3,3'-Diaminobenzidine
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Basic information
- CAS
91-95-2- Standard SMILES
Nc1ccc(-c2ccc(N)c(N)c2)cc1N- InChIKey
HSTOKWSFWGCZMH-UHFFFAOYSA-N- Molecular formula
- C12H14N4
- Average molar mass
- 214.27 g/mol
- Monoisotopic mass
- 214.12184646
Overview
3,3'-diaminobenzidine is a member of the class of biphenyls that is benzidine in which one of the hydrogens ortho to each of the amino groups has been replaced by an amino group. It has a role as a histological dye. It is a member of biphenyls and a substituted aniline.
Names & identifiers
- Preferred name
- 3,3'-Diaminobenzidine
- IUPAC
- 4-(3,4-diaminophenyl)benzene-1,2-diamine
- English name
- 3,3'-Diaminobenzidine
- Molecular formula
- C12H14N4
- Molecular weight
- 214.27
Names & synonyms
3,3'-Diaminobenzidine91-95-23,3-DIAMINOBENZIDINE3,3',4,4'-Tetraaminobiphenyl3,3',4,4'-Biphenyltetramine3,3',4,4'-Tetraaminodiphenyl3,3',4,4'-Diphenyltetramine3,3',4,4'-Tetraminobiphenyl[1,1'-Biphenyl]-3,3',4,4'-tetramineBiphenyl-3,3',4,4'-tetrayltetraamine(1,1'-Biphenyl)-3,3',4,4'-tetramineDTXSID2036827
Show more names
DABDIAMINOBENZIDINE[1,1'-biphenyl]-3,3',4,4'-tetraaMineTETRAAMINOBIPHENYL3,3'DAB BUFFERJACS-91-95-2TIMTEC-BB SBB0084273'-DiaMinobenzidine3,3'-Diaminobenzidin
2RV4T6KHQIDiaminobenzidine, 3,3NSC-76152DTXCID0016827CHEBI:909943,3 Diaminobenzidine3,3' diaminobenzidineDiaminobenzidine, 3,3'
Database identifiers
- CAS
91-95-2
Properties
Computed structural propertiesFilling in
- XLogP
- 0.9
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 209
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Benzidine and Derivatives
LogP0.09
SolubilitySolubility in water: very poor
Flash Point>200 °C
Melting Point176 °C
Physical Description
Dry Powder
Red to brown hygroscopic solid; [ICSC]
RED-TO-BROWN HYGROSCOPIC SOLID IN VARIOUS FORMS.
Autoignition Temperature560 °C
Physicochemical properties
- Melting point
- 175 · 175-177 °C(lit.)
- Boiling point
- 344.41 °C · 344.41°C (rough estimate)
- Density
- 1.1726 · 1.1726 (rough estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Danger
H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Hazard Traits - Carcinogenicity
[1,1'-Biphenyl]-3,3',4,4'-tetramine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of [1,1'-Biphenyl]-3,3',4,4'-tetramine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Biphenyl-3,3',4,4'-Tetrayltetraamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Fire HazardsCombustible.
Hazards Summary
Causes muscle weakness, cyanosis, and urine changes in inhalation lethal-dose study of rats; [RTECS] May cause eye irritation; A possible human carcinogen; [ICSC] May cause irritation; Possible teratogen and carcinogen; [Aldrich MSDS] See Benzidine.
Chemical DangersDecomposes on burning. This produces nitrogen oxides. Reacts with strong oxidants.
Hazard Classes and Categories
Muta. 2 (100%)
Carcinogenicity - category 1B
Carc. 1B
Safety & protection
Chemistry & industry
Uses & manufacturing
UsesUsed as a reagent; [REPROTOX]
U.S. Production2023: 140,461 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
General Manufacturing Information
Textiles, apparel, and leather manufacturing
[1,1'-Biphenyl]-3,3',4,4'-tetramine: ACTIVE
Applications
Description3,3'-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.
Uses3,3'-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.
Preparation methods
Preparation15 kg of 98.5% pure 3,3'-dinitro-4,4'-diaminobiphenyl tide product and 45 kg of methanol,0.075 kg of palladium carbon is mixed, and hydrogen gas of 0.85-0.9 MPa is introduced at 55-60 ° C, and stirred for 3 hours.At the end of the reaction, the catalyst was recovered, methanol was recovered, 30 kg of water was added, and the mixture was centrifuged and dried to obtain 9.3 kg of 3,3'-Diaminobenzidine having a purity of 99.3%.The yield was 90.6% (based on 3,3'-dinitro-4,4'-diacetylaminobiphenyl).
Related reactions
23 records
Compound notes
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