359-41-1

Basic information

• Product Name: 1,1,1-Trifluoro-2,3-epoxypropane
• Synonyms: 1,2-EPOXY-3,3,3-TRIFLUOROPROPANE;1,1,1-TRIFLUORO-2,3-EPOXYPROPANE;2-(TRIFLUOROMETHYL)OXIRANE;3,3,3-TRIFLUORO-1,2-EPOXYPROPANE;3,3,3-Trifluoro-1,2-epoxypropane~2-(Trifluoromethyl)oxirane;3,3,3-Trifluoro-1,2-epoxypropane, tech;1,2-EPOXY-3,3,3-TRIFLUOROPROPANE, 90+%;1,1,1-Trifluoro-2,3-epoxypropane,tech.
• CAS NO: 359-41-1
• Molecular Formula: C₃H₃F₃O
• Molecular Weight: 112.05
• EINECS: -0
• Product Categories: Fluorochemicals;organic chemical
• Mol File: 359-41-1.mol

Chemical Properties

• Melting Point: -80
• Boiling Point: 38 °C
• Flash Point: -40°C
• Appearance: colorless liquid
• Density: 1,3 g/cm3
• Vapor Pressure: 560mmHg at 25°C
• Refractive Index: 1.2997
• Storage Temp.: Keep Cold
• Water Solubility: Not miscible with water.
• Sensitive: Moisture Sensitive
• BRN: 103730
• CAS DataBase Reference: 1,1,1-Trifluoro-2,3-epoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-Trifluoro-2,3-epoxypropane(359-41-1)
• EPA Substance Registry System: 1,1,1-Trifluoro-2,3-epoxypropane(359-41-1)

Safety Data

• Hazard Codes: F,T
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36-36/37-9
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 359-41-1(Hazardous Substances Data)

Usage

Uses

1,2-Epoxy-3,3,3-trifluoropropane is used for the synthesis of trifluorolactic acid. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

InChI:InChI=1/C3H3F3O/c4-3(5,6)2-1-7-2/h2H,1H2/t2-/m0/s1

Synthetic route

2-bromo-1,1,1-trifluoropropan-3-ol (311-86-4) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
With calcium hydroxide In water at 38 - 40℃; for 1h; Concentration; Reagent/catalyst;	80.3%
With calcium hydroxide In water at 90℃; for 1h;	74%
With sodium hydroxide at 85℃;	70.2%

2-bromo-1,1,1-trifluoropropan-3-ol (311-86-4) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1) + 2-bromo-3,3,3-trifluoropropene (1514-82-5)

Conditions	Yield
With sodium hydroxide In water at 0 - 95℃;

3-bromo-1,1,1-trifluoropropan-2-ol (137429-44-8) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
With sodium hydroxide at 100℃;	88%

(+-)-3-bromo-1,1,1-trifluoro-propan-2-ol → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
With sodium hydroxide

3-acetoxy-2-bromo-1,1,1-trifluoropropane (383-68-6) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1) + 2-bromo-3,3,3-trifluoropropene (1514-82-5)

Conditions	Yield
With sodium hydroxide In water at 100℃; Title compound not separated from byproducts.;

1,1,1-trifluoropropylene (677-21-4) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
Stage #1: 1,1,1-trifluoropropylene With N-Bromosuccinimide; sulfuric acid; acetic acid at 65 - 70℃; for 11h; Stage #2: With sodium hydroxide In water at 120 - 130℃;	17.3 g
With dinitrogen monoxide at 20 - 300℃; under 750.075 Torr; for 4h; Kinetics; Reagent/catalyst; Inert atmosphere;

(+-)-2-bromo-3,3,3-trifluoro-propan-1-ol → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
With sodium hydroxide

(+-)-3-acetoxy-2-bromo-1,1,1-trifluoro-propane → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1)

Conditions	Yield
With sodium hydroxide

1,1,1-trifluoropropylene (677-21-4) → 1,1,1-trifluoro-2,3-epoxypropane (359-41-1) + 3,3,3-trifluoropropanal (460-40-2)

Conditions	Yield
With dinitrogen monoxide at 20 - 300℃; under 750.075 Torr; for 4h; Kinetics; Reagent/catalyst; Inert atmosphere;

Upstream product

• 311-86-4 2-bromo-3,3,3-trifluoropropan-1-ol 
• 677-21-4 1,1,1-trifluoropropylene 
• 137429-44-8 3-bromo-1,1,1-trifluoropropan-2-ol 
• 383-68-6 3-acetoxy-2-bromo-1,1,1-trifluoropropane 

Downstream Products

• 431-36-7 1,1,1-trifluoro-2-butanol 
• 374-01-6 1,1,1-trifluoroisopropanol 
• 431-38-9 3-amino-1,1,1-trifluoropropan-2-ol 
• 123271-24-9 Diphenyl-(3,3,3-trifluoro-2-trimethylsilanyloxy-propyl)-phosphane 
• 130748-17-3 Phenyl-(3,3,3-trifluoro-2-trimethylsilanyloxy-propyl)-trimethylsilanyl-phosphane 
• 460-40-2 3,3,3-trifluoropropanal 
• 421-50-1 1,1,1-trifluoro-2-propanone 
• 121170-45-4 (2R)-1,1,1-trifluorooctan-2-ol 
• 129443-08-9 (S)-(-)-1,1,1-trifluoro-2-octanol 
• 330-72-3 (S)-1,1,1-trifluoro-2-hydroxy-3-phenylpropane 
• 330-72-3 (R)-1,1,1-trifluoro-2-hydroxy-3-phenylpropane 
• 374-01-6 (S)-1,1,1-trifluoro-2-propanol 
• 374-01-6 (R)-1,1,1-trifluoropropanol 
• 160706-71-8 (S)-(-)-1-Amino-3,3,3-trifluoro-2-propanol 

Relevant articles and documents

Gas-phase epoxidation of 3,3,3-trifluoropropylene over Au/CuTiO2 catalysts with N2O as the oxidant

Gas-phase epoxidation of 3,3,3-trifluoropropylene (TFP) was conducted on a series of Au/CuTiO2 catalysts with different Cu contents with N 2O as the oxidant. These catalysts were effective for this reaction. The best catalytic performance was obtained on a catalyst containing 4.6 wt.% of Au and 0.9 wt.% of Cu (4.6Au/0.9CuTiO2), with a steady-state 3,3,3-trifluoropropylene oxide (TFPO) formation rate of 72.4g TFPOh-1kgcat-1, which was much higher than that on a 2.1Au/TiO2 catalyst (22.1gTFPOh-1kgcat-1). The enhancement was attributed to the higher Au content in the Cu-promoted catalyst and small Au particle size and more importantly to the complicated synergy between the AuCuTiO2 interaction which might be the active sites for epoxidation. Also, high selectivity to TFPO up to 88% was obtained on the Cu-promoted catalyst, due to the proper electronic structure induced by the interaction between Au and low valent Cu species. Catalyst deactivation was due to the significant growth of Au particles and loss of AuCuTiO2 interface because of the segregation of Cu species during the reaction.

Preparation method of 3,3,3-trifluoropropylene carbonate

The invention discloses a preparation method of 3,3,3-trifluoropropylene carbonate. The preparation method comprises the steps: with trifluoropropylene as a raw material, carrying out several simple reaction steps to obtain trifluoroepoxy propane, introducing carbon dioxide into a high-pressure reaction kettle by taking a metal conjugated microporous polymer complex as a catalyst, and preparing 3,3,3-trifluoropropylene carbonate at the temperature of 25-100 DEG C and the pressure of 0.1Mpa-3Mpa. Compared with the prior art, the method has the advantages that trifluoropropylene is taken as theraw material, so that the raw material cost is substantially lowered; and meanwhile, the yield is relatively high, and the catalyst can be repeatedly used, so that the method is suitable for industrial production.

A method for preparing three fluorine epoxy propane

The invention relates to a preparation method of trifluoro epoxypropane, which comprises the following steps: (1) in the presence of sulfuric acid, performing reflux reaction on 3,3,3-trifluoro-2-bromopropyl acetate and alcohol to prepare 3,3,3-trifluoro-2-bromopropanol; and (2) dropwisely adding the 3,3,3-trifluoro-2-bromopropanol into a mixture of alkali and water at 70-120 DEG C, and reacting to prepare trifluoro epoxypropane. According to the invention, the 3,3,3-trifluoro-2-bromopropyl acetate used as a raw material is subjected to ester exchange to obtain the 3,3,3-trifluoro-2-bromopropanol, the treatment method is simple, green and environment-friendly; a catalyst concentrated sulfuric acid is reusable; and the preparation efficiency of the 3,3,3-trifluoro-2-bromopropanol is high. Meanwhile, the trifluoro epoxypropane reaction yield is high.

Preparative-scale synthesis of 3,3,3-trifluoropropene oxide

Bromination of 3,3,3-trifluoropropene in 20% oleum, followed by treatment with acetic acid furnishes 2-bromo-3,3,3-trifluoropropyl acetate in quantitative yield, which upon acid hydrolysis and cyclization with alkali affords 3,3,3-trifluoropropene oxide (TFPO) in 63% overall yield.

Novel method for the synthesis of (trifluoromethyl)oxirane

The reaction of 3,3,3-trifluoropropene with N-bromosuccinimide in acetic acid at 65-70 deg C affords 3-acetoxy-2-bromo-1,1,1-trifluoropropane. When treated with an alkali, the latter is readily converted into (trifluoromethyl)oxirane.

The synthesis of fluorine-containing pterins

The synthesis of some 7,7-difluoro-7,8-dihydropterins and pterins with fluoroalkyl substituents at the 6 or 7 positions from fluorine-containing aliphatic precursors and suitably substituted pyrimidines is described. The fluorine-containing pterins were found to be very insoluble and also stable to nucleophiles and bases in dilute aqueous solution.