(4-Bromophenyl)hydrazine

Base Information

• Chemical Name: (4-Bromophenyl)hydrazine
• CAS No.: 589-21-9
• Molecular Formula: C6H7BrN2
• Molecular Weight: 187.039
• Hs Code.: 2928000090
• European Community (EC) Number: 209-640-7
• NSC Number: 190724
• UNII: 1D906VQ17M
• DSSTox Substance ID: DTXSID80207631
• Nikkaji Number: J94.986H
• Wikidata: Q27252272
• Mol file: 589-21-9.mol

Synonyms:(4-Bromophenyl)hydrazine;589-21-9;4-Bromophenylhydrazine;p-Bromophenylhydrazine;Hydrazine, (4-bromophenyl)-;(p-Bromophenyl)hydrazine;(4-Bromo-phenyl)-hydrazine;Hydrazine, (p-bromophenyl)-;MFCD01935685;1-(4-Bromophenyl)hydrazine;UNII-1D906VQ17M;1D906VQ17M;EINECS 209-640-7;NSC-190724;p-bromophenyl hydrazine;p-Bromphenylhydrazin;(4-bromophenyl)diazane;4-bromophenyl hydrazine;N(N)c1ccc(Br)cc1;4-bromo-phenyl hydrazine;(4-bromophenyl)-Hydrazine;SCHEMBL7151;TimTec1_005956;Hydrazine,(4-bromophenyl)-;1-(4-Bromophenyl)hydrazine #;Hydrazine, 1-(p-bromophenyl)-;DTXSID80207631;HMS1550O16;P-BROMOPHENYLHYDRAZINE [MI];BBL009630;NSC190724;STK697361;AKOS000312970;NSC 190724;PS-3070;NCGC00173351-01;SY101512;BB 0249756;CS-0060253;FT-0617693;W16688;2-IODOTETRAFLUOROETHYLTRIFLUOROMETHYLETHER;A832075;Q27252272

Chemical Property of (4-Bromophenyl)hydrazine

Chemical Property:

• Vapor Pressure: 0.00278mmHg at 25°C
• Melting Point: 102-104 °C
• Refractive Index: 1.68
• Boiling Point: 285.6 °C at 760 mmHg
• PKA: 4.93±0.20(Predicted)
• Flash Point: 126.5 °C
• PSA: 38.05000
• Density: 1.666 g/cm³
• LogP: 2.50800
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 185.97926
• Heavy Atom Count: 9
• Complexity: 79.1

Purity/Quality:

99%, ^*data from raw suppliers

(4-Bromophenyl)hydrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1NN)Br
• General Description: P-Bromophenyl hydrazine is a key intermediate used in the synthesis of eletriptan via Fischer indole cyclization. Its preparation involves the reduction of p-bromophenyldiazonium salts, optimized using L-ascorbic acid to enhance efficiency and sustainability. P-BROMOPHENYL HYDRAZINE serves as a crucial building block in the streamlined, cost-effective, and environmentally friendly production of eletriptan, demonstrating its importance in pharmaceutical synthesis.

Technology Process of (4-Bromophenyl)hydrazine

There total 29 articles about (4-Bromophenyl)hydrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

N-(4-bromophenyl)-nitramine (412328-47-3) → (4-bromophenyl)hydrazine (589-21-9)

Guidance literature:

With hydrogenchloride; tin(ll) chloride; In water; for 4h; Cooling with ice;

DOI:10.1016/j.tet.2013.11.084

Reference yield: 71.0%

4-bromobenzenediazonium tetrafluoroborate (673-40-5) → (4-bromophenyl)hydrazine (589-21-9)

Guidance literature:

With nickel dichloride; zinc; In tetrahydrofuran;

DOI:10.1039/a905588f

Reference yield:

4-bromophenylhydrazine hydrochloride (622-88-8,41931-18-4) → (4-bromophenyl)hydrazine (589-21-9)

Guidance literature:

With sodium carbonate; In dichloromethane; water;

upstream raw materials:

acetone p-bromophenylhydrazone

acetone phenylhydrazone

(4-bromophenyl)diazonium chloride

phenylhydrazine

Downstream raw materials:

1,5-bis-(4-bromo-phenyl)-formazan

(Z)-4-[2-(4-bromophenyl)hydrazino]-4-oxobut-2-enoic acid

5-nitro-thiophene-2-carbaldehyde-(4-bromo-phenylhydrazone)

4-nitro-thiophene-2-carbaldehyde-(4-bromo-phenylhydrazone)

Refernces

Second-generation process research towards eletriptan: A fischer indole approach

10.1021/op100251q

The study presents the development of a second-generation synthetic process for eletriptan, a drug used to treat migraines, employing a Fischer indole cyclization approach. The new process aims to overcome the limitations of the existing manufacturing route, which includes the use of expensive and harmful starting materials, and generates significant waste. The research details the synthesis of key intermediates, such as aldehyde 8 and hydrazine 10, and explores various methods to improve yield and scalability. The study also discusses the successful application of the Fischer indole reaction to synthesize eletriptan and the optimization of the process using L-ascorbic acid for the reduction of diazonium salts to aryl hydrazines, resulting in a more cost-effective, efficient, and environmentally friendly synthesis route. The final objective was achieved by synthesizing the single enantiomer of eletriptan (R)-7 through classical resolution techniques, offering a potentially more sustainable and scalable method for its production.

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