81927-55-1

Basic information

• Product Name: BENZYL 2,2,2-TRICHLOROACETIMIDATE
• Synonyms: Benzyl 2,2,2-trichloroethanimidoate;Benzyl trichloroacetimidate;TRICHLOROACETIMIDIC ACID BENZYL ESTER;LABOTEST-BB LT00455324;BENZYL 2,2,2-TRICHLOROACETIMIDATE;2,2,2-TRICHLOROACETIMIDIC ACID BENZYL ESTER;Benzyl 2,2,2-trichloroacetimidate, 98+%;Ethanimidic acid, 2,2,2-trichloro-, phenylmethyl ester
• CAS NO: 81927-55-1
• Molecular Formula: C₉H₈Cl₃NO
• Molecular Weight: 252.52
• Product Categories: Benzene series;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Amidates/Imidates;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 81927-55-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 3 °C
• Boiling Point: 106-114 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.359 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with cyclohexane/dichloromethane.
• PKA: 2.23±0.70(Predicted)
• Sensitive: Moisture Sensitive
• Stability: Moisture Sensitive
• BRN: 2525375
• CAS DataBase Reference: BENZYL 2,2,2-TRICHLOROACETIMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2,2,2-TRICHLOROACETIMIDATE(81927-55-1)
• EPA Substance Registry System: BENZYL 2,2,2-TRICHLOROACETIMIDATE(81927-55-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 81927-55-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

Different sources of media describe the Uses of 81927-55-1 differently. You can refer to the following data:
1. Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups.
2. 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.
3. 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.

Purification Methods

Purify the imidate by distillation to remove up to 1% of PhCH2OH as stabiliser. A solution in hexane can be stored for up to 2 months without decomposition. It is hygroscopic and has to be stored dry. [Wessel et al. J Chem Soc, Perkin Trans 1 2247 1985, Beilstein 6 IV 2265.]

InChI:InChI=1/C9H8Cl3NO/c10-9(11,12)8(13)14-6-7-4-2-1-3-5-7/h1-5,13H,6H2

Upstream product

• 545-06-2 trichloroacetonitrile 
• 100-51-6 benzyl alcohol 

Downstream Products

• 119788-82-8 (2R,5S)-3-Benzyloxy-5,6-dihydro-5-(3-hydroxypropyl)-2-methyl-2H-1,4-oxazin 
• 119788-83-9 (2R,5S)-5-(3-Benzyloxypropyl)-2-methyl-3-morpholinon 
• 119788-81-7 (2R,5S)-2-Methyl-5-(3-trichloracetimidoyloxypropyl)-3-morpholinon 
• 119788-86-2 (2R,5S)-3-(4-Benzyloxybutyloxy)-5-(3-hydroxypropyl)-2-methyl-5,6-dihydro-2H-1,4-oxazin 
• 119788-85-1 (2R,5S)-3-Benzyloxy-5-(3-benzyloxypropyl)-5,6-dihydro-2-methyl-2H-1,4-oxazin 
• 32780-08-8 (5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one 
• 77697-15-5 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 
• 54783-72-1 ethyl (S)-2-(benzyloxy)propionate 
• 103-50-4 dibenzyl ether 
• 112904-65-1 dimethyl 3-(benzyloxy)pentanedioate 
• 4817-93-0 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate 
• 181713-52-0 3-Benzyloxy-4-methyl-2-methylene-pentanoic acid methyl ester 
• 147914-42-9 2,3-bisbenzyloxy-1-chloropropane 
• 147879-18-3 (2S)-3,6-Dibenzyloxy-2,5-dihydro-2-isopropylpyrazine 

Relevant articles and documents

Hit-to-lead optimization of novel benzimidazole phenylacetamides as broad spectrum trypanosomacides

Trypanosoma cruzi and Trypanosoma brucei are the parasitic causative agents of Chagas disease and human African trypanosomiasis (HAT), respectively. The drugs currently used to treat these diseases are not efficacious against all stages and/or parasite sub-species, often displaying side effects. Herein, we report the SAR exploration of a novel hit, 2-(4-chlorophenyl)-N-(1-propyl-1H-benzimidazol-2-yl)acetamide previously identified from high throughput screens against T. cruzi, Trypanosoma brucei brucei and Leishmania donovani. An informative set of analogues was synthesized incorporating key modifications of the scaffold resulting in improved potency whilst the majority of compounds retained low cytotoxicity against H9c2 and HEK293 cell lines. The SAR observed against T. cruzi broadly matches that observed against T.b. brucei, suggesting the possibility for a broad-spectrum candidate. This class of compounds therefore warrants further investigation towards development as a treatment for Chagas disease and HAT. This journal is

Synthesis of 3-deoxy-2-uloses via the indium-mediated allylation reaction

Abstract: We utilized the indium-mediated allylation reaction for the synthesis of carbohydrate structures containing the 3-deoxy-2-ulose motif, a barely investigated compound class. The stereoselective outcome can be controlled by the presence or absence of a chelating group in α-position to the carbonyl function. By introduction of an UV-active allyl building block, we enabled epimer separation by HPLC towards the synthesis of 3-deoxy-d-glycero-d-galacto-2-nonulose, the carboxyl-reduced analogue of widely distributed 3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn). Ozonolysis of the introduced 2-C-methylidenepropan-1-ol motif provided the desired 3-deoxy-2-uloses. Graphical abstract: [Figure not available: see fulltext.].

Br?nsted acid catalyzed monoalkylation of anilines with trichloroacetimidates

Trichloroacetimidates are useful alkylating agents for aromatic amines, requiring only a catalytic amount of a Br?nsted acid to facilitate the reaction. Monoalkylation predominates under these conditions. Electron-poor anilines provide superior yields, with electron-rich anilines sometimes showing competitive Friedel-Crafts alkylation. A single flask protocol with formation of the imidate in situ is demonstrated, providing a convenient method for the direct substitution of alcohols with anilines. Reaction with a chiral imidate favors a mechanism that proceeds through a carbocation intermediate.