Basic information
- Standard SMILES
c1ccc([Se][Se]c2ccccc2)cc1- InChIKey
YWWZCHLUQSHMCL-UHFFFAOYSA-N- Molecular formula
- C12H10Se2
- Average molar mass
- 312.1 g/mol
- Monoisotopic mass
- 313.91129292
Overview
Diphenyl diselenide is an organic molecular entity.
Names & identifiers
- Preferred name
- Diphenyl diselenide
- IUPAC
- (phenyldiselanyl)benzene
- English name
- Diphenyl diselenide
- Molecular formula
- C12H10Se2
- Molecular weight
- 312.13
Names & synonyms
Show more names
Database identifiers
- CAS
1666-13-3- PubChem CID
- 15460
- DTXSID
DTXSID6061864- ChEMBL
CHEMBL3122204- ChEBI
CHEBI:232541- UNII
- 9ATU3Z459Q
- EC Number
- 216-780-2
- Nikkaji
- J31.930I
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 128
Physicochemical properties
- Melting point
- 60 °C · 60 °C
- Boiling point
- 202 °C · 202 °C / 11mmHg
- Density
- 1.557 · 1.5570
- refractive index
- 1.743 · 1.7430
- storage temp.
- 30 °C · Store below +30°C.
- form
- Powder
- color
- yellow
- Specific Gravity
- 1.84 · 1.84
- Water Solubility
- Insoluble
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 2047179 · 2047179
- Exposure limits
- 0.2 mg/m3NIOSH: · ACGIH: TWA 0.2 mg/m3NIOSH: IDLH 1 mg/m3; TWA 0.2 mg/m3
- InChI
- 1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
- InChIKey
- YWWZCHLUQSHMCL-UHFFFAOYSA-N
- SMILES
- [Se]([Se]c1ccccc1)c2ccccc2
- CAS DataBase Reference
- 1666 · 1666-13-3(CAS DataBase Reference)
- FDA UNII
- 9 ATU3Z459Q · 9ATU3Z459Q
- NIST Chemistry Reference
- Diselenide, diphenyl(1666-13-3)
- EPA Substance Registry System
- Diselenide, diphenyl (1666-13-3)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 330 · H330-H301-H373-H410
- Precautionary statements
- 501 · P501-P273-P260-P270-P271-P264-P284-P391-P314-P301+P310+P330-P304+P340+P310-P403+P233-P405
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T,N
- Risk Statements
- 23 · 23/25-33-50/53
- Safety Statements
- 20 · 20/21-28-45-60-61-28A
- RIDADR
- 3283 · UN 3283 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 9152500 · JM9152500
- TSCA
- TSCA listed
- HS Code
- 2931 · 2931 90 00
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 InhalationAcute · Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
- Limited Quantities
- 0.5 Kg · 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (97.9%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P319, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Diselenide, diphenyl
Diphenyl diselenide: Does not have an individual approval but may be used under an appropriate group standard
Safety & protection
Toxicology
Health Effects
Chronic oral exposure to high concentrations of selenium compounds can produce a disease called selenosis. The major signs of selenosis are hair loss, nail brittleness, and neurological abnormalities (such as numbness and other odd sensations in the extremities). Animal studies have shown that selenium may also affect sperm production and the female reproductive cycle. (L619)
Toxicity Summary
Selenium readily substitutes for sulfur in biomolecules and in many biochemical reactions, especially when the concentration of selenium is high and the concentration of sulfur is low. Inactivation of the sulfhydryl enzymes necessary for oxidative reactions in cellular respiration, through effects on mitochondrial and microsomal electron transport, might contribute to acute selenium toxicity. Selenomethionine (a common organic selenium compound) also appears to randomly substitute for methionine in protein synthesis. This substitution may affect the structure and functionability of the protein, for example, by altering disulfide bridges. Inorganic forms of selenium appear to react with tissue thiols by redox catalysis, resulting in formation of reactive oxygen species and causing damage by oxidative stress. (L619)
Signs and Symptoms
Short-term oral exposure to high concentrations of selenium may cause nausea, vomiting, and diarrhea. Brief exposures to high levels of elemental selenium or selenium dioxide in air can result in respiratory tract irritation, bronchitis, difficulty breathing, and stomach pains. Longer-term exposure to either of these air-borne forms can cause respiratory irritation, bronchial spasms, and coughing. (L619)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- JM9152500
- ridadr
- UN 3283 6.1/PG 2
- hs_code
- 2931 90 00
- risk_code
- 23/25-33-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08,GHS09
- hazard_code
- T,N
- safety_code
- 20/21-28-45-60-61-28A
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H330-H301-H373-H410
- Limited Quantities
- 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
- Precautionary statements
- P501-P273-P260-P270-P271-P264-P284-P391-P314-P301+P310+P330-P304+P340+P310-P403+P233-P405
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Selenium may be absorbed through inhalation and ingestion, while some selenium compounds may also be absorbed dermally. Once in the body, selenium is distributed mainly to the liver and kidney. Selenium is an essential micronutrient and is a component of glutathione peroxidase, iodothyronine 5'-deiodinases, and thioredoxin reductase. Organic selenium is first metabolized into inorganic selenium. Inorganic selenium is reduced stepwise to the intermediate hydrogen selenide, which is either incorporated into selenoproteins after being transformed to selenophosphate and selenocysteinyl tRNA or excreted into the urine after being transformed into methylated metabolites of selenide. Elemental selenium is also methylated before excretion. Selenium is primarily eliminated in the urine and feces, but certain selenium compounds may also be exhaled. (L619)
Uses & manufacturing
Applications
UsesDiphenyl diselenide is used in the methoxyselenenylation of alkenes, dihydroxylation of double bonds, hydrothiolation of terminal alkynes. It is used in the synthesis of the unsymmetrical diorganyl selenides, 1-(phenylselenomethyl)vinyl selenides, allylic phenyl selenides.
General DescriptionDiphenyl diselenide (Ph2Se2) is an organoselenium compound. Its crystalline structure, toxicokinetic properties, antioxidant and anti-inflammatory activities have been investigated. Its ability to reverse the oxidative brain damage and mitochondrial dysfunction induced by acetaminophen has been studied in mice. It reacts with thallium (Tl) to form TI (SePh). It participates in a four-component radical coupling to form substituted cyclopentanes.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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