4,4'-Dimethoxytrityl chloride CAS 40615-36-9
4,4'-Dimethoxytrityl chloride Basic information
| Product Name: | 4,4'-Dimethoxytrityl chloride |
| Synonyms: | 1,1'-(chlorophenylmethylene)bis[4-methoxybenzene];4,4'-DIMETHOXY-TRIPHENYLCHLOROMETHANE;4,4-DIMETHOXYTRITYL CHLORIDE;DMT-Cl (4,4-Dimethoxytrityl Chloride);4,4-Dimethoxytritylchloride98+%;Dimethoxy Trityl Chloride;Bis(4-methoxyphenyl)phenylmethyl chloride;Chlorobis(4-methoxyphenyl)phenylmethane |
| CAS: | 40615-36-9 |
| MF: | C21H19ClO2 |
| MW: | 338.83 |
| EINECS: | 255-002-6 |
| Product Categories: | OLED materials,pharm chemical,electronic;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Regant series;Coupling Reagent;N-Protecting Reagents;Organics |
| Mol File: | 40615-36-9.mol |
4,4'-Dimethoxytrityl chloride Chemical Properties
| Melting point | 123-125 °C |
| Boiling point | 455.07°C (rough estimate) |
| density | 1.0887 (rough estimate) |
| vapor pressure | 0Pa at 20℃ |
| refractive index | 1.5330 (estimate) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| form | Powder |
| color | Pink |
| Water Solubility | Soluble in chloroform and methanol. Partially soluble in water |
| Sensitive | Moisture Sensitive |
| BRN | 2471942 |
| Stability: | Hygroscopic, Moisture Sensitive |
| 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 |
| SMILES | COc1ccc(cc1)C(Cl)(c2ccccc2)c3ccc(OC)cc3 |
| LogP | 5.74 at 20℃ |
| CAS DataBase Reference | 40615-36-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Methane, chlorobis(p-methoxyphenyl)phenyl-(40615-36-9) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-34 |
| Safety Statements | 22-24/25-37/39-26-36-45-36/37/39 |
| RIDADR | 3261 |
| WGK Germany | 3 |
| F | 10-21 |
| HS Code | 29093090 |
| Storage Class | 8B - Non-combustible corrosive hazardous materials |
| Hazard Classifications | Aquatic Chronic 2 Eye Dam. 1 Skin Corr. 1B Skin Sens. 1 STOT SE 3 |
| Toxicity | A hallucinogenic (psychedelic)agent that may catalyze the onset of emotional problemsor psychosis in predisposed individuals. DMT is perhapsone of the least studied of the hallucinogens. It causes perceptualalterations and illusions, including changes in touch, taste,and odor. The thinking process is substantially altered; thereare hallucinations and loss of contact with reality. There havebeen no overdose deaths attributed to the direct effects ofDMT. The drug is very short-acting, with a duration of effectof about half an hour or less. |
| Chemical Properties | 4,4'-Dimethoxytrityl chloride is pink powder |
| Uses | 4,4'-Dimethoxytrityl chloride is a versatile protecting group for primary alcohols, specially useful in oligonucleotide synthesis |
| Uses | 4,4'-Dimethoxytrityl chloride is used as a protective reagent for oligonucleotide synthesis. It is used for selective protection and deprotection procedures for thiol and hydroxy groups in nucleoside derivatives. |
| Uses | Hydroxyl protecting group for nucleosides and nucleotides. |
| Flammability and Explosibility | Not classified |
| Synthesis | 100-66-3 98-07-7 40615-36-9 a. In a 500 L reactor, 75 kg of trichloromethylbenzene (M = 195.48, n = 383.67 mol) and 103.72 kg of anisole (M = 108.14, n = 959.17 mol) were added, followed by the addition of 53.35 kg of the catalyst aluminum chloride (M = 133.34, n = 400.1 mol). The reaction temperature was controlled to be 30 °C and the reaction was continuously stirred for 10 h to obtain the mixed reaction solution I.b. Add 475 kg of 5% dilute hydrochloric acid to the mixed reaction solution I at 30°C and transfer to a 1000 L reactor for hydrolysis reaction for 3 hours. Subsequently, 200 kg of dichloromethane was added, stirred well and stratified. After separating the organic phase, the aqueous phase was extracted twice with 200kg of dichloromethane. All organic phases were combined and dried with anhydrous sodium sulfate for 2 hours.c. Concentrate the dichloromethane to recover the solvent. 70.74 kg of epichlorohydrin (M = 126.93, n = 557.32 mol) was added and the reaction was carried out under reflux for 6 hours. After completion of the reaction, 130 kg of petroleum ether was added dropwise and cooled to 30°C for crystallization. Crude 4,4'-dimethoxytrityl chloride (DMT-Cl) was obtained by solid-liquid separation, and the HPLC purity of the crude product was 98.91%.d. The crude DMT-Cl was recrystallized with 4.5 times mass of dichloromethane and 20 times mass of petroleum ether, and the wet product was obtained by solid-liquid separation. The wet product was dried to give a final product DMT-Cl 110.66 kg with a purity of 99.95% and a yield of 85.13%. The recovered mixed solvent was quantitatively analyzed by gas chromatography (GC) and recycled. |
| Purification Methods | DMT crystallises from cyclohexane/acetyl chloride as the hydrochloride. Dry it over KOH pellets in a desiccator. When dissolved in *C6H6 and air is blown through, HCl is removed. It crystallises from Et2O. [Baeyer & Villiger Chem Ber 36 2788 1903, Smith et al. J Am Chem Soc 84 430 1962, Smith et al. J Am Chem Soc 85 3821 1963.] Ifit has hydrolysed considerably (see OH in IR), then repeat the crystallisation from cyclohexane/acetyl chloride — excess of AcCl is removed in a vacuum over KOH, then recrystallise it from Et2O. [Beilstein 6 IV 1042.] |
| References | [1] Patent: CN107056590, 2017, A. Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0028-0045 |
4,4'-Dimethoxytrityl chloride Preparation Products And Raw materials
| Raw materials | Anisole-->Benzotrichloride-->Hydrochloric acid |
| Preparation Products | 5''-O-(4,4''-Dimethoxytrityl)-inosine-->5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE-->DMT-DCYTIDINE (N6-BENZOYL) CYANOETHYL PHOSPHORAMIDITE)-->5'-O-(4,4'-DIMETHOXYTRITYL)-N4-BENZOYL-5-METHYL-2'-DEOXYCYTIDINE-->5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE-->DMT-dG(dmf) Phosphoramidite-->N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-->5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine-->Acetamide, N-[3-[bis(4-methoxyphenyl)phenylmethoxy]-2-hydroxypropyl]-2,2,2-trifluoro--->Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite], (S)- (9CI) |
