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

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

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 
• 104599-37-3 3,4-dibromo-5-nitro-1H-pyrazole 
• 67460-86-0 3,5-dibromo-1H-pyrazole 
• 1347628-00-5 8,9-dibromo-12-(4-methoxyphenyl)-12H-naphtho[1,2-e]pyrazolo[5,1-b][1,3]oxazine 

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.

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.

Compounds for treating spinal muscular atrophy

Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.

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.

Compounds derived from diaminopyrazoles substituted by an aminoalkyl or aminoalkenyl radical and their use in oxidation dyeing of keratinous fibres

The invention concerns compounds derived from diaminopyrazole of formula (I), wherein: R1 is a linear or branched radical selected among C2, C3, C4 aminoalkyl radicals or C2, C3, C4 aminoalkenyl radicals, or one of the physiologically acceptable salts thereof. The invention also concerns compositions containing said compound for dyeing keratinous fibres and the method using said compositions.

Diaminopyrazole derivatives and their use for oxidation dyeing of keratinous fibres

The invention relates to diaminopyrazole derivatives having the following structure (I), wherein R1 represents an alkyl or alkenyl radical bearing at least one substituent selected from among OR, NRR′, SR, SOR, SO2R, COOR, CONRR′, PO(OH)2, SO3X, NHCONRR, a non-cationic heterocycle, an aryl, a halogen. R2 and R3 are different from H and represent, independently of each other, an alkyl or alkenyl group; R2 and R3, together with the nitrogen atom to which they are attached, can form a heterocycle possibly comprising at least one other heteroatom selected from among N, O and S; R2 and R3 or the heterocycle that they form with the nitrogen to which they are attached can be substituted by at least one substituent defined above. The identical or different R, R′ groups are selected from a hydrogen atom, an alkyl or alkenyl group; R and R′, together with the nitrogen atom to which they are attached, can form a heterocycle having at least 4 ring members that can contain at least one additional heteroatom selected from among O, N and S. X represents a hydrogen, an alkaline-earth or alkali metal atom or an ammonium group. The invention also relates to the dyeing compositions and the dyeing methods using same.

Diaminopyrazole compounds and the use thereof in the oxidation dyeing of keratinous fibres

The invention relates to novel diaminopyrazole having formula (I), wherein: R1, R2, identical or different, represent a C3 C5 mono- or polyhydroxyalkyl, isopropyl, n-propyl or ethyl group, said groups being linear or branched, and their physiologically acceptable salts. The invention also relates to a composition for dyeing keratinous fibres containing a compound having formula (I) and the method for using same. 1

Diaminopyrazole compounds and the use thereof in the oxidation dyeing of keratinous fibres

The invention relates to novel diaminopyrazole compounds having formula (I): wherein R1 represents a linear or branched C4-C5 alkyl or n-propyl group, or a linear or branched C3-C5 mono or polyhydroxy alkyl group, and the addition salts thereof with a physiologically acceptable acid. The invention also relates to the compositions containing such a compound for the dyeing of keratinous fibers and the method for using said compositions.