Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > 4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine]

4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine]

4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine] structure

4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine] 

structure
  • CAS No:

    479-73-2

  • Formula:

    C19H17N3

  • Chemical Name:

    4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine]

  • Synonyms:

    Benzenamine,4,4′-[(4-imino-2,5-cyclohexadien-1-ylidene)methylene]bis-;C.I. Basic Red 9;Benzenamine,4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-;4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine];Homolka's Base;775235-15-9

  • Categories:

    Organic Chemistry  >  Amides

Description

ChEBI: An imine that is 4-methylidenecyclohexa-2,5-dien-1-imine in which both the hydrogens of the methylidene group are replaced by 4-aminophenyl groups. The hydrochloride salt is the histological dye 'pararosaniline'.


Pararosaniline free base is an imine that is 4-methylidenecyclohexa-2,5-dien-1-imine in which both the hydrogens of the methylidene group are replaced by 4-aminophenyl groups. The hydrochloride salt is the histological dye 'pararosaniline'. It has a role as a fluorochrome and a histological dye. It is a substituted aniline and an imine. It is a conjugate base of a pararosaniline(1+).

4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine] Basic Attributes

287.366

287.36

610-397-8

20N4C0M8NM

DTXSID5043845

COLORLESS TO RED CRYSTALS|Dark-green crystalline powder

Characteristics

75.9

-0.21

268-270 deg C (decomposes)

soluble in water (2-3 mg/ml), ethanol (2-25 mg/ml) ethylene glycol methyl ether (50-70 mg/ml) and methanol

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

CATIONIC|Destroyed by strong oxidizing agents; readily reduced to leuco-bases with a variety of reducing reagents sensitive to photochemical oxidation

Safety Information

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for C.I. BASIC RED 9 (6 total), please visit the HSDB record page.

DHHS/NTP; Toxicology & Carcinogenesis Studies of C.I Basic Red 9 Monohydrochloride (Pararosaniline) in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 285 (1986) NIH Publication No. 86-2541|National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. C.I. Basic Red 9 Monohydrochloride (569-61-9) is listed as reasonably anticipated to be a human carcinogen. /C.I. Basic Red 9 Monohydrochloride/[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s046ciba.pdf]

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

COMBUSTIBLE.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for C.I. BASIC RED 9 (9 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Toxicity

...0.01 MOLAR NEAR-NEUTRAL SOLN OF PARAROSANILINE...AFTER...BEEN REDUCED & RENDERED...COLORLESS BY ADDITION OF 1% TO 2% SODIUM HYDROSULFITE CAUSE RELATIVELY SLIGHT CORNEAL OPACIFICATION...WHEREAS...WITHOUT REDUCTION CAUSE SEVERE OPACIFICATION & VASCULARIZATION.

... Toxicology and carcinogenesis studies were conducted by administering the test chemical in feed to groups of 50 male and 50 female F344/N rats and B6C3F1 mice for 103 wk at concentrations of 0, 1,000 or 2,000 ppm for male rats and 0, 500 or 1,000 ppm for female rats and mice of each sex. The avg daily doses of C.I. Basic Red 9 monohydrochloride were estimated to be 49 and 103 mg/kg for male rats, 28 and 59 mg/kg for female rats, 196 and 379 mg/kg for male mice, and 149 and 407 mg/kg for female mice. Two lots of the test chemical were used in the 2 yr studies with purities of 93% (water content approx 9%) and 99%. ... Under the conditions of these 2 yr feed studies, there was ... evidence of carcinogenicity of C.I. Basic Red 9 monohydrochloride in male and female F344/N rats and in male and female B6C3F1 mice. In male rats, /the cmpd/ caused squamous cell carcinomas, trichoepitheliomas and sebaceous adenomas of the skin, subcutaneous fibromas, thyroid gland follicullar cell adenomas and follicular cell carcinomas, Zymbal gland carcinomas, and hepatocellular carcinomas. In female rats, /the cmpd/ caused subcutaneous fibromas, thyroid gland follicular cell adenomas or carcinomas (combined), and Zymbal gland carcinomas. In male mice, /the cmpd/ caused hepatocellular carcinomas. In female mice, /the cmpd/ caused hepatocellular carcinomas and adrenal gland pheochromocytomas or malignant pheochromocytomas (combined). ...

Drug Information

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)|Agents employed in the preparation of histologic or pathologic specimens for the purpose of maintaining the existing form and structure of all of the constituent elements. Great numbers of different agents are used; some are also decalcifying and hardening agents. They must quickly kill and coagulate living tissue. (See all compounds classified as Fixatives.)

4-((4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl)benzeneamine monohydrochloride

4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine] Use and Manufacturing

Methods of Manufacturing

REACTION OF ANILINE WITH FORMALDEHYDE, IN THE PRESENCE OF HYDROGEN CHLORIDE, FORMING P,P'-METHYLENEDIANILINE, WHICH IS THEN HEATED WITH ANILINE AND ANILINE HYDROCHLORIDE IN THE PRESENCE OF NITROBENZENE AND FERRIC CHLORIDE

Uses

DYE FOR TEXTILES (SILKS & ACRYLICS), LEATHER, & PAPER; COMPONENT OF MAGENTA (FUCHSIN) DYE; BIOLOGICAL STAIN|For staining bacilli, especially influenza and tubercle, in tissue and for acid-fast bacteria using methylene blue as counterstain.|For staining tubercle bacillus and in distinguishing between the coli and aerogenes types of bacteria in the Endo medium; also used in the periodic acid-Schiff (PAS) method, the Feulgen stain, and in Gomoris aldehyde- function method for staining elastic tissue|Have been used extensively as textile dyes...current use is mainly for non- textile purposes...such as printing inks, high-speed photoduplicating and photoimaging systems; specialty applications such as tinting automobile antifreeze solutions and toilet sanitary preparations, in the mfg of carbon paper, in ink and typewriter ribbons and in jet printing for high-speed computer printers; may be used to color other substrates; extensively used as microbiological stains /Triarylmethane dyes including Basic Parafuchsine/|Can be N-phenylated with excess aniline and benzoic acid to form CI Solvent Blue 23

Production

(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1992) No data|The 1977 production estimate was 1-10 million lbs

Available commercially as a certified biological stain at a purity of approximately 95%; it is also available at a purity of at least 88%|A mixture of three parts pararosaniline acetate and one part pararosaniline hydrochloride|Certifiable grade

Benzenamine, 4,4'-[(4-imino-2,5-cyclohexadien-1-ylidene)methylene]bis-, hydrochloride (1:1): ACTIVE|A TRIPHENYLMETHANE DYE. ... COMPONENT OF FUCHSIN.|BASIC FUCHSIN NF XIII [BASIC MAGENTA]- A MIXTURE OF ROSANILINE & PARAROSANILINE HYDROCHLORIDE. ... POSSESSES MODERATE ANTIFUNGAL & ANTIBACTERIAL ACTIVITY.|Produced by one company in Brazil and by two companies in the US (companies not reported)|No recent data available (1993) on production of CI Basic Red 9

A rapid method for assay (Knecht method) is titration with titanium trichloride to a colorless end-point

Computed Properties

Molecular Weight:287.4
XLogP3:3.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:287.142247555
Monoisotopic Mass:287.142247555
Topological Polar Surface Area:75.9
Heavy Atom Count:22
Complexity:457
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of 4,4′-[(4-Imino-2,5-cyclohexadien-1-ylidene)methylene]bis[benzenamine]

  • China CN

    5 YRS

    Business licensed Certified factory
    Manufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed Additive
    CAS No.: 479-73-2
    Grade: Industrial Grade
    Content: 99%
    Inquiry

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.