Monochlorobimane

Base Information

• Chemical Name: Monochlorobimane
• CAS No.: 76421-73-3
• Molecular Formula: C10H11 Cl N2 O2
• Molecular Weight: 226.663
• Hs Code.: 2933990090
• European Community (EC) Number: 687-817-1
• NSC Number: 602733
• DSSTox Substance ID: DTXSID90227249
• Nikkaji Number: J547.051J
• Wikidata: Q27123275
• Metabolomics Workbench ID: 58133
• Mol file: 76421-73-3.mol

Synonyms:monochlorobimane

Chemical Property of Monochlorobimane

Chemical Property:

• Vapor Pressure: 0.000453mmHg at 25°C
• Melting Point: 135-136 °C(lit.)
• Boiling Point: 314.9°C at 760 mmHg
• Flash Point: 144.2°C
• PSA: 42.96000
• Density: 1.4g/cm³
• LogP: 0.86100
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 226.0509053
• Heavy Atom Count: 15
• Complexity: 437

Purity/Quality:

98%Min ^*data from raw suppliers

Chlorobimane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(N2C(=C(C(=O)N2C1=O)C)CCl)C
• Uses: Cell-permeant probe for quantifying glutathione levels in cells. Generally suitable for the detection of thiol groups. Chlorobimane is a thiol-reactive fluorescent probe used for measuring glutathione levels in cells.

Technology Process of Monochlorobimane

There total 4 articles about Monochlorobimane 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: 64.0%

3-(hydroxymethyl)-2,5,6-trimethylpyrazolo[1,2-a]pyrazole-1,7-dione (76421-69-7) → Monochlorobimane (76421-73-3)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1021/jo00321a029

Reference yield: 54.0%

syn-(azidomethyl,methyl)(methyl,methyl)bimane (172327-11-6) → Monochlorobimane (76421-73-3) + Triphenylphosphine oxide (791-28-6) + syn-(acetamidomethyl,methyl)(methyl,methyl)bimane

Guidance literature:

With acetyl chloride; triphenylphosphine; In chloroform;

DOI:10.1021/jo950273q

Reference yield:

monobromobimane (71418-44-5) → Monochlorobimane (76421-73-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COONa, H₂O / acetonitrile / 15 h / Heating

2: 64 percent / SOCl₂ / Heating

With thionyl chloride; water; sodium 2,2,2-trifluoroacetate; In acetonitrile;

DOI:10.1021/jo00321a029

upstream raw materials:

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

syn-(azidomethyl,methyl)(methyl,methyl)bimane

monobromobimane

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

Refernces

• 1、 Kosower, Edward M.,Pazhenchevsky, Barak,Dodiuk, Hanna,Kanety, Hannah,Faust, Dov. "Bimanes. 6. Reactive halogen derivatives of syn- and anti-1,5-diazabicyclo[3.3.0]octadienediones (9,10-dioxabimanes)". . p. 1666 - 1673. Retrieved 2007/10/02.