BENZYL 2,2,2-TRICHLOROACETIMIDATE

Base Information

• Chemical Name: BENZYL 2,2,2-TRICHLOROACETIMIDATE
• CAS No.: 81927-55-1
• Molecular Formula: C9H8Cl3NO
• Molecular Weight: 252.528
• Hs Code.: 29252900
• European Community (EC) Number: 617-271-1
• DSSTox Substance ID: DTXSID301002319
• Nikkaji Number: J254.926C
• Wikidata: Q72443174
• Mol file: 81927-55-1.mol

Synonyms:Benzyl 2,2,2-trichloroacetimidate;Benzyltrichloroacetimidate;

Chemical Property of BENZYL 2,2,2-TRICHLOROACETIMIDATE

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 3 °C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 319.54 °C at 760 mmHg
• PKA: 2.23±0.70(Predicted)
• Flash Point: 106.952 °C
• PSA: 33.08000
• Density: 1.361 g/cm³
• LogP: 3.65040
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with cyclohexane/dichloromethane.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 250.967147
• Heavy Atom Count: 14
• Complexity: 197

Purity/Quality:

97% ^*data from raw suppliers

Benzyl 2,2,2-Trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=N)C(Cl)(Cl)Cl
• Uses: Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate. Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It was used in the acid-catalyzed benzylation of hydroxy groups.

Technology Process of BENZYL 2,2,2-TRICHLOROACETIMIDATE

There total 1 articles about BENZYL 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: 100.0%

trichloroacetonitrile (545-06-2) + benzyl alcohol (100-51-6,185532-71-2) → O-benzyl 2,2,2-trichloroacetimidate (81927-55-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In n-heptane; at 0 ℃; for 0.25h; Solvent;

DOI:10.1055/s-0037-1611551

Reference yield: 99.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + 1,2-diamino-benzene (95-54-5) → 2-trichloromethyl-1H-benzoimidazole (3584-65-4)

Guidance literature:

With acetic acid; at 20 ℃; for 1h;

DOI:10.1039/d0md00058b

Reference yield: 92.0%

methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate (17369-87-8,18951-36-5,23053-16-9,81872-27-7,87333-63-9,118204-68-5) + O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → dibenzyl ether (103-50-4) + methyl (2RS,3RS)-3-benzyloxy-2-tetradecyloctadecanoate

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane;

DOI:10.1016/0008-6215(93)80100-S

upstream raw materials:

trichloroacetonitrile

benzyl alcohol

Downstream raw materials:

tribenzylphosphate

benzyl 2,2,2-trichloroacetamide

(2R,5S)-3-Benzyloxy-5,6-dihydro-5-(3-hydroxypropyl)-2-methyl-2H-1,4-oxazin

(2R,5S)-5-(3-Benzyloxypropyl)-2-methyl-3-morpholinon