Sulphenone

HCID 6621CAS 80-00-2

Basic information

Standard SMILES
O=S(=O)(c1ccccc1)c1ccc(Cl)cc1
InChIKey
OFCFYWOKHPOXKF-UHFFFAOYSA-N
Molecular formula
C12H9ClO2S
Average molar mass
252.72 g/mol
Monoisotopic mass
252.00117821

Names & identifiers

Preferred name
Sulphenone
IUPAC
1-(benzenesulfonyl)-4-chlorobenzene
English name
Sulfenone
Molecular formula
C12H9ClO2S
Molecular weight
252.72

Names & synonyms

4-Chlorophenyl phenyl sulfone80-00-2SULPHENONESulfenone1-Chloro-4-(phenylsulfonyl)benzene4-Chlorodiphenyl sulfoneTrifensonSulfenonBenzene, 1-chloro-4-(phenylsulfonyl)-p-Chlorophenyl phenyl sulfoneCompound R-242p-Chlorophenyl phenyl sulphone
Show more names
r242r-242SULFERONEent17,941SulphenoneRr-242-b[qr]
Sulfone, p-chlorophenyl phenylp-Monochlorophenyl phenyl sulfoneR-242-B4-Chlorodiphenyl sulphone4-ChlordifenylsulfonENT 17,941Caswell No. 211DDTXSID9042259

Database identifiers

CAS
80-00-2
PubChem CID
6621
DTXSID
DTXSID9042259
ChEMBL
CHEMBL3188889
UNII
7NVM546U2M
EC Number
201-242-1
Nikkaji
J3.850D

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
42.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
16

Experimental & physicochemical properties

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticides -> Organochlorine Pesticides
LogPlog Kow = 3.25 /Estimated/
OdorSlight aromatic odor
TasteTasteless
Color/Form · 3 items

Dimorphic crystals

Colorless crystals

White solid

Physicochemical properties

Melting point
90 · 90-94 °C(lit.)
Boiling point
389 °C · 389 °C / 719mmHg
Density
1.3319 · 1.3319 (estimate)
storage temp.
-20 °C · -20°C Freezer, Under inert atmosphere
solubility
74.4 g/100ml · acetone: soluble74.4 g/100ml at 20°C(lit.)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (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.

Hazard information

Regulatory InformationBenzene, 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 SummaryEffects include weakness and weight loss in high-dose oral studies in dogs; [RTECS] An irritant; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Disposal Methods · 1 item

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Toxicology

Ecotoxicity Values · 4 items

LD50 House sparrows oral >100 mg/kg

LD50 Redwinged blackbirds oral >100 mg/kg

LC50 Fundulus similis (Longnose killifish) 7500 ug/L/24 hr; 6000 ug/L/48 hr; static /Formulated product/

LC50 Mugil curema (White mullet) 11900 ug/L/48 hr; static /Formulated product/

Environmental Fate · 3 items

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 · 1 item

/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 · 1 item

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 SourcesSulphenone'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 · 1 item

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).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
WR5775000
hs_code
2930909899
Toxicity
LD50 orally in mice: 2.7 g/kg (Hazleton)

Chemistry & industry

Pharmacology

Absorption, Distribution and ExcretionNo significant tissue storage in chronic feeding tests /in lab mammals/.

Uses & manufacturing

Uses · 5 items

Used as acaricide; Not currently registered with the EPA for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For sulphenone (USEPA/OPP Pesticide Code: 060510) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Acaricide

A miticide

Methods of Manufacturing · 2 items

Preparation: Bender, Pitt, US 2593001 (1952 to Stauffer Chem)

...By reaction of benzenesulfonic acid & chlorobenzene @ 250 °C...

Formulations/Preparations · 3 items

Emulsifiable concn 4 lb/US gal; 50% wettable powder; field concn (wp) of order of 2-3 lb/100 US gal

Commercial product contains 80% sulfenone and 20% related diaryl sulfones.

Technical material consists of about 80% of this compound, with small amount of o- & m-isomers, bis-(p-chlorophenyl) sulfone, & diphenyl sulfone.

General Manufacturing Information · 3 items

Benzene, 1-chloro-4-(phenylsulfonyl)-: ACTIVE

Insecticidal property of bis(p-chlorophenyl)sulfone: Unsymmetrical Deriv was developed for Insecticidal purposes by Stauffer chem. ...Compatible with all commonly-used spray materials. An acaricide with limited insecticidal properties, good residual & ovicidal activity on 2 spotted spider mite. Ovicide on apples & pears. No ...evidence of phytotoxicity except ...on sensitive greenhouse plants & certain sensitive varieties of apples or pears.

Discontinued by Stauffer Chemical Co.

Applications · 4 items

UsesSulfenone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.

UsesAcaricide.

Uses4-Chlorophenyl Phenyl Sulfone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.

General Description4-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.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
石家庄衍晟生物科技有限公司18332018567; 18332018567 · [email protected]

Related reactions

8 records

Linked notes

Loading…