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Tinopal DMS

HCID 6433657
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Basic information

CAS
16090-02-1
Standard SMILES
O=S(=O)([O-])c1cc(Nc2nc(Nc3ccccc3)nc(N3CCOCC3)n2)ccc1/C=C/c1ccc(Nc2nc(Nc3ccccc3)nc(N3CCOCC3)n2)cc1S(=O)(=O)[O-].[Na+].[Na+]
InChIKey
VUJGKADZTYCLIL-YHPRVSEPSA-L
Molecular formula
C40H38N12Na2O8S2
Average molar mass
924.9 g/mol
Monoisotopic mass
924.21723713

Names & identifiers

Preferred name
Tinopal DMS
IUPAC
disodium;5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(E)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate
English name
Fluorescent brightener 71
Molecular formula
C40H38N12Na2O8S2
Molecular weight
924.91486

Names & synonyms

Fluorescent brightener 71Tinopal DMSC.I. Fluorescent brightener 260C.I. Fluorescent Brightener 71C.I. Fluorescent Brightener 244C.I. Fluorescent Brightener 250CCRIS 3187HSDB 5061FBA-260EINECS 240-245-2TINOPAL DMS [HSDB]CI 40625
Show more names
MBBH 766BELOTEXKDUvitex SDGMikephor TBJADEADD CXTBelofor KD 2Heliofor 3BCHeliofor BDCKayaphor MASLeukopur PAM
2,2'-Stilbenedisulfonic acid, 4,4'-bis((4-anilino-6-morpholino-s-triazin-2-yl)amino)-, disodium saltEC 240-245-24,4'-Bis((4-anilino-6-morpholino-1,3,5-triazine-2-yl)amino)stilbene 2,2-disulfonate 2Na4,4'-Bis((4-anilino-6-morpholino-s-triazin-2-yl)-amino)-2,2'-stilbenedisulfonateDisodium 4,4'-bis((4-anilino-6-morpholino-1,3,5-triazin-2-yl)amino)stilbene-2,2'-disulphonate4,4'-Bis((2-anilino-4-morpholino-1,3,5-triazin-6-yl)amino)-2,2'-stilbenedisulfonic acid, disodium saltDisodium 4,4'-bis[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)amino]stilbene-2,2'-disulphonateBenzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis(5-((4-(4-morpholinyl)-6-(phenylamino)-1,3,5-triazin-2-yl)amino)-, sodium salt (1:2)

Properties

Computed structural properties

Topological polar surface area
282 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
20
Rotatable bonds
12
Heavy atoms
64
Formal charge
0
Complexity
1,490

Experimental & physicochemical properties

SolubilityIn water, 5 mg/l at 25 °C.
DecompositionWhen heated to decomposition it emits toxic vapaors of nitrous oxides and /hydrogen chloride/.
Melting Point>270 °C
Physical DescriptionDry Powder; Large Crystals
Dissociation Constantslog Kow = 1.48

Physicochemical properties

Melting point
270 °C · >270 °C
Density
0.417 · 0.417-1.54[at 20℃]
vapor pressure
0 · 0-0Pa at 25℃
storage temp.
Refrigerator
solubility
DMSO (Slightly), Methanol (Very Slightly, Heated)
form
Solid
color
Pale Yellow
Water Solubility
1.223 · 1.223-1.9g/L at 20-25℃

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 · 4 items

This chemical does not meet GHS hazard criteria for 62.1% (231 of 372) of all reports.

H412 (37.4%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 372 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-[[4-(4-morpholinyl)-6-(phenylamino)-1,3,5-triazin-2-yl]amino]-, sodium salt (1:2) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-[[4-(4-morpholinyl)-6-(phenylamino)-1,3,5-triazin-2-yl]amino]-, sodium salt (1:2) 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: Disodium 4,4'-bis[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)amino]stilbene-2,2'-disulphonate (EC: 240-245-2)

C.I. Fluorescent brightener 260: Does not have an individual approval but may be used under an appropriate group standard

EPA Safer ChemicalChemical: FWA-1
Hazard Classes and CategoriesAquatic Chronic 3 (37.4%)

Safety & protection

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.

Chemistry & industry

Pharmacology

Biological Half-LifeORAL DOSES OF 5 MG/KG (14)C-TINOPAL AMS TO RATS HAD RAPID & COMPLETE EXCRETION & RADIOACTIVITY T/2 OF 7-13 HR.
Absorption, Distribution and Excretion · 2 items

INTUBATION IN RATS SHOWED LITTLE ABSORPTION FROM INTESTINAL TRACT. EXCRETED RAPIDLY IN FECES. PARENTERAL ADMIN TO RATS, RAPIDLY EXCRETED IN FECES; SMALL AMT IN TISSUES & ORGANS. ABSORPTION BY SKIN: SLIGHT.

ORAL DOSES OF 5 MG/KG (14)C-TINOPAL AMS TO RATS HAD RAPID & COMPLETE EXCRETION. MOST EXCRETION WAS VIA FECES. NO RADIOACTIVITY WAS FOUND IN BLOOD, LIVER, KIDNEY, BRAIN, MUSCLE OR FAT 96 HR AFTER DOSING.

Uses & manufacturing

Uses · 2 items

DYE FOR COTTON FIBERS, SOAPS & DETERGENTS

IN HEAVY DUTY DETERGENT, TO WHITEN FABRICS; PLASTICS; FIBERS, COATINGS, WAXES... /TINOPAL/

U.S. Production · 3 items

2023: 1,000,000 - <2,500,000 lb

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Consumer UsesDye
Industry UsesDye
Household ProductsInformation on 53 consumer products that contain Tinopal DMS in the following categories is provided:
Use Classification · 2 items

EPA Safer Chemical Functional Use Classes -> Colorants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

General Manufacturing Information · 3 items

All Other Chemical Product and Preparation Manufacturing

Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-[[4-(4-morpholinyl)-6-(phenylamino)-1,3,5-triazin-2-yl]amino]-, sodium salt (1:2): ACTIVE

Related reactions

1 records
New reaction record
HRID 1836072 reaction equation
HRID 1836072As reactantuspto-grants-2004_08

Compound notes

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Database identifiers

CAS
16090-02-1
PubChem CID
6433657
UNII
Q1O8YPR146
EC Number
240-245-2
LogP
-1.58 · -1.58-1.186 at 25℃
CAS DataBase Reference
16090 · 16090-02-1(CAS DataBase Reference)
FDA UNII
1 O8YPR146 · Q1O8YPR146
EPA Substance Registry System
2 · Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-[[4-(4-morpholinyl)-6-(phenylamino)-1,3,5-triazin-2-yl]amino]-, sodium salt (1:2) (16090-02-1)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
TSCA
TSCA listed
Hazardous Substances Data
16090 · 16090-02-1(Hazardous Substances Data)
REACH Registrations
Active

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended regression classification scheme(1), an estimated Koc value of 1800 (SRC), determined from a measured water solubility of 5 mg/l(2) and a recommended regression-derived equation(3), indicates that C.I. Fluorescent Brightener will have low mobility in soil(SRC). In one experiment, clean water was percolated through sludge containing fluorescent whitening agents. After 68 days the total amount leached from the original 216 mg C.I. Fluorescent Brightener 260 in 20 kg sludge was only 0.02%(6). As C.I. Fluorescent Brightener 3 is an ionic compound at environmental pHs, volatilization of this compound will not be important from moist soil surfaces(4,SRC). Based on limited data, C.I. Fluorescent Brightener 260 is expected to be resistant to aerobic biodegradation(SRC); C.I. Fluorescent Brightener 260 was not biodegraded in a standard 5 day BOD test(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1800(SRC), determined from a measured water solubility(3) and a recommended regression-derived equation(2), indicates that C.I. Fluorescent Brightener 260 may adsorb to suspended solids and sediment in water(SRC). However, due to the ionic nature of C.I. Fluorescent Brightener, the retention of the brightener by ion-exchange processes(4,SRC), particularly on clay surfaces, and adsorption at mineral surfaces such as geothite(5,SRC), may lead to increased adsorption on some sediment and particulate surfaces(SRC). As C.I. Fluorescent Brightener 260 is an ionic compound, volatilization from water surfaces is not expected(4,SRC). According to a classification scheme(6), a BCF range of 1.4 to 28 in carp(3) suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, C.I. Fluorescent Brightener 260 is expected to be resistant to aerobic biodegradation in water(SRC); C.I. Fluorescent Brightener 260 was not biodegraded in a standard 5 day BOD test(7). In a river die-away test at which carbon dioxide production was measured in solutions of maximum 1000 ppb over a period of 35 days, no biodegradability was found(7).

ATMOSPHERIC FATE: The ionic state of C.I. Fluorescent Brightener 260 makes this compound essentially non-volatile(1,SRC), therefore this compound will only exist in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Fluorescent Brightener 260 may be physically removed from the air by wet and dry deposition(SRC).

Effluent ConcentrationsSamples of 35 US rivers in 1974 showed concentration of fluorescent whitening agents up to 0.6 ppb upstream of a sewage treatment plant. Downstream concentrations were never above 40 ppb for C.I. Fluorescent Brightener 260(1).
Soil Adsorption/Mobility · 1 item

The Koc of C.I. Fluorescent Brightener 260 is estimated as approximately 1800(SRC), using a water solubility of 5 mg/l(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that C.I. Fluorescent Brightener 260 is expected to have low mobility in soil(SRC). Due to the ionic nature of the brightener, the retention of C.I. Fluorescent Brightener 260 by ion-exchange processes(4,SRC), particularly on clay surfaces and adsorption at mineral surfaces such as geothite(5,SRC), may slow down or prevent leaching(SRC). In one experiment, clean water was percolated through sludge containing fluorescent whitening agents. After 68 days the total amount leached from the original 216 mg C.I. Fluorescent Brightener 260 in 20 kg sludge was only 0.02%(6).

Artificial Pollution SourcesC.I. Fluorescent Brightener 260's production and use in laundry detergents(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

Laboratory experiments showed that fluorescent whitening agents used in detergents are not readily biodegradable. Tests which used the oxygen consumption over 5 days as a measure of the ability of fluorescent agents to serve a substrate for bacterial growth gave no evidence of biodegradation; C.I. Fluorescent Brightener 260 had a BOD5 of zero. In a river die-away test at which carbon dioxide production was measured in solutions of maximum 1000 ppb over a period of 35 days, no biodegradability was found(1).

Sediment/Soil Concentrations · 1 item

Fluorescent whitening agents are strongly adsorbed to soil. In one experiment, clean water was percolated through sludge containing fluorescent whitening agents. After 68 days the total amount leached from the original 216 mg C.I. Fluorescent Brightener 260 in 20 kg sludge was only 0.02%. The sludge had been exposed to natural weather and non-agricultural conditions(1).

Environmental BioconcentrationA bioconcentration factor range of 1.4 to 28 in carp was determined for C.I. Fluorescent Brightener 260(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilSince C.I. Fluorescent Brightener 260 is an ionic compound, volatilization from water and moist soil surfaces is not expected to be an important fate process(1,SRC).
Non-Human Toxicity Excerpts · 5 items

FBA-260 GIVEN @ 40-1000 PPM IN DIET, HAD NO EFFECT ON REPRODUCTIVE PERFORMANCE OF RATS THROUGH 3 SUCCESSIVE 2-LITTER GENERATIONS.

NO SIGNIFICANT ADVERSE EFFECTS WHEN TINOPAL AMS WAS FED FOR 2 YR TO RATS @ LEVELS OF 40, 200 OR 1000 PPM & FED TO DOGS @ LEVELS OF 2000 PPM FOR 2 YR.

FBA-260 SHOWED NO MUTAGENICITY IN DOMINANT LETHAL TESTS WHEN GIVEN @ 5000 MG/KG, ORALLY, TO MICE.

SKIN TUMORS WERE PRODUCED IN HAIRLESS MICE AFTER SEVERAL MONTHS DAILY EXPOSURE TO UV, VISIBLE & IR IRRADIATION. PRETREATMENT WITH TINOPAL AMS DID NOT PRODUCE PHOTOTOXICITY OR ENHANCE PHOTOCARCINOGENESIS.

For more Non-Human Toxicity Excerpts (Complete) data for C.I. FLUORESCENT BRIGHTENER 260 (11 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 item

C.I. Fluorescent Brightener 260 is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1). Fluorescent whitening agents, which includes C.I. Fluorescent Brightener 260, have an UV absorption maximum between 340 to 360 nm in water and transform UV energy almost quantitatively into blue fluorescent light(2).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 231 workers (76 of these are female) are potentially exposed to C.I. Fluorescent Brightener 260 in the US(1). Occupational exposure to C.I. Fluorescent Brightener 260 may occur through dermal contact with this compound at workplaces where C.I. Fluorescent Brightener 260 is produced or used(SRC). The general population may be exposed to C.I. Fluorescent Brightener 260 via dermal contact with consumer products (i.e. detergents) containing C.I. Fluorescent Brightener 260(SRC).

Environmental Water ConcentrationsONLY TRACE QUANTITIES OF FLUORESCENT WHITENING AGENTS HAVE BEEN FOUND IN DRINKING WATER.

Safety data

tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazardous Substances Data
16090-02-1(Hazardous Substances Data)

"TINOPAL" /IS/ TRADEMARK FOR GROUP OF OPTICAL BRIGHTENERS, WHICH ABSORB UV LIGHT IN NEAR VISIBLE RANGE & RE-EMIT THE ENERGY AS VISIBLE LIGHT. /TINOPAL/

Applications · 1 item

Uses(Fluorescent brightener 71)Fluorescent (optical) brighteners are known for their characteristics of protecting baculoviruses against deactivation by UV light and enhancing the activity of these agents as microbial insecticides on hosts and semipermissive hosts. Fluorescent brighteners improve the bioinsecticidal activity of Anticarsia gemmatalis nucleopolyhedrovirus.