353-61-7

Usage

Uses

Used in Organic Synthesis:
TERT-BUTYL FLUORIDE is used as a reagent for various organic synthesis processes due to its high reactivity and ability to facilitate specific chemical reactions.
Used in Chemical Reactions as a Solvent:
TERT-BUTYL FLUORIDE is used as a solvent in different chemical reactions, providing a medium for the reactions to occur and enhancing the reaction rates.
Used in Pharmaceutical Production:
TERT-BUTYL FLUORIDE is used as a fluorinating agent in the production of pharmaceuticals, enabling the incorporation of fluorine atoms into drug molecules, which can improve their pharmacological properties.
Used in Agrochemical Production:
TERT-BUTYL FLUORIDE is used as a fluorinating agent in the production of agrochemicals, allowing for the development of more effective and targeted pesticides and other agricultural chemicals.

InChI:InChI=1/C4H9F/c1-4(2,3)5/h1-3H3

Upstream product

• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 78-83-1 2-methyl-propan-1-ol 
• 421-20-5 Methyl fluorosulfonate 
• 66950-72-9 isobutyl N,N-dimethylsulfamate 
• 507-20-0 tertiary butyl chloride 
• 78-77-3 Isobutyl bromide 
• 1634-04-4 tert-butyl methyl ether 
• 1584-03-8 perfluoro-2-methylpent-2-ene 
• 507-19-7 t-butyl bromide 
• 558-17-8 tert-Butyl iodide 
• 75-28-5 Isobutane 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 637-92-3 Ethyl tert-butyl ether 

Downstream Products

• 4210-60-0 t-butylmalonodinitrile 
• 141-70-8 1,1-dineopentylethylene 
• 27656-49-1 trans-2,2,4,6,6-pentamethyl-3-heptene 
• 420-45-1 2,2-difluoropropane 
• 1184-60-7 2-fluoropropene 
• 74-87-3 methylene chloride 
• 834-14-0 p-benzylanizole 
• 883-90-9 o-benzyl anisole 
• 144774-61-8 C₄H₉Cl*Cl^(1-) 
• 98-51-1 4-tert-butyltoluene 
• 1075-38-3 m-t-butyltoluene 

Relevant academic research and scientific papers

GROUP ADDITIVITY FOR THE BAND STRENGTH OF THE CF-CHROMOPHORE FOR IR-PHOTOCHEMISTRY.

Integrated band strengths for rovibrational absorption in the frequency range of the CF-chromophore (800 to 1300 cm** minus **1) have been obtained from vapor phase IR-spectra of twelve fluoroalkanes containing one or more CF groups. It is found that the chromophore band strength is about 1. 7 (pm)**2 for each CF group with some minor variations due to neighboring substituents at the CF carbon atom. These variations can be accounted for by a simple, empirical equation. The results are discussed in relation to the chromophore principle in IR-photochemistry. The frequency distribution of the chromophore absorption for primary, secondary, and tertiary alkyl fluorides is considered. The primary CF-chromophore (R-CH//2-F) is suggested to be a particularly useful general chromophore for CO//2-laser pumping. The foundations of the group additivity for chromophore band strengths and some further applications are discussed as well.

Synthesis, Bonding, and Reactivity of Vanadium(IV) Oxido-Fluorido Compounds with Neutral Chelate Ligands of the General Formula cis-[VIV(=O)(F)(LN-N)2]+

Reaction of the oxidovanadium(IV)-LN-N species (LN-N is bipy = 2,2′-bipyridine or bipy-like molecules) with either BF4- or HF and/or KF results in the formation of compounds of the general formula cis-[VIV(=O)(F)(LN-N)2]+. Structural and spectroscopic (electron paramagnetic resonance) characterization shows that these compounds are in the tetravalent oxidation state containing a terminal fluorido ligand. Density functional theory calculations reveal that the VIV-F bond is mainly electrostatic, which is reinforced by reactivity studies that demonstrate the nucleophilicity of the fluoride ligand in a halogen exchange reaction and in fluorination of various organic substrates.

METHOD FOR PRODUCING FLUORINATED HYDROCARBONS

Provided is a method for industrially advantageously producing a fluorinated hydrocarbon (3). The disclosed method for producing a fluorinated hydrocarbon represented by formula (3) includes bringing into contact, in a hydrocarbon-based solvent, a secondary or tertiary ether compound represented by formula (1) below with an acid fluoride represented by formula (2) in the presence of lithium salt or sodium salt (in the formulae, R1 and R2 each represent a C1-3 alkyl, and R1 and R2 may be bonded to each other to form a ring structure; R3 represents a hydrogen atom, methyl, or ethyl; and R4 and R5 each represent methyl or ethyl).

Catalytic Formation of C(sp3)-F Bonds via Heterogeneous Photocatalysis

Due to their chemical, physical, and biological properties, fluorinated compounds are widely employed throughout society. Yet, despite their critical importance, current methods of introducing fluorine into compounds suffer from severe drawbacks. For example, several methods are noncatalytic and employ stoichiometric equivalents of heavy metals. Existing catalytic methods, on the other hand, exhibit poor activity, generality, selectivity and/or have not been achieved by heterogeneous catalysis, despite the many advantages such an approach would provide. Here, we demonstrate how selective C(sp3)-F bond synthesis can be achieved via heterogeneous photocatalysis. Employing TiO2 as photocatalyst and Selectfluor as mild fluorine donor, effective decarboxylative fluorination of a variety of carboxylic acids can be achieved in very short reaction times. In addition to displaying the highest turnover frequencies of any reported fluorination catalyst to date (up to 1050 h-1), TiO2 also demonstrates excellent levels of durability, and the system is catalytic in the number of photons required; i.e., a photon efficiency greater than 1 is observed. These factors, coupled with the generality and mild nature of the reaction system, represent a breakthrough toward the sustainable synthesis of fluorinated compounds.

MANUFACTURING METHOD OF FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide a method for industrially advantageously manufacturing fluorinated hydrocarbon (3). SOLUTION: There is provided a method for manufacturing fluorinated hydrocarbon represented by the formula (3), including contacting a secondary or tertiary ether compound represented by the formula (1) and acid fluoride represented by the formula (2) in the presence of a silver salt in a hydrocarbon solvent. R1 and R2 are each independently a C1 to 3 alkyl group, R1 and R2 may bind to form a ring structure, R3 is H, a methyl group or an ethyl group, R4 and R5 are each independently a methyl group or an ethyl group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

METHOD FOR PRODUCING FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide a method for industrially advantageously producing a fluorinated hydrocarbon. SOLUTION: The method for producing a fluorinated hydrocarbon represented by formula (3) comprises bringing a secondary or tertiary ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in the presence of a compound having an N-X bond (X is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom) in a halogenated hydrocarbon-based solvent. (R1 and R2 are each independently a C1-C3 alkyl group; R3 is H, a methyl group, or an ethyl group; R4 and R5 are each a methyl group or an ethyl group; and R1 and R2 may be bonded together to form a ring structure.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Catalytic formation of C(sp3)-F bonds via decarboxylative fluorination with mechanochemically-prepared Ag2O/TiO2 heterogeneous catalysts

Mechanochemically-prepared, Ag2O-containing solid materials, are shown to be efficient heterogeneous catalysts for the synthesis of C(sp3)-F bonds via decarboxylative fluorination. Five catalytic cycles without loss of intrinsic activity could be performed with the optimal catalyst, composed of 1 wt% Ag2O supported on TiO2 (P25), despite the challenging conditions. The catalyst is easily prepared from the corresponding oxides in 20 minutes by simple mechanical mixing methods. In addition to ease of separation and re-use, the turnover numbers obtained over the solid catalyst are over one order of magnitude higher than those obtained with the state-of-the-art homogeneous catalyst, AgNO3, under otherwise identical conditions. To the best of our knowledge, this represents the first true heterogeneous catalyst for the selective formation of C(sp3)-F bonds with electrophilic fluorine donors, representing a major breakthrough in the field of catalytic fluorination.

Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: Reactivity and mechanistic studies

Cross dehydrogenative couplings on ethers occur very effectively using N-fluorobis(phenyl)sulfonimide (NFSI) as oxidizing agent under UVA irradiation in the presence of 2 mol% benzophenone. The reaction was shown to proceed first by fast radical fluorination of the α-C-H bond of ethers, followed by HF elimination to yield the highly electrophilic oxocarbenium ion as a key intermediate.

METHOD FOR PRODUCING FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide an industrially advantageous method for producing a fluorinated hydrocarbon such as 2-fluorobutane useful as etching gas for a dry etching process. SOLUTION: There is provided a method for producing a fluorinated hydrocarbon represented by formula (3) by bringing an ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in a halogenated hydrocarbon solvent in the presence of a metal halide represented by formula (4): MX3 (M represents a metal atom; X represents a chlorine atom or a bromine atom) (R1 and R2 each independently represent an alkyl group having 1-3 carbon atoms; R1 and R2 may be bonded to form a ring structure; R3 represents H, a methyl group or an ethyl group; R4 and R5 each independently represent a methyl group or an ethyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

METHOD FOR PRODUCING FLUORINATED HYDROCARBON

The present invention is a method for producing a fluorohydrocarbon represented by a structural formula (3) comprising bringing a secondary or tertiary ether compound represented by a structural formula (1) into contact with an acid fluoride represented by a structural formula (2) in a hydrocarbon-based solvent in the presence of a boron trifluoride complex. (In structural formulae (1) to (3), each of R1 and R2 represents an alkyl group having 1 to 3 carbon atoms, R3 represents a hydrogen atom, a methyl group, or an ethyl group, and each of R4 and R5 represents a methyl group or an ethyl group, provided that R1 and R2 are optionally bonded to each other to form a ring structure.)