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Home > Encyclopedia > 4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine

4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine

4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine structure

4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine 

structure
  • CAS No:

    3248-93-9

  • Formula:

    C20H19N3

  • Chemical Name:

    4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine

  • Synonyms:

    Benzenamine,4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methyl-;C.I. Solvent Red 41;C.I. Basic Violet 14,free base;4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine;C.I. 42510B;Brilliant Oil Crimson Base;Fuchsine HF Base;Rosaniline Base;Waxoline Red A;Fuchsine base;Magenta base;4-(4-Aminophenyl(4-iminocyclohexa-2,5-dienylidene)methyl)-2-methylaniline;714902-45-1

  • Categories:

    Dyes and Pigments  >  Dye

Description

ChEBI: An imine that is 4-methylidenecyclohexa-2,5-dien-1-imine in which the hydrogens of the methylidene group are replaced by 4-aminophenyl and 3-methyl-4-aminophenyl groups. The monohydrochloride salt is the histological dye 'rosanilin'.


Rosanilin free base is an imine that is 4-methylidenecyclohexa-2,5-dien-1-imine in which the hydrogens of the methylidene group are replaced by 4-aminophenyl and 3-methyl-4-aminophenyl groups. The monohydrochloride salt is the histological dye 'rosanilin'. It has a role as a histological dye, a fluorochrome and a carcinogenic agent. It is an imine and a substituted aniline. It is a conjugate base of a rosanilin(1+).

4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine Basic Attributes

301.38

301.39

221-832-2

I8F3948441

DTXSID0043844

2925290090

Characteristics

75.89000

6.17120

1.0962 (rough estimate)

268-270°C decomposes

570.8ºC at 760 mmHg

299ºC

1.6000 (estimate)

ALMOST INSOL IN ETHER /MAGENTA/

Safety Information

III

6.1

UN 2811 6.1/PG III

ZE9705000

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1. ...COMPETENT ENGINEERING... 2. ...ADEQUATE VENTILATION; 3. DAILY CHANGES OF FRESHLY LAUNDERED CLOTHING...& SHOWER BATH... @ END OF...WORK PERIOD; 4. ...MEDICAL DEPT FOR INSPECTION @ END OF...SHIFT; 5. INDIVIDUALS SHOWING GROSS EVIDENCE OF CYANOSIS...KEPT UNDER OBSERVATION. /AROMATIC AMINO COMPD/|6. WORKMEN SHOULD NEVER BE PERMITTED TO ENTER A VESSEL... UNTIL DEGREE OF ATMOSPHERIC CONCN HAS BEEN QUANT EST BY PLANT HYGIENIST; 7. ... COMPLETE PHYSICAL EXAM INCL HEMOGLOBIN DETERMINATIONS, RED, WHITE, & DIFFERENTIAL COUNTS, & COMPLETE URINALYSIS, EVERY 6 MO OR OFTENER. /AROMATIC AMINO COMPD/

Toxicity

MAGENTA HAS NOT BEEN REPORTED TO OCCUR AS SUCH IN NATURE. /MAGENTA/

...IT IS NOT POSSIBLE TO INDICATE WHETHER INDUSTRIAL BLADDER CANCER FOUND IN MAGENTA WORKERS IS ATTRIBUTABLE TO EXPOSURE TO MAGENTA ITSELF, OR TO ONE OR MORE OF ITS ASSOCIATED INTERMEDIATES & IMPURITIES. /MAGENTA/|...SHOWED THAT THERE WAS HIGHLY SIGNIFICANT RISK OF CONTRACTING BLADDER CANCER AMONG MEN ENGAGED IN MANUFACTURING, BUT NOT IN PURIFYING OR USING, MAGENTA. /MAGENTA/|THE MFR OF MAGENTA HAS CARRIED A CARCINOGENIC SUBSTANCES REGULATIONS 1967, BUT THERE APPEARS TO BE NO FIRM EVIDENCE THAT MAGENTA ITSELF IS CARCINOGENIC. /MAGENTA/

Drug Information

BASIC FUCHSIN...IS STILL MARKETED IN MIXT CONTAINING 0.3% BASIC FUCHSIN FOR TREATMENT OF TINEA PEDIS & TINEA CAPITIS.

CATIONIC DYES ARE WELL KNOWN TO BIND TO NUCLEIC ACIDS. /CATIONIC DYES/|CATIONIC DYES APPEAR TO HAVE SPECIAL ATTRIBUTE OF NITROGEN ATOM WHICH IS PART OF RESONANT SYSTEM RESPONSIBLE FOR COLOR, & WHICH APPEARS TO BE ASSOC WITH PROPENSITY TO VERY STRONG BINDING TO CARBOXYL GROUPS OF CORNEAL MUCOPROTEINS. /CATIONIC DYES/

IN TREATMENT OF EYES CONTAMINATED WITH CATIONIC DYES, FIRST AID MEASURES... INCLUDES COPIOUS IRRIGATION, MECHANICAL REMOVAL OF PARTICLES, & IN CASE OF IMBEDDED COLORED PENCIL MAY NECESSITATE SURGICAL EXPLORATION & CAREFUL REMOVAL OF PARTICLES. /CATIONIC DYES/

OF 85 MEN KNOWN TO HAVE BEEN ENGAGED IN MANUFACTURING MAGENTA...THERE WERE 5 CASES OF BLADDER CANCER. THREE OF THESE WERE RECORDED AS DYING OF BLADDER CANCER, WHEREAS ONLY 0.13 CASES WOULD HAVE BEEN EXPECTED (RELATIVE RISK= 23.0; P LESS THAN 0.005). /MAGENTA/

2-methyl-4,4'-((4-imino-2,5-cyclohexadien-1-ylidene)methylene)dianiline

4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine Use and Manufacturing

Methods of Manufacturing

OXIDATION OF A MIXTURE OF ANILINE, O(AND P)-TOLUIDINE & THEIR HYDROCHLORIDES WITH NITROBENZENE, OR A MIXTURE OF NITROBENZENE & O-NITROTOLUENE, IN PRESENCE OF FERROUS CHLORIDE, FERROUS OXIDE & ZINC CHLORIDE, FOLLOWED BY NEUTRALIZATION TO THE FREE BASE

Uses

AS DYE OR DYE INTERMEDIATE, COLORING TEXTILE FIBERS, FABRICS, PAPER PRODUCTS, TO DYE COTTON, WOOL, JUTE FIBERS, CHINA CLAY PRODUCTS, LEATHER; IN PRINTING INKS, AS A FILTER DYE IN PHOTOGRAPHY; BIOLOGICAL STAIN; LAB REAGENT, IN THIN-LAYER CHROMATOGRAPHY /MAGENTA/|DYE FOR OILS, FATS, WAXES (ESPECIALLY FOR POLISHES); DYE FOR CARBON PAPERS AND BALL POINT PEN INKS|MEDICATION

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

ESSENTIALLY 100% AS A DYE

A SYNTHETIC ROSANILINE DYESTUFF, A MIXTURE OF ROSANILINE & PARAROSANILINE HYDROCHLORIDES. ... GRADE NF.|MAGENTA, AS COMMERCIAL MATERIAL, IS MIXTURE OF...MAGENTA I, PARA-MAGENTA, & SMALL AMT OF MAGENTA II. MAGENTA...AVAILABLE IN US AS BASIC FUCHSIN NF... /CONTAINING/ A MAX LIMIT OF 8 PPM OF ARSENIC & 30 PPM OF LEAD (AMERICAN PHARMACEUTICAL ASSOC, 1970). /MAGENTA/

Benzenamine, 4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methyl-: ACTIVE

SPECTROPHOTOMETRIC METHODS ARE DESCRIBED...INDIVIDUAL BUT ABSORPTION MAXIMA DIFFER SLIGHTLY FOR INDIVIDUAL COMPONENTS OF MAGENTA. /MAGENTA/

Computed Properties

Molecular Weight:301.4
XLogP3:3.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:301.157897619
Monoisotopic Mass:301.157897619
Topological Polar Surface Area:75.9
Heavy Atom Count:23
Complexity:515
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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