Basic information
- CAS
81-11-8- Standard SMILES
Nc1ccc(C=Cc2ccc(N)cc2S(=O)(=O)O)c(S(=O)(=O)O)c1- InChIKey
REJHVSOVQBJEBF-UHFFFAOYSA-N- Molecular formula
- C14H14N2O6S2
- Average molar mass
- 370.4 g/mol
- Monoisotopic mass
- 370.02932817
Overview
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)
Names & identifiers
- Preferred name
- Diaminostilbenedisulfonic acid
- IUPAC
- 5-amino-2-[2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid
- English name
- 4,4'-Diamino-2,2'-stilbenedisulfonic acid
- Molecular formula
- C14H14N2O6S2
- Molecular weight
- 370.4
Names & synonyms
Show more names
Database identifiers
- CAS
81-11-8- PubChem CID
- 6668
- DTXSID
DTXSID5024926- ChEMBL
CHEMBL3185470- EC Number
- 201-325-2
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 178 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 606
Experimental & physicochemical properties
Solubility
less than 1 mg/mL at 73 °F (NTP, 1992)
VERY SLIGHTLY SOL IN WATER
SOL IN ALCOHOL & ETHER
Physical Description
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]
Physicochemical properties
- Melting point
- 300 °C · 300 °C
- Density
- 1.4732 · 1.4732 (rough estimate)
- vapor pressure
- 1.3 hPa · 1.3hPa at 25℃
- refractive index
- 1.651 · 1.6510 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Aqueous Base (Slightly)
- pka
- -1.58 · -1.58±0.50(Predicted)
- form
- Crystalline Powder
- color
- Cream to yellow-brown
- Water Solubility
- 0.1 g/100 · <0.1 g/100 mL at 23 ºC
- Merck
- 14 · 14,595
- BRN
- 629516 · 629516
- Stability
- 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 DataBase Reference
- 81 · 81-11-8(CAS DataBase Reference)
- FDA UNII
- 899 GJ5MP05 · 899GJ5MP05
- EPA Substance Registry System
- Amsonic acid (81-11-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- C,Xn
- Risk Statements
- 34 · 34-22-36/37/38-20/21/22
- Safety Statements
- 24 · 24/25-45-36/37/39-26-22
- RIDADR
- 2583 · UN 2583
- WGK Germany
- 1 · WGK 1
- RTECS
- 6603000 · WJ6603000
- TSCA
- TSCA listed
- HS Code
- 29215900 · 29215900
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Hazardous Substances Data
- 81 · 81-11-8(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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
Health Hazards
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
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]
Safety & protection
First Aid
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
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)
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
Ongoing Test Status
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
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
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.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- WGK 1
- tsca
- TSCA listed
- rtecs
- WJ6603000
- ridadr
- UN 2583
- hs_code
- 29215900
- risk_code
- 34-22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- C,Xn
- safety_code
- 24/25-45-36/37/39-26-22
- Storage Class
- 8A - Combustible corrosive hazardous materials
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- Hazardous Substances Data
- 81-11-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
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
(1977) No Data
(1979) No Data
U.S. Imports
(1977) 4.74X10+8 GRAMS (PRINCPL CUSTMS DISTS)
(1979) 4.42X10+8 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 1,000,000 - <5,000,000 lb
(1977) PROBABLY GREATER THAN 9.08X10+6 GRAMS
(1979) PROBABLY GREATER THAN 6.81X10+6 GRAMS
Methods of Manufacturing
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.
General Manufacturing Information
Paper Manufacturing
Benzenesulfonic acid, 2,2'-(1,2-ethenediyl)bis[5-amino-: ACTIVE
Applications
Uses4,4’-Diaminostilbene-2,2’-disulfonic Acid, 95+% (cas# 81-11-8) is a compound useful in organic synthesis.
UsesIn manufacture of dyes, bleaching agents.
General DescriptionOdorless yellowish microscopic needles or cream-colored powder. pH approximately 4.3 at 30 g/L water (suspension).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers101 total
Related reactions
Compound notes
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