50709-33-6

Basic information

• Product Name: 2-Bromophenylhydrazine hydrochloride
• Synonyms: 2-Bromophenylhydrazinehydrichloride;O-BROMOPHENYLHYDRAZINE HYDROCHLORIDE;2-BROMOPHENYLHYDRAZINE HCL;2-BROMOPHENYLHYDRAZINE HYDROCHLORIDE;1-(2-BROMOPHENYL)HYDRAZINE HYDROCHLORIDE;BIO-FARMA BF000755;2-Bromophenylhdrazine Hydrochloride;2-BROMOPHENYLHYDRAZINE HYDROCHLORIDE, 98 %
• CAS NO: 50709-33-6
• Molecular Formula: C₆H₈BrN₂*Cl
• Molecular Weight: 223.5
• EINECS: 256-728-6
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Phenylhydrazine;Hydrazines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 50709-33-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 189 °C (dec.)(lit.)
• Boiling Point: 275.7 °C at 760 mmHg
• Flash Point: 120.5 °C
• Appearance: white to light yellow crystal powder
• Vapor Pressure: 0.00502mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: slightly sol. in Methanol
• Sensitive: Hygroscopic
• BRN: 3628612
• CAS DataBase Reference: 2-Bromophenylhydrazine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromophenylhydrazine hydrochloride(50709-33-6)
• EPA Substance Registry System: 2-Bromophenylhydrazine hydrochloride(50709-33-6)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-20/21-31-20
• Safety Statements: 26-27-36/37/39-45-23
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅱ
• Hazardous Substances Data: 50709-33-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromophenylhydrazine hydrochloride is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. It plays a crucial role in the synthesis of 6-(3-bromophenylhydrazono)-7,8,9,11-tetrahydropyrido[2,1-b]quinazoline-11-one, which may have potential applications in the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 2-Bromophenylhydrazine hydrochloride serves as a valuable reagent for the synthesis of various organic compounds. Its unique chemical properties make it a versatile building block for creating complex molecules with specific functionalities.
Used in Analytical Chemistry:
2-Bromophenylhydrazine hydrochloride can also be employed in analytical chemistry as a derivatizing agent for the detection and quantification of specific compounds. Its reactivity with certain functional groups allows for the formation of derivatives that can be more easily analyzed using various analytical techniques.

InChI:InChI=1/C6H7BrN2.ClH/c7-5-3-1-2-4-6(5)9-8;/h1-4,9H,8H2;1H

Upstream product

• 615-36-1 2-bromoaniline 

Downstream Products

• 188181-16-0 2-(2-Bromo-phenyl)-3-oxo-3,5-dihydro-2H-pyridazino[4,3-b]indole-4-carboxylic acid 
• 188180-98-5 2-(2-Bromo-phenyl)-3-oxo-3,5-dihydro-2H-pyridazino[4,3-b]indole-4-carboxylic acid ethyl ester 
• 156941-60-5 7-bromotryptamine hydrochloride 
• 220000-30-6 ethyl 2-benzoylamino-3-[(2-bromophenyl)hydrazono]propanoate 
• 877165-58-7 7-formyl-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 877165-61-2 1-methyl-7-piperazin-1-ylmethyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215384-10-3 1-methyl-7-[4-(1-methyl-piperidine-4-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215384-48-7 7-[4-(azetidine-3-carbonyl)-piperazin-1-ylmethyl]-1-methyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215384-50-1 1-methyl-7-[4-(1-methyl-piperidine-3-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215384-57-8 7-{4-[2-(4-dimethylamino-piperidin-1-yl)-acetyl]-piperazin-1-ylmethyl}-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215384-61-4 1-methyl-7-[4-(2-piperazin-1-yl-acetyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215385-50-4 7-bromo-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 
• 1215385-53-7 tert-butyl 4-(2-{4-[2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-ylmethyl]-piperazin-1-yl}-2-oxo-ethyl)-piperazine-1-carboxylate 
• 1215385-55-9 7-hydroxymethyl-1-methyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 

Relevant articles and documents

Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode

A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.

Synthesis and biological evaluation of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone derivatives as tubulin inhibitors

A series of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanones (8a-p, 9a-p) and ketoxime (10c) derivatives were designed and synthesized as antitubulin agents. All of the target compounds were evaluated for the in vitro anti-proliferative activities against three tumor cell lines (A549, HT-1080, SGC-7901). The most promising compounds in this class were (1-(p-tolyl)-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone (9c) and its ketoxime derivative (10c), which significantly inhibited tumor cells growth with IC50 value of 0.054–0.16 μM. Meanwhile, compound 9c exhibited effectively inhibitory activity of tubulin polymerization. Consistent with its antitubulin activity, compound 9c could destructively damage microtubule network and arrest SGC-7901 cell cycle at G2/M phase significantly. The structure-activity relationship (SAR) and conformational analysis indicate that methyl group at C4-position of C-ring is critical for the activities and the amino group at the C5-position of B-ring plays a negative role in maintaining bioactivity. Furthermore, a molecular docking study was performed to elucidate its binding mode at the colchicine site in the tubulin heterodimer.

A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i

New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.

Ticyclic compd. and pharmaceutical composition containing the same

PROBLEM TO BE SOLVED: To provide a compound which provides EP3 receptor antagonism, and a pharmaceutical composition which contains the compound and is for prevention against and treatment of prostaglandin mediated disorders. SOLUTION: There is disclosed the compound represented by general formula (I), where R1and R2are a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, or a halogen atom, R3is a monocyclic or bicyclic aromatic ring or heterocyclic ring, or a cyclo ring, R4is a monocyclic or bicyclic aromatic ring or heterocyclic ring, X is -CH2- or a carbon atom having a lower alkyl group, Y is -CH2CH2-(CH2)m- or -CR5=CR6-(CH2)m- (R5and R6may be identical or different and a hydrogen atom or a halogen atom), -O-CH2-(CH2)m-, (cyclo ring (1-5 carbons))-(CH2)m-, or (monocyclic or bicyclic aromatic ring)-(CH2)m-, where m is 0-5, Z is a bond or -SO2-, and n is 0-5. COPYRIGHT: (C)2013,JPO&INPIT

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues

Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.

An straightforward entry to new pyrazolo-fused dibenzo[1,4]diazepines

A series of novel pyrazolodibenzo[1,4]diazepines has been synthesized with good overall yields. The diarylpyrazole intermediates, with structure similarity to biologically relevant compounds such as currently marketed drugs like rimonabant or celecoxib, were prepared by a tandem sequence amine-exchange/ heterocyclization starting from readily available enaminones and arylhydrazines. The key step of this efficient methodology was Caryl-N bond construction, accomplished by a palladium-catalyzed intramolecular N-arylation reaction, which was conducted in both homogeneous and polymer-supported versions. Reaction scope of such protocols and recycling of the heterogeneous catalyst were also examined.

Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid

A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.

Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues

A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.

Preparation of sodium-hydrogen exchanger type-1 inhibitors

This invention relates to methods of preparing sodium-hydrogen exchanger type 1 (NHE-1) inhibitors of formula I′ 1intermediates of the NHE-1 inhibitors and a new almost colorless form of the NHE-1 inhibitor N-(5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carbonyl)-guanidine.