HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulphenone
r242 · r-242 · r-242-b · sulfenon · Sulfenone · SULFERONE · ent17,941 · SULPHENONE
Identifiers & Physical Properties
| CAS No. | 80-00-2 |
|---|---|
| Molecular formula | C12H9ClO2S |
| Average molar mass | 252.72 g/mol |
| Monoisotopic mass | 252.00117821 g/mol |
| SMILES | O=S(=O)(c1ccccc1)c1ccc(Cl)cc1 |
| InChIKey | OFCFYWOKHPOXKF-UHFFFAOYSA-N |
| PubChem CID | 6621 |
| ChEMBL | CHEMBL3188889 |
| EC No. | 201-242-1 |
| DTXSID | DTXSID9042259 |
Chemical & Physical Properties
| XLogP | 3.1 |
|---|---|
| Topological polar surface area | 42.5 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 16 |
| Formal charge | 0 |
| Complexity | 306 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pesticides | Pesticides -> Organochlorine Pesticides |
| LogP (partition coefficient) | log Kow = 3.25 /Estimated/ |
| Odor | Slight aromatic odor |
| Taste | Tasteless |
| Color/Form | Dimorphic crystalsColorless crystalsWhite solid |
| Solubility | At 20 °C acetone (74.4 g/100mL), toluene (44.4 g/100mL), dioxane (65.6 g/100mL), isopropanol (21 g/100mL), hexane 0.4 g/100mL), xylene (18.2 g/100mL), carbon tetrachloride (4.9 g/100mL)slightly soluble in pet ether.Readily sol in polar and aromatic org solventsInsoluble in wateracetone: soluble74.4 g/100ml at 20°C(lit.) |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen chloride and sulfur oxides/. |
| Melting point | 98 °C90-94 °C(lit.) |
| Vapor pressure | 0.0000039 [mmHg]8.7X10-6 mm Hg at 25 °C /Estimated/ |
| Henry's law constant | Henry's Law constant = 1.9X10-7 atm-cu/mole at 25 °C /Estimated/5.2×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Physical Description | Colorless or white solid[HSDB] White powder[MSDSonline] |
| Boiling point | 389 °C / 719mmHg |
| Density | 1.3319 (estimate) |
| Storage conditions | -20°C Freezer, Under inert atmosphere |
| Physical state | Solid |
| Color | White to Off-White |
| Merck | 14,8988 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C12H9ClO2S/c13-10-6-8-12(9-7-10)16(14,15)11-4-2-1-3-5-11/h1-9H |
| InChIKey | OFCFYWOKHPOXKF-UHFFFAOYSA-N |
| SMILES | Clc1ccc(cc1)S(=O)(=O)c2ccccc2 |
| CAS DataBase Reference | 80-00-2(CAS DataBase Reference) |
| FDA UNII | 7NVM546U2M |
| NIST Chemistry Reference | Benzene, 1-chloro-4-(phenylsulfonyl)-(80-00-2) |
| EPA Substance Registry System | p-Chlorophenyl phenyl sulfone (80-00-2) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302+H312+H332 |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 20/21/22 |
| Safety statements (S) | 36 |
| Water hazard class (WGK) | 3 |
| RTECS number | WR5775000 |
| TSCA inventory status | TSCA listed |
| Customs code | 2930909899 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral |
| Hazardous substances data | 80-00-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice: 2.7 g/kg (Hazleton) |
Safety & Regulations
| GHS classification | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 45 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Benzene, 1-chloro-4-(phenylsulfonyl)-: 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. |
| Hazards summary | Effects include weakness and weight loss in high-dose oral studies in dogs[RTECS] An irritant[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Ecotoxicity values | LD50 House sparrows oral >100 mg/kgLD50 Redwinged blackbirds oral >100 mg/kgLC50 Fundulus similis (Longnose killifish) 7500 ug/L/24 hr6000 ug/L/48 hrstatic /Formulated product/LC50 Mugil curema (White mullet) 11900 ug/L/48 hr |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,700(SRC), determined from a structure estimation method(2), indicates that sulphenone is expected to have slight mobility in soil(SRC). Volatilization of sulphenone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Sulphenone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.7X10-6 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,700(SRC), determined from a structure estimation method(2), indicates that sulphenone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 64(SRC), from an estimated log Kow of 3.2(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulphenone, which has an estimated vapor pressure of 8.69X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase sulphenone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 23 days(SRC), calculated from its rate constant of 7.1X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase sulphenone may be removed from the air by wet and dry deposition(SRC). Sulphenone does not absorb light at wavelengths >290(4) and therefore, is not expected to be susceptible to direct photolysis by sunlight. |
| Ecotoxicity excerpts | /BIRDS and MAMMALS/ The acute oral toxicity, repellency and hazard potential of sulphenone to one or more of 68 species of wild and domestic birds was determined by standardized testing procedures. Redwinged blackbirds were the most sensitive of the bird species tested. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for sulphenone can be estimated to be 4,700(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulphenone is expected to have slight mobility in soil. |
| Artificial Pollution Sources | Sulphenone's former production and use as an acaricide(1) and miticide(2) resulted in its direct release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 64 was calculated for sulphenone(SRC), using an estimated log Kow of 3.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for sulphenone is estimated as 1.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sulphenone is expected to be essentially nonvolatile from water surfaces(2). Sulphenone's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Sulphenone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.7X10-6 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ ...Moderately low oral toxicity to lab mammals. No skin irritation. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of sulphenone with photochemically-produced hydroxyl radicals has been estimated as 7.1X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 23 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Sulphenone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Sulphenone does not absorb light at wavelengths >290(4) and therefore, is not expected to be susceptible to direct photolysis by sunlight. |
| Probable Routes of Human Exposure | Current occupational exposure and general population exposure should be low or non-existent since sulphenone is no longer produced or used in the US (May,2005). In the past, sulphenone was applied directly to apple and pears trees and green house plants as an acaricide and insecticide and exposure to this compound was primarily by inhalation and dermal contact. (SRC) |
| Environmental Fate/Exposure Summary | Sulphenone's former production and use as an acaricide and miticide resulted in its direct release to the environment through various wastes streams. If released to air, an estimated vapor pressure of 8.7X10-6 mm Hg at 25 °C indicates sulphenone will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase sulphenone will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 23 days. Particulate-phase sulphenone will be removed from the atmosphere by wet and dry deposition. Sulphenone does not absorb light at wavelengths >290nm and therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, sulphenone is expected to have slight mobility based upon an estimated Koc of 4700. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.9X10-7 atm-cu m/mole. Sulphenone is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, sulphenone is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 64 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Current occupational exposure and general population exposure should be low or non-existent since sulphenone is no longer produced or used in the US(5,2005). In the past, sulphenone was applied directly to apple and pears trees and green house plants as an acaricide and insecticide and exposure to this compound was primarily by inhalation and dermal contact. (SRC) |
| Antidote and Emergency Treatment | Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/ |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | WR5775000 |
| Customs code | 2930909899 |
| Toxicity | LD50 orally in mice: 2.7 g/kg (Hazleton) |
| Risk statements (R) | 20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302+H312+H332 |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312 |
| Hazardous substances data | 80-00-2(Hazardous Substances Data) |
Applications & Uses
Uses
Sulfenone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.
Uses
Acaricide.
Uses
4-Chlorophenyl Phenyl Sulfone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.
General Description
4-Chlorophenyl phenyl sulfone is also referred to as sulphenone. It participates in palladium-catalyzed amidation reaction in the presence of low CO pressures and an iodide salt.