3,3'-Diaminobenzidine Chemical Properties

Melting point:

175-177 °C(lit.)

Boiling point:

344.41°C (rough estimate)

Density 

1.1726 (rough estimate)

refractive index 

1.5000 (estimate)

Flash point:

12 °C

storage temp. 

room temp

solubility 

0.55g/l

form 

tablet

pka

4.39±0.10(Predicted)

color 

Crystals from MeOH

PH

7 (1g/l, H2O, 20℃)

Water Solubility 

0.55 g/L (20 ºC)

Sensitive 

Light Sensitive

BRN 

1212988

Stability:

Moisture and light sensitive. Incompatible with strong oxidizing agents.

InChIKey

HSTOKWSFWGCZMH-UHFFFAOYSA-N

CAS DataBase Reference

91-95-2(CAS DataBase Reference)

NIST Chemistry Reference

3,3'-Diaminobenzidine(91-95-2)

EPA Substance Registry System

3,3'-Diaminobenzidine (91-95-2)

Safety Information

Hazard Codes 

Xn,T,F,O

Risk 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

RIDADR 

UN 3316 9

WGK Germany 

1

RTECS 

DV8750000

F 

8-10-23

TSCA 

Yes

HS Code 

29214200

Toxicity

LDLo orl-rat: 3000 mg/kg CNREA8 26,619,66

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3,3'-Diaminobenzidine Usage And Synthesis

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.

Chemical Properties

Off-white to brown solid.

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.

Synthesis

3,3'-Diaminobenzidine can be synthesized by treating 3, 3'-dichlorobenzidine with ammonia in the presence of copper catalyst at high temperature and pressure.

Application

3,3'-Diaminobenzidine is used for preparation of high-strength material such as nucleic acid stain and resistance high-temperature polymers such as bullet-proof vests.?

Definition

ChEBI: 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member of the class of biphenyls that is benzidine in which one of the hydrogens ortho to each of the amino groups has been replaced by an amino group.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.

Application

3,3',4,4' -Tetraaminodiphenyl (3,3'-Diaminobenzidine) is suitable for the production of fibers based on polybenzimidazole. These fibers are resistant to high temperature and to chemicals. Fabrics made from them do not burn, do not melt in contact with a flame, and do not become hard when carbonized. They are suitable for the production of protective clothing and flue–gas filters and as substitutes for asbestos.

Preparation

15 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).

Biochem/physiol Actions

DAB (3,3′-Diaminobenzidine) is utilized in many applications for the visualization of peroxidase activity. In the peroxidase reaction, DAB serves as a hydrogen donor in the presence of peroxide. The oxidized DAB forms an insoluble brown end-product for use in the immunohistological and immunoblotting staining procedures.

Safety Profile

Suspected carcinogen withexperimental tumorigenic data. Moderately toxic byingestion. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

References

3,3′-Diaminobenzidine staining interferes with PCR-based DNA analysis
DOI:10.1038/s41598-018-19745-9
Transition metal complexes of novel binuclear Schiff base derived from 3,3′-diaminobenzidine: synthesis, characterization, thermal behavior, DFT, antimicrobial and molecular docking studies
DOI:10.1080/00958972.2020.1752372
3, 3′-Diaminobenzidine with dual o-phenylenediamine groups: two in one enables visual colorimetric detection of nitric oxide
DOI:10.1007/s00216-020-02482-2
A new sensitive colorimetric assay for peroxidase using 3,3'-diaminobenzidine as hydrogen donor.
DOI:10.1016/0003-2697(73)90144-9

3,3'-Diaminobenzidine (91-95-2)Related Product Information

• Benzidine dihydrochloride
• trans-Bifenthtin
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• Benzidine
• Bifonazole
• Biphenyl
• Bifendate
• Pigment Yellow 12
• FIREMASTER BP-6
• 2,3,3',4,4',5-HEXACHLOROBIPHENYL
• 3,3',4,4'-Biphenyltetramine tetrahydrochloride
• 2,2'-OXYDIANILINE
• 3,3'-Diaminobenzidine tetrahydrochloride dihydrate,3,3μ-Diaminobenzidine dihydrate tetrahydrochloride,3,3'-DIAMINOBENZIDINE TETRAHYDROCHLORIDE HYDRATE
• 3,3'-Diaminobenzidine tetrahydrochloride hydrate
• 3,3′-DIAMINOBENZIDINE TABLETS
• 3,3'-Diaminobenzidine
• 3,3μ-Diaminobenzidine (DAB) Liquid Substrate System tetrahydrochloride
• 3,3' DIAMINOBENZIDINE-TETRAHYDROCHLORID