68654-22-8

Basic information

• Product Name: syn-(Methyl,methyl)bimane
• Synonyms: syn-(Methyl,methyl)bimane;2,3,5,6-Tetramethyl-pyrazolo[1,2-a]pyrazole-1,7-dione;2,3,7,8-Tetramethyl-1,5-diaza-bicyclo(3.3.0)octa-2,7-dien-4,6-dione;3,4,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione;3,4,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione;2,3,5,6-Tetramethyl-pyrazolo[1,2-α]pyrazole-1,7-dione;methylbimane
• CAS NO: 68654-22-8
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.217
• Product Categories: Heterocyclic Compounds;Heterocycles
• Mol File: 68654-22-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 211-2120C
• Boiling Point: 280.817°C at 760 mmHg
• Flash Point: 116.704°C
• Appearance: /
• Density: 1.282g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: syn-(Methyl,methyl)bimane(CAS DataBase Reference)
• NIST Chemistry Reference: syn-(Methyl,methyl)bimane(68654-22-8)
• EPA Substance Registry System: syn-(Methyl,methyl)bimane(68654-22-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 68654-22-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

2,3,5,6-Tetramethylpyrazolo[1,2-a]pyrazole-1,7-dione (cas# 68654-22-8) is a compound useful in organic synthesis.

Definition

ChEBI: A pyrazolopyrazole that consists of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione bearing four methyl substituents at positions 2, 3, 5 and 6.

InChI:InChI=1/C10H12N2O2/c1-5-7(3)11-8(4)6(2)10(14)12(11)9(5)13/h1-4H3

Upstream product

• 107-03-9 1-thiopropane 
• 71418-44-5 monobromobimane 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 60178-92-9 4-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 759-65-9 diethyl oxalpropionate 
• 6628-22-4 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 79746-70-6 3-(carboethoxy)-4-chloro-4-methyl-2-pyrazolin-5-one 
• 79746-68-2 3-(carboethoxy)-4,4-dichloro-2-pyrazolin-5-one 
• 100130-07-2 4-bromo-3,4-dimethylpyrazol-5-one 
• 74235-66-8 1,2-dimethylene-4,4'-bis(3-methyl-4-chloro-2-pyrazolin-5-one) 
• 60848-28-4 3-methyl-4-phenyl-4-chloro-2-pyrazolin-5-one 
• 33549-66-5 4,4-dibromo-5-methyl-2,4-dihydro-3H-pyrazol-3-one 

Downstream Products

• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 74235-78-2 9,10-dioxa-anti-(bromomethyl,methyl)(methyl,methyl)bimane 
• 220357-74-4 9,10-dioxa-syn-(methyl,phenyl)(methyl,methyl)bimane 
• 74235-89-5 9,10-dioxa-anti-(methyl,methyl)(methyl,phenyl)bimane 
• 74235-81-7 9,10-dioxa-syn-(bromomethyl, methyl)(methyl,phenyl)bimane 
• 76421-73-3 Monochlorobimane 
• 76421-90-4 9,10-dioxa-syn-(aminomethyl,methyl)(methyl,methyl)bimane 

Relevant articles and documents

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.

Highly sensitive detection of cobalt through fluorescence changes in β-cyclodextrin-bimane complexes

A supramolecular complex ofsyn-(methyl,methyl)bimane (1) and β-cyclodextrin demonstrates a sensitive (limit of detection = 0.60 nM) and selective fluorescence turn-off response in the presence of cobalt in aqueous media, with calibration curves enabling quantitation in solution and using filter papers on which bimane and cyclodextrin were adsorbed.1H NMR spectroscopy provides insight into interactions underlying the sensor performance.

Bimanes. 14. Synthesis and Properties of 4,6-Bis(carboalkoxy)-1,5-diazabicycloocta-3,6-diene-2,8-diones . Preparation of the Parent syn-Bimane, syn-(Hydrogen,hydrogen)bimane.

The 3-(carboalkoxy)pyrazolin-5-ones derived from dialkyl oxaloacetates or diethyl α-methyloxaloacetate through reaction with hydrazine can be converted into the strongly fluorescent 4,6-bis(carboalkoxy)-1,5-diazabicycloocta-3,6-diene-2,8-diones 1)B (6), R=CH3 or CH3CH2, R1=CH3, Cl, Br> by base treatment of the corresponding chloro or bromo derivative.The structure of one bis ester, 4,6-bis(carbomethoxy)-3,7-dimethyl-1,5-diazabicycloocta-3,6-diene-2,8-dione , has beendetermined by X-ray crystallography.Lithium bromide and the esters in CH3CN or DMF yield via dealkylation and decarboxylation the corresponding syn-(H,R1)B (11), (R1=H, CH3, Cl, Br, I) or the "mixed" bimanes syn-(EtOOC,R1)(H,R1)B (10, R1=Cl or CH3).A dicarboxylic acid (R1=CH3; LiBr/CH3CN/60 deg C; two COOCH3's) readily decarboxylates.Hydrogenation of halogenated bimanes over Pd/C(AcOH) replaces one or both halogens, the 2H product from syn-(H,Cl)B being the parent syn-bimane, syn-(H,H)B, syn-(COOR,H)B and ICl yield syn-(COOR,I)B, which gives syn-(H,I)B on dealkylation-decarboxylation.Replacement of Cl in syn-(COOCH2CH3,Cl)B by C6H5S(1-) yields syn-(COOCH2CH3,C6H5S)B.Both ester groups and halogens shift absorption and fluorescence maxima to longer wavelengths than those recorded for syn-(CH3,CH3)B.In 1H NMR spectra, the β-hydrogens of the syn-bimane appear at considerably lower fields (7.52-8.21 ppm) than the α-hydrogens (5.42-6.13 ppm).