866683-57-0

Usage

Uses

Used in Organic Synthesis:
1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is used as a key intermediate in organic synthesis for the creation of a variety of complex organic molecules. Its ethynyl and trifluoromethoxy functionalities contribute to the diversity of synthetic pathways and the properties of the resulting compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE serves as a valuable precursor for the synthesis of potential pharmaceutical agents. Its unique structural features allow for the development of new molecules with therapeutic potential.
Used in the Synthesis of Pharmaceuticals:
1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is utilized as a building block in the synthesis of pharmaceuticals, where its trifluoromethoxy group can impart specific biological activities and improve pharmacokinetic properties of the resulting drugs.
Used in Agrochemicals Development:
1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is also used in the development of agrochemicals, where its structural elements can be leveraged to create new pesticides or herbicides with enhanced efficacy and selectivity.
Used as a Fluorinated Ligand in Transition Metal Catalysis:
1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE's trifluoromethyl group makes it a candidate for use as a fluorinated ligand in transition metal catalysis, potentially influencing the reactivity and selectivity of catalytic reactions in various chemical processes.
Used in the Creation of Diverse Molecules:
Due to its unique structure and reactivity, 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is employed in the creation of molecules with a wide range of properties and applications, contributing to the advancement of material science and chemical research.

InChI:InChI=1/C9H5F3O/c1-2-7-4-3-5-8(6-7)13-9(10,11)12/h1,3-6H

Synthetic route

trimethyl-(3-trifluoromethoxyphenylethynyl)-silane (866683-58-1) → 1-ethynyl-3-trifluoromethoxybenzene (866683-57-0)

Conditions	Yield
With potassium carbonate In ethanol for 16h;	83%

1-ethynyl-3-trifluoromethoxybenzene (866683-57-0) + methyl 5-azido-4'-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)-[1,1',-biphenyl]-3-carboxylate → methyl 5-(4-(3-(trifluoromethoxy)phenyl)-1H-1,2,3-triazol-1-yl)-4'-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)-[1,1'-biphenyl]-3-carboxylate

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 12h; Huisgen Cycloaddition;	84%

5-bromopyridine-3-carbonitrile (35590-37-5) + 1-ethynyl-3-trifluoromethoxybenzene (866683-57-0) → 5-(3-trifluoromethoxyphenylethynyl)-nicotinonitrile (866685-98-5)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In ethyl acetate at 50℃; for 18h; Sonogashira Coupling;	15%

1-ethynyl-3-trifluoromethoxybenzene (866683-57-0) + 2-iodophenylamine (615-43-0) → 3-(2-(3-(trifluoromethoxy)phenyl)-1H-indole-1-yl)isobenzofuran-1(3H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 24 h / 20 °C / Inert atmosphere 2: palladium diacetate / toluene / 6 h / 10 °C / Sealed tube View Scheme

1-ethynyl-3-trifluoromethoxybenzene (866683-57-0) + 2-iodophenylamine (615-43-0) → 2-((3-(trifluoromethoxy)phenyl)ethynyl)aniline

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 24h; Inert atmosphere;

Upstream product

• 597-64-8 tetraethyltin 
• 20525-62-6 dibutyldiethylstannane 
• 3682-12-0 diethyltin(IV) oxide 
• 4282-05-7 dimethyl diethyl tin 
• 98-13-5 Phenyltrichlorosilane 
• 7719-09-7 thionyl chloride 
• 19411-60-0 tributylethylstannane 
• 1066-57-5 ethyltintrichloride 
• 10294-34-5 boron trichloride 
• 7446-70-0 aluminium trichloride 
• 7646-78-8 tin(IV) chloride 
• 104923-33-3 mercury(I) chloride 
• 98-88-4 benzoyl chloride 
• 13453-32-2 thallium (III) chloride 

Relevant academic research and scientific papers

PYRIDYL DERIVATIVES AND THEIR USE AS MGLU5 RECEPTOR ANTAGONISTS

The present invention is directed toward pyridyl derivatives of formula (I) as antagonists of the mGlu5 receptor. As such the compounds may be useful for treatment or prevention of disorders remedied by antagonism of the mGlu5 receptor, wherein Ar is phenyl or napthyl each of which may be substituted by one or more C1-C4 alkyl, C1-C4 alkoxy, C1-C5 acyl, halo, amino, nitro, cyano, hydroxy, C1-C5 acylamino, C1-C4 alkylsulfonylamino, mono-, di- or trifluorinated C1-C3 alkyl, substituents which may be the same or different and may bear a CONH2, CONHCH3, CON(CH3)2, CO2H, CO2CH3, OCF3, CH2NHCOCH3, CH2NH2, CH2N(CH3)2, CH2CN, CH2OH, CH2NHSO2CH3, CH2N(CH3)(CH2)2 CN, CH2N(CH3)CH(CH3)2, CH2NHCH(CH3)2, CH2NH(CH2)2CH3, CH2NHCO2R4, CH2NHCH2CH3, CH2NHCH3 NHCOC(CH3)2, or N(S(O)2CH3)2 substituent; R1 is hydrogen, halo, R4, CN, C(NOH)R3, C(NO-R4)R3, (CH)2CO2R4 , (CH2)n OR3 , COR3 , CF3,SR4 , S(O)R4, S(O)2R4, COCH2CO2R3 , NHSO2R4 , NHCOR3, C(NOR3)NH2, CH2OCOR3,(CH2)n NH2, CON(CH3)2 (CH2)nNHCO2R4 , CO2R3, CONH2, CSNH2, C(NH)NHOR3, (CH2)nN(CH3)2, or CONHNHCOR3; R2 is 1,2-ethenediyl or 1,2-ethynediyl; R3 is hydrogen or C1-C4 alkyl; R4 is C1-C4 alkyl; and n is 0, 1, 2,3 or 4; or a pharmaceutically acceptable salt thereof, or an N-oxide thereof.

Organotin compounds in synthesis of surface-modified silica materials

Use of alkyl chlorostannanes for obtaining silica materials modified with organic compounds was investigated. The hydrolytic stability of the obtained modified silicas was studied.

Reactions of Thionyl Chloride with Tetraorganotin(IV) Compounds

The reactions of thionyl chloride with tetraorganotin(IV) derivatives (R4Sn where R = CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H4CH3) bring about cleavage of tin-carbon bonds to give dialkyl/aryltin(IV) and alkyl/aryl sulphinyl chlorides.The ease of cleavage observed on the basis of the reactivities of R4Sn follows the order: n-C4H9 > n-C3H7 > C2H5 > CH3 > C6H5CH2 >> C6H4CH3.This order is not the same as commonly known in literature.

Donor-Acceptor Complexes of Organometals and Iodine. Alkyl Ligands as Probes for Steric Effects in Charge Transfer

Charge-transfer (CT) absorptions are observed between iodine and a variety of homoleptic alkylmetals including dialkylmercury (R2Hg) and tetraalkylmetals (R4M) of the group 4A elements (where M = lead, tin, germanium, and silicon) in carbon tetrachloride solutions.These alkylmetal-iodine complexes are all classified as weak, the formation constants, K, being generally less than 5 M-1 for dialkylmercury and less than 3 M-1 for the methylethyllead compounds.The formation constants of tetraalkyltin, -germanium, and -silicon are too small to measure (K -1).The frequency of the charge-transfer bands (hνCT) varies lineary with the vertical ionization potential (ID) of the alkylmetal, determined independently from the photoelectron spectra.However, two separate correlations are required for these alkylmetals-one for the series of two-coordinate, linear dialkylmercury compound and another for the series of four-coordinate, tetrahedral tetraalkylmetals corresponding to a sterically open and a quasi-spherical configuration of electron donors, respectively.Steric effects in these alkylmetal-iodine complexes may be evaluated in two ways.By the direct method, the role of steric effects in determining the charge transfer transition energy is associated with the Coulombic term (e2/rDA) in the first-order treatment of weak complexes according to the Mulliken theory.The mean separation rDAin the CT complexes of R2Hg and R4M, calculated from the measured values of βCT, ID, and the vertical electron affinity of iodine, shows two paralell trends, both increasing with decreasing values of the ionization potentials.This behavior is the same as that evaluated for the CT complexes of tetracyanoethylene (TCNE) with the same series of alkylmetals, in which K is larger and can be measured for as well as complexes.By the indirect method, steric effects are evaluated relative to a reference alkylmetal (Me2Hg for R2Hg and Me4Sn for R4M).The difference ΔE, taken as the relative change in steric effects, is shown to be essentially the same in TCNE and iodine complexes.The later bears on the general question as to whether small (intermediant) values of K (-1) or -ΔH (-1) can be used as adequate criteria for contact charge transfer.