Benzyl 2,2,2-trichloroacetimidate
Benzyl 2,2,2-trichloroacetimidate (CAS: 81927-55-1) is an organic compound with the molecular formula CCl3C(=NH)OCH2C6H5 and a molecular weight of 252.52 g/mol. This amidate is a valuable reagent in organic synthesis, particularly for the benzylation of hydroxy groups under acidic conditions. It has been employed in the preparation of complex molecules, including natural products and chiral intermediates.
- IUPAC
- 2,2,2-Trichloroacetimidic acid benzyl ester
- Synonyms
- 81927-55-1CCl3C(=NH)OCH2C6H52,2,2-Trichloroacetimidic acid benzyl ester
Reagent in Organic Synthesis
Benzyl 2,2,2-trichloroacetimidate serves as a key reagent in various organic transformations. Its structure facilitates the introduction of a benzyl protecting group onto hydroxyl functionalities, a common strategy in multi-step synthesis.
Synthesis of Natural Products
This compound has been utilised in the synthesis of complex natural products. For instance, it was a reagent in the preparation of funiculosin dimethyl ether, demonstrating its utility in intricate synthetic routes.
Preparation of Chiral Intermediates
Benzyl 2,2,2-trichloroacetimidate has been employed in the synthesis of chiral building blocks, such as (S)-3-(benzyloxy)-2-methylpropanal. This highlights its role in asymmetric synthesis and the preparation of enantiomerically pure compounds.
| Molecular weight | 252.52 |
|---|---|
| Linear formula | CCl3C(=NH)OCH2C6H5 |
| Assay | 99% |
| Boiling point | 106-114 °C/0.5 mmHg(lit.) |
| Density | 1.359 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.545(lit.) |
| Storage temperature | 2-8°C |
| Impurities tested | <1% benzyl alcohol |
| Application | Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether1 and (S)-3-(benzyloxy)-2-methylpropanal2. It was used in the acid-catalyzed benzylation of hydroxy groups3. |
Hazard statements
- H302Harmful if swallowed
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 113 °C / 235.4 °F |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22-36/37/38 |
| Safety statements (S) | 26 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
| Transition Temp | solidification point 3-4 °C |
|---|
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Benzyl 2,2,2-trichloroacetimidate used for?
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Benzyl 2,2,2-trichloroacetimidate is primarily used as a reagent in organic synthesis for the acid-catalyzed benzylation of hydroxy groups. It has been utilised in the preparation of natural products like funiculosin dimethyl ether and chiral intermediates such as (S)-3-(benzyloxy)-2-methylpropanal.
What are the CAS number and formula for Benzyl 2,2,2-trichloroacetimidate?
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The CAS number for Benzyl 2,2,2-trichloroacetimidate is 81927-55-1. Its linear formula is CCl3C(=NH)OCH2C6H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Benzyl 2,2,2-trichloroacetimidate with an assay of 99% and less than 1% benzyl alcohol as an impurity. This is a technical/research grade product, and TSS does not represent it as USP, BP, or EP grade.
What are the safety considerations for handling Benzyl 2,2,2-trichloroacetimidate?
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Benzyl 2,2,2-trichloroacetimidate is classified with a GHS07 symbol and a 'Warning' signal word. It carries hazard statements H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Appropriate personal protective equipment, including eyeshields, face shields, gloves, and suitable respiratory protection, should be used. Store at 2-8°C.
Is Benzyl 2,2,2-trichloroacetimidate a controlled substance?
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The provided data does not indicate that Benzyl 2,2,2-trichloroacetimidate is a controlled substance.
How is Benzyl 2,2,2-trichloroacetimidate packed, shipped, and exported?
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Tech Serve Solutions, as a global supplier and exporter, ensures appropriate packing and shipping for Benzyl 2,2,2-trichloroacetimidate according to international regulations for chemical substances. Please contact us for specific export details.
How can I request a sample or quote for Benzyl 2,2,2-trichloroacetimidate?
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To request a sample or a quote for Benzyl 2,2,2-trichloroacetimidate, please contact our sales department through the website or by phone. Our team will be pleased to assist you with your requirements.
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