Dibromobimane

Base Information

• Chemical Name: Dibromobimane
• CAS No.: 68654-25-1
• Molecular Formula: C10H10 Br2 N2 O2
• Molecular Weight: 350.00
• Hs Code.: 29339900
• European Community (EC) Number: 636-186-0
• NSC Number: 608550
• DSSTox Substance ID: DTXSID70218736
• Nikkaji Number: J777.662D
• Wikidata: Q27132207
• Metabolomics Workbench ID: 62448
• ChEMBL ID: CHEMBL2158899
• Mol file: 68654-25-1.mol

Synonyms:dibromobimane

Chemical Property of Dibromobimane

Chemical Property:

• Vapor Pressure: 1.01E-05mmHg at 25°C
• Melting Point: 170-172oC(lit.)
• Boiling Point: 371.8°Cat760mmHg
• PKA: -4.55±0.70(Predicted)
• Flash Point: 178.6°C
• PSA: 42.96000
• Density: 1.98g/cm³
• LogP: 1.60360
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 349.90885
• Heavy Atom Count: 16
• Complexity: 414

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dibromobimane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• 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)CBr)CBr
• Uses: A cross linking reagent for proteins, thiols in myosin, hemoglobin and mitochondrial ATPase multiple labeled product that can be fixed with aldehydes A cross linking reagent for proteins, thiols in myosin, hemoglobin and mitochondrial ATPase. Dibromobimane, a bifunctional thiol reagent, is used as a cross-linking agent for cysteine mapping and studies on protein structure/conformation and cross-linking processes.

Technology Process of Dibromobimane

There total 6 articles about Dibromobimane 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: 76.0%

9,10-dioxa-syn-(methyl,methyl)bimane (68654-22-8) → syn-4,6-bis(bromomethyl)-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione (68654-25-1)

Guidance literature:

With bromine; In dichloromethane; for 0.5h; Product distribution; Ambient temperature; other reaction time; chemical properties of 9,10-dioxabimanes: electrophylic reactions, reduction and oxidation, reactions with bases, thermal reactions;

DOI:10.1021/ja00535a028

Reference yield: 2.2%

9,10-dioxa-syn-(methyl,methyl)bimane (68654-22-8) → monobromobimane (71418-44-5) + syn-4,6-bis(bromomethyl)-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione (68654-25-1)

Guidance literature:

With bromine; In dichloromethane; Ambient temperature;

DOI:10.1021/ja00535a028

Reference yield:

2-acetylpropanoic acid ethyl ester (609-14-3) → syn-4,6-bis(bromomethyl)-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione (68654-25-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NH₂NH₂ / ethanol / 1 h / Heating

2: 73.1 percent / Cl₂ / 1,2-dichloro-ethane / Heating

3: 12.5 percent / hydrated potassium carbonate / CH₂Cl₂ / 12 h / Ambient temperature

4: 2.2 percent / Br₂ / CH₂Cl₂ / Ambient temperature

With bromine; chlorine; potassium carbonate; hydrazine; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja00535a028

upstream raw materials:

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

2-acetylpropanoic acid ethyl ester

3,4-dimethyl-4-chloro-2-pyrazolin-5-one

3,4-dimethyl-4-chloro-2-pyrazolin-5-one

Downstream raw materials:

9,10-dioxa-syn-bimane

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

9,10-dioxa-syn-(trimethylammoniomethyl,methyl)(bromomethyl,methyl)bimane bromide

9,10-dioxa-μ-methylthianio-syn-(methylene,methyl)bimane fluorosulfate

Refernces

• 1、 -. "Preparation process of acetic acid". . . Retrieved 2008/06/13.