4-(tert-Butyl)benzyl mercaptan

Base Information

• Chemical Name: 4-(tert-Butyl)benzyl mercaptan
• CAS No.: 49543-63-7
• Molecular Formula: C11H16S
• Molecular Weight: 180.314
• Hs Code.: 2930909090
• European Community (EC) Number: 628-884-9
• DSSTox Substance ID: DTXSID50373791
• Nikkaji Number: J268.480B
• Mol file: 49543-63-7.mol

Synonyms:(4-tert-Butylphenyl)methanethiol;4-tert-Butylbenzenemethanethiol;4-tert-Butylbenzyl mercaptan;4-tert-Butylbenzylthiol;p-tert-Butylbenzenemethanethiol;p-tert-Butylbenzylmercaptan;

Chemical Property of 4-(tert-Butyl)benzyl mercaptan

Chemical Property:

• Vapor Pressure: 0.0251mmHg at 25°C
• Refractive Index: n20/D 1.5430(lit.)
• Boiling Point: 256.2 °C at 760 mmHg
• PKA: 9.83±0.10(Predicted)
• Flash Point: 102.3 °C
• PSA: 38.80000
• Density: 0.966 g/cm³
• LogP: 3.41390
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 180.09727168
• Heavy Atom Count: 12
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

(4-tert-Butylphenyl)methanethiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)CS
• Uses: 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.

Technology Process of 4-(tert-Butyl)benzyl mercaptan

There total 3 articles about 4-(tert-Butyl)benzyl mercaptan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

p-tert-butylbenzyl alcohol (877-65-6) → 4-tert-butylbenzyl mercaptan (49543-63-7)

Guidance literature:

With Lawessons reagent; In toluene; for 48h; Reflux;

DOI:10.1002/adsc.201701518

Reference yield:

4-tert-Butylbenzaldehyde (939-97-9) → 4-tert-butylbenzyl mercaptan (49543-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol

2: Lawessons reagent / toluene / 48 h / Reflux

With Lawessons reagent; sodium tetrahydroborate; In methanol; toluene;

DOI:10.1002/adsc.201701518

Reference yield:

1-tert-Butyl-4-octylsulfanylmethyl-benzene → dioctyl disulfide (822-27-5) + Octanethiol (111-88-6) + 1,2-bis(4-tert-butylphenyl)ethane (22927-07-7) + 4-tert-butyltoluene (98-51-1) + 4-tert-butylbenzyl mercaptan (49543-63-7) + 1-tert-butyl-4-nonylbenzene

Guidance literature:

With hydrogen; In acetone; at -78 ℃; under 3.5 Torr; Mechanism; Product distribution; other alkyl substituted-benzyl sulfides and alkyl sulfides, competition with n-octyl benzyl sulfide, reaction rate relative to n-octyl benzyl sulfide, microwave generation of H from H₂, reaction time 5-10 min;

DOI:10.1021/jo9615615

upstream raw materials:

p-tert-butylbenzyl alcohol

4-tert-Butylbenzaldehyde

Downstream raw materials:

2-(4-tert-Butyl-benzylsulfanylcarbonyl)-propionic acid ethyl ester

5-(4-tert-butyl-benzylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde

2-(4-tert-butylbenzyl)thio-3-((2-tetrahydropyranyloxy)methyl)chromen-4-one

5-(4-t-butylbenzylthio)-4-chloro-2-[(2,2-dichloro-1,1-dimethyl)-ethyl]-3(2H)-pyridazinone

Refernces

• 1、 Tanner, Dennis D.,Koppula, Sudha,Kandanarachchi, Pramod. "Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate". . p. 4210 - 4215. Retrieved 2007/10/03.