Basic information
- CAS
3248-93-9- Standard SMILES
CC1=CC(=C(c2ccc(N)cc2)c2ccc(N)cc2)C=CC1=N- InChIKey
YDCMWLQSPFTWCS-UHFFFAOYSA-N- Molecular formula
- C20H19N3
- Average molar mass
- 301.4 g/mol
- Monoisotopic mass
- 301.15789762
Overview
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 carcinogenic agent, a fluorochrome and a histological dye. It is an imine and a substituted aniline. It is a conjugate base of a rosanilin(1+).
Names & identifiers
- Preferred name
- Magenta Base
- IUPAC
- 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline
- English name
- Solvent Red 41
- Molecular formula
- C20H19N3
- Molecular weight
- 301.39
Names & synonyms
3248-93-9Solvent Red 41Fuchsine BaseRosaniline baseMAGENTA BASEWaxoline Red AFuchsive basepara-RosanilineC.I. Solvent Red 41CI Solvent Red 41Fuchsin (basic)Fuchsine HF Base
Show more names
ci42510bfuchsivebasefuchsinebaseMagenta Powdercisolventred41fuchsinehfbaseien-1-ylidene)-FUCHSIN,NEUTRAL
C.I. Basic Violet 14, free baseCI 42510BCI Basic Violet 41, free baseHSDB 2955EINECS 221-832-2BRN 2814815MAGENTA BASE [HSDB]Benzenamine, 4-((4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl)-2-methyl-
Database identifiers
- CAS
3248-93-9- PubChem CID
- 12448
- ChEMBL
CHEMBL220998、CHEMBL4303311- ChEBI
CHEBI:87666- UNII
- I8F3948441
- EC Number
- 221-832-2、684-520-9
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 75.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 515
Experimental & physicochemical properties
Chemical ClassesDyes -> Di- and Triaryl Dyes
SolubilityALMOST INSOL IN ETHER /MAGENTA/
Physical DescriptionDark green powder or greenish crystals with a bronze luster; [MSDSonline]
Physicochemical properties
- Melting point
- 268 · 268-270°C decomposes
- Boiling point
- 432.52 °C · 432.52°C (rough estimate)
- Density
- 1.0962 · 1.0962 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 15 °C · Store at +15°C to +30°C.
- solubility
- 10 g/L · 10 g/L
- form
- solid
- Colour Index
- 42510 · 42510
- pka
- 6.81 · 6.81±0.20(Predicted)
- PH
- 5 · 5-6 (1g/l, H2O, 25°C)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: Benzenamine, 4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-2-methyl-
Hazards SummaryMild skin irritant; Oral LDLo (rabbit) = 180 mg/kg; [RTECS] An irritant; [MSDSonline] See Magenta.
Safety & protection
Preventive Measures
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/
Toxicology
Natural Pollution SourcesMAGENTA HAS NOT BEEN REPORTED TO OCCUR AS SUCH IN NATURE. /MAGENTA/
Human Toxicity Excerpts
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/
Non-Human Toxicity Excerpts
...INJECTED 10 MG PARA-MAGENTA AS 1% SOLN SC WEEKLY...INTO 20 BD III RATS. FIRST LOCAL SARCOMA...@ 300 DAYS, AFTER TOTAL DOSE OF 370 MG OF DYE. TOTAL OF 7 SARCOMAS...IN 12 RATS SURVIVING AFTER APPEARANCE OF FIRST TUMOR, COMPARED TO SPONTANEOUS INCIDENCE OF SARCOMAS IN THESE RATS OF LESS THAN 5%.
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
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/
Uses & manufacturing
Uses
Used as dye for oils, fats, waxes (especially polishes), carbon papers, and ball point pen inks; [HSDB]
Pulp and Paper Processing [Category: Industry]
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
U.S. Exports
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Consumption PatternsESSENTIALLY 100% AS A DYE
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
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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