252581
2-Phenylethanethiol
98%
Synonym(s):
2-Phenylethyl mercaptan, Phenethyl mercaptan
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About This Item
Linear Formula:
C6H5CH2CH2SH
CAS Number:
Molecular Weight:
138.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
224-563-9
Beilstein/REAXYS Number:
1446618
MDL number:
Assay:
98%
Quality Level
assay
98%
refractive index
n20/D 1.560 (lit.)
bp
217-218 °C (lit.)
density
1.032 g/mL at 25 °C (lit.)
functional group
phenyl, thiol
SMILES string
SCCc1ccccc1
InChI
1S/C8H10S/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChI key
ZMRFRBHYXOQLDK-UHFFFAOYSA-N
General description
2-Phenylethanethiol serves as a building block in organic synthesis to incorporate a thiol functional group into molecules. Structures of 2-phenylethanethiol and its 1:1 water clusters have been studied using resonant two-photon ionization spectroscopy.
Application
2-Phenylethanethiol has been used:
- in preparation of biicosahedral Au (25) clusters protected with various types of thiol ligands
- as derivatization reagent for phosphorylated sequences of peptides, for enhancing ionization efficiency in matrix-assisted laser desorption/ionization mass spectrometry
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
194.0 °F - closed cup
flash_point_c
90 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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Articles
Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.
Clementine Klemm et al.
Rapid communications in mass spectrometry : RCM, 18(22), 2697-2705 (2004-10-16)
The identification of phosphorylation sites is essential for a full understanding of the cellular functions of proteins. However, mass spectrometric analysis is often hampered by the low abundance of phosphoproteins, the difficulty of obtaining full sequence coverage by specific proteolysis
Differential reactivity of the inner and outer positions of Au 25 (SCH 2 CH 2 Ph) 18 dimeric staples under place exchange conditions
P Pengo, et al.
Chemical Communications (Cambridge, England), 51, 3204-3207 (2015)
SunYoung Park et al.
Langmuir : the ACS journal of surfaces and colloids, 28(17), 7049-7054 (2012-04-12)
The synthesis and electrochemical and spectroscopic characterization of biicosahedral Au(25) clusters with a composition of [Au(25)(PPh(3))(10)(thiolate)(5)Cl(2)](2+) are described. The biicosahedral Au(25) clusters protected with various types of thiol ligands including alkanethiols, 2-phenylethanethiol, 11-mercaptoundecanoic acid, and 11-mercapto-1-undecanol were synthesized in high