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Sigma-Aldrich

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
Beilstein:
1446618
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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

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General description

2-Phenylethanethiol serves as a building block in organic synthesis to incorporate a thiol functional group into molecules.[1] Structures of 2-phenylethanethiol and its 1:1 water clusters have been studied using resonant two-photon ionization spectroscopy[2].

Application

2-Phenylethanethiol has been used:
  • in preparation of biicosahedral Au (25) clusters protected with various types of thiol ligands[3]
  • as derivatization reagent for phosphorylated sequences of peptides, for enhancing ionization efficiency in matrix-assisted laser desorption/ionization mass spectrometry[4]

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
Danielle E Martin et al.
The Journal of chemical physics, 128(16), 164301-164301 (2008-05-02)
The structures of 2-phenylethanethiol (PET, PhCH(2)CH(2)SH) and its 1:1 water clusters have been studied using resonant two-photon ionization spectroscopy including band contour analysis and UV-UV holeburning, combined with extensive ab initio calculations on ground and excited states. The most populated
Sanghwa Lee et al.
Journal of the American Chemical Society, 142(32), 13974-13981 (2020-07-17)
Atomically precise coinage metal (Au, Ag, and Cu) nanoclusters (NCs) have been the subject of immense interest for their intriguing structural, photophysical, and catalytic properties. However, the synthesis of Cu NCs is highly challenging because of low reduction potential and

Articles

Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.

Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.

Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.

Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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