1-[chloro(4-methoxyphenyl)benzyl]-4-methoxybenzene

• ChemBase ID: 68203
• Molecular Formular: C21H19ClO2
• Molecular Mass: 338.82736
• Monoisotopic Mass: 338.10735753
• SMILES: C(c1ccc(cc1)OC)(c1ccc(cc1)OC)(c1ccccc1)Cl
• Canonical SMILES: COc1ccc(cc1)C(c1ccc(cc1)OC)(c1ccccc1)Cl
• InChI: InChI=1S/C21H19ClO2/c1-23-19-12-8-17(9-13-19)21(22,16-6-4-3-5-7-16)18-10-14-20(24-2)15-11-18/h3-15H,1-2H3
• InChIKey: JBWYRBLDOOOJEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[chloro(4-methoxyphenyl)benzyl]-4-methoxybenzene
• IUPAC Traditional name: 1-[chloro(4-methoxyphenyl)benzyl]-4-methoxybenzene
• Synonyms: 4,4'-Dimethoxytriphenylmethyl chloride; 4,4'-Dimethoxytrityl chloride; 4,4′-Dimethoxytrityl chloride; DMT; 4,4′-Dimethoxytrityl chloride; Chloro-4,4′-dimethoxytriphenylmethane; 4,4′-Dimethoxytriphenylmethyl chloride; 4,4'-Dimethoxytrityl chloride; DMT-Cl; 4,4'-二甲氧基三苯基氯甲烷; 4,4′-二甲氧基氯化三苯甲烷; 4,4′-二甲氧基氯化三苯甲烷; 氯-4,4′-二甲氧基三苯基甲烷; 4,4′-二甲氧基三苯甲基氯

Database IDs

• CAS Number: 40615-36-9
• EC Number: 255-002-6
• MDL Number: MFCD00008409
• Beilstein Number: 2471942
• PubChem SID: 24864217; 162033935; 24846511
• PubChem CID: 96831

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.6776276
• LogD (pH = 7.4): 5.6776276
• Log P: 5.6776276
• Molar Refractivity: 99.2889 cm^3
• Polarizability: 38.210403 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 119-123 °C(lit.); 121-127°C; 123-125 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: IRRITANT; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-37; S:20-25-26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... HTR2A(3356), HTR2B(3357), HTR2C(3358)rat ... Htr1a(24473), Htr2a(29595)

Product Information

• Purity: ≥97.0% (HPLC); 95%; 95+%; 97%; 98%
• Linear Formula: C6H5C(C6H4OCH3)2Cl
• Empirical Formula (Hill Notation): C21H19ClO2

DETAILS

MP Biomedicals - 02150925

Protecting reagent for oligonucleotide synthesis.

Sigma Aldrich - 100013

Packaging
5, 25 g in glass bottle
Application
Hydroxyl protecting group for nucleosides1,2,3 and nucleotides.4

Sigma Aldrich - 38827

Other Notes
Useful protecting-group reagent1,2,3; Removal4
Packaging
10, 50 g in glass bottle

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).