4-Azidophenacyl bromide

Base Information

• Chemical Name: 4-Azidophenacyl bromide
• CAS No.: 57018-46-9
• Molecular Formula: C8H6BrN3O
• Molecular Weight: 240.059
• Hs Code.: 29299090
• European Community (EC) Number: 260-519-5
• UNII: POZ2E56V0Y
• DSSTox Substance ID: DTXSID30205627
• Nikkaji Number: J267.368A
• Wikidata: Q27286681

Synonyms:4-azidophenacyl bromide;4-azidophenacylbromide;APA bromide;p-azidophenacyl bromide

Chemical Property of 4-Azidophenacyl bromide

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Melting Point: 64-65 °C
• PSA: 66.82000
• LogP: 2.65876
• Storage Temp.: 2-8°C
• Solubility.: methanol: 50 mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 238.96942
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

98%,99%, ^*data from raw suppliers

p-Azidophenacyl Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-34-42/43
• Safety Statements: 16-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CBr)N=[N+]=[N-]
• Uses: 4-AZIDOPHENACYL BROMIDE is a versatile photolabile bifunctional reagent. Useful for investigating the active sites of sulfhydryl enzymes-particularly those which posess a particularly reactive cysteine residue at the active site. Used to study the nature of the ribosomal binding site of E. coli tRNAVal. Photoactive, heterobifunctional cross-linking reagent. Typically, the initial reaction couples to sulfhydryl in the pH range 7.0-8.0. Second bonding occurs during UV irradiation (250 nm) via reactive nitrene. The latter bonding is rapid and non-specific.

Technology Process of 4-Azidophenacyl bromide

There total 5 articles about 4-Azidophenacyl bromide 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: 86.0%

4-azidoacetophenone (20062-24-2) → 4-azidophenacyl bromide (57018-46-9)

Guidance literature:

With bromine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jm010153c

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 4-azidobenzoyl chloride (14848-01-2) → 4-azidophenacyl bromide (57018-46-9)

Guidance literature:

diazomethane; 4-azidobenzoyl chloride; In diethyl ether; dichloromethane; at 0 ℃; for 1h;

With hydrogen bromide; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2010.04.042

Reference yield:

p-aminobenzophenone (99-92-3) → 4-azidophenacyl bromide (57018-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium nitrite / water / 0.5 h / 0 °C / Acidic conditions

1.2: 3 h / 0 °C

2.1: bromine / dichloromethane / 2 h / 20 °C

With bromine; sodium nitrite; In dichloromethane; water;

DOI:10.1021/jacs.1c08723

upstream raw materials:

4-azidoacetophenone

diazomethane

4-azidobenzoyl chloride

4-azidobenzoic acid

Downstream raw materials:

S-(4-azidophenacyl)glutathione

1-(4-azidophenyl)-2-(morpholin-4-yl)ethanone

2-amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester

C₁₇H₁₄N₈O₄

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