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4,4'-Diaminostilben-2,2'-disulfonsure

Diaminostilbenedisulfonic acid

HCID 6668
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Grundinformationen

CAS
81-11-8
Standard-SMILES
Nc1ccc(C=Cc2ccc(N)cc2S(=O)(=O)O)c(S(=O)(=O)O)c1
InChIKey
REJHVSOVQBJEBF-UHFFFAOYSA-N
Summenformel
C14H14N2O6S2
Durchschnittliche Molmasse
370,4 g/mol
Monoisotopische Masse
370,02932817

Überblick

4,4'-diamino-2,2'-stilbenedisulfonic acid appears as odorless yellowish microscopic needles or cream-colored powder. pH approximately 4.3 at 30 g/L water (suspension). (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Diaminostilbenedisulfonic acid
IUPAC
5-amino-2-[2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid
Lokaler Name
4,4'-Diaminostilben-2,2'-disulfonsure
Englischer Name
4,4'-Diamino-2,2'-stilbenedisulfonic acid
Summenformel
C14H14N2O6S2
Molmasse
370.4

Namen und Synonyme

4,4'-DIAMINO-2,2'-STILBENEDISULFONIC ACIDAmsonic acidDTXSID5024926AmsonsaeureDiaminostilbenedisulfonic acidBenzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino-NCI-C60162DTXCID2049262,2'-(1,2-Ethylenediyl)bis(5-aminobenzenesulfonic acid)Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis(5-amino-NSC-163899GJ5MP05
Weitere Namen anzeigen
DASDSD ACIDDASDA4,4'-Diaminostilbene-2,2'-disulfonic AcidDASD1,2-bis(4-amino-2-sulfophenyl)ethene4',4" Diamino stillbene 2'2" disulphonic acidbenedisuL
DADSDASSARefChem:9200034,4'-diacetamido-2,2'-stilbene disulfonate201-325-22,2'-Disulfo-4,4'-stilbenediamine2,2'-Stilbenedisulfonic acid, 4,4'-diamino-4,4-diaminostilbene-2,2'-disulfonic acid

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,3
Polarare Oberfläche (TPSA)
178 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
24
Formalladung
0
Komplexität
606

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Aminobenzoic Acids
LogP-1.7
Color/FormYELLOW NEEDLES
Solubility · 3 Einträge

less than 1 mg/mL at 73 °F (NTP, 1992)

VERY SLIGHTLY SOL IN WATER

SOL IN ALCOHOL & ETHER

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Pointgreater than 617 °F (NTP, 1992)
Physical Description · 3 Einträge

4,4'-diamino-2,2'-stilbenedisulfonic acid appears as odorless yellowish microscopic needles or cream-colored powder. pH approximately 4.3 at 30 g/L water (suspension). (NTP, 1992)

Dry Powder; Large Crystals; Liquid

Yellow solid; [Merck Index]

Other Experimental PropertiesFORMS SPARINGLY WATER SOL CRYSTALLINE SALTS WITH MANY BISQUATERNARY AMMONIUM BASES

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 1% (2 of 210) of reports.

Warning

H302 (18.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 210 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino-

Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino- 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)

Status: Cease Manufacture Update: 15-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30493

Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include irritation, burning, reddening, tearing and possible swelling of the eyes, irritation of the respiratory tract, runny nose, sore throat, coughing, chest discomfort and shortness of breath. Persons with impaired pulmonary function or with preexisting eye conditions may be more susceptible to the effects of this compound.

Hazards Summary · 1 Eintrag

An eye and respiratory tract irritant; [CAMEO] There have been reports of decreased libido in male workers handling this chemical; [REPROTOX] An irritant; Effects in high-dose animal studies include abnormal liver and kidney function tests; [MSDSonline]

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

Used as a chemical intermediate for dyes, bleaching agents, and fluorescent brighteners; [HSDB]

IN MFR OF DYES, BLEACHING AGENTS

CHEM INT FOR DYES (EG, CI DIRECT YELLOW 12) & FLUORESCENT BRIGHTENERS

U.S. Exports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Imports · 2 Einträge

(1977) 4.74X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 4.42X10+8 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 Einträge

2023: 1,000,000 - <5,000,000 lb

(1977) PROBABLY GREATER THAN 9.08X10+6 GRAMS

(1979) PROBABLY GREATER THAN 6.81X10+6 GRAMS

Consumption PatternsESSENTIALLY 100% AS A CHEM INT
Industry UsesIntermediate
Methods of Manufacturing · 3 Einträge

CATALYTIC REDUCTION OF 4,4'-DINITRO-2,2'-STILBENEDISULFONIC ACID

BENDER, SCHULTZ, BER 19, 3234 (1886); HE FIERZ-DAVID, L BLANGEY, GRUNDLEGENDE OPERATONEN DER FARBENCHEMIE (SPRINGER-VERLAG, VIENNA, 7TH ED, 1947) P 161; SPIEGLER, US PATENT 2,784,220 (1957 TO DUPONT).

BOILING SODIUM SALT OF PARA-NITROTOLUENE-ORTHO-SULFONATE IN WATER WITH CAUSTIC SODA & REDN WITH ZINC DUST.

Household ProductsInformation on 13 consumer products that contain Diaminostilbenedisulfonic acid in the following categories is provided:
General Manufacturing Information · 2 Einträge

Paper Manufacturing

Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino-: ACTIVE

Anwendungen

Zugehörige Reaktionen

7
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 277579
HRID 277579als Eduktuspto-grants-2002_03
Reaktionsgleichung von HRID 648847
HRID 648847als Eduktuspto-grants-1988_04
Reaktionsgleichung von HRID 850904
HRID 850904als Produktuspto-grants-1983_05
Reaktionsgleichung von HRID 1415380
HRID 1415380als Eduktuspto-grants-1977_01
Reaktionsgleichung von HRID 1606232
HRID 1606232als Eduktuspto-grants-1976_04
Reaktionsgleichung von HRID 1663278
HRID 1663278als Eduktuspto-grants-2011_10
Reaktionsgleichung von HRID 1663287
HRID 1663287als Eduktuspto-grants-2011_10

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Datenbank-Bezeichner

CAS
81-11-8
PubChem CID
6668
DTXSID
DTXSID5024926
ChEMBL
CHEMBL3185470
EC Number
201-325-2

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · 300 °C
Dichte
1.4732 · 1.4732 (rough estimate)
Dampfdruck
1.3 hPa · 1.3hPa at 25℃
Brechungsindex
1.651 · 1.6510 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Aqueous Base (Slightly)
pka
-1.58 · -1.58±0.50(Predicted)
Aggregatzustand
Crystalline Powder
Farbe
Cream to yellow-brown
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 23 ºC
Merck
14 · 14,595
BRN
629516 · 629516
Stabilität
Stable. Combustible. Incompatible with iron, strong oxidizing agents.
InChI
1S/C14H14N2O6S2/c15-11-5-3-9(13(7-11)23(17,18)19)1-2-10-4-6-12(16)8-14(10)24(20,21)22/h1-8H,15-16H2,(H,17,18,19)(H,20,21,22)/b2-1+
InChIKey
REJHVSOVQBJEBF-OWOJBTEDSA-N
SMILES
Nc1ccc(\C=C\c2ccc(N)cc2S(O)(=O)=O)c(c1)S(O)(=O)=O
LogP
-1.7 · -1.7--1.42 at 25℃
CAS Datenbank
81 · 81-11-8(CAS DataBase Reference)
EPA chemische Informationen
Amsonic acid (81-11-8)
Reactive GroupHydrocarbons, Aliphatic Unsaturated
Reactivity Profile4,4'-DIAMINO-2,2'-STILBENEDISULFONIC ACID is incompatible with iron. It forms sparingly water-soluble, crystalline salts with many bisquaternary ammonium bases. (NTP, 1992)
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (18.6%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 Eintrag

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 Eintrag

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.

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1 Eintrag

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. /4,4'-Diamino-2,2'-stilbenedisulfonic acid, disodium salt/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=7336-20-1]

Human Toxicity Excerpts · 2 Einträge

RESULTS OF MEDICAL SURVEYS & STUDIES ON SAFETY OF FLUORESCENT WHITENING AGENTS (FWA'S) CONTAINING DIAMINOSTILBENE DISULFONATE WERE COMPILED & CRITICIZED. CONCLUSION THAT FWA'S ARE PRACTICALLY NONTOXIC.

HAZARD: TOXIC BY INGESTION.

Non-Human Toxicity Excerpts · 1 Eintrag

4,4'-Diamino-2,2'-stilbenedisulfonic acid was evaluated for mutagenicity in the Salmonella/microsome preincubation assay using a standard protocol approved by the National Toxicology Program. Doses of 0, 100, 333, 3333, 4000, 4500, and 5000 ug/plate were tested in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. These tests were negative and the highest ineffective dose level tested in any Salmonella tester strain was 5000 ug/plate.

Sicherheitsdaten

wgk
WGK 1
tsca
TSCA listed
ridadr
UN 2583
hs_code
29215900
RTECS-Nr.
WJ6603000
risk_code
34-22-36/37/38-20/21/22
hazard_code
C,Xn
safety_code
24/25-45-36/37/39-26-22
Speicherklasse
8A - Combustible corrosive hazardous materials
Giftige Stoffe Daten
81-11-8(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 Oral

VerwendenIn manufacture of dyes, bleaching agents.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

4-Nitrotoluol

Nachgelagerte Produkte

fluorescent whitening agent PRSfluorescent whitening agent JD-3Fluorescent Brightener BCDirect Red Brown RNfluorescent whitening agent SBADirect Red 227Fluorescent Brightener VBUReactive Yellow KE-4RNFluorescent brightener No.31fluorescent bleaches Rfluorescent whitening agent RADirect Blending Brilliant Red D-5BLDinatrium-4,4'-bis[(4-ethoxyphenyl)azo]stilben-2,2'-disulfonatReactive Yellow 179fluorescent whitening agent DMSReactive Red KD-8BReactive Orange KE-2GFluorescent brightener 85fluorescent bleaches BRDirect Blending Yellow D-3RNL4,4'-Bis[4-[bis(2-hydroxyethyl)amino]-6-anilino-1,3,5-triazin-2-yl]amino]stilben-2,2'-disulfonsureReactive Yellow 84Reactive Yellow KE-RNPROCION YELLOW H-E3G