68654-25-1

Basic information

• Product Name: DIBROMOBIMANE
• Synonyms: syn(bromomethyl,methyl)bimane;1H,7H-Pyrazolo[1,2-a]pyrazole-1,7-dione, 3,5-bis(bromomethyl)-2,6-dimethyl-;3,5-Bis(broMoMethyl)-2,6-diMethyl-1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione;NSC 608550;Thiolyte BB;bBBr [DibroMobiMane];BBBR;DBBR
• CAS NO: 68654-25-1
• Molecular Formula: C₁₀H₁₀Br₂N₂O₂
• Molecular Weight: 350.01
• Product Categories: NONE;Pyrazole;Nitric Oxide Reagents;Cross Linking Reagents;Fluorescent Labels & Indicators;MTS & Sulfhydryl Active Reagents;Biochemicals and Reagents;DetectionFluorescent Probes, Labels, Particles and Stains;Fluorescent Labels;Fluorescent Probes, Labels, Particles and Stains;Functional Group Reactive Labels;Functional Group Reactive Labels for SpectroscopyFluorescent Probes, Labels, Particles and Stains;Other Fluorescent Labels;Other
• Mol File: 68654-25-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 170-172 °C(lit.)
• Boiling Point: 371.8°Cat760mmHg
• Flash Point: 178.6°C
• Appearance: /
• Density: 1.98g/cm³
• Vapor Pressure: 1.01E-05mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: 2-8°C
• Solubility: DMF: soluble
• PKA: -4.55±0.70(Predicted)
• Stability: Light Sensitive
• BRN: 4189453
• CAS DataBase Reference: DIBROMOBIMANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBROMOBIMANE(68654-25-1)
• EPA Substance Registry System: DIBROMOBIMANE(68654-25-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 68654-25-1(Hazardous Substances Data)

Usage

Description

DIBROMOBIMANE, also known as a pyrazolopyrazole, is a chemical compound that consists of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione with two methyl substituents at positions 2 and 6, and two bromomethyl substituents at positions 3 and 5. It is a yellow solid and is widely used as a cross-linking reagent in various applications.

Uses

Used in Biochemical Applications:
DIBROMOBIMANE is used as a cross-linking reagent for proteins and thiols in myosin, hemoglobin, and mitochondrial ATPase. It helps in the study of protein structure, conformation, and cross-linking processes.
Used in Fluorescent Labeling:
DIBROMOBIMANE is used as a multiple labeled product that can be fixed with aldehydes, making it a valuable tool in the detection and analysis of various biomolecules.
Used in Cysteine Mapping:
DIBROMOBIMANE, being a bifunctional thiol reagent, is used as a cross-linking agent for cysteine mapping, which is essential for understanding the structure and function of proteins.
Used in Research and Development:
DIBROMOBIMANE is employed in research and development for its ability to cross-link proteins and thiols, making it a useful tool in the study of protein interactions and modifications.

InChI:InChI=1/C10H10Br2N2O2/c1-5-7(3-11)13-8(4-12)6(2)10(16)14(13)9(5)15/h3-4H2,1-2H3

Upstream product

• 6628-22-4 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 

Downstream Products

• 76421-97-1 9,10-dioxa-syn-bimane 
• 76421-60-8 6-(4-Chloro-phenyl)-1,4,6-trimethyl-2,3-dioxo-3,5,6,7-tetrahydro-2H-2a,7b-diaza-6-azonia-cyclopenta[cd]indene; bromide 
• 76421-49-3 9,10-dioxa-μ-(4-methoxybenzyl)imino-syn-(methylene,methyl)bimane 
• 76421-68-6 9,10-dioxa-μ-methylthianio-syn-(methylene,methyl)bimane fluorosulfate 
• 71418-45-6 9,10-dioxa-syn-(trimethylammoniomethyl,methyl)(bromomethyl,methyl)bimane bromide 
• 76421-53-9 9,10-dioxa-μ-(4-cyanophenyl)imino-syn-(methylene,methyl)bimane 
• 76421-48-2 9,10-dioxa-μ-benzylimino-syn-(methylene,methyl)bimane 
• 76421-96-0 9,10-dioxa-syn-(N-phenyl-N-methylaminomethyl,methyl)bimane 
• 76421-56-2 9,10-dioxa-μ-<4-(carboethoxy)phenyl>imino-syn-(methylene,methyl)bimane 
• 76421-51-7 9,10-dioxa-μ-(4-methoxyphenyl)imino-syn-(methylene,methyl)bimane 
• 76421-55-1 9,10-dioxa-μ-(4-chlorophenyl)imino-syn-(methylene,methyl)bimane 
• 76421-52-8 9,10-dioxa-μ-(4-methylphenyl)imino-syn-(methylene,methyl)bimane 
• 74317-61-6 9,10-dioxa-μ-thia-syn-(methylene,methyl)bimane 
• 76421-61-9 1,4,6-Trimethyl-2,3-dioxo-6-p-tolyl-3,5,6,7-tetrahydro-2H-2a,7b-diaza-6-azonia-cyclopenta[cd]indene; bromide 

Relevant articles and documents

Bimane: A Visible Light Induced Fluorescent Photoremovable Protecting Group for the Single and Dual Release of Carboxylic and Amino Acids

A series of ester conjugates of carboxylic and amino acids were synthesized based on bimane fluorescent photoremovable protecting group (FPRPG). The photorelease of single and dual (same as well as different) carboxylic and amino acids is demonstrated from a single bimane molecule on irradiation with visible light (λ ≥ 410 nm). The detailed mechanistic study of photorelease revealed that the release of two caged acids is simultaneous but in a stepwise pathway.

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.