Benzidine

Base Information

• Chemical Name: Benzidine
• CAS No.: 92-87-5
• Deprecated CAS: 46310-07-0,56481-94-8,56481-94-8
• Molecular Formula: C12H12N2
• Molecular Weight: 184.241
• Hs Code.: 29215900
• European Community (EC) Number: 202-199-1
• ICSC Number: 0224
• NSC Number: 146476
• UN Number: 1885
• UNII: 2X02101HVF
• DSSTox Substance ID: DTXSID2020137
• Nikkaji Number: J3.933K
• Wikipedia: Benzidine
• Wikidata: Q410066
• NCI Thesaurus Code: C44335
• Metabolomics Workbench ID: 49570
• ChEMBL ID: CHEMBL15901
• Mol file: 92-87-5.mol

Synonyms:benzidine;benzidine acetate;benzidine dihydrochloride;benzidine hydrochloride;benzidine monosulfate

Chemical Property of Benzidine

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 2.5E-05mmHg at 25°C
• Melting Point: 127-128 °C
• Refractive Index: 1.667
• Boiling Point: 358.7 °C at 760 mmHg
• PKA: 4.66(at 30℃)
• Flash Point: 203.5 °C
• PSA: 52.04000
• Density: 1.156 g/cm³
• LogP: 3.68040
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol (U.S. EPA, 1985) and ether (1 g/50 mL) (Windholz et al., 1983)
• Water Solubility.: Sparingly soluble.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 145
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Benzidine,95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F,Xn
• Hazard Codes: T,N,F,Xn
• Statements: 45-22-50/53-52/53-39/23/24/25-23/24/25-11-36/37/38-20/21/22-51/53-67
• Safety Statements: 53-45-60-61-36/37-16-7-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Benzidine and Derivatives
• Canonical SMILES: C1=CC(=CC=C1C2=CC=C(C=C2)N)N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Long Term Exposure: This substance is carcinogenic to humans.
• Uses: Important dye intermediates, benzidine and its derivatives can be used to make direct dyes, acid dyes, vat dyes, ice dyed dyes, sulfur dyes, reactive dyes and organic pigments. More than 250 dyes are made from benzidine, of which the most important is the direct black EW. The benzidine yellow is a widely used organic pigment. Benzidine was used extensively in the manu facture of dyes. Because of its cancer-causingeffects in humans, its application in dyes hasbeen curtailed. Other uses of this compoundare in chemical analysis: as a reagent for thedetermination of hydrogen peroxide in milkand in the analysis of nicotine. Its hydrochlo ride is used as a reagent to analyze metalsand sulfate. Manufacture of dyestuffs; hardener for rubber; laboratory reagent Potentially mutagenic compound.
• Description: Benzidine is a white, greyish-yellow, or slightly reddish crystalline solid or powder. The major use for benzidine is in the production of dyes, especially azo dyes in the leather, textile, and paper industries and as a synthetic precursor in the preparation and manufacture of dyestuffs. It is also used in the manufacture of rubber, as a reagent, and as a stain in microscopy. It is slightly soluble and slowly changes from a solid to a gas.
• Physical properties: Grayish-yellow to pale reddish powder or crystals. Darkens on exposure to air or light. Odorless.

Technology Process of Benzidine

There total 209 articles about Benzidine 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: 55.0%

p-nitrobenzene iodide (636-98-6) → p,p'-diaminobiphenyl (92-87-5) + p-aminoiodobenzene (540-37-4)

Guidance literature:

With hydrazine hydrate; In ethanol; at 70 ℃; for 4h; chemoselective reaction;

DOI:10.1016/j.apcata.2016.04.004

Reference yield: 48.0%

nitrobenzene (98-95-3,26969-40-4) → aniline (62-53-3) + Azobenzene (1227476-15-4) + p,p'-diaminobiphenyl (92-87-5)

Guidance literature:

With lithium aluminium tetrahydride; titanium tetrachloride; In diethyl ether; at 20 ℃; for 15h; Solvent; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.07.089

Reference yield: 40.0%

4-bromo-aniline (106-40-1) + zinc (7440-66-6) → NH2C6H4ZnBr (301300-48-1) + aniline (62-53-3) + p,p'-diaminobiphenyl (92-87-5)

Guidance literature:

With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; In acetonitrile; the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;

DOI:10.1021/ja0289494

upstream raw materials:

pyridine

4,4'-Bis-(N'-phenyl-hydrazino)-biphenyl

acetic acid

p-nitrobenzene iodide

Downstream raw materials:

N,N'-biphenyl-4,4'-diyl-bis-acetoacetamide

4,4'-bis-(2-pyridinethiocarboxamido)-biphenyl

1,1'-biphenyl-4,4'-diyl-bis-pyrrolidin-2-one

difurfurylidene-benzidine

Refernces

• 1、 Bloink,Pausacker. "-". . p. 950,951, 952, 953. Retrieved 1950.
• 2、 Khan, Mohammad Naved,Bashir, Ommer,Khan, Tabrez Alam,Al-Thabaiti, Shaeel Ahmed,Khan, Zaheer. "Catalytic Activity of Cobalt Nanoparticles for Dye and 4-Nitro Phenol Degradation: A Kinetic and Mechanistic Study". . p. 438 - 454. Retrieved 2017.
• 3、 Hughes,Ingold. "-". . p. 608. Retrieved 1941.
• 4、 McConnell, Anna J.,Aitchison, Catherine M.,Grommet, Angela B.,Nitschke, Jonathan R.. "Subcomponent Exchange Transforms an FeII4L4 Cage from High- to Low-Spin, Switching Guest Release in a Two-Cage System". . p. 6294 - 6297. Retrieved 2017.
• 5、 Pizarro,Molina,Rodriguez. "Decoloration of azo and triarylmethane dyes in the aqueous phase by catalytic hydrotreatment with Pd supported on pillared clays". . p. 113820 - 113825. Retrieved 2016.
• 6、 Prasanna,Bhat, Shrikanth K.,Usha,Hegde. "Ligand and Base Free Synthesis of Biaryls from Aryl Halides in Aqueous Media with Recyclable Ti0.97Pd0.03O1.97 Catalyst". . p. 3313 - 3322. Retrieved 2021/03/04.
• 7、 Meng, Xiangzhi,Klaasen, Henning,Viergutz, Lena,Schulze Lammers, Bertram,Witteler, Melanie C.,M?nig, Harry,Amirjalayer, Saeed,Liu, Lacheng,Neugebauer, Johannes,Gao, Hong-Ying,Studer, Armido,Fuchs, Harald. "Azo bond formation on metal surfaces". supporting information. p. 1458 - 1464. Retrieved 2020/12/14.