HC Blue 2
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HC Blue 2
structure -
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CAS No:
33229-34-4
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Formula:
C12H19N3O5
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Chemical Name:
HC Blue 2
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Synonyms:
Ethanol,2,2′-[[4-[(2-hydroxyethyl)amino]-3-nitrophenyl]imino]bis-;Ethanol,2,2′-[[4-[(2-hydroxyethyl)amino]-3-nitrophenyl]imino]di-;2,2′-[[4-[(2-Hydroxyethyl)amino]-3-nitrophenyl]imino]bis[ethanol];N1,N4,N4-Tris(2-hydroxyethyl)-2-nitro-p-phenylenediamine;N,N′,N′-Tris(2-hydroxyethyl)-2-nitro-p-phenylenediamine;N1,N4,N4-Tris(2′-hydroxyethyl)-2-nitro-p-phenylenediamine;HC Blue No. 2;HC Blue 2;2,2′-[4-(2-Hydroxyethylamino)-3-nitrophenylimino]diethanol;Covarine Blue W 6122;Colorex HCB 2;N,N,N′-Tris(2-hydroxyethyl)-3-nitrobenzene-1,4-diamine;2,2′-((4-((2-Hydroxyethyl)amino)-3-nitrophenyl)azanediyl)diethanol;2-[4-[Bis(2-hydroxyethyl)amino]-2-nitroanilino]ethanol
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CAS No:
Description
Blue-violet crystal powder
Hc blue 2 is a dark blue to dark brown microcrystalline powder. (NTP, 1992)
Hc blue 2 is a dark blue to dark brown microcrystalline powder. (NTP, 1992)|HC Blue No. 2 is a C-nitro compound.
HC Blue 2 Basic Attributes
285.3
285.30
251-410-3
6C0EL1931V
DTXSID6020193
Dark-blue microcrystalline (75% pure) or blackish-blue amorphous powder (98% pure), with a copper cast.
29221990
Characteristics
122
0.4
Hc blue 2 is a dark blue to dark brown microcrystalline powder. (NTP, 1992)
1.421 g/cm3
93-98 °C
582.7°C at 760 mmHg
1.672
water: soluble (lit.)
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
May be sensitive to prolonged exposure to air. Slow oxidation. Insoluble in water.
Alcohols and Polyols
A nitrated aromatic, amine and alcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Safety Information
NONH for all modes of transport
1
36/37/38
26-36
KL2880000
Xi
P261-P305 + P351 + P338
H315-H319-H335
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.
Toxicology & Carcinogenesis Studies of HC Blue No. 2 in F344/N Rats and B6C3F1 Mice. Technical Report Series No.293 (1985) NIH Publication No. 85-2549 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Warning|H315 (60.91%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 111 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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 keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicity
Toxicology and carcinogenesis studies of HC Blue No. 2 (approx 98% pure) ... were conducted by admin the test chemical in feed for 103 wk to groups of 50 F344/N rats of each sex and for 104 wk to groups of 50 B6C3F1 mice of each sex. The dietary concn used were 0, 5,000 or 10,000 ppm for male rats and male mice and 0, 10,000 or 20,000 ppm for female rats and female mice. ... The avg daily doses were approx 195 and 390 mg/kg in male rats, 465 and 1,000 mg/kg in female rats, 1,320 and 2,240 mg/kg in male mice and 2,330 and 5,600 mg/kg in female mice. ... Under the conditions of these studies, there was no evidence of carcinogenicity in male or female F344/N rats or in male or female B6C3F1 mice receiving HC Blue No. 2 in the diet at concn of 0.5% and 1.0% for males and 1.0% and 2.0% for females for 2 yr.
Drug Information
About 85 g of a commercial semi-permanent hair dye formulation containing 1.77% HC Blue No. 2 enriched with 378.6 uCi/mg (14)C-labelled HC Blue No. 2 was applied to the hair of human volunteers, worked in gently for 5-8 min and allowed to remain in contact with the hair and scalp for an additional 30 min. After 30 days, radiolabel accounting for less than 0.1% of that applied was detected in the urine; half was excreted in urine after 52 hr. (The Working Group noted that urinary metabolites were not identified, so that the metabolic fate of HC Blue No. 2 in humans remains unknown.)|Up to 40% of radiolabel was recovered in the urine of B6C3F1 mice and Fischer 344/N rats after oral administration by gavage of 100 mg/kg bw (14)C-labelled HC Blue No. 2 (0.1 mCi/mmol (35 uCi/mg); 98% pure).|The safety of HC Blue No 2 for use as a colorant in hair dyes was evaluated, based on a review of available data. ... An in vivo metabolic radioassay with B6C3F1 mice indicated less than 5% of the initial radioactivity was excreted as the parent cmpd; the remainder was excreted as more polar metabolites, with the majority in one peak. An in vitro metabolic study indicated the production of a beta-glucuronidase metabolite. ...
Metabolism of HC Blue No. 2 (200 uM (57 mg) by hepatocytes isolated from mice and rats yielded profiles similar to those seen in vivo. High performance liquid chromatography separation showed that HC Blue No. 2 is metabolized extensively in mice to one major metabolite, which has not been characterized.|Previous studies indicated that HC Blue 1 induced hepatocellular carcinomas in B6C3F1 mice whereas the structurally similar nitroaromatic amine HC Blue 2 did not. ... Comparative metabolism and genetic toxicity studies were undertaken. Eighteen hour urinary recovery of admin radioactivity was equivalent for both cmpd following oral gavage (100 mg/kg) in female B6C3Fl mice. By HPLC analysis, HC Blue 1 yielded 3 major polar metabolite peaks, one of which was susceptible to glucuronidase. In vivo metabolism of HC Blue 2 yielded a single major metabolite peak which was not hydrolyzed by glucuronidase. Metabolism by B6C3Fl mouse hepatocytes yielded metabolite profiles which were qualitatively similar to the profiles observed after in vivo metabolism. HC Blue 1 was metabolized by hepatocytes at approximately twice the rate of HC Blue 2. Cytogenetic evaluations of mouse hepatocytes after in vitro treatment indicated HC Blue 1 was more potent than HC Blue 2 in inducing chromosomal aberrations while both chemicals showed weak activity for inducing sister-chromatid exchanges. Furthermore, in the V79 cell metabolic cooperation assay, HC Blue 1, but not HC Blue 2, inhibited cell-to-cell communication suggesting a non-genotoxic activity may be present for HC Blue 1. ...
HC Blue #2 is available commercially with a purity greater than or equal to 95% with possible impurities, including methylamine (<1%), 1,2-dihydroxyethane (<1%), and water (<1%). It is also available in a technical grade containing 55-90% dye, 10-30% inorganic salts and 2,2-((4-amino-3-nitrophenyl)imino)bis (ethanol) (<7%) as a possible impurity.
SYMPTOMS: Symptoms of exposure to this compound may include eye inflammation and dermatitis. Exposure to this type of compound can cause irritation or injury to corneas, conjunctiva and lids, and ocular injuries. ACUTE/CHRONIC HAZARDS: This compound may be absorbed through the skin. When heated to decomposition it emits toxic fumes of nitrogen oxides. (NTP, 1992)
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. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)
2,2'-((4-((2-hydroxyethyl)amino)-3-nitrophenyl)imino)bis(ethanol)
HC Blue 2 Use and Manufacturing
4 g of 2, 2?-[4-(2-hydroxyethylamino)-3-nitrophe- nylimino]diethanol were dissolved in 75 ml of anhydrous tetrahydroffiran. 4.51 g of N-(5-isocyanatopentyl)-N?-(6-iso- propyl-4-oxo- 1 , 4-dihydropyrimidin-2-yl)urea were added portionwise, under an argon atmosphere and with stirring, followed by addition of 3 drops of dibutyltin dilaurate (DBTDL). The reaction medium was then stirred at this temperature for 3 hours; the disappearance of the isocyanate function was monitored by infrared. After total disappearance of the isocyanate function, the reaction medium was filtered through Celite and then concentrated to half its volume. The reaction medium was then poured into 800 ml of ethyl ether with vigorous stirring and the precipitate obtained was filtered off on a sinter funnel. The product was then dried under vacuum to give 7 g of a violet powder, in a yield of about 80%. 10909] Analysis by HPLC coupled to a mass spectrometer shows the predominant formation of the desired product [M+H] +=607 and also a remaining amount of starting material and of double-reaction product of mass M=928.10910] 15 mg of dye thus prepared are placed in a 25 ml flask, and 100 tl ofbenzyl alcohol and 400 tl of ethyl alcohol are added. The mixture is heated slightly to 40 C. in order to dissolve the dye (ultrasonication if necessary). Finally, 1000 tl of water are added. An opaque violet solution is obtained.
Used as medicine and dye intermediate
(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US
Production and use of HC Blue #2 began in the late 1950s. Approximately 9-11 tons are used annually in the USA, according to industry estimates.
Cosmetics -> Hair dyeing
Computed Properties
Molecular Weight:285.30
XLogP3:0.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:285.13247072
Monoisotopic Mass:285.13247072
Topological Polar Surface Area:122
Heavy Atom Count:20
Complexity:281
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of HC Blue 2
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5 YRS
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