Monobromobimane

Base Information

• Chemical Name: Monobromobimane
• CAS No.: 71418-44-5
• Molecular Formula: C10H11 Br N2 O2
• Molecular Weight: 271.114
• NSC Number: 608544
• UNII: V23UK0CYXL
• DSSTox Substance ID: DTXSID70221609
• Nikkaji Number: J546.912K
• Wikipedia: Bromobimane
• Wikidata: Q4973726
• Metabolomics Workbench ID: 62447
• ChEMBL ID: CHEMBL1649730
• Mol file: 71418-44-5.mol

Synonyms:bromobimane;MBBR;monobromobimane;Thiolyte MB

Chemical Property of Monobromobimane

Chemical Property:

• Vapor Pressure: 0.000197mmHg at 25°C
• Melting Point: 152-154oC
• Boiling Point: 327.8°C at 760 mmHg
• PKA: -3.36±0.70(Predicted)
• Flash Point: 152.1°C
• PSA: 42.96000
• Density: 1.66g/cm³
• LogP: 1.01710
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 270.00039
• Heavy Atom Count: 15
• Complexity: 437

Purity/Quality:

99% ^*data from raw suppliers

Monobromobimane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(N2C(=C(C(=O)N2C1=O)C)CBr)C
• Description: Monobromobimane is a thiol-reactive fluorogenic probe. It is cell-permeable, reacts rapidly at physiological pH with available thiol groups, and generates a stable fluorescent signal. Monobromobimane can be used to evaluate or quantify a variety of compounds containing reactive sulfur or thiol groups, including H2S, glutathione, proteins, and nucleotides. The absorption and emission maxima for monobromobimane are 398 and 490 nm, respectively.
• Uses: Monobromobimane readily reacts with low molecular weight thiols. Bimanes are useful for detecting the distribution of protein thiols in cells before and after chemical reduction of disulfides. Fluorescence: max. Abs. 398nm; e x 10-3: 5.0 Monobromobimane is essentially nonfluorescent until conjugated to target molecule. It readily reacts with several low molecular weight thiols, including glutathione, mercaptopurine, peptides and plasma thiols, as well as with carboxylic acids. double labeled product that can be fixed with aldehydes for cell-lineage tracing1, neuronal tracing2 and transplantation3. Monobromobimane is a thiol-reactive fluorogenic probe. It is cell-permeable, reacts rapidly at physiological pH with available thiol groups, and generates a stable fluorescent signal. Monobromobimane can be used to evaluate or quantify a variety of compounds containing reactive sulfur or thiol groups, including H2S, glutathione, proteins, and nucleotides. The absorption and emission maxima for monobromobimane are 398 and 490 nm, respectively.

Technology Process of Monobromobimane

There total 7 articles about Monobromobimane 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: 53.1%

3,4-dimethyl-4-chloro-2-pyrazolin-5-one (68654-32-0) → monobromobimane (71418-44-5)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 0 - 20 ℃; for 24h;

DOI:10.1039/d1cc06218b

Reference yield: 50.0%

9,10-dioxa-syn-(methyl,methyl)bimane (68654-22-8) → monobromobimane (71418-44-5)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 0 - 20 ℃; for 12.5h;

DOI:10.1055/s-0036-1591964

Reference yield: 39.0%

3-(hydroxymethyl)-2,5,6-trimethylpyrazolo[1,2-a]pyrazole-1,7-dione (76421-69-7) → monobromobimane (71418-44-5)

Guidance literature:

With phosphorus tribromide; In dichloromethane;

DOI:10.1021/jo00321a029

upstream raw materials:

3-(hydroxymethyl)-2,5,6-trimethylpyrazolo[1,2-a]pyrazole-1,7-dione

9,10-dioxa-syn-(methyl,methyl)bimane

2-acetylpropanoic acid ethyl ester

3,4-dimethyl-4-chloro-2-pyrazolin-5-one

Downstream raw materials:

9,10-dioxa-syn-(1-propylthiomethyl,methyl)(methyl,methyl)bimane

9,10-dioxa-syn-(methyl,methyl)bimane

9,10-dioxa-syn-(aminomethyl,methyl)(methyl,methyl)bimane

9,10-dioxa-syn-(cyano,methyl)(methyl,methyl)bimane