58244-27-2

Basic information

• Product Name: TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE
• Synonyms: TRIS[(TRIFLUOROETHOXY)METHANE];TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE;Tris(2,2,2-trifluoroethyl)orthoformate 97%;Tris(2,2,2-trifluoroethyl)orthoformate97%;Tris(2,2,2-trifluoroethoxy)methane, 2-[Bis(2,2,2-trifluoroethoxy)methoxy]-1,1,1-trifluoroethane
• CAS NO: 58244-27-2
• Molecular Formula: C₇H₇F₉O₃
• Molecular Weight: 310.11
• Mol File: 58244-27-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 144-146°C
• Flash Point: 59.5°C
• Appearance: /
• Density: 1.457g/cm³
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE(58244-27-2)
• EPA Substance Registry System: TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE(58244-27-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 58244-27-2(Hazardous Substances Data)

Usage

Description

TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE is a chemical compound with unique properties that make it suitable for various applications, particularly in the field of energy storage and battery technology.

Uses

Used in Energy Storage Industry:
TRIS(2,2,2-TRIFLUOROETHYL)ORTHOFORMATE is used as an electrolyte additive for enhancing the performance and safety of lithium metal batteries. Its high concentration electrolyte behavior near the lithium metal anode surface helps improve the battery's efficiency and stability, making it a valuable component in the development of advanced energy storage solutions.

Synthetic route

chloroform (67-66-3) + 2,2,2-trifluoroethanol (75-89-8) → tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2)

Conditions	Yield
With iron(III) chloride

2,2,2-trifluoroethanol (75-89-8) + trifluoroethoxyfluorodiazirine (154914-84-8) → tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2)

Conditions	Yield
Irradiation;

2,2,2-trifluoroethanol (75-89-8) + bis-trifluoroethoxydiazirine (154914-85-9) → tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2)

Conditions	Yield
Ambient temperature; Yield given;

3-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy]-1,2-propanediol (126814-93-5) + tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) → 4-(((3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy)methyl)-2-(2,2,2-trifluoroethoxy)-1,3-dioxolane

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane for 3h; Dean-Stark; Reflux;	74%

tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) + 5,5,6,6,7,7,8,8,9,9,10,10,10-Tridecafluorodecane-1,2-diol (147274-18-8) → 4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-(2,2,2-trifluoroethoxy)-1,3-dioxolane

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane for 1h; Dean-Stark; Reflux;	44%

tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) + 1H,1H,2H,3H,3H-perfluoroheptane-1,2-diol (125070-38-4) → 4-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-2-(2,2,2-trifluoroethoxy)-1,3-dioxolane

Conditions	Yield
With Amberlyst 15 (H form, Aldrich) In cyclohexane for 4h; Dean-Stark; Reflux;	39%

tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) + 5,5,6,6,7,7,8,8,8-Nonafluorooctane-1,2-diol (269394-13-0) → 4-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-2-(2,2,2-trifluoroethoxy)-1,3-dioxolane

Conditions	Yield
With Amberlyst 15 (H form, Aldrich) In cyclohexane Dean-Stark; Reflux;	20%

tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) + (4-nitrophenyl)ethanone (100-19-6) → 1-[1,1-Bis-(2,2,2-trifluoro-ethoxy)-ethyl]-4-nitro-benzene (64600-24-4)

tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) + (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8, 8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (445312-74-3) → (R,Z)-2-tert-butyl 8a-methyl 7-(hydroxymethylene)-6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (864973-65-9)

Conditions	Yield
Stage #1: (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8, 8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate With n-butyllithium; diisopropylamine In diethyl ether at -78℃; for 0.333333h; Stage #2: tris(2,2,2-trifluoroethyl)orthoformate In diethyl ether for 1.5h;

(S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (864973-62-6) + tris(2,2,2-trifluoroethyl)orthoformate (58244-27-2) → (S)-7-[1-hydroxy-meth-(Z)-ylidene]-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (864973-64-8)

Conditions	Yield
Stage #1: (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester With n-butyllithium; diisopropylamine In diethyl ether at -78℃; for 0.333333h; Stage #2: tris(2,2,2-trifluoroethyl)orthoformate In diethyl ether for 1.5h;

Upstream product

• 67-66-3 chloroform 
• 75-89-8 2,2,2-trifluoroethanol 
• 154914-84-8 trifluoroethoxyfluorodiazirine 
• 154914-85-9 bis-trifluoroethoxydiazirine 

Downstream Products

• 64600-24-4 1-[1,1-Bis-(2,2,2-trifluoro-ethoxy)-ethyl]-4-nitro-benzene 

Relevant articles and documents

A family of trifluoroethoxycarbenes

-