71418-44-5

Basic information

• Product Name: MONOBROMOBIMANE
• Synonyms: MONOBROMOBIMANE;MMB;THIOLYTE MONOBROMOBIMANE REAGENT;THIOLYTE(R) MB;THIOLYTE(R) MB REAGENT;THIOLYTE(R) MONOBROMOBIMANE REAGENT;THIOLYTE(R) MONOBROMOBIMANE REAGENT, FLUORESCENT LABELING COMPOUND;MBBR
• CAS NO: 71418-44-5
• Molecular Formula: C₁₀H₁₁BrN₂O₂
• Molecular Weight: 271.11
• Product Categories: Fluorescent Labels and Indicators;Fluorescent Labels & Indicators;MTS & Sulfhydryl Active Reagents;Pyrazole
• Mol File: 71418-44-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152-154 °C(lit.)
• Boiling Point: 327.8°C at 760 mmHg
• Flash Point: 152.1°C
• Appearance: Yellow/powder
• Density: 1.66g/cm³
• Vapor Pressure: 0.000197mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: 2-8°C
• Solubility: DMF: soluble
• PKA: -3.36±0.70(Predicted)
• Stability: Light Sensitive
• BRN: 4430959
• CAS DataBase Reference: MONOBROMOBIMANE(CAS DataBase Reference)
• NIST Chemistry Reference: MONOBROMOBIMANE(71418-44-5)
• EPA Substance Registry System: MONOBROMOBIMANE(71418-44-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 71418-44-5(Hazardous Substances Data)

Usage

Description

Monobromobimane is a thiol-reactive fluorogenic probe that is cell-permeable and reacts rapidly at physiological pH with available thiol groups, generating a stable fluorescent signal. It 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. It is a yellow powder in appearance and is defined as a pyrazolopyrazole with specific substituents.

Uses

1. Used in Chemical Analysis:
Monobromobimane is used as a detection agent for identifying and quantifying compounds with reactive sulfur or thiol groups, such as H2S, glutathione, proteins, and nucleotides.
2. Used in Cellular Studies:
Monobromobimane is used as a fluorescent probe for tracing cell-lineages, neuronal tracing, and transplantation due to its ability to generate a stable fluorescent signal upon reaction with thiol groups.
3. Used in Protein Studies:
Monobromobimane is used as a detection tool for identifying the distribution of protein thiols in cells before and after the chemical reduction of disulfides.
4. Used in Drug Delivery Systems:
Monobromobimane is used as a carrier for low molecular weight thiols, including glutathione, mercaptopurine, peptides, and plasma thiols, as well as with carboxylic acids, to improve their delivery, bioavailability, and therapeutic outcomes.
5. Used in Research and Development:
Monobromobimane is used as a research tool for studying the interactions of various organic and metallic nanoparticles with thiol groups, which can be beneficial in developing novel drug delivery systems and understanding cellular processes.

InChI:InChI=1/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3

Upstream product

• 76421-69-7 3-(hydroxymethyl)-2,5,6-trimethylpyrazolo[1,2-a]pyrazole-1,7-dione 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 6628-22-4 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 

Downstream Products

• 76421-84-6 9,10-dioxa-syn-(1-propylthiomethyl,methyl)(methyl,methyl)bimane 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 
• 76421-90-4 9,10-dioxa-syn-(aminomethyl,methyl)(methyl,methyl)bimane 
• 76421-91-5 9,10-dioxa-syn-(cyano,methyl)(methyl,methyl)bimane 
• 119843-35-5 9,10-dioxa-syn-(carboxymethylthiomethyl, methyl)(methyl, methyl)-bimane 
• 158761-05-8 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside 
• 418785-19-0 diethylphophoryl cyanide 
• 76421-73-3 Monochlorobimane 
• 87623-39-0 C₁₃H₁₇N₃O₄S 

Relevant articles and documents

A β-hairpin peptide with pH-controlled affinity for tumor cells

Considering that the pH in the tumor microenvironment is dysregulated, we designed a β-hairpin peptide (SSRFEWEFESSDPRGDPSSRFEWEFESS). The configuration of the peptide switched from a flexible linear to a rigid loop structure under weakly acidic conditions. The peptide internalized by tumor cells increased significantly under weakly acidic conditions.

Visible Light Activation of Nucleophilic Thiol-X Addition via Thioether Bimane Photocleavage for Polymer Cross-Linking

On-demand photo-uncaging of reactive thiols have been employed in engineering biomaterial scaffolds for regulation of cellular activities. A drawback of the current photo-uncaging chemistry is the utilization of high energy UV light or 2-photon laser light, which may be harmful to cells and cause undesired side reactions within the biological environment. We introduce an effective approach for the caging of thiol using monobromobimane, which can be removed under irradiation of light at = 420 nm and in the presence of electrophiles, such as acrylate, propiolate and maleimide, for trapping of the newly release thiol. This chemical approach can be used in visible light-induced polymer coupling and cross-linking for the preparation of cell-laden hydrogels.

Bimanes. 6. Reactive halogen derivatives of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes)

The preparation of reactive halogen derivatives of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes) is accomplished through the intermediate monobromo- and dibromobimanes previously described. Mono- and dihydroxy compounds are produced from the bromides by reaction with wet sodium trifluoroacetate in CH3CN and are used to prepare the (a) monochlorides and dichlorides (SOCl2) and (b) the monofluorides and difluorides (Et2NSF3). Monofunctional halides react with nucleophiles (amines, thiols, carboxylates) to yield direct substitution products, with some reduction accompanying the thiol reaction. Difunctional halides react with excess nucleophile to give direct disubstitution products. syn-Dihalides react with difunctional nucleophiles (actual or potential, e.g., RNH2, S2-, (CN)2C2,CH3)B are markedly affected by the nature of X. Most syn-bromobimanes are nonfluorescent and are moderately photosensitive, due to thermally reversible isomerizations and additional irreversible reactions. syra-Chlorobimanes are nonfluorescent to weakly fluorescent. syn-Monofluoro- and difluorobimanes are strongly fluorescent. At 77 K, the halogenated compounds are all phosphorescent to some extent and many of the syn derivatives are strongly fluorescent.