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6160-65-2 - 1,1'-Thiocarbonyldiimidazole, tech 90% - B22008 - Alfa Aesar

B22008 1,1'-Thiocarbonyldiimidazole, tech 90%

CAS Number
6160-65-2
Synonyms

Size Price ($) Quantity Availability
10g 88.15
50g 293.55
250g 775.20
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1,1'-Thiocarbonyldiimidazole, tech 90%

MDL
MFCD00005289
EINECS
228-183-4

Chemical Properties

Formula
C7H6N4S
Formula Weight
178.22
Melting point
98-102°
Sensitivity
Moisture Sensitive
Solubility
Soluble in terahydrofuran, toluene and dichloromethane.

Applications

1,1'-Thiocarbonyldiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. It is also used to deoxygenate carboxylic monosaccharide analogues. Further, it is a useful reagent involved in biochemical synthesis. In addition to this, it is used to prepare 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol.

Notes

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Store in a cool place. Incompatible with strong oxidizing agents and strong acids.

Literature References

Reacts with diols to give cyclic thionocarbonates which are desulfurized by trialkyl phosphites to give alkenes by cis-elimination of CO2 from the intermediate carbene (Corey-Winter olefination): J. Am. Chem. Soc., 85, 2677 (1963); Angew. Chem. Int. Ed., 14, 753 (1975). For a modified procedure involving ring-opening of the thionocarbonate intermediate with an alkyl iodide, followed by Zn reduction of the resulting iodo ester, see: Tetrahedron Lett., 3793 (1973). Alternatively, the thionocarbonate of a 1,2-diol can be selectively reduced to the methylenedioxy group with Triphenyl­tin hydride, L00163, under free-radical conditions: J. Org. Chem., 62, 4159 (1997).

Can be used to deoxygenate carbocyclic monosaccharide analogues: Tetrahedron., 48, 2349 (1992).

Ivanov, A. V.; Virus, E. D.; Luzyanin, B. P.; Kubatiev, A. A. Capillary electrophoresis coupled with 1,1'-thiocarbonyldiimidazole derivatization for the rapid detection of total homocysteine and cysteine in human plasma. J. Chromatogr. B 2015, 1004, 30-36.

Chaurand, P. Introducing specificity and sensitivity in imaging MS. Bioanalysis 2015, 7 (18), 2279-2281.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
609349
Harmonized Tariff Code
2933.29
TSCA
No

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