3,3'-Diaminobenzidine

Base Information

• Chemical Name: 3,3'-Diaminobenzidine
• CAS No.: 91-95-2
• Deprecated CAS: 1458011-73-8
• Molecular Formula: C12H14N4
• Molecular Weight: 214.27
• Hs Code.: 29214200
• European Community (EC) Number: 202-110-6
• ICSC Number: 1666
• NSC Number: 76152
• UNII: 2RV4T6KHQI
• DSSTox Substance ID: DTXSID2036827
• Nikkaji Number: J3.927F
• Wikipedia: 3,3%27-Diaminobenzidine,3'-Diaminobenzidine
• Wikidata: Q4030650
• ChEMBL ID: CHEMBL1396955
• Mol file: 91-95-2.mol

Synonyms:3,3 Diaminobenzidine;3,3' Diaminobenzidine;3,3'-Diaminobenzidine;3,3-Diaminobenzidine;Diaminobenzidine, 3,3;Diaminobenzidine, 3,3'

Chemical Property of 3,3'-Diaminobenzidine

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 175-177 °C(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 481.7 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 282.7oC
• PSA: 104.08000
• Density: 1.307 g/cm³
• LogP: 4.00720
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: 0.55g/l
• Water Solubility.: 0.55 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 214.121846464
• Heavy Atom Count: 16
• Complexity: 209

Purity/Quality:

DAB ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F,O
• Statements: 36/37/38-40-22-20/21/22-68-45-67-37-34-11-8
• Safety Statements: 26-36/37-45-36/37/39-22-53-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Benzidine and Derivatives
• Canonical SMILES: C1=CC(=C(C=C1C2=CC(=C(C=C2)N)N)N)N
• Recent ClinicalTrials: Study to Evaluate the Effect of SCY-078 on the PK of Dabigatran in Healthy Subjects
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly.
• Effects of Short Term Exposure: May cause mechanical irritation to the eyes.
• Effects of Long Term Exposure: This substance is possibly carcinogenic to humans.
• Description: 3,3'-Diaminobenzidine (DAB) is a precursor to polybenzimidazole. DAB is frequently used in the immunohistochemical staining of nucleic acids and proteins. It can also be used to detect fingerprints in blood because that it can be oxidized by hydrogen peroxide in the presence of hemoglobin to give a dark-brown color.
• Uses: 3,3'-Diaminobenzidine is used as peroxidase substrate and a reagent for spectrophotometric determination of selenium. DAB is used for the immunohistochemical staining of nucleic acids and proteins. As a dark brown dye, was used as an antibody-specific stain to identify the paired antibodies in breast tissue. It may be used for the synthesis of a useful, linear, Schiff-base coordination polymer.

Technology Process of 3,3'-Diaminobenzidine

There total 14 articles about 3,3'-Diaminobenzidine 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: 93.1%

3,3'-dichlorobenzidine (91-94-1) → 3,3',4,4'-tetraaminobiphenyl (91-95-2)

Guidance literature:

With ammonium hydroxide; tetrabutyl-ammonium chloride; ammonia; copper dichloride; at 10 - 180 ℃; for 7.5h; under 20252 - 24002.4 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere; Autoclave;

Reference yield: 90.6%

3,3'-dinitrobenzidine (6271-79-0) → 3,3',4,4'-tetraaminobiphenyl (91-95-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 55 - 60 ℃; for 3h; under 6375.64 - 6750.68 Torr; Large scale;

Reference yield: 80.0%

3,3'-diamino-4,4'-dinitrobiphenyl (74959-03-8) → 3,3',4,4'-tetraaminobiphenyl (91-95-2)

Guidance literature:

With hydrogenchloride; tin(ll) chloride; In ethanol; at 0 ℃; for 10.5 - 12.5h; Heating / reflux;

upstream raw materials:

3,3'-dinitrobenzidine

hydrogenchloride

4-iodo-2-nitroaniline

2-nitro-aniline

Downstream raw materials:

Biphenyl-3,4,3',4'-tetraamine; compound with 2,4-dinitro-phenol

Biphenyl-3,4,3',4'-tetraamine; compound with 1,3,5-trinitro-benzene

2-Chloro-1,3,5-trinitro-benzene; compound with biphenyl-3,4,3',4'-tetraamine

Biphenyl-3,4,3',4'-tetraamine; compound with 1-methyl-2,4-dinitro-benzene

Refernces

• 1、 -. "Preparation method of 3,3',4,4'-tetraaminobiphenyl". Paragraph 0061-0076. . Retrieved 2021/06/09.
• 2、 Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.. "A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments". supporting information. p. 1403 - 1416. Retrieved 2013/02/23.