Pararosaniline
-
Pararosaniline
structure -
-
CAS No:
569-61-9
-
Formula:
C19H17N3.ClH
-
Chemical Name:
Pararosaniline
-
Synonyms:
Benzenamine,4,4′-[(4-imino-2,5-cyclohexadien-1-ylidene)methylene]bis-,hydrochloride (1:1);Para Magenta;C.I. Basic Red 9,monohydrochloride;Benzenamine,4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl]-,monohydrochloride;Benzenamine,4,4′-[(4-imino-2,5-cyclohexadien-1-ylidene)methylene]bis-,monohydrochloride;C.I. 42500;Calcozine Magenta N;Fuchsine DR 001;Fuchsine SP;Fuchsine SPC;Parafuchsin;Pararosaniline chloride;Pararosaniline hydrochloride;Parafuchsine;Pararosaniline;C.I. Basic Red 9;Basic Parafuchsine;p-Fuchsin;p-Rosaniline hydrochloride;p-Fuchsine;Orient Para Magenta Base;Basic Red 9;NSC 10460;131883-55-1;70426-60-7;187112-40-9
- Categories:
-
CAS No:
Description
green crystalline powder C.I. Basic red 9 is a colorless to red crystalline solid or green powder.
Pararosaniline hydrochloride appears as colorless to red crystals or green powder. (NTP, 1992)
Pararosaniline hydrochloride appears as colorless to red crystals or green powder. (NTP, 1992)|Pararosaniline is a hydrochloride that is the monohydrochloride of 4,4'-[(4-iminocyclohexa-2,5-dien-1-ylidene)methanediyl]dianiline. One of the major constituents of Basic fuchsin, together with rosanilin, magenta II and new fuchsin. It has a role as a histological dye and a fluorochrome. It contains a pararosaniline(1+).
Pararosaniline Basic Attributes
323.82
323.118927
4164603
211-189-6
444C2M8JKN
10460
DTXSID1021247
COLORLESS TO RED CRYSTALS|Dark-green crystalline powder
32041300
Characteristics
75.9
log Kow = -0.21
metallic green Solid
0.999 g/mL at 20 °C
268-270 °C (decomp)
568.2°C at 760 mmHg
11 °C
n20/D 1.334
H2O: 10 g/L (25 ºC);ethanol: soluble 1mg/mL
Store at RT.
CATIONIC|Destroyed by strong oxidizing agents; readily reduced to leuco-bases with a variety of reducing reagents sensitive to photochemical oxidation
Insoluble in water.
Salts, Acidic
Safety Information
Ⅲ
UN 2924 3/PG 2
3
40-45-11
7-16-53-45-36/37
CX9850000
F,T,Xn
Stable. Incompatible with strong oxidizing agents.
P201-P308 + P313
H350
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]
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Danger|H350: May cause cancer [Danger Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|H350 (100%): May cause cancer [Danger Carcinogenicity]|Aggregated GHS information provided by 51 companies from 3 notifications to the ECHA C&L Inventory.|Warning|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P281, P308+P313, P312, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|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
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.)|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.)
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of hydrogen chloride and nitrogen oxides. (NTP, 1992)|Carcinogens
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
4-((4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)methyl)benzeneamine monohydrochloride
Pararosaniline Use and Manufacturing
The preparation method of alkaline pay magenta is that methylene diphenylamine and aniline are catalyzed by catalytic oxidation in air using the catalyst, which comprises the following steps:(1) A mixture of methylene diphenylamine and aniline in a weight ratio of 20: 1 was placed in a four-necked flask to obtain a mixture A; four ports in a four-necked flask were provided with a condenser, a water separator, a thermometer and an air Introduction tube, four-necked flask with a stirrer;(2) mixing the mixture A with stirring in a concentration of 30percent HCl to obtain solution B; wherein the weight of 30percent HCl used is 0.77 times the weight of methylene aniline;(3) adding a catalyst to solution B to obtain solution C, the weight of which is 1percent to 4percent by weight of methylene aniline; the catalyst is cesium vanadate;(4) to the side of the solution C while heating into the air, to be heated to 140 when the temperature and continue to pass into the air for 5 hours until no moisture generated, the end of the reaction to get the material D;(5) the material D for azeotropic distillation to remove and recover excess aniline, get the crude, the crude material poured out of the four-necked flask, the crude will cool brittle;(6) grinding the crude product and stirring with a dilute hydrochloric acid solution to obtain a solution E of pH ≤ 1;(7) The solution E is continuously stirred for 6.5 hours and then filtered through celite. The filtrate is filtered to obtain solution F;(8) the solution F with 0.4mol / L NaOH solution and to PH = 5, the temperature is 24 , filter and filter cake after the filtrate to get the material G;(9) The material G was dissolved in boiling water of PH = 4, cooled to room temperature for 16 hours to crystallize, and finally filtered. The solid product was alkaline quasi-red crystals with a yield of 70percent.The preparation method of alkaline pay magenta is that methylene diphenylamine and aniline are catalyzed by catalytic oxidation in air using the catalyst, which comprises the following steps:(1) A mixture of methylene diphenylamine and aniline in a weight ratio of 20: 1 was placed in a four-necked flask to obtain a mixture A; four ports in a four-necked flask were provided with a condenser, a water separator, a thermometer and an air Introduction tube, four-necked flask with a stirrer;(2) mixing the mixture A with stirring in a concentration of 30percent HCl to obtain solution B; wherein the weight of 30percent HCl used is 0.77 times the weight of methylene aniline;(3) adding a catalyst to solution B to obtain solution C, the weight of which is 1percent to 4percent by weight of methylene aniline; the catalyst is cesium vanadate;(4) to the side of the solution C while heating into the air, to be heated to 140 when the temperature and continue to pass into the air for 5 hours until no moisture generated, the end of the reaction to get the material D;(5) the material D for azeotropic distillation to remove and recover excess aniline, get the crude, the crude material poured out of the four-necked flask, the crude will cool brittle;(6) grinding the crude product and stirring with a dilute hydrochloric acid solution to obtain a solution E of pH ' 1;(7) The solution E is continuously stirred for 6.5 hours and then filtered through celite. The filtrate is filtered to obtain solution F;(8) the solution F with 0.4mol / L NaOH solution and to PH = 5, the temperature is 24 , filter and filter cake after the filtrate to get the material G;(9) The material G was dissolved in boiling water of PH = 4, cooled to room temperature for 16 hours to crystallize, and finally filtered. The solid product was alkaline quasi-red crystals with a yield of 70percent.Triethylamine (15.15g, 0.15mol) was added to a solution of
It can be used as a biological stain and can be used in spectrophotometric detection in analytical detection.
(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
Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:323.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:323.1189253
Monoisotopic Mass:323.1189253
Topological Polar Surface Area:75.9
Heavy Atom Count:23
Complexity:457
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Recommended Suppliers of Pararosaniline
-
CN
5 YRS
Business licensed Certified factoryManufactory Supplier of Custom Synthetic Chemicals,Biological Stains,Pharmaceutical Intermediates,Cosmetic Grade Chemicals,Enzyme,Nucleosides,Indicators,Speciality Chemicals,Biological Chemicals,Enzyme Substrates -
CN
5 YRS
Business licensedTrader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives -
CN
5 YRS
Business licensedTrader Supplier of PVC resin,pvc paste resin,melamine -
IN
4 YRS
Business licensed Certified factoryManufactory Supplier of Chemical Reagents,Speciality Cheicals,Stains and indicators,Metal Salts,Fine Chemicals
Learn More Other Chemicals
-
Pararosaniline acetate
6035-94-5
-
4,4′-Diaminobenzenesulfonanilide
16803-97-7
-
(4-methylphenyl)methyl thiocyanate
18991-39-4
-
(1s,4r)-4-Butyl-4'-(3,4,5-trifluorophenyl)-1,1'-bi(cyclohexyl) Formula
139420-31-8
-
2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-4-[(4-methyl-2-sulfophenyl)amino]-9,10-dioxo-, sodium salt (1:2) Formula
6408-80-6
-
4-Cyclohexylphenol Formula
1131-60-8
-
4-(Benzoylamino)-5-hydroxy-2,7-naphthalenedisulfonic acid Structure
117-46-4
-
Ethyl3,4-diaminobenzoate Structure
37466-90-3
-
What is Direct Blue 6
2602-46-2
-
What is 3,3-bis(1-butyl-2-methyl-1H-indol-3-yl)phthalide
50292-91-6