Basic information
- Standard SMILES
c1ccc(SSc2ccccc2)cc1- InChIKey
GUUVPOWQJOLRAS-UHFFFAOYSA-N- Molecular formula
- C12H10S2
- Average molar mass
- 218.3 g/mol
- Monoisotopic mass
- 218.02239232
Overview
Diphenyl disulfide is a member of benzenes.
Names & identifiers
- Preferred name
- Diphenyl disulfide
- IUPAC
- (phenyldisulfanyl)benzene
- English name
- Diphenyl disulfide
- Molecular formula
- C12H10S2
- Molecular weight
- 218.34
Names & synonyms
DIPHENYL DISULFIDEPhenyl disulfide882-33-7(Phenyldisulfanyl)benzeneDisulfide, diphenylDiphenyl disulphideBiphenyl disulfidePhenyldithiobenzeneDisulfide diphenylFEMA No. 3225DTXSID6022131NSC-2689
Show more names
FEMA 3225PHENYL DISULPHIDEDiphenyl disulfide ,99%Nelfinavir Related CoMpound Eusafe-1AKOS 94361
7P54H519IJDTXCID702131RefChem:588825212-926-41,2-diphenyldisulfanediphenyldisulfideUSAF E-1Phenyldisulfide
Database identifiers
- CAS
882-33-7- PubChem CID
- 13436
- DTXSID
DTXSID6022131- ChEMBL
CHEMBL462861- ChEBI
CHEBI:174102- UNII
- 7P54H519IJ
- EC Number
- 212-926-4
- Nikkaji
- J2.117B
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 50.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 128
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Sulfur Compounds
SpringerMaterials PropertiesBoiling point
LogP
4.41
4.41
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.353 (20 °C)
Flavoring AgentsEU Flavoring substances
Solubility
insoluble in water; soluble in alcohol, ether, carbon disulfide
(in ethanol)
Boiling Point
310.00 °C. @ 760.00 mm Hg
310 °C; 192 °C (15 mm Hg)
Melting Point62 - 63 °C
Physical Description
Colorless solid; [Merck Index] White crystalline powder with an unpleasant odor; [Alfa Aesar MSDS]
Solid
orthorhombic needles
Physicochemical properties
- Melting point
- 58 · 58-60 °C (lit.)
- Boiling point
- 191 · 191-192 °C (15 mmHg)
- Density
- 1.353 · 1.353
- refractive index
- 1 · 1,441-1,444
- FEMA
- 3225 · 3225 | PHENYL DISULFIDE
- FLAVIS Number
- 12.043 · 12.043 | Diphenyl disulfide
- Flash point
- 310 °C · 310°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 3 %, · xylene: soluble3%, clear, colorless to yellow
- form
- Crystalline Solid
- color
- White to off-white
- Specific Gravity
- 1.353 · 1.353
- Odor
- 0.1 % · at 0.10 % in propylene glycol. sulfurous earthy burnt
- Odor Type
- sulfurous
- Water Solubility
- Insoluble in water.
- JECFA Number
- 578 · 578
- BRN
- 639794 · 639794
- Stability
- Stable. Incompatible with strong oxidizing agents, strong bases.
- InChI
- 1S/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
- InChIKey
- GUUVPOWQJOLRAS-UHFFFAOYSA-N
- SMILES
- S(Sc1ccccc1)c2ccccc2
- LogP
- 4.41 · 4.41
- CAS DataBase Reference
- 882 · 882-33-7(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- PHENYL DISULFIDE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 P54H519IJ · 7P54H519IJ
- NIST Chemistry Reference
- Disulfide, diphenyl(882-33-7)
- EPA Substance Registry System
- Diphenyl disulfide (882-33-7)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H410
- Precautionary statements
- 264 · P264-P270-P273-P301+P312-P391-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,N
- Risk Statements
- 36 · 36/37/38-50/53
- Safety Statements
- 26 · 26-37/39-36-61-60
- RIDADR
- 3335 · UN 3335
- WGK Germany
- 3 · 3
- RTECS
- 6825000 · SS6825000
- F
- 13 · 13
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- IRRITANT, STENCH
- PackingGroup
- III
- HS Code
- 29093090 · 29093090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 141 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: Disulfide, diphenyl
Disulfide, diphenyl: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Oral LD50 (female rat) > 300-2,000 mg/kg; Anemia and changes of the liver and kidney observed in repeated-dose oral study of rats at 30 mg/kg/day; No adverse effects on reproductive or developmental toxicity parameters seen at doses up to 30 mg/kg/day; No evidence of mutagenicity; [JECDB] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Diallyl disulfide and Benzyl disulfide.
Hazard Classes and Categories
Skin Irrit. 2 (98.6%)
Acute toxicity (Oral) - Category 4
Safety data
- F
- 13
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SS6825000
- ridadr
- UN 3335
- hs_code
- 29093090
- risk_code
- 36/37/38-50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi,N
- hazard_note
- Irritant
- safety_code
- 26-37/39-36-61-60
- hazard_class
- IRRITANT, STENCH
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H302-H410
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P264-P270-P273-P301+P312-P391-P501
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
UsesUsed as a reagent in organic synthesis; [Merck Index] Used as a flavoring agent; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationDisulfide, diphenyl: ACTIVE
Applications
DescriptionDiphenyl disulfide is a colorless crystalline material with the formula (C6H5S)2 and often abbreviated Ph2S2. It is most commonly utilized as a reagent for integration of a phenylthio functionality into molecules. The phenylthio group in the compound has a useful function due to the numerous of reaction that it can facilitate in organic chemistry. Phenysulfides, for instance, undergo oxidative elimination, producing alkenes under relatively mild, normal conditions. Also phenyl sulfides can serve as a source of carbon-centered radicals in radical reactions. Diphenyl disulfide is usually synthesized by the oxidation of thiophenol: 2 PhSH + I2 → Ph2S2 + 2 HI
OccurrenceNaturally occurring phytoalexin-like substan
UsesDiphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.
Preparation methods
PreparationBy heating and passing a stream of air over an ammoniacal solution of thiophenol.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Diphenyl disulfide is a member of benzenes.
Related reactions
33 records
Linked notes
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