Chloro(dimethylsulfide)gold(I)

Base Information

• Chemical Name: Chloro(dimethylsulfide)gold(I)
• CAS No.: 29892-37-3
• Molecular Formula: C2H6AuClS
• Molecular Weight: 294.555
• European Community (EC) Number: 627-889-3
• DSSTox Substance ID: DTXSID001029475
• Wikipedia: Chloro(dimethyl_sulfide)gold(I)
• Wikidata: Q5102987
• Mol file: 29892-37-3.mol

Synonyms:Chloro(dimethylsulfide)gold(I);29892-37-3;chlorogold;methylsulfanylmethane;(Dimethylsulfide)gold(I) chloride;chloro(dimethyl sulfide)gold(i);AuCl(SMe2);(dimethylsulfide)gold(i)chloride;DTXSID001029475;(methylsulfanyl)methane;AKOS024259170;SC10720;D78287;(Dimethylsulfide)gole(I)chloride, (CH3SCH3)AuCl;A924875;Q5102987;(DIMETHYLSULFIDE)GOLD(I) CHLORIDE;CHLORO(DIMETHYLSULFIDE)GOLD(I);[AU(SME2)CL];(Dimethylsulfide)gole(I)chloride,? (CH3SCH3)AuCl

Chemical Property of Chloro(dimethylsulfide)gold(I)

Chemical Property:

• Melting Point: 160°C(dec.)(lit.)
• PSA: 25.30000
• LogP: 1.66620
• Storage Temp.: 0-10°C
• Sensitive.: light sensitive, store cold
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 293.954444
• Heavy Atom Count: 5
• Complexity: 4.8

Purity/Quality:

99%, ^*data from raw suppliers

Chloro(dimethylsulfide)gold(I) >97.0%(T) ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC.Cl[Au]
• General Description: (Dimethylsulfide)gold(I) chloride (AuCl·SMe₂) is a gold(I) precursor used in coordination chemistry, characterized by its linear geometry around the gold center when bound to ligands such as axially chiral oxazoline-carbenes. It reacts with these ligands to form stable Au(I) complexes, with the coordination behavior and yields influenced by the stereochemistry of the chiral framework. The resulting complexes exhibit distinct structural properties, as confirmed by NMR and X-ray crystallography, highlighting the role of ligand geometry in complex formation.

Technology Process of Chloro(dimethylsulfide)gold(I)

There total 16 articles about Chloro(dimethylsulfide)gold(I) 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: 99.0%

gold(III) tetrachloride trihydrate + dimethylsulfide (75-18-3) → chloro(dimethylsulfide) gold(I) (29892-37-3)

Guidance literature:

In ethanol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c8dt00109j

Reference yield: 99.0%

potassium tetrachloroaurate(III) (13682-61-6) + dimethylsulfide (75-18-3) → chloro(dimethylsulfide) gold(I) (29892-37-3)

Guidance literature:

In methanol; for 0.5h; Darkness;

DOI:10.1002/chem.201804378

Reference yield: 93.0%

hydrogenchloride (7647-01-0,15364-23-5) + dimethylsulfide (75-18-3) + gold (7440-57-5,457905-15-6) → chloro(dimethylsulfide) gold(I) (29892-37-3)

Guidance literature:

With aqua regia; In methanol; water; dissolving of Au in boiling aqua regia, redn. of vol. by boiling, addn. concd. HCl, redn. of volume; repeat this procedure; cooling to room tempp., addn. of CH3OH, dropwise addn. of SMe2 with min. light exposure withcontinous stirring; pptn., filtration, washing with methanol, diethyl ether and pentane, drying under vac.;

DOI:10.1039/b005251p

upstream raw materials:

hydrogenchloride

dimethylsulfide

gold

potassium tetrachloroaurate(III)

Downstream raw materials:

gold

(triphenylphosphine)gold(I) chloride

(bis(diphenylphosphino)methane)bis(chlorogold(I))

(trimethylphosphine)gold(I) chloride

Refernces

Synthesis of axially chiral oxazoline-carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

10.3762/bjoc.8.81

The research focuses on the synthesis and coordination behavior of axially chiral oxazoline-carbene ligands with an N-naphthyl framework, specifically their interaction with AuCl·SMe2 to form Au(I) complexes. The main reactants used in the synthesis include methyl 1-hydroxy-2-naphthoate, trifluoromethylation reagents, 2-nitroaniline, Pd/C for reduction, triethyl orthoformate, TsOH for cyclization, and (S)-2-amino-2-phenylethanol, among others. The synthesis process involved several steps, including trifluoromethylation, coupling reactions, reduction, cyclization, and amide formation, leading to the formation of axially chiral ligands. The coordination study with AuCl·SMe2 was conducted using NaOAc in acetonitrile, and the Au(I) complexes were isolated by flash column chromatography. The analysis of the complexes was performed using 1H NMR spectroscopy to compare the chemical shifts of protons on the oxazoline ring before and after complexation, and single-crystal X-ray diffraction studies were employed to confirm the structure of the complexes, revealing a nearly linear coordination geometry around the gold(I) center. The study found that the geometry of the chiral N-naphthyl axis significantly influenced the yields of the Au(I) complexes, with (Sa,S)-7 yielding higher complex yields than (Ra,S)-7.

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