6160-65-2 Usage
Description
1,1'-ThiocarbonylDiimidazole is an organic compound that serves as a versatile reagent in various chemical and biochemical synthesis processes. It is known for its ability to deoxygenate carboxylic monosaccharide analogues and is used in conjunction with other reagents for the deoxygenation of alcohols and diols.
Uses
Used in Chemical Synthesis:
1,1'-ThiocarbonylDiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. This property makes it a valuable tool in the synthesis of various organic compounds, particularly in the removal of oxygen-containing functional groups.
Used in Biochemical Synthesis:
1,1'-ThiocarbonylDiimidazole is used as a reagent in biochemical synthesis, where it aids in the formation of desired products by facilitating specific chemical reactions. Its ability to deoxygenate carboxylic monosaccharide analogues is particularly useful in the synthesis of complex biological molecules.
Used in the Preparation of 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole:
1,1'-ThiocarbonylDiimidazole is used in the preparation of 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol. This application highlights its versatility in the synthesis of diverse chemical compounds with potential applications in various fields.
Synthesis Reference(s)
The Journal of Organic Chemistry, 43, p. 337, 1978 DOI: 10.1021/jo00396a035
Purification Methods
It forms yellow crystals on recrystallisation from tetrahydrofuran or by sublimation at 10-3torr (bath temperature 70-80o). It is hydrolysed by H2O and should be stored dry. [Staab & Walther Justus Liebigs Ann Chem 657 98 1962; Pullukat et al. Tetrahedron Lett 1953 1967, Hanessian et al. Can J Chem 65 1859 1987, Rajanbabu et al. J Am Chem Soc 111 1759 1989.] Thiochrome {2,7-dimethyl-5H -thiachromine-8-ethanol; 3,8-dimethyl-2-hydroxyethyl-5H -
Check Digit Verification of cas no
The CAS Registry Mumber 6160-65-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,6 and 0 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 6160-65:
(6*6)+(5*1)+(4*6)+(3*0)+(2*6)+(1*5)=82
82 % 10 = 2
So 6160-65-2 is a valid CAS Registry Number.
6160-65-2Relevant articles and documents
Conversion of D-(-)-quinic acid into an enantiopure C-4 functionalized 2-iodocyclohexenone acetal
Su,Paquette
, p. 764 - 766 (1995)
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Origin of the "β-oxygen effect" in the Barton deoxygenation reaction
Crich, David,Beckwith, Athelstan L. J.,Chen, Chen,Yao, Qingwei,Davison, Ian G. E.,Longmore, Robert W.,De Parrodi, Cecilia Anaya,Quintero-Cortes, Leticia,Sandoval-Ramirez, Jésus
, p. 8757 - 8768 (2007/10/02)
Photolysis of O-neopentyl S-tributylstannyl dithiocarbonate with hexaphenyl distannane, and 4-methoxyacetophenone as sensitizer, results in crossover of the stannyl groups. The reaction of O-octyl O′-(2-butoxyethyl) thiocarbonate with tributyltin deuteride or tris(trimethylsilyl)silane and a radical initiator shows no significant preference for the cleavage of either C-O bond. Intermolecular competitions between O-octyl O′-phenyl thiocarbonate and O-(2-butoxyethyl) O′-phenyl thiocarbonate for a deficiency of stannane or silane also indicated no significant preference for reaction of the β-oxygen-substituted substrate, leading to the conclusion that in conformationally unrestricted systems there is no significant β-oxygen effect in the Barton deoxygenation reaction. Competition experiments between the cis- and trans-O-(4-phenylcyclohexyl) S-methyl dithiocarbonates and the cis- and trans-O-(2-phenyl1,3-dioxan-5-yl) S-methyl dithiocarbonates for reaction with tributylstannane reveal that in every case the heterocyclic system is more reactive. The cis-isomers of 4-phenylcyclohexyl S-methyl dithiocarbonate and O-(2-phenyl-1,3-dioxan-5-yl) 5-methyl dithiocarbonate, with their axial xanthates, are more reactive than the corresponding transisomers. Molecular mechanics calculations suggest that the greater reactivity of the cis-series with respect to the trans is due to the greater relief of strain on fragmentation.