• Name

  3-Hydroxyphenylacetylene

• EINECS
• CAS No. 10401-11-3
• Article Data11
• CAS DataBase
• Density 1.12g/cm³
• Solubility
• Melting Point 64-66 °C
• Formula C8H6 O
• Boiling Point 230.9°Cat760mmHg
• Molecular Weight 118.135
• Flash Point 106.1°C
• Transport Information
• Appearance Clear yellow liquid
• Safety

  Hazard Codes	Xn
  Risk Statements	22-41-52/53
  Safety Statements	26-37/39
  RIDADR	2810
  WGK Germany	2

• Risk Codes 22-41-52/53
• Molecular Structure
• Hazard Symbols
• Synonyms Phenol,m-ethynyl- (7CI,8CI); 3-Ethynylphenol; 3-Hydroxy-1-ethynylbenzene;3-Hydroxyphenylacetylene; m-Ethynylphenol; m-Hydroxyethynylbenzene
• PSA 20.23000
• LogP 1.37350

Synthetic route

3-(2-triisopropylsilylethynyl)phenol

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	95%

388061-72-1

3-[2-(trimethylsilylethynyl)]phenol

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With methanol; potassium hydroxide In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	88%
Stage #1: 3-[2-(trimethylsilylethynyl)]phenol With potassium hydroxide In tetrahydrofuran; methanol; water for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water	70%
With potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;

3-methyl-4-(3-hydroxyphenyl)methylene-isoxazole-5(4H)-one

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
at 800℃; under 0.000750075 Torr;	87%

3-(3-hydroxy-3-methylbut-1-ynyl)phenol

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With potassium hydroxide In toluene for 3h; Heating;	43%

138769-95-6

(1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With potassium carbonate In methanol for 12h;

(1R,2S)-3-Ethynyl-cyclohexa-3,5-diene-1,2-diol

A

5101-44-0

2-ethynyl-phenol

B

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With perchloric acid at 25℃; Rate constant;

591-20-8

3-Bromophenol

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)palladium(II) dichloride; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 3 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine / 1,4-dioxane / 1.33 h / 70 °C / Inert atmosphere; Microwave irradiation 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme

100-83-4

meta-hydroxybenzaldehyde

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 24 h / Cooling with ice; Inert atmosphere; Darkness 2: 800 °C / 0 Torr View Scheme

4-(3-ethynylphenoxy)-2,3,5,6-tetrafluoropyridine

10401-11-3

3-hydroxy phenylacetylene

Conditions

Conditions	Yield
With potassium fluoride; 18-crown-6 ether; Methyl thioglycolate In water; acetonitrile at 50℃;

10401-11-3

3-hydroxy phenylacetylene

121-71-1

3-Hydroxyacetophenone

Conditions

Conditions	Yield
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation;	100%
With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 1h; Catalytic behavior; Temperature; Microwave irradiation; Inert atmosphere;	92%
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25℃; for 24h; Sealed tube; regioselective reaction;	87%
With water at 60℃; for 20h; Sealed tube;	63%
With methanesulfonic acid; iron(II) chloride tetrahydrate In 1,2-dichloro-ethane at 60℃; for 2h; Inert atmosphere;	49%

1193784-38-1

2,2‘,4,4’,5,5‘,6,6‘-hexa-O-acetyl-3,3‘-diazido-3,3‘-dideoxy-1,1‘-sulfanediyl-di-β-D-galactopyranoside

10401-11-3

3-hydroxy phenylacetylene

1421638-22-3

bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 80℃; for 0.666667h; Microwave irradiation;	100%

1239028-00-2

5-azido-2-hydroxy-N-(3-(trifluoromethyl)phenyl)benzamide

10401-11-3

3-hydroxy phenylacetylene

1239028-13-7

2-hydroxy-5-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-N-(3-trifluoromethylphenyl)benzamide

Conditions

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; dimethyl sulfoxide; tert-butyl alcohol at 20℃; for 96h; Inert atmosphere;	99%

2689-88-5

diethyl 2,2-di(prop-2-yn-1-yl)malonate

10401-11-3

3-hydroxy phenylacetylene

1214275-19-0

diethyl 5-(3-hydroxyphenyl)-1H-indene-2,2(3H)-dicarboxylate

Conditions

Conditions	Yield
With cobalt(II) chloride hexahydrate; 2-(2,6-diisopropylphenyliminomethyl)pyridine; zinc In tetrahydrofuran at 40℃; Inert atmosphere;	99%

10401-11-3

3-hydroxy phenylacetylene

620-18-8

3-hydroxystyrene

Conditions

Conditions	Yield
With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 40℃; for 5h; Inert atmosphere;	99%
Stage #1: 3-hydroxy phenylacetylene With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;	91%
With hydrogen In ethanol at 40℃; under 760.051 Torr; for 1.5h; Schlenk technique; Sealed tube; chemoselective reaction;	95 %Chromat.
With Dimethylphenylsilane; water In dimethyl sulfoxide at 70℃; for 0.333333h; Inert atmosphere; stereoselective reaction;

10401-11-3

3-hydroxy phenylacetylene

1617539-93-1

(Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

(Z)-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-6-[4-(3-hydroxyphenyl)-1,2,3-triazole-1-yl]-L-ascorbic acid

Conditions

Conditions	Yield
With copper diacetate In methanol at 50℃; Temperature; Flow reactor; Sonication;	99%
With copper diacetate In methanol

10401-11-3

3-hydroxy phenylacetylene

18162-48-6

tert-butyldimethylsilyl chloride

163233-08-7

3-tert-butyldimethylsilyloxyphenylacetylene

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h;	98%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	86%

874347-26-9

C14H16INO4

10401-11-3

3-hydroxy phenylacetylene

874680-87-2

C22H21NO5

Conditions

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide for 6h;	98%

10401-11-3

3-hydroxy phenylacetylene

98-83-9

isopropenylbenzene

1235453-96-9

3-(3-methyl-3-phenylcyclobut-1-enyl)phenol

Conditions

Conditions	Yield
With (acetonitrile)[(2',4',6'-triisopropyl-1,1'-biphenyl-2-yl)di-tert-butylphosphine]gold(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In dichloromethane at 23℃; Inert atmosphere; regioselective reaction;	98%
With (acetonitrile)[2-di-tert-butyl(2′,4′,6′-triiso-propylbiphenyl)phosphine]gold(I) hexafluoroantimonate In dichloromethane at 20℃; for 26h; Inert atmosphere; regioselective reaction;	74%

124-38-9

carbon dioxide

10401-11-3

3-hydroxy phenylacetylene

10401-10-2

3-(3-hydroxyphenyl)-2-propynoic acid

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 16h; Sealed tube;	98%
With caesium carbonate In N,N-dimethyl-formamide at 24℃; for 20h;	92%
With caesium carbonate; silver(I) iodide In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 16.25h; Inert atmosphere; Schlenk technique;	90%

636-98-6

p-nitrobenzene iodide

10401-11-3

3-hydroxy phenylacetylene

3-{1-(4-nitrophenyl)-[1,2,3]triazol-4-yl}phenol

Conditions

Conditions	Yield
With sodium azide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium L-ascorbate; copper(l) iodide In dimethyl sulfoxide at 20℃; for 1h;	97%

10401-11-3

3-hydroxy phenylacetylene

610-97-9

o-iodo-methyl-benzoic acid

methyl 2-[(2-hydroxyphenyl)ethynyl]benzoate

Conditions

Conditions	Yield
Stage #1: 3-hydroxy phenylacetylene; o-iodo-methyl-benzoic acid With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.25h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 1h; Sonogashira Cross-Coupling; Inert atmosphere;	97%

10401-11-3

3-hydroxy phenylacetylene

91-56-5

indole-2,3-dione

(S)-3-hydroxy-3-((3-hydroxyphenyl)ethynyl)indolin-2-one

Conditions

Conditions	Yield
With C36H29N2O2P; cobalt(II) diacetate tetrahydrate In ethanol at 30℃; for 20h; Schlenk technique; Glovebox; Inert atmosphere; enantioselective reaction;	97%

625-86-5

2,5-dimethylfuran

10401-11-3

3-hydroxy phenylacetylene

C14H14O2

Conditions

Conditions	Yield
With 1,3‐bis[2,6‐bis(propan‐2‐yl)phenyl]‐2‐[(phenylformonitrile)aurio]‐2,3‐dihydro‐1H‐imidazol‐2‐yl hexafluorostibane In dichloromethane at 23℃; Inert atmosphere;	96%

10401-11-3

3-hydroxy phenylacetylene

146846-56-2

3-(4-(3-hydroxyphenyl)buta-1,3-diynyl)phenol

Conditions

Conditions	Yield
With oxygen; potassium carbonate In dimethyl sulfoxide at 50℃; for 8h;	95%

3-Ethynylphenol Chemical Properties

3-Ethynylphenol Safety Profile

3-Ethynylphenol Specification