12-(4-methoxyphenyl)-12H-naphtho[1,2-e]pyrazolo[5,1-b][1,3]oxazine 
• 67460-86-0 3,5-dibromo-1H-pyrazole 
• 104599-37-3 3,4-dibromo-5-nitro-1H-pyrazole 

Relevant articles and documents

The N-vinyl group as a protection group of the preparation of 3(5)-substituted pyrazoles via bromine-lithium exchange

Treatment of 3,4,5-tribromopyrazole with 1,2-dibromoethane and triethylamine gave 3,4,5-tribromo-1-vinylpyrazole, which underwent regioselective bromine-lithium exchange at the 5-position. Subsequent addition of an electrophile gave 5-substituted 3,4-dibr

METHODS FOR THE PREPARATION OF 5-BROMO-2-(3-CHLORO-PYRIDIN-2-YL)-2H-PYRAZOLE-3-CARBOXYLIC ACID

Described herein are novel methods of synthesizing 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid from pyrazole or pyrazole derivatives. Also described herein are novel reaction intermediates.

Discovery and Optimization of Small Molecule Splicing Modifiers of Survival Motor Neuron 2 as a Treatment for Spinal Muscular Atrophy

The underlying cause of spinal muscular atrophy (SMA) is a deficiency of the survival motor neuron (SMN) protein. Starting from hits identified in a high-throughput screening campaign and through structure-activity relationship investigations, we have developed small molecules that potently shift the alternative splicing of the SMN2 exon 7, resulting in increased production of the full-length SMN mRNA and protein. Three novel chemical series, represented by compounds 9, 14, and 20, have been optimized to increase the level of SMN protein by >50% in SMA patient-derived fibroblasts at concentrations of 160 nM. Daily administration of these compounds to severe SMA Δ7 mice results in an increased production of SMN protein in disease-relevant tissues and a significant increase in median survival time in a dose-dependent manner. Our work supports the development of an orally administered small molecule for the treatment of patients with SMA.