359-13-7

Basic information

• Product Name: 2,2-Difluoroethanol
• Synonyms: CHF2CH2OH;Ethanol, 2,2-difluoro-;2,2-Difluoroethanol,95%;2,2-Difluoroethanol 97%;2,2-Difluoroethanol97%;2,3-Difluoroethanol;2,2-difluoroethan-1-ol;1,1-Difluoro-2-hydroxyethane
• CAS NO: 359-13-7
• Molecular Formula: C₂H₄F₂O
• Molecular Weight: 82.05
• EINECS: -0
• Product Categories: Four-membered heterocyclic compound
• Mol File: 359-13-7.mol
• Article Data: 36

Chemical Properties

• Melting Point: -28°C
• Boiling Point: 95 °C
• Flash Point: 3°C
• Appearance: /
• Density: 1.296
• Vapor Pressure: 25.1mmHg at 25°C
• Refractive Index: 1.338
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: soluble in chloroform, ethanol.
• PKA: 13.00±0.10(Predicted)
• BRN: 1731617
• CAS DataBase Reference: 2,2-Difluoroethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Difluoroethanol(359-13-7)
• EPA Substance Registry System: 2,2-Difluoroethanol(359-13-7)

Safety Data

• Hazard Codes: F,T
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-36/37/39-45-60-37-33-26-7
• RIDADR: 1987
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 359-13-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2,2-Difluoroethanol is used as a chemical intermediate for the synthesis of various compounds, contributing to the development of new materials and products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-difluoroethanol is utilized as a building block for the creation of novel drugs and drug candidates, taking advantage of its unique chemical properties to enhance the effectiveness and safety of medications.
Used in Fluoropolymer Industry:
2,2-Difluoroethanol is employed as a key component in the production of fluoropolymers, which are known for their exceptional chemical resistance, thermal stability, and non-stick properties. These polymers find applications in a wide range of sectors, such as automotive, aerospace, electronics, and consumer goods.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 23, p. 985, 1980 DOI: 10.1021/jm00183a005

InChI:InChI=1/C2H2ClFO/c3-1-2(4)5/h1H2

Upstream product

• 381-72-6 difluoroacetyl chloride 
• 359-07-9 2-bromo-1,1-difluoroethane 
• 74427-22-8 2,2-difluoroethyl triflate 
• 454-31-9 ethyl difluoroacetate 
• 433-53-4 difluoroacetic acid methyl ester 
• 1550-44-3 2,2-difluoroethyl acetate 
• 67-56-1 methanol 
• 1137875-58-1 2,2-difluoroethyl formate 
• 2925-22-6 2,2-difluoroacetyl fluoride 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 
• 338-65-8 1-chloro-2,2-difluoroethane 
• 79667-91-7 2,2-difluoroethylamine hydrochloride 
• 354-24-5 chlordifluoroacetyl chloride 
• 106-95-6 allyl bromide 

Downstream Products

• 79-14-1 glycolic Acid 
• 358-64-5 tris(2,2-difluoroethyl) phosphate 
• 338-65-8 1-chloro-2,2-difluoroethane 
• 75-71-8 Dichlorodifluoromethane 
• 354-24-5 chlordifluoroacetyl chloride 
• 332-38-7 (4-ethoxy-phenyl)-carbamic acid-(2,2-difluoro-ethyl ester) 
• 32778-16-8 2-difluoromethoxy-1,1-difluoroethane 
• 74427-22-8 2,2-difluoroethyl triflate 
• 381-73-7 Difluoroacetic acid 
• 359-07-9 2-bromo-1,1-difluoroethane 
• 874974-22-8 benzyl 4,4-difluoro-2-butenoate 
• 163035-65-2 methanesulfonic acid 2,2-difluoroethyl ester 
• 391663-89-1 2-amino-6-(2,2-difluoroethoxy)-4-(2-fluorophenyl)pyridine-3,5-dicarbonitrile 
• 219714-96-2 penoxsulam 

Relevant articles and documents

In situ generation of difluoromethyl diazomethane for [3+2] cycloadditions with alkynes

A novel approach to agrochemically important difluoromethyl-substituted pyrazoles has been developed based on the elusive reagent CF2HCHN2, which was synthesized (generated in situ) for the first time and employed in [3+2] cycloaddition reactions with alkynes. The reaction is extremely practical as it is a one-pot process, does not require a catalyst or the isolation of the potentially toxic and explosive gaseous intermediate, and proceeds in a common solvent, namely chloroform, in air. The reaction is also scalable and allows for the preparation of the target pyrazoles on gram scale. A new reagent: The elusive chemical reagent CF2HCHN2 was generated in situ for the first time and further reacted with alkynes in a [3+2] cycloaddition reaction. This transformation constitutes a novel and efficient approach to agrochemically important difluoromethylated pyrazoles.

Synthesis and Biological Activity of Fluoroalkylamine Derivatives of Narcotic Analgesics

N-Ethyl-, N-(2-fluoroethyl)-, N-(2,2-difluoroethyl)-, and N-(2,2,2-trifluoroethyl)-substituted normeperidine (1b-e) and normetazocine (2b-e) derivatives were prepared.The analgesic activities of the compounds were determined in mice.Opiate receptor binding studies, in the presence and absence of sodium ion, were carried out.The antagonist activities of normetazocine derivatives were studied in monkeys.These were further examined in the isolated guinea pig ileum for agonist activity.These pKa values were measured in vivo agonist activity was lost with the weakly bas ic derivatives.For the normetazocine derivatives, opiate receptor binding data were consistent with guinea pig ileum agonist potency and mouse vas deferens antagonist potency but not in vivo data.Opiate receptor binding was reduced for the less basic normetazocine derivatives.In the normeperidine series, there was no apparent direct relationship between pKa and opiate receptor binding.However, a relationship involving the hydrophobic character of the N-substituent is discussed.The N-(2-fluoroethyl) derivatives in both series were found to cause convulsions in rats at doses of 40-45 mg/kg ip.Elevated serum citrate levels were found in these rats, implicating in vivo oxidative deamination of the N-(fluoroalkyl) substituent to fluoroacetate.

Gas phase hydrogenolysis of methyl difluoroacetate to 1,1-difluoroethanol over Ru/C catalysts

Ru/C catalysts were prepared by an impregnation method and their catalytic properties were tested for hydrogenolysis methyl difluoroacetate to difluoroethanol. The catalysts were characterized by X-ray powder diffraction (XRD), transmission electron microscopy (TEM), CO chemisorption and H 2 temperature-programmed reduction (H2-TPR). The effects of reaction temperature, Ru content and reduction temperature of the Ru/C catalysts on the reaction were investigated. It was found that with increasing Ru contents in the Ru/C catalysts, the methyl difluoroacetate conversion, the selectivity to difluoroethanol and the TOF value first increased and then decreased. A 3Ru/C catalyst reduced at 400 °C exhibited the highest selectivity to difluoroethanol (93.5%) and the highest activity (39.5%). It was also found that the Ru/C catalyst showed a good stability of catalytic hydrogenolysis of methyl difluoroacetate within 100 h.

Hydrogen Bonding in Low-Temperature Matrices: 1. Proton Donor Abilities of Fluoroalcohols. Comparative Infrared Studies of ROH...O(CH3)2 Complex Formation in the Gas Phase, in CCl4 Solution, and in Solid Argon

The proton donor-acceptor complexes formed by a series of fluoroalcohols with systematically increasing acidity (pKa's from 14.5 to 5.4) have been studied with dimethyl ether (DME) as a reference base in argon matrices, in CCl4 solutions, and in the gas phase.The intermolecular bond formation O-H...O is discussed on the basis of changes of the O-H stretching absorptions in the infrared spectra.A stepwise increase of the proton donor abilities of the fluoroalcohols is achieved by successively introducing fluorine in β-position of the alcohols as indicated by the increasing frequency shift of the O-H stretching vibrations in the O-H...O complexes.The observed frequency shifts Δν increases as one passes from the gas phase to CCl4 solutions and argon matrices.Data for ΔH0, ΔS0, and ΔG0 have been derived from the solution measurements on the basis of the temperature-dependent intensity changes of the "free" O-H stretching bands.A comparison of the O-H stretching frequencies of the alcohol monomers obtained from the three phases has also been made.The small shifts observed in argon matrices on the order of 19 +/- 4 cm-1 are characteristic for weak interactions of the van der Waals type.The solvent shift in CCl4 is about twice as high and was found to be on the order of 45 +/- 8 cm-1, indicating a much stronger interaction with the solute molecules.It is concluded that it is advantageous, where possible, to study a particular hydrogen-bonded system in different phases in order to get a deeper insight into intermolecular interactions ranging from very weak to very strong and to distinguish hydrogen bond interaction in condensed phases from other intermolecular forces or environmental effects.

Method for preparing 2,2-difluoroethanol

The invention discloses a method for preparing 2,2-difluoroethanol. The method for preparing 2,2-difluoroethanol comprises the following steps: step (i): performing transesterification on 2,2-difluoroethyl acetate in the presence of ethanol and optionally a base.

Engineering Catalysts for Selective Ester Hydrogenation

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.

SYNTHESIS OF FLUORO HEMIACETALS VIA TRANSITION METAL-CATALYZED FLUORO ESTER AND CARBOXAMIDE HYDROGENATION

This application is directed to use of transition metal-ligand complexes to hydrogenate fluorinated esters and carboxamides into fluorinated hemiacetals. Methods for synthesis of certain ligands are also provided.

Method for synthesizing 2,2-difluoroethanol from R142

The invention provides a method for synthesizing 2,2-difluoroethanol from R142. The method comprises the following steps: reacting the R142 with alkali metal formate or alkali metal acetate to preparean intermediate; and reacting the intermediate with alcohol under the catalysis of an oxide carrier loaded metal element catalyst to prepare 2,2-difluoroethanol. In the oxide carrier loaded metal element catalyst, the oxide carrier is aluminum oxide, magnesium oxide or zirconium dioxide, and the metal element is one or a combination of two or more of Mg, Ca, Sr, Ba, Na, K, Rb, Cs, La, Nd, Y and Ce. The oxide carrier loaded metal elements are used as the catalyst, so that the catalyst can be recycled, no alkaline waste liquid is generated, and the catalyst is environment-friendly and low in cost; and the reaction temperature is proper, side reactions are few, and the yield and purity of the obtained target product are high.

Diaminodiphosphine tetradentate ligand and ruthenium complex thereof, and preparation methods and applications of ligand and complex

The invention discloses a diaminodiphosphine tetradentate ligand and a ruthenium complex thereof, and preparation methods and applications of the ligand and the complex, and provides a ruthenium complex represented by a formula I, wherein L is a diaminodiphosphine tetradentate ligand represented by a formula II, and X and Y are respectively and independently chlorine ion, bromine ion, iodine ion,hydrogen negative ion or BH4. According to the present invention, the ruthenium complex exhibits excellent catalytic activity in the catalytic hydrogenation reactions of ester compounds, has high yield and high chemical selectivity, is compatible with conjugated and non-conjugated carbon-carbon double bond, carbon-carbon triple bond, epoxy, halogen, carbonyl and other functional groups, and hasgreat application prospects.

Method for synthesizing difluoroethanol

The invention relates to a method for synthesizing difluoroethanol, and aims to solve the problems of multiple steps, complicated process, low product purity and low yield in the prior art. The methodcomprises the following steps: (1) adding gamma-butyrolactone and alkali metal hydroxide into a reaction kettle under anhydrous and vacuum conditions; (2) feeding 2,2-difluoro-1-halothane, and then quickly heating to reaction temperature for reaction; (3) filtering, rectifying and drying obtained reaction liquid to obtain a difluoroethanol product. The difluoroethanol synthesized by the method has the purity more than or equal to 99.9 percent and the yield more than or equal to 92 percent.