3398-16-1

Basic information

• Product Name: 4-Bromo-3,5-dimethylpyrazole
• Synonyms: VITAS-BB TBB000654;4-BROMO-3,5-DIMETHYL-1H-PYRAZOLE;4-BROMO-3,5-DIMETHYLPYRAZOLE;AKOS B001459;AKOS PAO-1351;IFLAB-BB F0900-0030;BUTTPARK 47\04-31;4-bromo-3,5-dimethyl-pyrazol
• CAS NO: 3398-16-1
• Molecular Formula: C₅H₇BrN₂
• Molecular Weight: 175.03
• EINECS: 222-263-2
• Product Categories: Halides;Pyrazoles & Triazoles;Pyrazoles & Triazoles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks;Building Blocks;C3 to C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 3398-16-1.mol

Chemical Properties

• Melting Point: 123-125 °C(lit.)
• Boiling Point: 269.1 °C at 760 mmHg
• Flash Point: 116.5 °C
• Appearance: pale white or light yellow crystal powder
• Density: 1.595
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 13.83±0.50(Predicted)
• BRN: 108534
• CAS DataBase Reference: 4-Bromo-3,5-dimethylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3,5-dimethylpyrazole(3398-16-1)
• EPA Substance Registry System: 4-Bromo-3,5-dimethylpyrazole(3398-16-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: UQ6210000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3398-16-1(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C5H7BrN2/c1-3-5(6)4(2)8-7-3/h1-2H3,(H,7,8)

Upstream product

• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 934-48-5 3,5-dimethylpyrazole-1-carboxamide 
• 130874-32-7 4-bromo-3,5-dimethyl-1-phenylsulphonylpyrazole 
• 84691-20-3 4,4-Dibromo-3,5-dimethyl-4H-pyrazole 
• 61857-80-5 4-bromo-3,5-dimethyl-pyrazole-1-carboxylic acid anilide 
• 7732-18-5 water 
• 107520-99-0 4-bromo-3,5-dimethyl-pyrazole-1-carboxylic acid diphenylamide 
• 7803-57-8 hydrazine hydrate 
• 106-49-0 p-toluidine 
• 270588-85-7 3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine 
• 30169-25-6 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine 
• 123-54-6 acetylacetone 
• 64-17-5 ethanol 
• 32551-34-1 3-methylfurazancarboxylic hydrazide 

Downstream Products

• 130874-32-7 4-bromo-3,5-dimethyl-1-phenylsulphonylpyrazole 
• 49764-18-3 di-(1-adamantyl) ether 
• 768-95-6 1-adamanthanol 
• 15801-69-1 4-bromo-1,3,5-trimethylpyrazole 
• 575489-77-9 (E)-4-bromo-1-[3-(4-bromophenyl)-2-propenoyl]-3,5-dimethylpyrazole 
• 575489-74-6 (E)-4-bromo-1-(3-cyclohexyl-2-propenoyl)-3,5-dimethylpyrazole 
• 575489-76-8 (E)-4-bromo-1-(3-phenyl-2-propenoyl)-3,5-dimethylpyrazole 
• 850011-37-9 5-bromo-1-[3-(4-bromo-2-methoxyphenyl)-2-propenoyl]-3,5-dimethylpyrazole 
• 850011-38-0 5-bromo-1-[3-(3,5-dibromophenyl)-2-propenoyl]-3,5-dimethylpyrazole 
• 847818-62-6 (1,3,5-trimethyl-1H-pyrazol-4-yl)boronic acid 
• 444177-50-8 3-(4-bromo-3,5-dimethylpyrazol-1-yl)-1-(2-hydroxy-5-methylphenyl)-1-propanone oxime 
• 444177-54-2 3-(4-bromo-3,5-dimethylpyrazol-1-yl)-1-(2-hydroxy-5-methylphenyl)-1-propanone oxime acetate 
• 74731-15-0 4-Bromo-3,5-dimethyl-pyrazole-1-carbonyl chloride 
• 28188-06-9 4-bromo-1-methoxycarbonyl-3,5-dimethylpyrazole 

Relevant articles and documents

Tumor microenvironment and NIR laser dual-responsive release of berberine 9-: O -pyrazole alkyl derivative loaded in graphene oxide nanosheets for chemo-photothermal synergetic cancer therapy

A berberine 9-O-pyrazole alkyl derivative, a chemical compound (called B3) previously synthesized by our group, shows anti-cancer activity. However, B3 lacks targeting cytotoxicity to cancer cells, leading to obvious toxic side effects on normal cells. To solve this problem, here, we prepared a drug delivery system, namely, AS1411-GO/B3 for tumor targeting, in which nano-graphene oxide (GO) sheets were employed as the drug carrier, and the aptamer AS1411 was conjugated onto GO for tumor targeting. GO also had a photothermal effect, which helped the release of B3 from GO as well as the thermal cytotoxicity to cells. We found that the release of B3 could respond to acid conditions, indicating that the tumor intracellular environment could promote the release of B3, thus allowing it to perform chemotherapy effects. This system could also release B3 in response to photothermal heating, moreover, combined photothermal therapy and chemotherapy to improve the anticancer activity was achieved. This AS1411-GO/B3 platform with chemo-photothermal synergetic therapy provides a very promising treatment for tumors.

R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond

A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

Identification of Isoform 2 Acid-Sensing Ion Channel Inhibitors as Tool Compounds for Target Validation Studies in CNS

Acid-sensing ion channels (ASICs) are a family of ion channels permeable to cations and largely responsible for the onset of acid-evoked ion currents both in neurons and in different types of cancer cells, thus representing a potential target for drug discovery. Owing to the limited attention ASIC2 has received so far, an exploratory program was initiated to identify ASIC2 inhibitors using diminazene, a known pan-ASIC inhibitor, as a chemical starting point for structural elaboration. The performed exploration enabled the identification of a novel series of ASIC2 inhibitors. In particular, compound 2u is a brain penetrant ASIC2 inhibitor endowed with an optimal pharmacokinetic profile. This compound may represent a useful tool to validate in animal models in vivo the role of ASIC2 in different neurodegenerative central nervous system pathologies.

A mild halogenation of pyrazoles using sodium halide salts and Oxone

A mild, inexpensive, and operationally simple pyrazole halogenation method utilizing Oxone and sodium halide salts is reported. This work documents 17 examples of alkyl, aryl, allyl, and benzyl substituted 4-chloro and 4-bromopyrazoles, obtained in up to 93% yield. Reactions are performed in water under ambient conditions and generation of organic byproducts is avoided.

Discovery of DS79182026: A potent orally active hepcidin production inhibitor

Hepcidin has emerged as the central regulatory molecule of systemic iron homeostasis. Inhibition of hepcidin could be a strategy favorable to treating anemia of chronic disease (ACD). We report herein the synthesis and structure-activity relationships (SARs) of a series of benzisoxazole compounds as orally active hepcidin production inhibitors. The optimization study of multi kinase inhibitor 1 led to a potent and bioavailable hepcidin production inhibitor 38 (DS79182026), which showed serum hepcidin lowering effects in a mouse IL-6 induced acute inflammatory model.

A two-valence sulfonyl isoxazole derivatives and use thereof

The invention discloses a bi-titer sulfonyl isoxazole derivative in the technical field of organic compound weedicides, and application thereof. The bi-titer sulfonyl isoxazole derivative has a molecular structural formula shown as a general formula I. The invention further discloses a preparation method of the bi-titer sulfonyl isoxazole derivative. The bi-titer sulfonyl isoxazole derivative has very high activity of inhibiting weed growth and killing and removing weeds, and can be used in agricultural production, and is classified as a novel active component for weedicides.

Synthesis and characterization of some symmetrical substituted 1-(2-chloroethyl)pyrazole-based chalcogenides

The present paper describes the synthesis of some symmetrical substituted 1-(2-chloroethyl) pyrazole-based dichalcogenides and monochalcogenides by reacting different 3,4,5-trisubstituted 1-(2-chloroethyl) pyrazole derivatives with in situ prepared Na2E2 (E = S, Se, Te) and sodium hydrogen selenide, respectively. All compounds were fully characterized by different spectroscopic techniques, namely, IR, 1H, 13C, 77Se nuclear magnetic resonance, and mass spectrometry. X-ray crystal structure determination of 1,2-bis(2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)ethyl)diselane (10b) reveals intermolecular Se·N·H interactions between two molecules.

Synthesis of [1,2,4]triazolo[4,3-b]-s-tetrazines with incorporated furazan ring

Furazancarboxylic hydrazides can serve as nucleophiles to substitute for one dimethylpyrazole fragment in bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine, giving the corresponding N-[6-(3,5-dimethylpyrazol-1-yl)-s-tetrazin-3-yl] -4-R-furazan-3-carbohydrazides i

α-Substituted boron difluoride acetylacetonates

By treatment of α-substituted acetylacetone derivatives with boron trifluoride etherate a series of earlier unknown boron difluoride complexes is obtained. The series includes binuclear complexes containing boron in the chelate fragment connected via sulfur or selenium atom. Gas chromatographic and spectral characteristics of the obtained compounds were investigated. By means of chromato-mass spectrometry their reaction with hydrazine in acidic and alkaline media was studied.

Halogenation of pyrazoles using N-halosuccinimides in CCl4 and in water

Reaction of pyrazoles with N-halosuccinimides (NXS, X=Br, Cl) in either CCl4 or water gave 4-halopyrazoles in excellent yields. The reaction was carried out under mild conditions and did not require any catalysts or special precautions. The reaction provides an efficient method for 4-C halogenation of pyrazoles. Copyright Taylor & Francis Group, LLC.