76421-73-3

Basic information

• Product Name: MONOCHLOROBIMANE
• Synonyms: MBCL;MCB;CHLOROBIMANE;THIOLYTE(R) MONOCHLOROBIMANE REAGENT;THIOLYTE(R) MONOCHLOROBIMANE REAGENT, FLUORESCENT LABELING COMPOUND;THIOLYTE(R) MC;THIOLYTE(R) MC REAGENT;MONOCHLOROBIMANE
• CAS NO: 76421-73-3
• Molecular Formula: C₁₀H₁₁ClN₂O₂
• Molecular Weight: 226.66
• Product Categories: DetectionAntibody Modification;Labeling with FluorochromesFluorescent Probes, Labels, Particles and Stains;Antibody Labeling;Biochemicals and Reagents;Fluorescent Labels;Fluorescent Probes, Labels, Particles and Stains;Other Fluorescent Labels
• Mol File: 76421-73-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 135-136 °C(lit.)
• Boiling Point: 314.9°C at 760 mmHg
• Flash Point: 144.2°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 0.000453mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• Solubility: DMF: soluble
• BRN: 4440901
• CAS DataBase Reference: MONOCHLOROBIMANE(CAS DataBase Reference)
• NIST Chemistry Reference: MONOCHLOROBIMANE(76421-73-3)
• EPA Substance Registry System: MONOCHLOROBIMANE(76421-73-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 76421-73-3(Hazardous Substances Data)

Usage

Description

MONOCHLOROBIMANE, also known as Chlorobimane, is a thiol-reactive fluorescent probe commonly used for the detection and quantification of thiol groups, particularly glutathione levels in cells. It exhibits cell permeability and is widely employed in various applications across different industries due to its unique properties.

Uses

Used in Research and Diagnostic Applications:
MONOCHLOROBIMANE is used as a cell-permeant probe for quantifying glutathione levels in cells, allowing researchers and diagnosticians to assess the antioxidant capacity and overall health of cells.
Used in Analytical Chemistry:
In the field of analytical chemistry, MONOCHLOROBIMANE serves as a thiol-reactive fluorescent probe, enabling the detection and measurement of thiol groups. This is particularly useful in studying the role of thiols in various chemical reactions and processes.
Used in Pharmaceutical and Biomedical Research:
MONOCHLOROBIMANE is utilized as a valuable tool in pharmaceutical and biomedical research for evaluating the efficacy of drugs and other compounds that target thiol groups. Its ability to detect and quantify glutathione levels can provide insights into the antioxidant properties of these compounds and their potential therapeutic applications.
Used in Environmental Monitoring:
In environmental monitoring, MONOCHLOROBIMANE can be employed as a sensitive and selective probe for detecting thiol-containing compounds in various samples, such as water, soil, and air. This can help in assessing the presence of pollutants and contaminants, as well as monitoring the overall health of ecosystems.
Used in Food Industry:
In the food industry, MONOCHLOROBIMANE can be used as a tool for detecting and quantifying thiol compounds, which are important for flavor, aroma, and preservation. This can help in ensuring the quality and safety of food products, as well as in developing new food preservation techniques.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care products industry, MONOCHLOROBIMANE can be employed for assessing the antioxidant properties of ingredients and formulations. Its ability to detect and quantify thiol groups can provide valuable information on the effectiveness of antioxidants in skincare and other personal care products.

InChI:InChI=1/C10H11ClN2O2/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 
• 172327-11-6 syn-(azidomethyl,methyl)(methyl,methyl)bimane 
• 71418-44-5 monobromobimane 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 

Relevant articles and documents

Sequence of reactant combination alters the course of the Staudinger reaction of azides with acyl derivatives. Bimanes. 30

The Staudinger reaction of azides has now been followed by NMR and other spectroscopic techniques. syn-(Azidomethyl,methyl)(methyl,methyl)(bimane (1) and Ph3P form a triazaphosphadiene intermediate 2 and then the bimane P-triphenyliminophosphorane 3. The iminophosphorane reacts with an acyl chloride to yield an iminophosphonium salt 4 which then forms the oxazaphosphetane 13. The latter undergoes an electrocyclic reversion to form the phosphine oxide and the chloroimines 7E and 7Z, the last being hydrolyzed to the (acylamido)bimane 6. This set of reactions constitutes the "iminophosphorane pathway". A significant diversion of the reaction path to an (N-alkylamino)-phosphonium chloride 8 occurs through reaction of 4 with H2O present in the CDCl3 and through reaction of 3 with HCl. A different azide (α-azido-o-xylene 1b) produces the (acylamido)-o-xylene as the sole product. A less sterically hindered phosphine (tri-2-furylphosphine) reacts more slowly to form the iminophosphorane 3a from the azidobimane 1. Reaction of the bimane P-tri-2-furyliminophosphorane with acyl chloride gives only the (acylamido)bimane 6. If the acyl chloride is mixed with 1, followed by addition of the Ph3P, the triazaphosphadiene adduct 5 is formed via the triazaphosphadiene. The adduct 5 is converted rapidly into a six-membered cyclic compound 11. The latter either loses nitrogen to yield 6 via 7Z and 7E and the phosphine oxide or loses chloride 10 through a novel chloride-induced elimination reaction from its protonated form. The change in procedure thus results in a dramatic change in the reaction pathway, a reaction set that constitutes the "triazaphosphadiene adduet pathway". In the case of α-azido-o-xylene, α-chloro-o-xylene (10b) is the only product. The reactions of the azides 1 or 1b with tri-2-furylphosphine also produce chlorides as the major products accompanied by some acetamido derivatives. The nucleophile-induced reaction explains a "surprising result" (formation of ester rather than amide) reported by Sahlberg et al. (Sahlberg, C.; Jackson, A. M.; Claesson, A. Acta Chem. Scand. 1988, B42, 556-562). The intramolecular "aza-Wittig" reaction may depend on the nucleophilicity of the triazaphosphadiene. A comprehensive mechanistic scheme for the Staudinger reaction of azides is conveniently divided into the following: (A) formation of the triazaphosphadiene (Scheme 1), (B) reactions of the triazaphosphadiene (Scheme 2), and (C) reactions via the iminophosphorane (Scheme 3). Some approximate kinetic parameters are reported for some of the reactions.