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E50604

Sigma-Aldrich

Ethyltriphenylphosphonium bromide

99%

Synonym(s):

TEP

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About This Item

Linear Formula:
[(C6H5)3P+C2H5]Br-
CAS Number:
Molecular Weight:
371.25
Beilstein:
3599630
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

reaction suitability

reaction type: C-C Bond Formation

mp

203-205 °C (lit.)

SMILES string

[Br-].CC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C20H20P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h3-17H,2H2,1H3;1H/q+1;/p-1

InChI key

JHYNXXDQQHTCHJ-UHFFFAOYSA-M

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Application

Reactant for synthesis of:
  • D-amino acids from L-cysteine-derived thiazolidines
  • Leiodolide A via aldol reactions and Horner-Wadsworth-Emmons olefination
  • Cycloalkanoindolines via diastereoselective intramolecular inimo-ene reactions
  • WXYZA′ domain of maitotoxin using the coupling of key building blocks

Reactant for:
  • Solid-state metathesis polycondensation to form alkyl-dipropenylthiophene monomers
  • Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization / lactonization cyclization reactions for synthesis of an ABC ring system

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 2

Flash Point(F)

401.0 °F

Flash Point(C)

205 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zhu Xiong et al.
Scientific reports, 7(1), 14099-14099 (2017-10-28)
Instability of superwetting surface is the stumbling block of flexible polymeric membranes for continuous separation of water-in-oil or oil-in-water emulsions. Manipulation of rigid superwetting nano-TiO
Yoshihiro Noda et al.
Depression and anxiety, 35(5), 448-456 (2018-04-11)
Dysfunctional neuroplasticity may be one of the pathophysiological mechanisms underlying major depression. We have previously established methods to assess neuroplasticity from the dorsolateral prefrontal cortex (DLPFC) using a paired associative stimulation (PAS) paradigm, which pairs a preceding peripheral nerve stimulation
Aru Panwar et al.
Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery, 158(1), 103-109 (2017-08-16)
Objectives To identify differences in postoperative wound complications associated with a primary tracheoesophageal puncture (TEP) at the time of laryngectomy versus no TEP. Study Design Retrospective review of large national data set. Setting Academic and nonacademic health care facilities in
Yoshihiro Noda et al.
Aging, 9(2), 556-572 (2017-02-18)
Gamma-aminobutyric acid (GABA)ergic and glutamatergic neurotransmissions in the prefrontal cortex decreases with age. Further, cognitive function mediated through the dorsolateral prefrontal cortex (DLPFC) also declines with age. Although neuroimaging studies have demonstrated decreased levels of these substances, direct neurophysiological data
Chaozheng Li et al.
Developmental and comparative immunology, 70, 45-58 (2017-01-11)
Thioester-containing proteins (TEPs) are present in a wide range of species from deuterostomes to protostomes and are thought to be involved in innate immunity. In the current study, a TEP gene homologous to insect TEPs (iTEP) from the crustacean Litopenaeus

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