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Diphenyl diselenide

HCID 15460
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1666-13-3
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

Diphenyl diselenide1666-13-3Diselenide, diphenylPhenyl diselenide1,2-Diphenyldiselane(phenyldiselanyl)benzeneDiphenyldiselenideBis(phenylselenide)9ATU3Z459QDTXSID6061864NSC-49763RefChem:134644
Show more names
diseLTwo phenyltwo sediphenyl-diseleniddiphenyl disenenideDiselenide,diphenylDiphenyl perselenide
DTXCID3035347216-780-2diphenyldiselaneC12H10Se2MFCD00003001CHEMBL3122204CCRIS 9227EINECS 216-780-2

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 propertiesFilling in

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)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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 · 2 items

Chemical: Diselenide, diphenyl

Diphenyl diselenide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesAcute Tox. 3 (97.9%)

Safety & protection

Minimum Risk LevelChronic Oral: 0.005 mg/kg/day (L134)

Toxicology

Health Effects · 1 item

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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

UsesDiphenyl diselenide is a useful reagent in organic synthesis. (L623)
General Manufacturing InformationDiselenide, diphenyl: INACTIVE
Applications · 2 items

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.

Related reactions

13 records
New reaction record
HRID 3901 reaction equation
HRID 3901As reactantuspto-grants-1988_02
HRID 36040 reaction equation
HRID 36040As reactantuspto-grants-1995_05
HRID 186939 reaction equation
HRID 186939As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 256381 reaction equation
HRID 256381As reactantuspto-grants-1987_10
HRID 728426 reaction equation
HRID 728426As reactantuspto-grants-1991_09
HRID 846685 reaction equation
HRID 846685As reactantuspto-grants-1992_08
HRID 846968 reaction equation
HRID 846968As reactantuspto-grants-1992_08
HRID 870037 reaction equation
HRID 870037As reactantuspto-grants-2015_03
Page 1 of 2

Compound notes

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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)
Exposure RoutesOral (L619) ; inhalation (L619) ; dermal (L619)
Toxicity Summary · 1 item

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 · 1 item

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)

Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)

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

Upstream & downstream products

Upstream raw materials

SeleniumGrignard reagentBromobenzene

Downstream products

MethylphenylselenidePhenylselenolBenzene, [(phenylmethyl)seleninyl]-