866683-57-0

Basic information

• Product Name: 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE
• Synonyms: 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE;3-(TRIFLUOROMETHOXY)PHENYLACETYLENE;Benzene, 1-ethynyl-3-(trifluoroMethoxy)-;1-Ethynyl-3-(trifluoromethoxy)benzene, 3-Ethynyl-alpha,alpha,alpha-trifluoroanisole;1-Ethynyl-3-(trifluoromethoxy)benzene, 3-Ethynylphenyl trifluoromethyl ether;3-(Trifluoromethoxy)phenylacetylene98%
• CAS NO: 866683-57-0
• Molecular Formula: C₄H₁₀Cl₂Sn
• Molecular Weight: 186.13
• Mol File: 866683-57-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 166.3°C at 760 mmHg
• Flash Point: 60.5°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 2.36mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE(866683-57-0)
• EPA Substance Registry System: 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE(866683-57-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 866683-57-0(Hazardous Substances Data)

Usage

General Description

1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is a chemical compound with the molecular formula C10H5F3O. It is a derivative of benzene, with a trifluoromethoxy group (-OCHF3) attached to the third position and an ethynyl group (-C≡CH) attached to the first position. 1-ETHYNYL-3-(TRIFLUOROMETHOXY)-BENZENE is commonly used in organic synthesis and medicinal chemistry research. The presence of the trifluoromethoxy group makes it a valuable building block for the synthesis of pharmaceuticals and agrochemicals, as well as a potential fluorinated ligand in transition metal catalysis. Its unique structure and reactivity make it a valuable tool for creating new molecules with diverse properties and applications.

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

• 3682-12-0 diethyltin(IV) oxide 
• 597-64-8 tetraethyltin 
• 98-13-5 Phenyltrichlorosilane 
• 7719-09-7 thionyl chloride 
• 20525-62-6 dibutyldiethylstannane 
• 19411-60-0 tributylethylstannane 
• 1066-57-5 ethyltintrichloride 
• 7446-70-0 aluminium trichloride 
• 7647-01-0 hydrogenchloride 
• 110167-95-8 [(C₂H₅)2SnCl₂(C₃H₃N₂)3CH] 
• 866683-58-1 trimethyl-(3-trifluoromethoxyphenylethynyl)-silane 
• 10203-52-8 diethyl(diphenyl)tin 
• 7646-78-8 tin(IV) chloride 
• 878-51-3 triethyl(phenyl)stannane 

Relevant articles and documents

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.

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.

Synthesis of organotin mixed dihalides

-