3,3'-Diaminobenzidine (HCID 7071)

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member of the class of biphenyls that is benzidine in which one of the hydrogens ortho to each of the amino groups has been replaced by an amino group.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'-tetramine(1,1'-Biphenyl)-3,3',4,4'-tetramineDTXSID2036827Biphenyl-3,3',4,4'-tetrayltetraamine

Show more names

DABDIAMINOBENZIDINE[1,1'-biphenyl]-3,3',4,4'-tetraaMineTETRAAMINOBIPHENYL3,3'DAB BUFFERJACS-91-95-2TIMTEC-BB SBB0084273'-DiaMinobenzidine3,3'-Diaminobenzidin

2RV4T6KHQINSC-76152DTXCID0016827CHEBI:909943,3 Diaminobenzidine3,3' diaminobenzidineDiaminobenzidine, 3,3Diaminobenzidine, 3,3'

Database identifiers

CAS: 91-95-2
PubChem CID: 7071
DTXSID: DTXSID2036827
ChEMBL: CHEMBL1396955
ChEBI: CHEBI:90994
UNII: 2RV4T6KHQI
EC Number: 202-110-6
Nikkaji: J3.927F

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 104 Å²
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 · 3 items

Dry Powder

Red to brown hygroscopic solid; [ICSC]

RED-TO-BROWN HYGROSCOPIC SOLID IN VARIOUS FORMS.

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)
refractive index: 1.5 · 1.5000 (estimate)
Flash point: 12 °C · 12 °C
storage temp.: room temp
solubility: 0.55 g/l · 0.55g/l
form: tablet
pka: 4.39 · 4.39±0.10(Predicted)
color: Crystals from MeOH
PH: 7 · 7 (1g/l, H2O, 20℃)
Water Solubility: 0.55 g/L · 0.55 g/L (20 ºC)
Sensitive: Light Sensitive
BRN: 1212988 · 1212988
Stability: Moisture and light sensitive. Incompatible with strong oxidizing agents.
Major Application: diagnostic assay manufacturinghematologyhistology
InChI: 1S/C12H14N4/c13-9-3-1-7(5-11(9)15)8-2-4-10(14)12(16)6-8/h1-6H,13-16H2
InChIKey: HSTOKWSFWGCZMH-UHFFFAOYSA-N
SMILES: NC1=C(N)C=CC(C2=CC(N)=C(N)C=C2)=C1
CAS DataBase Reference: 91 · 91-95-2(CAS DataBase Reference)
FDA UNII: 2 RV4T6KHQI · 2RV4T6KHQI
NIST Chemistry Reference: 3 · 3,3'-Diaminobenzidine(91-95-2)
EPA Substance Registry System: 3 · 3,3'-Diaminobenzidine (91-95-2)
UNSPSC Code: 12352204 · 12352204
NACRES: 83 · NA.83
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 302 · H302-H319-H341-H350
Precautionary statements: 202 · P202-P264-P270-P301+P312-P305+P351+P338-P308+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn,T,F,O
Risk Statements: 36 · 36/37/38-40-22-20/21/22-68-45-67-37-34-11-8
Safety Statements: 26 · 26-36/37-45-36/37/39-22-53-16
RIDADR: 3316 · UN 3316 9
WGK Germany: 1 · 1
RTECS: 8750000 · DV8750000
F: 8 · 8-10-23
TSCA: TSCA listed
HS Code: 29214200 · 29214200
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 4 OralCarc · Acute Tox. 4 OralCarc. 1BEye Irrit. 2Muta. 2
Toxicity: 3000 mg/kg · LDLo orl-rat: 3000 mg/kg CNREA8 26,619,66

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 2 items

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)

Fire HazardsCombustible.

Hazards Summary · 1 item

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 · 3 items

Muta. 2 (100%)

Carcinogenicity - category 1B

Carc. 1B

Safety & protection

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Safe StorageDry. Well closed. Separated from food and feedstuffs and strong oxidants. Store in an area without drain or sewer access.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Eye PreventionWear safety spectacles.

Fire PreventionNO open flames.

Toxicology

Exposure RoutesThe substance can be absorbed into the body in hazardous amounts by inhalation of its aerosol and by ingestion.

Signs and SymptomsRedness.

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.

Toxicity DataLCLo (rat) = 260 mg/m3/4hr

Safety data

F: 8-10-23
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 1
tsca: TSCA listed
rtecs: DV8750000
ridadr: UN 3316 9
hs_code: 29214200
Toxicity: LDLo orl-rat: 3000 mg/kg CNREA8 26,619,66
risk_code: 36/37/38-40-22-20/21/22-68-45-67-37-34-11-8
Signal word: Danger
Symbol(GHS): GHS07,GHS08
hazard_code: Xn,T,F,O
safety_code: 26-36/37-45-36/37/39-22-53-16
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements: H302-H319-H341-H350
Hazard Classifications: Acute Tox. 4 OralCarc. 1BEye Irrit. 2Muta. 2
Precautionary statements: P202-P264-P270-P301+P312-P305+P351+P338-P308+P313

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 · 2 items

Textiles, apparel, and leather manufacturing

[1,1'-Biphenyl]-3,3',4,4'-tetramine: ACTIVE

Applications · 2 items

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 · 1 item

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).

Upstream & downstream products

Upstream raw materials

Benzidine

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 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.