BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

Base Information

• Chemical Name: BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
• CAS No.: 88738-78-7
• Molecular Formula: C7H9F6O5P
• Molecular Weight: 318.11
• Hs Code.: 29319090
• Mol file: 88738-78-7.mol

Synonyms:Aceticacid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester (9CI);Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate;Bis(2,2,2-trifluoroethyl) methyl phosphonoacetate;Methyl(bis(2,2,2-trifluoroethoxy)phosphinyl)acetate;Methyl[bis(2,2,2-trifluoroethyl)phosphono]acetate;NSC 634137;[(Methoxycarbonyl)methyl]phosphonic acid bis(2,2,2-trifluoroethyl) ester;[Bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid methyl ester;[Bis(2,2,2-trifluoroethyl)phosphono]acetic acid methyl ester;

Chemical Property of BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

Chemical Property:

• Appearance/Colour: clear orange to dark orange-brown liquid
• Vapor Pressure: 4.23E-09mmHg at 25°C
• Refractive Index: n20/D 1.370(lit.)
• Boiling Point: 246.6 °C at 760 mmHg
• Flash Point: 102.9 °C
• PSA: 71.64000
• Density: 1.464 g/cm³
• LogP: 2.51030
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate >95.0%(GC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl?P,P-bis(2,2,2-trifluoroethyl)phosphonoacetate can be used:In one of the key synthetic steps for the preparation of?trans-hydrindanes and (R)-(+)-umbelactone.To prepare a cis-olefinic ester derivative by Still–Gennari olefination of an aldehyde derivative using 18-crown ether and potassium bis(trimethylsilyl)amide (KHMDS).In the synthesis of (?)-(6S,2′S)-epi?cryptocaryalactone.

Technology Process of BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE

There total 5 articles about BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE 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: 94.0%

2,2,2-trifluoroethanol (75-89-8) + methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate (67605-34-9) → bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7)

Guidance literature:

methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate; With iodine; triphenylphosphine; In chloroform; at 20 ℃; for 0.25h; Inert atmosphere;

With 1H-imidazole; In chloroform; at 20 - 50 ℃; for 0.75h; Inert atmosphere;

2,2,2-trifluoroethanol; In chloroform; at 60 ℃; for 5h; Inert atmosphere;

DOI:10.1055/s-0036-1591566

Reference yield: 86.0%

2,2,2-trifluoroethanol (75-89-8) + (methoxycarbonylmethyl)phosphonic dichloride (31460-11-4) → bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00163

Reference yield: 68.0%

2,2,2-trifluoroethanol (75-89-8) + phosphonoacetic acid trimethyl ester (40962-37-6) → bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7)

Guidance literature:

phosphonoacetic acid trimethyl ester; With iodine; triphenylphosphine; In chloroform; at 20 ℃; for 0.25h; Inert atmosphere;

With 1H-imidazole; In chloroform; at 20 - 50 ℃; for 0.75h; Inert atmosphere;

2,2,2-trifluoroethanol; In chloroform; at 60 ℃; for 5h; Inert atmosphere;

DOI:10.1055/s-0036-1591566

upstream raw materials:

2,2,2-trifluoroethanol

(methoxycarbonylmethyl)phosphonic dichloride

methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate

phosphonoacetic acid trimethyl ester

Downstream raw materials:

(2Z)-decenoic acid methyl ester

methyl (E)-dec-2-enoate

(R)-methyl-4,5-dibenzyloxy-2-(Z)-pentenoate

(R)-methyl-4,5-dibenzyloxy-2-(E)-pentenoate

Refernces

• 1、 Kurzawa, Timon,Harms, Klaus,Koert, Ulrich. "Stereoselective Synthesis of the Benzodihydropentalene Core of the Fijiolides". supporting information. p. 1388 - 1391. Retrieved 2018/03/09.
• 2、 Messik, Frauke,Oberthuer, Markus. "An expedient access to still-gennari phosphonates". . p. 167 - 170. Retrieved 2013/03/13.