88738-78-7 | Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$8.00	$5.00
1g	95%	in stock	$12.00	$9.00
5g	95%	in stock	$30.00	$21.00
10g	95%	in stock	$52.00	$37.00
15g	95%	in stock	$78.00	$55.00
25g	95%	in stock	$129.00	$91.00
100g	95%	in stock	$385.00	$270.00

Description

• Catalog Number: AB76043
• Chemical Name: Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate
• CAS Number: 88738-78-7
• Molecular Formula: C7H9F6O5P
• Molecular Weight: 318.1075
• MDL Number: MFCD00009901
• SMILES: COC(=O)CP(=O)(OCC(F)(F)F)OCC(F)(F)F
• NSC Number: 634137

Computed Properties

• Complexity: 329
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 19
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• XLogP3: 1.6

Upstream Synthesis Route

The upstream synthesis of Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate involves the following steps:

1. Synthesis of Dimethyl Methylphosphonate:
Start with phosphorus trichloride (PCl3) reacting with methanol (CH3OH) to form dimethyl methylphosphonate (DMMP) via methylation.

2. Conversion to Diethyl Methylphosphonate (if needed):
DMMP is then subjected to an alcohol exchange reaction with ethanol to produce diethyl methylphosphonate. This step is conditional and dependent on the necessity of the ethyl group in the target molecule.

3. Halogenation:
Introduce trifluoroethanol to the phosphonate compound under halogenating conditions to replace the ethyl/methyl groups with 2,2,2-trifluoroethyl groups.

4. Transesterification with Methoxycarbonylation:
The di-trifluoroethylated compound is then reacted with methyl chloroformate in the presence of a base (such as triethylamine) through a transesterification reaction to introduce the methoxycarbonylmethyl group, yielding the final product, Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate.

Throughout this synthesis, maintain anhydrous and aprotic conditions to prevent side reactions. Use appropriate inert atmospheres (like argon or nitrogen) when necessary to avoid oxidation or hydrolysis of intermediates and reagents. The reaction temperatures, stoichiometry, and choice of solvents must be controlled according to the sensitivity of the functional groups involved and the volatility of the reagents.

Literature

• A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones.

  Chemical & pharmaceutical bulletin 20020501