3,3'-Dimethoxybenzidine

Base Information

• Chemical Name: 3,3'-Dimethoxybenzidine
• CAS No.: 119-90-4
• Deprecated CAS: 59777-10-5
• Molecular Formula: C14H16N2O2
• Molecular Weight: 244.293
• Hs Code.: 29222990
• European Community (EC) Number: 204-355-4
• ICSC Number: 1582
• NSC Number: 3168
• UN Number: 2811,2431,3077
• UNII: MJY508JZXV
• DSSTox Substance ID: DTXSID3025091
• Nikkaji Number: J3.253K
• Wikipedia: O-Dianisidine
• Wikidata: Q222968
• NCI Thesaurus Code: C44365
• ChEMBL ID: CHEMBL398363
• Mol file: 119-90-4.mol

Synonyms:3,3' Dimethoxybenzidine;3,3'-Dimethoxybenzidine;Dianisidine;Dianisidine Dihydrochloride;Dianisidine Hydrochloride;Dianisidine Sulfate;Dihydrochloride, Dianisidine;Hydrochloride, Dianisidine;O Dianisidine;O-Dianisidine;Sulfate, Dianisidine

Chemical Property of 3,3'-Dimethoxybenzidine

Chemical Property:

• Appearance/Colour: Grey fine crystals
• Vapor Pressure: 2.49E-06mmHg at 25°C
• Melting Point: 137-138 °C(lit.)
• Refractive Index: 1.618
• Boiling Point: 391.3 °C at 760 mmHg
• PKA: 4.71±0.10(Predicted)
• Flash Point: 202.8 °C
• PSA: 70.50000
• Density: 1.178 g/cm³
• LogP: 3.69760
• Storage Temp.: Store at RT.
• Solubility.: H2O: slightly soluble
• Water Solubility.: Soluble in alcohol, benzene, ether, chloroform, acetone, most organic solvents and lipids. Slightly soluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 236
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

o-Dianisidine 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-22
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)OC)N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans.
• Uses: o-Dianisidine is used almost exclusively as a chemical intermediate for producing dyes and pigments. In 1971, the Society of Dyers and Colourists reported its use in the production of 89 dyes (see Dyes Metabolized to o-Dianisidine, below). o-Dianisidine is also used as a chemical intermediate to produce o-dianisidine diisocyanate for use in adhesives and as a component of polyurethanes. Other uses are as a dye for paper, plastics, rubber, and textiles and as a test substance for detection of metals, thiocyanates, and nitrites (IARC 1974, HSDB 2009). o-Dianisidine is a starting material for the production of disazo dyes and pigments. Like benzidine and o-tolidine, o-dianisidine forms colors with numerous oxidizing agents, e.g., copper, cobalt, and gold ions. o-Dianisidine is quantitatively determined by titration with nitrite using potassium iodide and starch paper as the indicator. o-Dianisidine can be detected in the urine using potassium 1,2-naphthoquinone4-sulfonate after extraction. A rapid and easy method is based on the color formed with cyanogen bromide. Its detection limit is 0.05 mg/kg. The free o-dianisidine base and the dihydrochloride are marketed in moist forms with a 10-30% water content. o-Dianisidine is used as a redox indicator. It is used as an intermediate for the preparation of azo dyes, pigments and o-dianisidine diisocyanate, which finds application in adhesives, polyurethane elastomers and resins. It is also used in various industries like leather, paper, plastics, rubber, and textiles. It acts as a reagent to detect metals, thiocyanates, and nitrites.

Technology Process of 3,3'-Dimethoxybenzidine

There total 9 articles about 3,3'-Dimethoxybenzidine 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: 60.3%

N,N'-bis-(2-methoxy-phenyl)-hydrazine (787-77-9) → 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine (119-90-4)

Guidance literature:

N,N'-bis-(2-methoxy-phenyl)-hydrazine; With hydrogenchloride; In water; at 30 - 90 ℃; for 2h;

With water; sodium hydroxide; pH=9 - 10;

Reference yield:

2,2'-dimethoxyazoxybenzene (13620-57-0) → 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine (119-90-4) + 2-methoxy-phenylamine (90-04-0)

Guidance literature:

Reference yield:

2-Nitroanisole (91-23-6) → 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine (119-90-4)

Guidance literature:

With sodium hydroxide; palladium; isopropyl alcohol; at 50 - 60 ℃; und Behandeln der abgekuehlten Reaktionsloesung mit wss.Salzsaeure;

upstream raw materials:

2-Nitroanisole

N,N'-bis-(2-methoxy-phenyl)-hydrazine

2,2'-dimethoxyazobenzene

2,2'-dimethoxyazoxybenzene

Downstream raw materials:

3,3'-dimethoxy-N,N'-bis-(pyridine-2-thiocarbonyl)-benzidine

N,N'-bis-(4'-amino-3,3'-dimethoxy-biphenyl-4-yl)-urea

N,N,N'N'-Tetrakis--3,3'-dimethoxy-benzidin

{4'-[Bis-(3-dimethylamino-phenoxy)-thiophosphorylamino]-3,3'-dimethoxy-biphenyl-4-yl}-thiophosphoramidic acid O,O'-bis-(3-dimethylamino-phenyl) ester

Refernces

• 1、 Sharma, Laxmi Kant,Kumar, Sanjeev,Singh,Siddiqui. "Electrochemical oxidation of o-anisidine, p-anisidine, diphenylamine and o-toluidine at platinum electrode". experimental part. p. 1117 - 1123. Retrieved 2011/05/05.
• 2、 -. "Basic azo dyestuffs of the 3-cyano-2,4,6-triamino pyridine series". . . Retrieved 2008/06/13.