O-ALLYL-2,2,2-TRICHLOROACETIMIDATE

Base Information

• Chemical Name: O-ALLYL-2,2,2-TRICHLOROACETIMIDATE
• CAS No.: 51479-73-3
• Molecular Formula: C5H6 Cl3 N O
• Molecular Weight: 202.468
• Hs Code.: 2925290090
• Mol file: 51479-73-3.mol

Synonyms:Acetimidicacid, 2,2,2-trichloro-, allyl ester (6CI); Ethanimidic acid, 2,2,2-trichloro-,2-propenyl ester (9CI); Allyl alcohol, 2,2,2-trichloroacetimidate (6CI); Allyl2,2,2-trichloroacetimidate; Allyl trichloroacetimidate; NSC 245512

Chemical Property of O-ALLYL-2,2,2-TRICHLOROACETIMIDATE

Chemical Property:

• Vapor Pressure: 6.11mmHg at 25°C
• Refractive Index: n20/D 1.489
• Boiling Point: 145.5°Cat760mmHg
• PKA: 2?+-.0.70(Predicted)
• Flash Point: 41.8°C
• PSA: 33.08000
• Density: 1.36g/cm³
• LogP: 2.63620
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

2,2,2-TrichloroacetimidicAcidAllylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: O-ALLYL-2,2,2-TRICHLOROACETIMIDATE is a reactive electrophilic allylating agent used in Lewis acid-catalyzed reactions, particularly for the synthesis of 3,3'-disubstituted oxindoles. It serves as a precursor to generate allylic carbocation intermediates under mild conditions, enabling efficient C–C bond formation with nucleophilic substrates like oxindoles. O-ALLYL-2,2,2-TRICHLOROACETIMIDATE is valuable for constructing pharmacologically relevant scaffolds, demonstrating broad substrate compatibility and high functional group tolerance in synthetic applications.

Technology Process of O-ALLYL-2,2,2-TRICHLOROACETIMIDATE

There total 1 articles about O-ALLYL-2,2,2-TRICHLOROACETIMIDATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.5%

allyl alcohol (107-18-6) + trichloroacetonitrile (545-06-2) → allyl trichloroacetimidate (51479-73-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;

DOI:10.3390/molecules131102837

Reference yield: 93.0%

1-methyl-3-phenylindolin-2-one (3335-97-5) + allyl trichloroacetimidate (51479-73-3) → 3-allyl-1-methyl-3-phenyl-1,3-dihydro-indol-2-one

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.01.155

Reference yield: 90.0%

allyl trichloroacetimidate (51479-73-3) + 5-fluoro-1-methyl-3-phenylindolin-2-one → 3-allyl-5-fluoro-1-methyl-3-phenylindolin-2-one

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.01.155

upstream raw materials:

allyl alcohol

trichloroacetonitrile

Downstream raw materials:

Acetic acid 4-((R)-allyloxy-cyano-methyl)-phenyl ester

methyl 2,4-di-O-allyl-3,6-di-O-benzoyl-α-D-mannopyranoside

methyl 4-O-acetyl-3-O-allyl-2-O-benzoyl-α-L-rhamnopyranoside

methyl 2-O-acetyl-3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

Refernces

BF₃·Et₂O catalyzed allylation of oxindoles with allyl trichloroacetimidate

10.1016/j.tetlet.2015.01.155

The research aims to develop an efficient Lewis acid catalyzed allylation method for 3-substituted oxindoles using allyl trichloroacetimidate as the electrophile under mild conditions. The study's purpose is to provide a general and efficient way to synthesize 3,3'-disubstituted oxindole derivatives, which are important structural motifs in many alkaloid natural products and pharmaceutically active compounds. The researchers optimized the reaction conditions, finding that BF3·Et2O as a catalyst, along with dichloromethane (DCM) as the solvent and a 3.0 equivalent of allyl trichloroacetimidate, yielded the best results. They tested various substrates with different substitution patterns and found that the reaction tolerated various substituents on the aromatic ring, with generally higher yields for 3-phenyl substituted oxindole substrates compared to 3-benzyl substituted ones. The proposed mechanism involves the formation of an allylic carbocation intermediate from the imidate, which is captured by the enolized oxindole. The study concludes that this method allows for the facile synthesis of 3-allyl-3'-substituted oxindoles, which are fundamental units of many pharmaceutically important molecules, and further investigations to extend the scope and develop new applications are underway.

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