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Direct Blue 218

HCID 34237
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Basic information

CAS
28407-37-6
Standard SMILES
Nc1cc(S(=O)(=O)[O-])cc2cc(S(=O)(=O)[O-])c(N=Nc3ccc(-c4ccc(N=Nc5c(S(=O)(=O)[O-])cc6cc(S(=O)(=O)[O-])cc(N)c6c5O)c(O)c4)cc3O)c(O)c12.[Cu].[Cu].[Na+].[Na+].[Na+].[Na+]
InChIKey
UIECJCJNZREJPJ-UHFFFAOYSA-J
Molecular formula
C32H20Cu2N6Na4O16S4
Average molar mass
1,091.9 g/mol
Monoisotopic mass
1,089.800135

Overview

C.I. Direct Blue 218 can cause cancer according to The National Toxicology Program.

Names & identifiers

Preferred name
Direct Blue 218
IUPAC
tetrasodium;5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-hydroxyphenyl]-2-hydroxyphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate;copper
English name
tetrasodium [mu-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxynaphthalene-2,7-disulphonato]](8-)]]dicuprate(4-)
Molecular formula
C32H16Cu2N6NaO16S4(-3)
Molecular weight
1018.83

Names & synonyms

DIRECT BLUE 21828407-37-6Fastusol Blue 9GLPSolantine Blue 10GLPontamine Bond Blue BAmanil Supra Blue 9GLCI Direct Blue 218Pontamine Fast Blue 7GLNRR3V5FL20NCCRIS 6142C.I. 24401HSDB 4223
Show more names
C.I. Direct Blue 218Direct blue 218 (C.I. 24401)C.I.Direct Blue 218:C.I.24401Direct Blue 218 (Technical Grade)[3,3'-[(3,3'-Dihydroxy-1,1'-biphenyl-4,4'-diyl)bis(azo)bis(5-amino-2,7-naphthalenedisulfonato-(O4,O3)]]dicopper, tetrasodium saltCuprate, [μ-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxy-2,7-naphthalenedisulfonato]]]]di-, tetrasodiumTetrasodium [μ-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis [5-amino-4-hydroxynaphthalene-2,7-disulphonato]](8-)]]dicuprateTetrasodium [μ-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxynaphthalene-2,7-disulphonato]](8-)]]dicuprate(4-)

Properties

Computed structural properties

Topological polar surface area
445 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
22
Rotatable bonds
1
Heavy atoms
64
Formal charge
0
Complexity
1,810

Experimental & physicochemical properties

Chemical ClassesDyes -> Benzidine Dyes
Solubility10 to 50 mg/mL at 63 °F (NTP, 1992)
Physical Description · 3 items

C.i. direct blue 218 is a deep purple to dark blue amorphous powder. (NTP, 1992)

Dry Powder; Liquid

Deep purple to dark blue solid; [CAMEO]

Physicochemical properties

Boiling point
1560 ℃[at · 1560℃[at 101 325 Pa]
Density
2.8 · 2.8[at 20℃]
vapor pressure
0 Pa · 0Pa at 25℃
solubility
DMSO (Sparingly), Methanol (Slightly), Water (Sparingly)
form
Solid
color
Very Dark Blue to Black
Water Solubility
10 g/L · 10g/L at 17℃
LogP
-0.77 at · -0.77 at 25℃
Toxicology and Carcinogenesis
218 · Toxicology and Carcinogenesis Studies of C.I. Direct Blue 218 (CASRN 28407-37-6) in F344/N Rats and B6C3F1 Mice (Feed Studies)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 3.3% (4 of 121) of reports.

Danger

H350 (86.8%): May cause cancer [Danger Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 121 reports by companies from 6 notifications to the ECHA C&L Inventory.

Danger

Hazard information

Regulatory Information · 5 items

Chemical: Cuprate(4-), [.mu.-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxy-2,7-naphthalenedisulfonato]](8-)]]di-, tetrasodium

Hazard Traits - Carcinogenicity

Cuprate(4-), [.mu.-[[3,3'-[[3,3'-di(hydroxy-.kappa.O)[1,1'-biphenyl]-4,4'-diyl]bis(2,1-diazenediyl-.kappa.N1)]bis[5-amino-4-(hydroxy-.kappa.O)-2,7-naphthalenedisulfonato]](8-)]]di-, sodium (1:4) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cuprate(4-), [.mu.-[[3,3'-[[3,3'-di(hydroxy-.kappa.O)[1,1'-biphenyl]-4,4'-diyl]bis(2,1-diazenediyl-.kappa.N1)]bis[5-amino-4-(hydroxy-.kappa.O)-2,7-naphthalenedisulfonato]](8-)]]di-, sodium (1:4) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Tetrasodium [μ-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxynaphthalene-2,7-disulphonato]](8-)]]dicuprate(4-) (EC: 249-008-8)

Cuprate(4-), [.mu.-[[3,3'-[[3,3'-di(hydroxy-.kappa.O)[1,1'-biphenyl]-4,4'-diyl]bis(azo-.kappa.N1)]bis[5-amino-4-(hydroxy-.kappa.O)-2,7-naphthalenedisulfonato]](8-)]]di-, tetrasodium: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Cuprate(4-), [.mu.-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxy-2,7-naphthalenedisulfonato]](8-)]]di-, tetrasodium: Environment tier I assessment

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as dye for cellulose, acetate, nylon, silk, wool, tissue, fine papers, and textile goods with a urea-formaldehyde finish; [HSDB]

Pulp and Paper Processing [Category: Industry]

DYE FOR CELLULOSE, ACETATE, NYLON, SILK, WOOL, TISSUE, & FINE PAPERS, FOR TEXTILE GOODS WITH A UREA-FORMALDEHYDE FINISH

U.S. Production · 4 items

2023: <75,000 lb

(1977) 4.03X10+8 GRAMS (SALES)

(1979) 3.54X10+8 GRAMS

(1985) 3.33X10+8 g

Consumer UsesDye
Industry UsesDye
Methods of Manufacturing · 2 items

CONDENSATION OF TETRAZOTIZED O-DIANISIDINE WITH 8-AMINO-1-N APHTHOL-3,6-DISULFONIC ACID UNDER ALKALINE CONDITIONS, FOLLOWED BY CONVERSION INTO THE COPPER COMPLEX

Direct Blue 218 is produced by coupling o-dianisidine to two moles of H acid, 4-amino-5-hydroxy-2,7-naphthalene disulfonic acid under alkaline pH conditions followed by metallizing and elimination of methyl groups from the methoxides (R6 and R7) to form the copper complex

General Manufacturing Information · 2 items

Synthetic Dye and Pigment Manufacturing

Cuprate(4-), [.mu.-[[3,3'-[[3,3'-di(hydroxy-.kappa.O)[1,1'-biphenyl]-4,4'-diyl]bis(2,1-diazenediyl-.kappa.N1)]bis[5-amino-4-(hydroxy-.kappa.O)-2,7-naphthalenedisulfonato]](8-)]]di-, sodium (1:4): ACTIVE

Applications · 2 items

UsesDirect Blue 218 is an azo dye used in diagnostic imaging. Used in the prediction of rat carcinogenisis. Also used in textile dyes contributing to textile effluents and wastewaters.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.

General DescriptionDeep purple to dark blue amorphous powder.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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tetrasodium [mu-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxynaphthalene-2,7-disulphonato]](8-)]]dicuprate(4-)
Cuprate(4-) [μ-[[3,3'-[(3,3'-dihydroxy[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxy-2,7-naphthalenedisulfonato]](8-)]]di-, tetrasodium
NCI C60877EINECS 249-008-8(3,3'-((3,3'-Dihydroxy-1,1'-biphenyl-4,4'-diyl)bis(azo)bis(5-amino-2,7-naphthalenedisulfonato-(O4,O3)))dicopper, tetrasodium saltCopper, (mu-((tetrahydrogen 3,3'-((3,3'-dihydroxy-4,4'-biphenylene)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulfonato))(4-)))di-, tetrasodium saltCuprate(4-) (mu-((3,3'-((3,3'-dihydroxy(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulfonato))(8-)))di-, tetrasodiumCuprate(4-), (mu-((3,3'-((3,3'-di(hydroxy-kappaO)(1,1'-biphenyl)-4,4'-diyl)bis(2,1-diazenediyl-kappaN1))bis(5-amino-4-(hydroxy-kappaO)-2,7-naphthalenedisulfonato))(8-)))di-, sodium (1:4)Cuprate(4-), (mu-((3,3'-((3,3'-di(hydroxy-kappaO)(1,1'-biphenyl)-4,4'-diyl)bis(azo-kappaN1))bis(5-amino-4-(hydroxy-kappaO)-2,7-naphthalenedisulfonato))(8-)))di-, tetrasodiumCuprate(4-), (mu-((3,3'-((3,3'-dihydroxy(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulfonato))(8-)))di-, tetrasodium

Database identifiers

CAS
28407-37-6
PubChem CID
34237
EC Number
249-008-8
FDA UNII
3 V5FL20N · RR3V5FL20N
Proposition 65 List
218 · C.I. Direct Blue 218
EPA Substance Registry System
218 · C.I. Direct Blue 218 (28407-37-6)
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
350 · H350
TSCA
TSCA listed
Hazardous Substances Data
28407 · 28407-37-6(Hazardous Substances Data)
REACH Registrations
Inactive
Fire HazardsFlash point data for this chemical are not available, however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: This compound may cause skin sensitization.
Hazards Summary · 1 item

One of the azo dyes metabolized to o-dianisidine--reasonably anticipated to be a human carcinogen; [NTP] May cause skin sensitization; [CAMEO] No results for the search: ((Direct Blue 218) OR 28407-37-6[EC/RN Number]) AND Dermatitis, Allergic Contact[Mesh]; [PubMed]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Special Reports · 1 item

Toxicology & Carcinogenesis Studies of C.I. Direct Blue 218 in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 430 (1994) NIH Publication No. 94-3161 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

Reactivity AlertsExplosive
Reactivity Profile · 1 item

C.I. DIRECT BLUE 218 is a diazo compound. Azo, diazo, azido compounds can detonate. The nitro groups would facilitate rapid decomposition. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Air and Water ReactionsWater soluble. Azo dyes can be explosive when suspended in air at specific concentrations.
Hazard Classes and Categories · 3 items

Carc. 1A (86.8%)

Carcinogenicity - category 1B

Acute toxicity (Oral) - Category 5

Safety & protection

Fire FightingFires involving this chemical should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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.

Nonfire Spill Response · 1 item

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.

Disposal Methods · 1 item

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.

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=28407-37-6]

TSCA Test Submissions · 5 items

C.I. direct blue 218 (CAS # 28407-37-6) was evaluated for acute dermal toxicity. The test substance was applied to the clipped backs of New Zealand white rabbits (1/sex abraded; 1/sex intact) at a dose level of 2.0 g/kg of body weight. The test site was covered for 24-hours. Diarrhea, bloated abdomen and few feces was noted in animal #1; and lethargy in animal #2. All other animals appeared normal. Necropsy findings concluded that all animals appeared normal. No mortality occurred and the dermal LD50 was determined to be greater than 2.0 g/kg b.w.

C.I. direct blue 218 (CAS # 28407-37-6) was evaluated for acute inhalation toxicity. The test substance was administered by a direct dust-feed system to Holtzman Sprague-Dawley rats (5/sex) at a concentration of 11.71 mg/l for 4-hours. No mortality occurred. No clinical signs occurred during exposure or the 14-day observation period. Body weights of males were normal, but 2 females exhibited slight depressed weight gain. Necropsy findings found macroscopic lesions in the lungs of all animals. These findings included hemorrhagic spots and foci, a purplish discoloration and rough texture of lobes or portions of lobes, and nodular masses or growths with a shrunken appearance. These findings were not considered treatment-related because it was concluded that these findings were typical of chronic murine pneumonia complex.

C.I. direct blue 218 (CAS # 28407-37-6) was evaluated for eye irritation. The test substance was instilled in the lower conjunctival sac of one eye of each of 6 New Zealand white rabbits at a dosage of 0.1 ml (liquid) or 0.1 g (solid). The lids were held closed for 1-second for even distribution of the test substance. The test substance was determined to be moderately irritating. No further information was submitted.

C.I. direct blue 218 (CAS # 28407-37-6) was evaluated for primary dermal irritation. The test substance was applied to the clipped back and sides (one-side was abraded) to 6 New Zealand white rabbits at a dosage of 0.5 ml (liquid) or 0.5 g (solid) and covered for 24-hours. The test substance was determined to be non-irritating. No further information was submitted.

For more TSCA Test Submissions (Complete) data for DIRECT BLUE 218 (12 total), please visit the HSDB record page.

Carcinogen Classification · 6 items

CI Direct Blue 218

Group 2B: Possibly carcinogenic to humans

Volume 129: (2022) Gentian Violet, Leucogentian Violet, Malachite Green, Leucomalachite Green, and CI Direct Blue 218

2022 online

2021

C.I. Direct Blue 218

Non-Human Toxicity Excerpts · 3 items

Direct Blue 218 was evaluated for the induction of sex-linked recessive lethal mutations in Drosophila melanogaster by the National Toxicology Program. Canton-S wild-type males were treated with concentrations of Direct Blue 218 that result in approximately 30% mortality. Following treatment, males were mated individually to 3 harems of Basc virgin females to produce 3 broods for analysis. The concentrations of Direct Blue 218 tested by injection (1000 ppm) or feeding (10,000 ppm) were negative in this assay.

Under the conditions of these 2 yr feed studies, there was some evidence of carcinogenic activity of C.I. Direct Blue 218 in male F344/N rats based on the occurrence of pharyngeal neoplasms. Squamous cell neoplasms of the forestomach may have been chemical related. There was no evidence of carcinogenic activity of C.I. Direct Blue 218 in female F344/N rats given 1,000, 3,000 or 10,000 ppm. There was clear evidence of carcinogenic activity of C.I. Direct Blue 218 in male and female B6C3F1 mice based upon incr incidences of hepatocellular adenomas and carcinomas. The occurrence of a few neoplasms of the kidney and small intestine in male mice may have been related to C.I. Direct Blue 218 treatment. ...

C.I Direct Blue 218 was not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, or TA1537 tested with and without exogenous metabolic activation (S9). It was also tested in a modified Salmonella test protocol which employed reductive metabolism supplied by flavin mononucleotide or rat cecal bacteria, followed by oxidative metabolism; results of this test using strain TA1538 were also negative. C.I. Direct Blue 218 induced a small but significant increase in sister chromatid exchanges in Chinese hamster ovary cells at the highest dose tested without S9. No increase in chromosomal aberrations were observed in Chinese hamster ovary cells with or without S9. C.I. Direct Blue 218 did not induce sex linked recessive lethal mutations in germ cells of male Drosophila melanogaster.

National Toxicology Program Studies · 1 item

... Toxicology and carcinogenesis studies were conducted by admin C.I. Direct Blue 218 in feed to groups of male and female F344/N rats and B6C3F1 mice for ... 2 yr. ... Groups of 60 male and 60 female rats were fed diets containing 0, 1,000, 3,000 or 10,000 ppm C.I. Direct Blue 281 for 103 wk. ... Groups of 60 male and 60 female mice were fed diets containing 0, 1,000, 3,000 or 10,000 ppm C.I. Direct Blue 218 for 103 wk. ... Under the conditions of these 2 yr feed studies, there was some evidence of carcinogenic activity of C.I. Direct Blue 218 in male F344/N rats based on the occurrence of pharyngeal neoplasms. Squamous cell neoplasms of the forestomach may have been chemical related. There was no evidence of carcinogenic activity of C.I. Direct Blue 218 in female F344/N rats given 1,000, 3,000 or 10,000 ppm. There was clear evidence of carcinogenic activity of C.I. Direct Blue 218 in male and female B6C3F1 mice based upon incr incidences of hepatocellular adenomas and carcinomas. The occurrence of a few neoplasms of the kidney and small intestine in male mice may have been related to C.I. Direct Blue 218 treatment. ...

RAIS Toxicity Values · 4 items

0.14000000000000001

CALEPA

500

CALEPA

Safety data

tsca
TSCA listed
Signal word
Danger
Symbol(GHS)
GHS08
Hazard statements
H350
REACH Registrations
Inactive
Hazardous Substances Data
28407-37-6(Hazardous Substances Data)

Preparation methods

Preparation3,3′-Dimethoxylbenzidine double nitriding, in alkaline conditions and 4-Amino-5-hydroxynaphthalene-2,7-disulfonic acid(2 Moore) coupling, and then will product into copper complex.