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Sigma-Aldrich

4-tert-Butylbenzyl mercaptan

Synonym(s):

4-tert-Butylbenzenemethanethiol, 4-tert-Butylbenzylthiol, 4-tert-Butylphenylmethanethiol, p-tert-Butylbenzenemethanethiol, p-tert-Butylbenzyl mercaptan

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About This Item

Linear Formula:
(CH3)3CC6H4CH2SH
CAS Number:
49543-63-7
Molecular Weight:
180.31
MDL number:
MFCD00068220
UNSPSC Code:
12352100
PubChem Substance ID:
24879053
NACRES:
NA.22

refractive index

n20/D 1.5430 (lit.)

bp

102-103 °C/3.1 mmHg (lit.)

density

0.966 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)c1ccc(CS)cc1

InChI

1S/C11H16S/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-7,12H,8H2,1-3H3

InChI key

UIYKSYBJKIMANV-UHFFFAOYSA-N

General description

4-tert-Butylbenzyl mercaptan is a benzyl mercaptan derivative that is commonly used as a ligand for synthesizing metal clusters.

Application

4-tert-Butylbenzyl mercaptan (BBSH) may be used in the preparation of N-Me-aminopyrimidinone derivatives, which are potent state-dependent inhibitor of Nav1.7 (Nav= voltage-gated sodium channel). It may also be used to synthesize organic-soluble, atomically precise array of silver clusters via a novel approach based on the miscibility principle while avoiding the use of phase-transfer agents.
Reactant for:
  • Stereoselective thiourea-catalyzed sulfa-Michael addition
  • Nucleophilic substitution reactions
  • Urea-catalyzed trans-thioesterification
  • Sc-catalyzed Michael addition
  • Copper-catalyzed decarboxylative cross-coupling

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

162.0 °F - closed cup

Flash Point(C)

72.2 °C - closed cup

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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Luminescent AgAu Alloy Clusters Derived from Ag Nanoparticles-Manifestations of Tunable AuI-CuI Metallophilic Interactions.
Krishnadas KR, et al.
European Journal of Inorganic Chemistry, 2014(5), 908-916 (2014)
Hanh Nho Nguyen et al.
Bioorganic & medicinal chemistry letters, 22(2), 1055-1060 (2012-01-03)
Clinical genetic data have shown that the product of the SCN9A gene, voltage-gated sodium ion channel Nav1.7, is a key control point for pain perception and a possible target for a next generation of analgesics. Sodium channels, however, historically have
C K Manju et al.
Dalton transactions (Cambridge, England : 2003), 48(24), 8664-8670 (2019-05-29)
Recent reports have shown that the intercluster reaction is a new synthetic strategy to prepare alloy clusters. In this work, we performed an intercluster reaction between silver clusters and produced highly ionizable Ag-S-type clusters; we examined their formation by mass
Synthesis of atomically precise silver clusters by using the miscibility principle.
Ghosh A and Pradeep T.
European Journal of Organic Chemistry, 2014(31), 5271-5275 (2014)
Gui-Nan Shen et al.
Experimental and therapeutic medicine, 20(5), 82-82 (2020-09-25)
The aim of the present study was to verify the pro-apoptotic anticancer potential of several 5,8-dimethoxy-1,4-phthoquinone (DMNQ) derivatives in Ras-mediated tumorigenesis. MTT assays were used to detect cellular viability and flow cytometry was performed to assess intracellular reactive oxygen species
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