4,4'-Dimethoxytrityl chloride

• Catalog No.: A11626
• CAS Number: 40615-36-9
• M. F.: C21H19ClO2
• M. W.: 338.82736
• Purity: 98%

SYNONYMS

• Title: 4,4'-二甲氧基三苯基氯甲烷
• IUPAC name: 1-[chloro(4-methoxyphenyl)benzyl]-4-methoxybenzene
• IUPAC Traditional name: 1-[chloro(4-methoxyphenyl)benzyl]-4-methoxybenzene
• Synonyms: 4,4'-Dimethoxytriphenylmethyl chloride; DMT

DATABASE IDS

• EC Number: 255-002-6
• Beilstein Number: 2471942
• MDL Number: MFCD00008409
• CAS Number: 40615-36-9

PROPERTIES

• Purity: 98%
• Melting Point: 121-127°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否

REFERENCES

• Reagent for protection of alcohols, compare Chlorotriphenylmethane, A11799 as their dimethoxytrityl (Dmt) ethers. Mono-, di- and trimethoxytrityl chlorides form ethers of increasing acid-lability, each MeO group increasing the rate of cleavage by ca x10: J. Am. Chem. Soc., 84, 430 (1962); 85, 3821 (1963). The group is introduced e.g. by reaction with the alcohol in pyridine solution. For use of DMAP as catalyst, see: J. Am. Chem. Soc., 104, 1316 (1982), or of silver nitrate: Can. J. Chem., 60, 1106 (1982).
• For selective protection and deprotection procedures for SH and OH groups in nucleoside derivatives, see: Synlett, 83 (1993).
• In a comparison with Mmt for N-protection during solid-phase peptide synthesis, the N-Mmt group was found to survive intact whereas N-Dmt derivatives decomposed slowly in protic solvents: Tetrahedron. Lett., 39, 1733 (1998).
• Selective cleavage in acid-sensitive nucleosides and nucleotides without competing N-glycosyl cleavage has also been accomplished by the use of 1,1,1,3,3,3-Hexafluoro-2-propanol, A12747: Tetrahedron Lett., 36, 7833 (1995). For deprotection with montmorillonite K 10 clay, see: J. Org. Chem., 61, 9026 (1996).