374822
4-Bromopyrazole
99%
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About This Item
Empirical Formula (Hill Notation):
C3H3BrN2
CAS Number:
Molecular Weight:
146.97
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
99%
Form:
solid
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InChI
1S/C3H3BrN2/c4-3-1-5-6-2-3/h1-2H,(H,5,6)
SMILES string
Brc1cn[nH]c1
InChI key
WVGCPEDBFHEHEZ-UHFFFAOYSA-N
assay
99%
form
solid
bp
250-260 °C (lit.)
mp
93-96 °C (lit.)
functional group
bromo
Quality Level
1 of 4
This Item | |||
|---|---|---|---|
| assay 99% | assay 97% | assay ≥95% | assay 97% |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 200 |
| form solid | form solid | form flakes | form - |
| bp 250-260 °C (lit.) | bp - | bp - | bp - |
| mp 93-96 °C (lit.) | mp 60-65 °C | mp 141-146 °C | mp 243 °C (dec.) (lit.) |
| functional group bromo | functional group bromo | functional group - | functional group amine, ester |
General description
4-Bromopyrazole is a heteroaryl halide and its cyanation in the presence of palladium catalysts has been reported.[1]
4-Bromopyrazole is a pyrazole derivative. It is reported to react with titanium tetrachloride to afford binary adducts.[2] Mutagenicity of 4-bromopyrazole has been tested using the L-arabinose forward mutation assay of Salmonella typhimurium.[3] It is reported to inhibit the oxidative phosphorylation, the ATP-32P exchange reaction, and energy dependent and independent calcium uptake.[4]
Application
4-Bromopyrazole may be used in the preparation of solid hexacoordinate complexes by reaction with dimethyl- and divinyl-tindichloride.
4-Bromopyrazole may be used in the preparation of 4-bromo-1-(2-chloroethyl)-1H-pyrazole.[5] It may be used as starting material in the synthesis of 1,4′-bipyrazoles.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Todd D Senecal et al.
Angewandte Chemie (International ed. in English), 52(38), 10035-10039 (2013-08-13)
Playing it safe: The nontoxic cyanide source K4 [Fe(CN)6]·3H2O can be used for the cyanation of (hetero)aryl halides. The application of palladacycle catalysts prevents poisoning during catalyst formation, thereby allowing for low catalyst loadings, fast reaction times, and wide heterocyclic
Kamal Nayan Sharma et al.
Dalton transactions (Cambridge, England : 2003), 42(11), 3908-3918 (2013-01-19)
The reactions of 4-bromo-1-(2-chloroethyl)-1H-pyrazole prepared from 4-bromopyrazole with the in situ generated PhSNa, PhSeNa, Na(2)S and Na(2)Se have resulted in thio/selenoether ligands L1-L4 respectively. The complexes [PdL1/L2Cl(2)](1-2) and [PdL3/L4Cl]BF(4) (3-4) of these ligands have been synthesized by reacting them with
Effects of pyrazole, 4-bromopyrazole and 4-methylpyrazole on mitochondrial function.
A I Cederbaum et al.
Biochemical pharmacology, 23(2), 203-213 (1974-01-15)
Dichlorodialkyltin complexes with 4-bromopyrazole. The crystal structure of bis(4-bromopyrazole- N2)dichlorodimethyltin(IV).
Casellato U, et al.
Journal of Organometallic Chemistry, 486(1-2), 105-107 (1995)
Ilia A. Guzei et al.
Inorganic chemistry, 36(20), 4415-4420 (2001-10-24)
Treatment of titanium tetrachloride with 3,5-di-tert-butylpyrazole affords the complexes [3,5-(C(CH(3))(3))(2)C(3)H(3)N(2)](2)[TiCl(6)] and (3,5-(C(CH(3))(3))(2)C(3)HN(2))(2)TiCl(2) in 37 and 42% yields, respectively. An analogous reaction with 3,5-dimethylpyrazole, 3-methylpyrazole, 4-bromopyrazole, and 4-iodopyrazole leads to the formation of corresponding TiCl(4)L(2) binary adducts in 30-86% yields. Crystal
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