4-Hydroxybenzolsulfonsure

4-Hydroxybenzenesulfonic acid

HCID 4765CAS 98-67-9

Grundinformationen

Standard-SMILES
O=S(=O)(O)c1ccc(O)cc1
InChIKey
FEPBITJSIHRMRT-UHFFFAOYSA-N
Summenformel
C6H6O4S
Durchschnittliche Molmasse
174,18 g/mol
Monoisotopische Masse
173,99867984

Namen und Bezeichner

Bevorzugter Name
4-Hydroxybenzenesulfonic acid
IUPAC
4-hydroxybenzenesulfonic acid
Lokaler Name
4-Hydroxybenzolsulfonsure
Englischer Name
4-Hydroxybenzenesulfonic acid
Summenformel
C6H6O4S
Molmasse
174.17

Namen und Synonyme

4-Hydroxybenzenesulfonic acid98-67-9p-Phenolsulfonic acidphenolsulfonic acid4-Phenolsulfonic acidSulfocarbolic acidp-Sulfophenolp-Hydroxybenzenesulfonic acidBenzenesulfonic acid, 4-hydroxy-4-HYDROXYPHENYLSULFONIC ACIDPhenol-4-sulfonic acidBenzenesulfonic acid, p-hydroxy-
Weitere Namen anzeigen
p-PhenoLARADUR 5003-1 BDC12849
4-hydroxybenzene-1-sulfonic acid4-Hydroxybenzenesulphonic acidHydroxybenzene-4-sulfonic acidp-PhenolsulfonateNSC 227908DTXSID1046421para-phenolsulfonic acidNSC-227908

Datenbank-Bezeichner

CAS
98-67-9
PubChem CID
4765
DTXSID
DTXSID1046421
ChEMBL
CHEMBL1398657
ChEBI
CHEBI:32354
UNII
L74LRO149A
EC Number
202-691-6
Nikkaji
J4.956E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
83 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

Density · 2 Einträge

1.337

1.337 @25 °C

Color/FormNEEDLES
SolubilityMISCIBLE WITH WATER, ALCOHOL
Vapor Pressure0.00000033 [mmHg]
Refractive IndexIndex of Refraction = 1.4890 at 20 °C
Physical Description · 2 Einträge

Liquid

Deliquescent solid; [Merck Index] Viscous brown liquid (65% wt. solution in water); [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
52 °C · 52 °C
Siedepunkt
275.14 °C · 275.14°C (rough estimate)
Dichte
1.337 g/mL · 1.337 g/mL at 25 °C
Dampfdruck
69.8 Pa · 69.8Pa at 20℃
Brechungsindex
20 · n20/D 1.489
Löslichkeit
Water (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 0.3% (1 of 341) of reports.

Danger

H290 (68.9%): May be corrosive to metals [Warning Corrosive to Metals];H302 (48.7%): Harmful if swallowed [Warning Acute toxicity, oral];H314 (99.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H318 (87.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H335 (30.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P234, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 341 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 341 reports by companies.;There are 16 notifications provided by 340 of 341 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzenesulfonic acid, 4-hydroxy-

Benzenesulfonic acid, 4-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-hydroxy- 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: Active Update: 31-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14998;Status: Active Update: 05-01-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18559

Benzenesulfonic acid, 4-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 1 Eintrag

· Combustible material: may burn but does not ignite readily.;· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Corrosives in contact with metals may evolve flammable hydrogen gas.;· Containers may explode when heated.;· Runoff may pollute waterways.;· Substance may be transported in a molten form.

Health Hazards · 1 Eintrag

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.;· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).;· Contact with molten substance may cause severe burns to skin and eyes.;· Avoid any skin contact.;· Fire may produce irritating, corrosive and/or toxic gases.;· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

Hazards Summary · 1 Eintrag

A skin irritant; [Merck Index] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; [MSDSonline] Oral LD50 (mouse) = 6400 mg/kg; Mild irritant effect to human skin after contact with 0.5% solution; [RTECS]

DOT ID and Guide1803 153
Hazard Classes and CategoriesMet. Corr. 1 (68.9%);Acute Tox. 4 (48.7%);Skin Corr. 1B (99.7%);Eye Dam. 1 (87.7%);STOT SE 3 (30.8%)

Sicherheit und Schutzausrüstung

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· DO NOT GET WATER INSIDE CONTAINERS.

First Aid · 1 Eintrag

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

Exposure Control and Personal Protection · 1 Eintrag

· Wear positive pressure self-contained breathing apparatus (SCBA).;· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

Disposal Methods · 1 Eintrag

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.

Preventive Measures · 1 Eintrag

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and Evacuation · 1 Eintrag

Immediate precautionary measure;· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;Spill;· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.;· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.;Fire;· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: An estimated Koc of 3.0(1,SRC), based on an estimated log Kow(2,SRC) indicates that 4-hydroxyphenylsulfonic acid will have very high mobility in soil(3,SRC). As this compound is miscible in water(4), leaching may be an important fate process(SRC). In moist soils 4-hydroxyphenylsulfonic acid should quickly dissociate(5,SRC). Biodegradation of this compound may be an important fate process; 4-hydroxyphenylsulfonic acid at 75 ug/l showed complete degradation within 32 days using a soil inoculum(6). 4-Hydroxyphenylsulfonic acid at 100 mg/l was biodegraded by an activated sludge inoculum over 14 days(7). A long lag period of 76-95 hours was measured with complete biodegradation requiring a total of 190 to 195 hours; these results suggested that 4-hydroxyphenylsulfonic acid is biodegraded completely over a long time by acclimatized microorganisms(7). Other aerobic biodegradation experiments using higher concentrations of 4-hydroxyphenylsulfonic acid (500 mg/l) and shorter incubation times (70 hours) determined that 4-hydroxyphenylsulfonic acid was not biodegraded under these conditions(8,9). Under anaerobic conditions, using an aquifer slurry as an inoculum, 4-hydroxyphenylsulfonic acid at 35 mg/l was not biodegraded over a period of 13 months(10). 4-Hydroxyphenylsulfonic acid will not volatilize from moist soil surfaces(SRC) based on an estimated Henry's Law constant of 2.62X10-13 atm-cu/mole(11).

AQUATIC FATE: If released to water, 4-hydroxyphenylsulfonic acid is expected to dissociate(1). Aerobic biodegradation is expected to be a major fate process for 4- hydroxyphenylsulfonic acid. 4-Hydroxyphenylsulfonic acid at 100 mg/l was incubated over 14 days with a non-acclimatized activated sludge inoculum. Complete biodegradation required 190-195 hours including a 76-95 hour lag time; this indicates that an initial acclimatization period prior to biodegradation of this compound is necessary(2). When inoculated with an activated sludge culture which was acclimatized to benzene, 4-hydroxyphenylsulfonic acid, at a concentration of 500 mg/l, was not biodegraded within the time period of 70 hours(3). A pure culture of Pseudomonas H-8, a known benzene sulfonate oxidizer isolated from pond water, was unable to biodegrade 4-hydroxyphenylsulfonic acid over an unreported period of time(4). 4-Hydroxyphenylsulfonic acid at 35 mg/l was not biodegraded under anaerobic conditions for a 13 month period using an aquifer slurry as an inoculum(5). An estimated BCF value of 0 indicates that 4-hydroxyphenylsulfonic acid will not bioconcentrate in an aquatic system(6,7,SRC). 4-Hydroxyphenylsulfonic acid is not expected to volatilize from water surfaces(SRC) based on an estimated Henry's Law constant of 2.62X10-13 atm-cu/mole (8).

ATMOSPHERIC FATE: Based on an estimated vapor pressure of 3.33X10-7 mm Hg at 25 °C(1,SRC), 4-hydroxyphenylsulfonic acid will exist both in the vapor phase and in the particulate phase(2,SRC). In the vapor phase it will degrade fairly rapidly by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 2 days(3,SRC). Particulate phase 4-hydroxyphenylsulfonic acid may be removed physically from air by wet and dry deposition(SRC).

Adverse EffectsDermatotoxin - Skin burns.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Soil Adsorption/Mobility · 1 Eintrag

Based on an estimated log Kow of -1.65(1), the Koc of 4-hydroxyphenylsulfonic acid is estimated as approximately 3.0 using a regression-derived equation(2,SRC). According to a suggested classification scheme, this estimated Koc value suggests that 4-hydroxyphenylsulfonic acid has very high mobility in soil(3).

Human Toxicity Excerpts...IRRITATING TO SKIN.
Artificial Pollution Sources · 1 Eintrag

4-Hydroxyphenylsulfonic acid's production and subsequent use mainly as an additive for electroplating baths(1), but also in the manufacture of synthetic tanning agents(1), as a chemical intermediate used to improve the dyeing properties of polyamide fibers(1) or used in the manufacture of polyesters with improved affinity for basic dyes(1), and during its use in the process of granulation of blast furnace slag(2) may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation · 3 Einträge

4-Hydroxyphenylsulfonic acid at a concentration of 75 ug/ml was incubated aerobically with a mixed culture of soil microorganisms for a time period ranging from 3 hours to 64 days. Total loss of this compound, followed by measuring the loss in absorbance of the benzene ring, was complete within 32 days(1). 4-Hydroxyphenylsulfonic acid at a concentration of 100 mg/l was incubated over 14 days with a non-acclimated activated sludge inoculum(2). The degradation ratio of 4-hydroxyphenylsulfonic acid (at 100 mg/l), defined as the BOD/Theoretical BOD, was determined to be 0.76 to 0.78; a lag time of 76-95 hours was measured, total biodegradation of this compound required 190-195 hours including the lag period(2). This indicates that this compound is biodegraded completely over a long time by acclimated microorganisms(2).

No biodegradation of 4-hydroxyphenylsulfonic acid at a concentration of 500 mg/l was seen over a period of one hour using a pure culture of Pseudomonas acclimatized to p-toluenesulfonate as its sole carbon and sulfur source(1). A pure culture of Pseudomonas strain H-8, a known benzene sulfonate oxidizer isolated from pond water, was unable to grow when given 4-hydroxyphenylsulfonic acid, at an unreported concentration, as the sole carbon source(2). 4-Hydroxyphenylsulfonic acid was not biodegraded using the agar plate method after a few days by a pure culture isolated for its ability to biodegrade benzenesulfonic acid(3).

4-Hydroxyphenylsulfonic acid, present at a concentration of 500 mg/l, was not used as a carbon source over a period of 70 hours using activated sludge acclimatized to benzene as an inoculum under aerobic conditions(2). In a compilation of chemicals, 4-hydroxyphenylsulfonic acid is listed as a chemical which should be degradable by biological sewage treatment provided suitable acclimatization of the microbial population is reached(2). The biodegradability of 4-hydroxyphenylsulfonic acid was measured under anaerobic conditions using two aquifer slurries, one from a sulfate reducing site, the other from a methanogenic site. 4-Hydroxyphenylsulfonic acid was added at a concentration of 200 uM to a slurry from each site and monitored from 0 to 13 months. Under sulfate reducing conditions, 4-hydroxyphenylsulfonic acid was present at 188 uM and at 198 uM after 0 to 13 months respectively. Under methanogenic conditions, 4-hydroxyphenylsulfonic acid was present at 194 uM and at 235 uM after 0 to 13 months respectively(3).

Regulatorische Informationen

Regulatory Information · 4 Einträge

Chemical: Benzenesulfonic acid, 4-hydroxy-

Benzenesulfonic acid, 4-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-hydroxy- 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: Active Update: 31-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14998;Status: Active Update: 05-01-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18559

Benzenesulfonic acid, 4-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
-
tsca
TSCA listed
ridadr
UN 1803 (PHENOLSULPHONIC ACID, LIQUID)
hs_code
29089990
RTECS-Nr.
DB6970000
risk_code
34-68

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used as a component of metal plating baths (tin and copper); as a chemical intermediate for pharmaceuticals and dyestuffs; in granulation of blast furnace slag; and as an analytical reagent; [HSDB]

Electroplating [Category: Plate];Cleaning Furnaces or Flues [Category: Clean]

INT IN MFG OF PHARMACEUTICALS, DYESTUFFS; IN FERROSTAN PROCESS OF TIN PLATING (US STEEL)

P-PHENOLSULFONIC ACID IS USED IN GRANULATION OF BLAST FURNACE SLAG.

CHEM INT FOR DYE INTS, EG, ITS 2-AMINO-6-NITRO DERIV

CHEM INT FOR 2-ALKYLPHENOLSULFONIC ACIDS

U.S. Production · 3 Einträge

2023: 500,000 - <1,000,000 lb;2022: 500,000 - <1,000,000 lb;2021: 1,000,000 - <8,500,000 lb;2020: 500,000 - <1,000,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Consumer UsesMonomers
Industry UsesMonomers
Methods of Manufacturing · 2 Einträge

PREPN BY HYDROLYSIS OF P-CHLORO- OR P-BROMOBENZENESULFONIC ACID; BY SULFONATION OF PHENOL.

Phenol (25 kg) and 96% sulfuric acid (28 kg) are heated to 50 °C; then 1.25 kg additional sulfuric acid is added and the reaction mixture is heated at 110 °C for 5-6 hours. Reaction water, together with about 5% of the phenol, is distilled off during this period. Yield 95%.

Formulations/PreparationsCOMMERCIAL AVAILABLE AS A 65% SOLN.
Anwendungen · 2 Einträge

Beschreibung4-hydroxybenzenesulfonic acid is an arenesulfonic acid that is phenol substituted by a sulfo group at C-4. It is functionally related to a phenol. Results obtained in a comparative study using the disulfide-bridge containing peptide deaminoarginine-vasopressin and several commonly used matrices indicate that the reduction-inhibiting efficiency of 4-hydroxy benzene sulfonic acid is comparable to that of 3-nitrobenzyl alcohol while reduction is found to be important in matrices such as thioglycerol and glycerol. Experiments conducted on peptides such as met-enkephalin and bradykinin, nucleosides and other polar compounds reveal that 4-hydroxybenzenesulfonic acid is a good solvent and has physical properties similar to glycerol. This new matrix material is a radical scavenger, is surface active, allows persistent secondary-ion beams, and produces a low background signal[1].

Verwenden4-Hydroxybenzenesulfonic Acid is used as a redox-mediator in the laccase-catalyzed degradation of indigo, a textile dye. Also used in oilfield chemicals, metal working, and as a polymerization catalyst.

Anbieter50 Anbieter

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河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An arenesulfonic acid that is phenol substituted by a sulfo group at C-4.

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