2,5-Dibromohexanediamide

Base Information

• Chemical Name: 2,5-Dibromohexanediamide
• CAS No.: 99584-96-0
• Molecular Formula: C₆H₁₀Br₂N₂O₂
• Molecular Weight: 301.966
• NSC Number: 126275
• DSSTox Substance ID: DTXSID701313350
• Nikkaji Number: J3.269.709G
• Mol file: 99584-96-0.mol

Synonyms:2,5-dibromohexanediamide;99584-96-0;DBHDA;C6H10Br2N2O2;NSC126275;2,5-Dibromoadipamide;SCHEMBL17545277;DTXSID701313350;2,5-Dibromohexanediamide, >=95%;MFCD27976335;AKOS024257945;AS-3291;NSC-126275;CS-0022004;EN300-269698

Chemical Property of 2,5-Dibromohexanediamide

Chemical Property:

• Melting Point: 196 °C
• Boiling Point: 492.8±45.0 °C(Predicted)
• PKA: 14.36±0.50(Predicted)
• Density: 1.932±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 301.90885
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

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

DBHDA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CC(C(=O)N)Br)C(C(=O)N)Br
• Uses: DBHDA was used as a catalyst in synthesis of advanced activity-based probes. This compound has been shown to be a useful reagent for the conversion of cysteine to dehydroalanine (DHA) in peptides or proteins. This enables chemical mutagenesis in which DHA can be efficiently reacted with iodide building blocks to add various natural and unnatural side chains on proteins. It was also shown that other modifications could be added through DHA such as phosphorylation, methylation, and glycosylation. In other research it was shown that DHA can be used to make ubiquitin conjugates that have a bond that mimics the native isopeptide bond.

Technology Process of 2,5-Dibromohexanediamide

There total 5 articles about 2,5-Dibromohexanediamide 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: 55.0%

Adipic acid dichloride (111-50-2) → 2,5-dibromohexanediamide (99584-96-0)

Guidance literature:

Adipic acid dichloride; With N-Bromosuccinimide; hydrogen bromide; In tetrachloromethane; water; for 2h; Reflux;

at 0 - 20 ℃;

DOI:10.1039/d0cc04969g

Reference yield:

2,5-dibromohexanedioyl dichloride (29548-86-5,137300-49-3) → 2,5-dibromohexanediamide (99584-96-0)

Guidance literature:

With ammonium hydroxide; In water; at 0 ℃; for 1.33333h;

DOI:10.1002/anie.201106432

Reference yield:

Adipic acid (124-04-9) → 2,5-dibromohexanediamide (99584-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 1.5 h / Reflux

2: N-Bromosuccinimide; water; hydrogen bromide / tetrachloromethane / 2 h / Reflux

3: ammonium hydroxide / water / 1.33 h / 0 °C

With ammonium hydroxide; N-Bromosuccinimide; thionyl chloride; water; hydrogen bromide; In tetrachloromethane; water;

DOI:10.1002/anie.201106432

upstream raw materials:

Adipic acid

2,5-dibromohexanedioyl dichloride

Adipic acid dichloride