40615-36-9

Basic information

• Product Name: 4,4'-Dimethoxytrityl chloride
• Synonyms: (DMT-C1) 4,4'-DiMethoxytrityl chloride;4,4'-(Chloro(phenyl)Methylene)bis(Methoxybenzene);DMT-Cl)D;4,4- twoMethoxy threephenylMethyl chloride;DMT-Cl, 98%, pink color;4,4'-DiMethoxytrityl chloride SynonyMs 1,1'-(ChlorophenylMethylene)bis[4-Methoxybenzene];Anti-Dematin, C-Terminal antibody produced in rabbit;EPB49
• CAS NO: 40615-36-9
• Molecular Formula: C₂₁H₁₉ClO₂
• Molecular Weight: 338.83
• EINECS: 255-002-6
• Product Categories: OLED materials,pharm chemical,electronic;Organics;Coupling Reagent;N-Protecting Reagents;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
• Mol File: 40615-36-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 455.07°C (rough estimate)
• Flash Point: 155.6 °C
• Appearance: Pink/Powder
• Density: 1.0887 (rough estimate)
• Vapor Pressure: 0Pa at 20℃
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: Store at 0°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in chloroform and methanol. Partially soluble in water
• Sensitive: Moisture Sensitive
• Stability: Hygroscopic, Moisture Sensitive
• BRN: 2471942
• CAS DataBase Reference: 4,4'-Dimethoxytrityl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethoxytrityl chloride(40615-36-9)
• EPA Substance Registry System: 4,4'-Dimethoxytrityl chloride(40615-36-9)

Safety Data

• Hazard Codes: Xi
• 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
• Hazardous Substances Data: 40615-36-9(Hazardous Substances Data)

Usage

Chemical Properties

4,4'-Dimethoxytrityl chloride is pink powder

Uses

Different sources of media describe the Uses of 40615-36-9 differently. You can refer to the following data:
1. 4,4'-Dimethoxytrityl chloride is a versatile protecting group for primary alcohols, specially useful in oligonucleotide synthesis
2. 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.
3. Hydroxyl protecting group for nucleosides and nucleotides.

Flammability and Explosibility

Notclassified

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.]

Synthetic route

4,4'-dimethoxytrityl alcohol (40615-35-8) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
With thionyl chloride In n-heptane 1.) 0 deg C, 10 min, 2.) RT, 10 min, 3.) reflux, 1 h;	91%
With acetyl chloride In toluene for 2h; Inert atmosphere; Reflux;	89.7%
With thionyl chloride In diethyl ether Heating;	82%

methoxybenzene (100-66-3) + Benzotrichlorid (98-07-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Stage #1: methoxybenzene; Benzotrichlorid With aluminum (III) chloride at 30℃; for 10h; Large scale; Stage #2: With hydrogenchloride In water at 30℃; for 3h; Large scale; Stage #3: With oxalyl dichloride for 6h; Temperature; Concentration; Reflux; Large scale;	85.13%

4,4'-dimethoxytrityl cation (14039-15-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
With perchloric acid; water; sodium chloride In methanol at 25℃; Equilibrium constant; other temperatures;

methoxybenzene (100-66-3) + 2-chloro-decalin → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) AlCl3, 2.) aq. H2SO4 / 1.) 2 h 2: AcCl / 1.5 h / Heating View Scheme

Benzotrichlorid (98-07-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) AlCl3, 2.) aq. H2SO4 / 1.) 2 h 2: AcCl / 1.5 h / Heating View Scheme

4-Methoxybenzophenone (611-94-9) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Grignard reaction 2: 82 percent / SOCl2 / diethyl ether / Heating View Scheme

1-bromo-4-methoxy-benzene (104-92-7) + sodium → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Grignard reaction 2: 82 percent / SOCl2 / diethyl ether / Heating View Scheme

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)thymine (140858-91-9) → 1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>thymine (140859-04-7)

Conditions	Yield
With pyridine for 1.5h; Ambient temperature;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine (146954-74-7)

Conditions	Yield
With pyridine at 20℃; for 3h; Inert atmosphere;	100%
With pyridine at 20℃; for 3h; Inert atmosphere;	100%
With dmap at 20℃; for 16h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 4-[4-(4-Hydroxy-butylcarbamoyloxymethyl)-2-methoxy-5-nitro-phenoxy]-butyric acid methyl ester (176375-53-4) → 4-(4-{4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-butylcarbamoyloxymethyl}-2-methoxy-5-nitro-phenoxy)-butyric acid methyl ester (176375-44-3)

Conditions	Yield
With pyridine at 50℃; for 1h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + (R)-oxiranemethanol (57044-25-4) → (S)-glycidyl 4,4’-dimethoxytrityl ether (834906-31-9)

Conditions	Yield
With triethylamine In dichloromethane for 12h;	100%
With pyridine at 20℃;	89%
In dichloromethane; triethylamine Ambient temperature;	65%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5',3'-O-(tetraisopropyldisiloxane-1,3-di-yl)-1-β-D-arabinofuranosyl-uracil (104477-70-5) → 1-[2'-O-(4,4'-Dimethoxytrityl)-3',5',-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil (194031-42-0)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-phenylselanyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide (201420-68-0) → N-(9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-phenylselanyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (201420-69-1)

Conditions	Yield
In pyridine for 48h; Ambient temperature;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5'-O-(4-nitrobenzoyl)thymidine (5983-14-2) → 3'-O-(4,4'-dimethoxytrityl)-5'-O-(4-nitrobenzoyl)thymidine (180335-81-3)

Conditions	Yield
With pyridine; dmap at 20℃; for 49h; tritylation;	100%

methyl (R)-3-hydroxy-2-methylpropionate (72657-23-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester (286458-65-9)

Conditions	Yield
With 2,3,5-trimethyl-pyridine In dichloromethane at 25℃; Substitution;	100%
With pyridine at 20℃; for 4h;
With 2,4,6-trimethyl-pyridine In dichloromethane at 0℃;

4,4'-dimethoxytrityl chloride (40615-36-9) + N-[6-dimethylamino-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide (375345-64-5) → N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-dimethylamino-9H-purin-2-yl)-2-phenoxy-acetamide (375345-67-8)

Conditions	Yield
With pyridine at 20℃; for 2h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil (129399-14-0) → Benzoic acid (2R,3R,5R)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone (402859-75-0) → 2-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone (600707-57-1)

Conditions	Yield
With pyridine at 20℃; for 3h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-06-0) → 5'-O-(dimethoxytrityl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-07-1)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2-O,2-C-propano-β-D-arabinofuranosyl)uracil (664333-53-3) → 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil (664333-54-4)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2-[(2S,3R,5S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-isoindole-1,3-dione → 1-[2,3-dideoxy-6-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine (676132-95-9)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran at 20℃; for 48h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O,4'-C-propylene-5-methyluridine (634153-97-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-propylene-5-methyluridine (634153-98-3)

Conditions	Yield
With pyridine at 40℃;	100%

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine (69304-45-6) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-6-N-(4,4'-dimethoxytrityl)-adenosine (874889-86-8)

Conditions	Yield
With pyridine at 20℃; for 14h;	100%
With pyridine at 20℃; for 14h;	91%

2,2-Dimethyl-propionic acid 4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-imidazol-1-ylmethyl ester + 4,4'-dimethoxytrityl chloride (40615-36-9) → [4-(5-O-DMT-2-deoxy-D-β-ribofuranosyl)imidazolyl]methyl 2,2-dimethylpropionate (872088-48-7)

Conditions	Yield
With pyridine; dmap; triethylamine at 20℃; for 2h;	100%
With pyridine; dmap; triethylamine at 20℃;	146 mg

[4-(2-O-allyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate (872088-52-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 2,2-Dimethyl-propionic acid 4-{(2S,3R,4R,5R)-3-allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-imidazol-1-ylmethyl ester (872088-53-4)

Conditions	Yield
With pyridine; dmap; triethylamine at 20℃; for 19h;	100%

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(1,2-dihydroxy-ethyl)-tetrahydro-furan-2-yl]-6-methyl-1H-pyrimidine-2,4-dione + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[5-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-hydroxy-ethyl}-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-6-methyl-1H-pyrimidine-2,4-dione

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine (519056-25-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine (519056-26-9)

Conditions	Yield
With pyridine at 20℃; for 3h;	100%
With pyridine In nitrogen at 20℃; for 3h;	100%

N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide (138406-86-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N-[9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2-cyano-ethylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide (138406-87-8)

Conditions	Yield
With pyridine at 20℃; for 2h;	100%

N-1-{(1R,2S,3S,4R)-2,3-bis(methoxymethoxy)-4-(hydroxymethyl)cyclopentyl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (933060-58-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (CH3)3CSi(CH3)2OCH2C5H4O3(CH3)2C5H3N5C5H6CH2OC(C6H4OCH3)2C6H5(OCH2OCH3)2

Conditions	Yield
With pyridine at 20℃; for 0.166667h;	100%

N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-(hydroxymethyl)cyclopentyl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (933060-59-4) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (CH3)3CSi(CH3)2OCH2C5H4O3(CH3)2C5H3N5C5H6CH2OC(C6H4OCH3)2C6H5OCH3OCH2OCH3

Conditions	Yield
With pyridine at 20℃;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3-hydroxymethyl-benzoic acid (3006-96-0) → triethylammonium 4-[[(4,4'-dimethoxytrityl)oxy]methyl]benzoate (403730-30-3)

Conditions	Yield
Stage #1: 4,4'-dimethoxytrityl chloride; 3-hydroxymethyl-benzoic acid In pyridine at 20℃; Stage #2: With triethylammonium acetate In methanol; dichloromethane; water	100%

2-(2-hydroxyethoxy)acetic acid (13382-47-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → triethylammonium 2-[2-(4,4'-dimethoxytrityloxy)ethoxy] acetate (403730-25-6)

Conditions	Yield
Stage #1: 2-(2-hydroxyethoxy)acetic acid; 4,4'-dimethoxytrityl chloride In pyridine at 20℃; Stage #2: With triethylammonium acetate In methanol; dichloromethane; water	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + (4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidin-2-one (1020110-06-8) → C26H27NO5 (1020110-07-9)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

N-1-{(1R,2S,3R)-4-hydroxymethyl-2,3-isopropylidenedioxycyclopent-4-en-1-yl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (1022895-51-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → C49H61N5O9Si

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃; for 10h;

1-(2-deoxy-2-fluoro-4-thio-β-D-ribofuranosyl)uracil (1030358-61-2) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[5-O-(4,4'-dimethoxytrityl)-2-deoxy-2-fluoro-4-thio-β-D-ribofuranosyl]uracil

Conditions	Yield
In pyridine at 20℃; for 2h;	100%

3-(2-hydroxyethoxy)propionic acid (89211-34-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) + triethylammonium acetate (5204-74-0) → triethylammonium 3-[2-[2-(4,4'-dimethoxytrityloxy)]ethoxy]propionate (403730-26-7)

Conditions	Yield
Stage #1: 3-(2-hydroxyethoxy)propionic acid; 4,4'-dimethoxytrityl chloride In pyridine at 20℃; Stage #2: triethylammonium acetate In methanol; dichloromethane; water	100%

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol (91547-59-0) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5-O-(4,4'-dimethoxytriphenylmethyl)-1,4-anhydro-2-deoxy-D-ribitol (95049-01-7)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%
With pyridine at 20℃; for 12h;	75%
With pyridine at 20℃; for 12h;	75%
With pyridine at 20℃; for 12h;

Upstream product

• 98-07-7 Benzotrichlorid 
• 100-66-3 methoxybenzene 
• 14039-15-7 4,4'-dimethoxytrityl cation 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 611-94-9 4-Methoxybenzophenone 

Downstream Products

• 68892-41-1 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine 
• 133931-96-1 (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3-ol 
• 111727-01-6 6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine 
• 163882-50-6 (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3-ol 
• 114827-15-5 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-2-(4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-2-oxo-2H-pyrimidin-1-yl)-5-(2,2-dimethyl-propionyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester 
• 105038-56-0 1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(3,4-dimethoxy-benzyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-3-(2-methoxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 105014-98-0 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(3,4-dimethoxy-benzyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 
• 117901-70-9 1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-3-tritylsulfanyl-1H-pyrimidine-2,4-dione 
• 103022-75-9 N₆,N₆,3'-O-tribenzoyl-5'-O-dimethoxytrityladenosine 
• 119722-75-7 1-{(2R,3S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one 
• 124040-44-4 N⁶,O⁵'-bis(4,4'-dimethoxytrityl)-9-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine 
• 143308-75-2 Methyl 5-O-acetyl-3-O-(dimethoxytrityl)-(-)-shikimate 
• 143632-19-3 1-<5-O--2-deoxy-β-D-ribofuranosyl>-4-phenylimidazole 
• 148504-72-7 1-{(2R,3R,4R,5R)-3-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-prop-1-ynyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Process for the capture and reuse of the 4,4′-dimethoxytriphenylmethyl group during manufacturing of oligonucleotides

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