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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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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
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)
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)
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
Nan Yan et al.
Science advances, 4(10), eaat7259-eaat7259 (2018-10-20)
The transition from nanocluster to nanocrystal is a central issue in nanoscience. The atomic structure determination of metal nanoparticles in the transition size range is challenging and particularly important in understanding the quantum size effect at the atomic level. On
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