Benzoic acid,4-ethynyl-, methyl ester supplier

Name
4-ETHYNYL-BENZOIC ACID METHYL ESTER
EINECS
CAS No. 3034-86-4
Article Data112
CAS DataBase
Density 1.11 g/cm³
Solubility Sparingly soluble in water (0.16 g/L at 25°C).
Melting Point 103-105℃
Formula C₁₀H₈O₂
Boiling Point 239.4 °C at 760 mmHg
Molecular Weight 160.172
Flash Point 92 °C
Transport Information
Appearance
Safety 22-26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzoicacid, p-ethynyl-, methyl ester (7CI,8CI);4-(Methoxycarbonyl)phenylacetylene;Methylp-ethynylbenzoate;Methyl 4-ethynylbenzoate;4-Ethynylbenzoic acid methyl ester;p-Ethynylbenzoic acid methyl ester;methyl 4-ethynylbenzoate;benzoic acid, 4-ethynyl-, methyl ester;methyl 4-ethynylbenzoate;
PSA 26.30000
LogP 1.45450

Synthetic route

: 33577-98-9
methyl 4-(3-hydroxy-3-methylbut-1-ynyl)benzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium phosphate; potassium hydroxide In toluene for 0.0833333h; Reagent/catalyst; Time; Inert atmosphere; Reflux;	100%
With sodium hydride In toluene at 110℃;	98%
With potassium phosphate; potassium carbonate In toluene Inert atmosphere;	92%

: 75867-41-3
4-trimethylsilanylethynyl-benzoic acid methyl ester

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In methanol for 2h;	100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 0.5h;	99%
With potassium carbonate In methanol; dichloromethane	99%

: 356759-39-2
(Z)-4-(β-bromovinyl)benzoic acid methyl ester

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 1h; microwave irradiation;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0166667h; microwave irradiation;
With sodium ethanolate In N,N-dimethyl-formamide at 120℃; for 12h;

: 67-56-1
methanol

: 150969-54-3
ethyl 4-(trimethylsilylethynyl)benzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 2h;	99%
With potassium carbonate at 20℃; for 0.5h;	91%
With potassium carbonate at 20℃; for 2h;	90%
With potassium carbonate at 10 - 20℃; for 3.86667h; Inert atmosphere; Schlenk technique;	12.3 g

: 3609-53-8
methyl 4-acetylbenzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane In N,N-dimethyl-formamide at -10 - 20℃;	97%

: 619-44-3
methyl 4-iodobenzoate

: 1066-54-2
trimethylsilylacetylene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: methyl 4-iodobenzoate; trimethylsilylacetylene With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride for 24h; Stage #2: With potassium carbonate In methanol for 48h;	91%
Stage #1: methyl 4-iodobenzoate; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 90℃; for 24h; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;	70%
Stage #1: methyl 4-iodobenzoate; trimethylsilylacetylene With copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; triethylamine In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h;

: 4-(methoxycarbonyl)phenylethynyldiphenylphosphine oxide

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With methylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 0℃; for 0.25h; Inert atmosphere;	91%

: 619-44-3
methyl 4-iodobenzoate

: ethynylzinc bromide

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 22℃; for 1h;	86%

: 90965-06-3
dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

: 1571-08-0
methyl 4-formylbenzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium tert-butylate In methanol at 100℃; for 0.5h;	84%
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h;
With potassium carbonate In tetrahydrofuran; methanol at 20℃;	23 mg

: 619-42-1
4-methoxycarbonylphenyl bromide

: 1066-54-2
trimethylsilylacetylene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine at 20℃; for 24.5h; Inert atmosphere; Reflux;	83.1%
Stage #1: 4-methoxycarbonylphenyl bromide; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Stage #2: With methanol; potassium hydroxide In tetrahydrofuran at 20℃; for 0.5h;	30%

: 529-20-4
2-methylphenyl aldehyde

: (4-methoxycarbonylphenyl)ethynyl iodide

: 762-72-1
allyl-trimethyl-silane

A: 3034-86-4
4-ethynylbenzoic acid methyl ester

B: methyl 4-(3-(o-tolyl)hex-5-en-1-yn-1-yl)benzoate

Conditions

Conditions	Yield
Stage #1: 2-methylphenyl aldehyde; (4-methoxycarbonylphenyl)ethynyl iodide With bis(cyclopentadienyl)titanium dichloride; P(p-CH3OC6H4)3; zinc In dichloromethane at 20℃; Inert atmosphere; Stage #2: allyl-trimethyl-silane With acetic anhydride In dichloromethane at 0℃; Inert atmosphere;	A n/a B 81%

...Expand

: 6908-41-4
4-(methoxycarbonyl)benzyl alcohol

: 90965-06-3
dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With manganese(IV) oxide; potassium carbonate In tetrahydrofuran; methanol at 20℃;	78%
With manganese(IV) oxide; potassium carbonate In tetrahydrofuran; methanol at 20℃; for 18h;	78%

: 253684-21-8
1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With caesium carbonate; dimethyl sulfoxide at 115℃; for 12h;	78%
With caesium carbonate In dimethyl sulfoxide at 115℃; Sealed tube; Inert atmosphere;	33%

: (2RS,3SR)-2,3-dibromo-3-(4-methoxycarbonylphenyl)propanoic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h;	75%
Multi-step reaction with 2 steps 1: 99 percent / triethylamine / dimethylformamide / 0.02 h / microwave irradiation 2: 99 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 1 h / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dimethylformamide / 1 h / microwave irradiation 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 0.02 h / microwave irradiation View Scheme

: 61266-36-2
methyl 4-(3-hydroxypropynyl)benzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With manganese(IV) oxide; potassium hydroxide In benzene for 0.25h; Ambient temperature;	72%
With manganese(IV) oxide; potassium hydroxide In benzene at 20℃; for 0.25h;	72%

: 67-56-1
methanol

: 10602-00-3
4-Ethynyl-benzoic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	72%

: 15164-44-0
p-(iodophenyl)carboxaldehyde

: 1066-54-2
trimethylsilylacetylene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: p-(iodophenyl)carboxaldehyde; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 90℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;	70%

: 619-44-3
methyl 4-iodobenzoate

: 471-25-0
Propiolic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 0 - 60℃; for 5h; Sealed flask;	42%

: 67-56-1
methanol

: 90347-86-7
1-carboxamido-4-ethynylbenzene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid

: 6929-96-0
2-ethynyl-1,3-butadiene

: 922-67-8
propynoic acid methyl ester

A: 10602-06-9
methyl 3-ethynylbenzoate

B: 3034-86-4
4-ethynylbenzoic acid methyl ester

C: 4-Ethynyl-cyclohexa-1,4-dienecarboxylic acid methyl ester

D: 5-Ethynyl-cyclohexa-1,4-dienecarboxylic acid methyl ester

Conditions

Conditions	Yield
In toluene at 75℃; for 6h; Title compound not separated from byproducts;

...Expand

: 6908-41-4
4-(methoxycarbonyl)benzyl alcohol

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: MnO2 / tetrahydrofuran / 4 h / 20 °C 2: 23 mg / K2CO3 / tetrahydrofuran; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: MnO2 / tetrahydrofuran / 20 °C 2: K2CO3 / methanol; tetrahydrofuran / 12 h / 20 °C View Scheme

: 619-44-3
methyl 4-iodobenzoate

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / Pd(PPh3)2Cl2; CuI; triethylamine / 2 h / 20 °C 2: 81 percent / sodium carbonate / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / (Ph3)2PdCl2; Ph3P; CuI / Et3N / 68 h / Heating 2: 98 percent / NaH / toluene / 110 °C View Scheme
Multi-step reaction with 2 steps 1: 95 percent / Pd(PPh3)2Cl2; CuI; triethylamine / tetrahydrofuran / 1.5 h / 80 °C 2: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / -20 °C View Scheme

: 117390-07-5
(E)-4-(methoxycarbonyl)cinnamic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / CHCl3 2: 99 percent / triethylamine / dimethylformamide / 0.02 h / microwave irradiation 3: 99 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 1 h / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: chloroform / 20 - 60 °C / Irradiation; Bromination 2: potassium carbonate / dimethyl sulfoxide / 12 h / 115 °C View Scheme

: 619-42-1
4-methoxycarbonylphenyl bromide

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / CuI; PPh3; Pd(PPh3)2Cl2 / triethylamine; tetrahydrofuran / Heating 2: 99 percent / K2CO3 / methanol; CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: 94 percent Chromat. / PdCl2(1,1'-bis(diphenylphosphino)ferrocene), CuI, Et3N / benzene / 2 h / 70 °C 2: 72 percent / MnO2, KOH powder / benzene / 0.25 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / Pd(OAc)2, PPh3 / tetrahydrofuran / 4 h / Heating 2: Bu4NF / tetrahydrofuran / 0.33 h View Scheme

: 619-58-9
4-iodobenzoic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / K2CO3 / dimethylsulfoxide 2: 95 percent / Pd(PPh3)2Cl2; CuI; triethylamine / tetrahydrofuran / 1.5 h / 80 °C 3: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / -20 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 20 °C / Inert atmosphere; Sealed tube; Schlenk technique 3: potassium carbonate / dichloromethane; methanol / 6 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: acetyl chloride / 12 h / 60 °C 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / 12 h / 75 °C 3: methanol; potassium carbonate / 6 h / 25 °C View Scheme

: 619-44-3
methyl 4-iodobenzoate

Co2(CO)8: Co2(CO)8

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / copper(I) iodide; diisopropylethylamine / bis(triphenylphosphine)palladium(II) dichloride / tetrahydrofuran / 18 h / 60 °C 2: 0.49 g / potassium carbonate / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

: 1443-80-7
4-cyanophenyl methyl ketone

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. H2SO4 / 150 °C 2: (i) PCl5, POCl3, (ii) NaNH2, liq. NH3, Et2O 3: H2SO4 View Scheme

: 586-89-0
4-acetyl-benzoic acid

1.4-diacetyl-benzene; terephthalic acid: 1.4-diacetyl-benzene; terephthalic acid

: 3034-86-4
4-ethynylbenzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) PCl5, POCl3, (ii) NaNH2, liq. NH3, Et2O 2: H2SO4 View Scheme

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 518980-39-7
1-iodo-2-nitro-4-phenylethynyl-benzene

: 546112-69-0
4-(2-nitro-4-phenylethynylphenylethynyl)benzoic acid methyl ester

Conditions

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 1h; Sonogashira-Castro-Stephens coupling;	100%

: 3058-39-7
4-iodobenzonitrile

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: methyl 4-((4-cyanophenyl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran for 5h; Inert atmosphere;	100%

: 624-38-4
para-diiodobenzene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 848850-13-5
dimethyl 4,4′-[1,4-phenylenebis(ethyne-2,1-diyl)]dibenzoate

Conditions

Conditions	Yield
Stage #1: 4-ethynylbenzoic acid methyl ester With triethylamine for 0.166667h; Stage #2: para-diiodobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 50℃; Inert atmosphere;	99%
With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride In triethylamine at 50℃; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira cross-coupling reaction;	46%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: (4-methoxycarbonylphenyl)ethynyl iodide

Conditions

Conditions	Yield
With aluminum oxide; N-iodo-succinimide In acetonitrile at 80℃; for 1h; Molecular sieve;	99%
With N-chlorobenzenesulfonamide; potassium iodide In acetonitrile at 20℃; for 2h;	97%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;	97%

: 870-46-2
t-butoxycarbonylhydrazine

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: (E)-tert-butyl 2-(1-(4-(methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate

Conditions

Conditions	Yield
With [(THD-Dipp)AuOTf] In neat (no solvent) at 100℃; Green chemistry; regioselective reaction;	99%

: 288-32-4
1H-imidazole

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: (E)-methyl 4-(2-(1H-imidazole-1-yl)vinyl)benzoate

Conditions

Conditions	Yield
With hexa[tri(dimethylamino)phosphazene]cyclotriphosphazene In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Glovebox; stereoselective reaction;	99%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 10602-00-3
4-Ethynyl-benzoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	98.64%
With lithium hydroxide In methanol; water for 2h;	77%
With lithium hydroxide In methanol; water for 2h;	77%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 3609-53-8
methyl 4-acetylbenzoate

Conditions

Conditions	Yield
With 5,10,15-tris(pentafluorophenyl)corrole cobalt(III) triphenyl phosphine; sulfuric acid; water In methanol at 80℃; for 36h;	98%
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25 - 70℃; for 45h; Sealed tube; regioselective reaction;	94%
With indium(III) triflate; water; toluene-4-sulfonic acid In 1,2-dichloro-ethane for 19h; Sealed tube; Reflux; regioselective reaction;	77%
With methanol; platinum(IV) oxide; water; toluene-4-sulfonic acid at 90℃; for 5h; Sealed tube;	68%
With 2CHF3O3S*C29H35NO6P2Pt; water; sodium dodecyl-sulfate at 80℃; Micellar solution;	26 %Chromat.

: 4897-68-1
2-iodo-4-methoxybromobenzene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 1378284-25-3
methyl 4-[(2-bromo-5-methoxyphenyl)ethynyl]benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	98%

: 1309763-77-6
4'-azido-2,2'-bipyridine-N'-oxide

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 1309763-84-5
4'-(4-(4-(methoxycarbonyl)phenyl)-1H-1,2,3-triazol-1-yl)-2,2'-bipyridine N'-oxide

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 20h; Inert atmosphere;	98%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 107864-71-1
1,3,5-tris(azidomethyl)benzene

: C39H33N9O6

Conditions

Conditions	Yield
With triethylamine In water; tert-butyl alcohol at 50℃; for 7h; Schlenk technique;	98%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 7-(diethylamino)-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate

: methyl 4-((7-(diethylamino)-2-oxo-2H-chromen-4-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Sonogashira Cross-Coupling; Inert atmosphere; Microwave irradiation;	98%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 171197-80-1
2-fluoro-5-iodopyridine

: methyl 4-((6-fluoropyridin-3-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 16h;	98%

: 609-14-3
2-acetylpropanoic acid ethyl ester

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: ethyl 2-acetyl-2-methyl-3-(4-methoxycarbonylphenyl)-3-butenoate

Conditions

Conditions	Yield
In(OSO2CF3)3 at 140℃; for 18h;	97%
indium(III) triflate at 140℃; for 18h;	97%
With indium(III) triflate	97%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 622-79-7
benzyl azide

: 76003-76-4
1-benzyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With copper(l) iodide; 1-decylimidazole at 25℃; for 2h; neat (no solvent);	97%

: 1394173-31-9
5-iodo-1,1,3,3-tetramethyl-1,3-disilaindane

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 1394173-35-3
methyl 4-(1,1,3,3-tetramethyl-1,3-disilaindan-5-ylethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 17h; Sonogashira Cross-Coupling; Inert atmosphere;	97%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 95-54-5
1,2-diamino-benzene

: C16H12N2O3

Conditions

Conditions	Yield
With oxygen; potassium carbonate; copper(l) chloride In methanol; acetonitrile at 25℃; for 2.5h; Irradiation; Green chemistry;	97%

: 253687-41-1
[RuCl(dppe)2]OTf

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: trans-[Ru(dppe)2(C≡CC6H4CO2Me)Cl]

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;	97%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: C20H16O4

Conditions

Conditions	Yield
With C17H37FeN3P2 In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox; stereoselective reaction;	97%
With [CoBr2(TriPhos)]; zinc(II) iodide; zinc In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique; diastereoselective reaction;	67%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: Methyl 4-(1,2,2-triiodovinyl)benzoate

Conditions

Conditions	Yield
Stage #1: 4-ethynylbenzoic acid methyl ester With [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 3h; Stage #2: With [bis(acetoxy)iodo]benzene; potassium iodide In water; acetonitrile at 20℃; for 15h;	97%
Stage #1: 4-ethynylbenzoic acid methyl ester With [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 3h; Stage #2: With [bis(acetoxy)iodo]benzene; potassium iodide In water; acetonitrile at 20℃; for 15.3333h; chemoselective reaction;	91%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: C10H7(2)HO2

Conditions

Conditions	Yield
With water-d2; silver trifluoroacetate In dichloromethane at 25℃; for 16h;	97%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 421554-58-7
2-bromo-5-(4-n-hexylphenylethynyl)-4-nitro-N-acetylaniline

: methyl 4-[2-acetamido-4-(4-n-hexylphenylethynyl)-5-nitro]phenylethynylbenzoate

Conditions

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 75℃; for 72h; Castro-Stephens/Sonogashira coupling;	96%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: dimethyl 4,4′-(buta-1,3-diyne-1,4-diyl)dibenzoate

Conditions

Conditions	Yield
With copper oxide supported on mesoporous manganese oxide; air In toluene at 105℃; for 4h;	96%
With piperidine In toluene at 60℃; under 760.051 Torr; for 24h;	95%
With copper diacetate In pyridine at 20℃; for 46h; Eglinton Coupling; Schlenk technique; Inert atmosphere;	89%

: 392-57-4
1,4-diiodo-2,3,5,6-tetrafluorobenzene

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 1,4-bis(4-carbomethoxyphenylethynyl)-2,3,5,6-tetrafluorobenzene

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 3h; Sonogashira cross-coupling reaction; Heating;	96%
With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride In triethylamine at 50℃; Inert atmosphere;	91%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 827574-12-9
3-butylamino-N,N-dimethyl-(Z)-2-butenamide

: 2-acetyl-3-(4-methoxyvarbonylphenyl)-N,N-dimethyl-2-butenamide

Conditions

Conditions	Yield
Stage #1: 4-ethynylbenzoic acid methyl ester; 3-butylamino-N,N-dimethyl-(Z)-2-butenamide With diethylzinc In hexane at 70℃; for 15h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃;	96%

Benzoic acid,4-ethynyl-, methyl ester Specification

The Benzoic acid,4-ethynyl-, methyl ester, with the CAS registry number 3034-86-4, has the systematic name of methyl 4-ethynylbenzoate. It is a kind of organics, and should be stored in the dry and cool environment. And the molecular formula of the chemical is C₁₀H₈O₂.

The characteristics of Benzoic acid,4-ethynyl-, methyl ester are as followings: (1)ACD/LogP: 2.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.38; (4)ACD/LogD (pH 7.4): 2.38; (5)ACD/BCF (pH 5.5): 37.76; (6)ACD/BCF (pH 7.4): 37.76; (7)ACD/KOC (pH 5.5): 468.22; (8)ACD/KOC (pH 7.4): 468.22; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.537; (14)Molar Refractivity: 44.92 cm³; (15)Molar Volume: 143.7 cm³; (16)Polarizability: 17.81×10^-24cm³; (17)Surface Tension: 42.5 dyne/cm; (18)Density: 1.11 g/cm³; (19)Flash Point: 92 °C; (20)Enthalpy of Vaporization: 47.62 kJ/mol; (21)Boiling Point: 239.4 °C at 760 mmHg; (22)Vapour Pressure: 0.0403 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(OC)c1ccc(C#C)cc1
(2)InChI: InChI=1/C10H8O2/c1-3-8-4-6-9(7-5-8)10(11)12-2/h1,4-7H,2H3
(3)InChIKey: JPGRSTBIEYGVNO-UHFFFAOYAK

Product Name

4-ETHYNYL-BENZOIC ACID METHYL ESTER

Synthetic route

Benzoic acid,4-ethynyl-, methyl ester Specification

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