10401-11-3

Basic information

• Product Name: 3-Hydroxyphenylacetylene
• Synonyms: 3-ETHYNYLPHENOL;3-HYDROXYPHENYLACETYLENE;4-ETHYNYL-PHENOL;TIMTEC-BB SBB005886;3-HYDROXYPHENYLACETYLENE (3-Ethynylphenol);Phenol, 3-ethynyl- (9CI);M-HYDROXYPHENYLACETYLENE;3-HYDROXYPHENYLACETYLENE, 95+%
• CAS NO: 10401-11-3
• Molecular Formula: C8H6O
• Molecular Weight: 118.13
• Mol File: 10401-11-3.mol

Chemical Properties

• Melting Point: 64-66 °C
• Boiling Point: 75°C 3mm
• Flash Point: 218 °F
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0424mmHg at 25°C
• Refractive Index: n20/D 1.5840(lit.)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Miscible with dimethylformamide.
• PKA: 9.30±0.10(Predicted)
• BRN: 2076613
• CAS DataBase Reference: 3-Hydroxyphenylacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyphenylacetylene(10401-11-3)
• EPA Substance Registry System: 3-Hydroxyphenylacetylene(10401-11-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41-52/53
• Safety Statements: 26-37/39
• RIDADR: 2810
• WGK Germany: 2
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 10401-11-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical and Analytical Applications:
3-Hydroxyphenylacetylene is used as a fluorogenic and chromogenic probe for bacterial enzymes. Its ability to change color or fluorescence in response to the presence of specific enzymes makes it a valuable tool in the detection and analysis of bacterial activity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Hydroxyphenylacetylene may be utilized for the development of new drugs or as a component in drug formulations due to its unique chemical properties and potential interactions with biological systems.
Used in Research and Development:
3-Hydroxyphenylacetylene's properties also make it a promising candidate for research and development in various scientific fields, including biochemistry, microbiology, and materials science, where its reactivity and detection capabilities can be further explored and optimized.

InChI:InChI=1/C8H6O/c1-2-7-4-3-5-8(9)6-7/h1,3-6,9H

Synthetic route

3-(2-triisopropylsilylethynyl)phenol → 3-hydroxy phenylacetylene (10401-11-3)

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

3-[2-(trimethylsilylethynyl)]phenol (388061-72-1) → 3-hydroxy phenylacetylene (10401-11-3)

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 → 3-hydroxy phenylacetylene (10401-11-3)

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

3-(3-hydroxy-3-methylbut-1-ynyl)phenol → 3-hydroxy phenylacetylene (10401-11-3)

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

(1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol (138769-95-6) → 3-hydroxy phenylacetylene (10401-11-3)

Conditions	Yield
With potassium carbonate In methanol for 12h;

(1R,2S)-3-Ethynyl-cyclohexa-3,5-diene-1,2-diol → 2-ethynyl-phenol (5101-44-0) + 3-hydroxy phenylacetylene (10401-11-3)

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

3-Bromophenol (591-20-8) → 3-hydroxy phenylacetylene (10401-11-3)

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

meta-hydroxybenzaldehyde (100-83-4) → 3-hydroxy phenylacetylene (10401-11-3)

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 → 3-hydroxy phenylacetylene (10401-11-3)

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

3-hydroxy phenylacetylene (10401-11-3) → 3-Hydroxyacetophenone (121-71-1)

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%

2,2‘,4,4’,5,5‘,6,6‘-hexa-O-acetyl-3,3‘-diazido-3,3‘-dideoxy-1,1‘-sulfanediyl-di-β-D-galactopyranoside (1193784-38-1) + 3-hydroxy phenylacetylene (10401-11-3) → bis-{2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-β-D-galactopyranosyl}sulfane (1421638-22-3)

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

5-azido-2-hydroxy-N-(3-(trifluoromethyl)phenyl)benzamide (1239028-00-2) + 3-hydroxy phenylacetylene (10401-11-3) → 2-hydroxy-5-[4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl]-N-(3-trifluoromethylphenyl)benzamide (1239028-13-7)

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

diethyl 2,2-di(prop-2-yn-1-yl)malonate (2689-88-5) + 3-hydroxy phenylacetylene (10401-11-3) → diethyl 5-(3-hydroxyphenyl)-1H-indene-2,2(3H)-dicarboxylate (1214275-19-0)

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

3-hydroxy phenylacetylene (10401-11-3) → 3-hydroxystyrene (620-18-8)

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;

3-hydroxy phenylacetylene (10401-11-3) + (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (1617539-93-1) → (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	Yield
With copper diacetate In methanol at 50℃; Temperature; Flow reactor; Sonication;	99%
With copper diacetate In methanol

3-hydroxy phenylacetylene (10401-11-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-tert-butyldimethylsilyloxyphenylacetylene (163233-08-7)

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%

C14H16INO4 (874347-26-9) + 3-hydroxy phenylacetylene (10401-11-3) → C22H21NO5 (874680-87-2)

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

3-hydroxy phenylacetylene (10401-11-3) + isopropenylbenzene (98-83-9) → 3-(3-methyl-3-phenylcyclobut-1-enyl)phenol (1235453-96-9)

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%

carbon dioxide (124-38-9) + 3-hydroxy phenylacetylene (10401-11-3) → 3-(3-hydroxyphenyl)-2-propynoic acid (10401-10-2)

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%

p-nitrobenzene iodide (636-98-6) + 3-hydroxy phenylacetylene (10401-11-3) → 3-{1-(4-nitrophenyl)-[1,2,3]triazol-4-yl}phenol

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%

3-hydroxy phenylacetylene (10401-11-3) + o-iodo-methyl-benzoic acid (610-97-9) → methyl 2-[(2-hydroxyphenyl)ethynyl]benzoate

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%

3-hydroxy phenylacetylene (10401-11-3) + indole-2,3-dione (91-56-5) → (S)-3-hydroxy-3-((3-hydroxyphenyl)ethynyl)indolin-2-one

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

2,5-dimethylfuran (625-86-5) + 3-hydroxy phenylacetylene (10401-11-3) → C14H14O2

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%

3-hydroxy phenylacetylene (10401-11-3) → 3-(4-(3-hydroxyphenyl)buta-1,3-diynyl)phenol (146846-56-2)

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

Upstream product

• 138769-95-6 (1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 10401-10-2 3-(3-hydroxyphenyl)-2-propynoic acid 
• 626-02-8 3-Iodophenol 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 
• 33696-06-9 3-benzoyloxybenzaldehyde 
• 388061-72-1 3-[2-(trimethylsilylethynyl)]phenol 
• 591-20-8 3-Bromophenol 
• 100-83-4 meta-hydroxybenzaldehyde 

Downstream Products

• 165404-92-2 tert-Butyl-[6-(3-ethynyl-phenoxymethyl)-[1,2]dithiin-3-ylmethoxy]-dimethyl-silane 
• 121-71-1 3-Hydroxyacetophenone 
• 163233-08-7 m-(tert-butyldimethylsiloxy)phenylacetylene 
• 868861-83-0 1-(4-methylthiophenyl)-2-(3-hydroxyphenyl)acetylene 
• 868861-92-1 1-(2-methylthiophenyl)-2-(3-hydroxyphenyl)acetylene 
• 868861-88-5 1-(3-methylthiophenyl)-2-(3-hydroxyphenyl)acetylene 
• 1013941-11-1 3-benzyloxy-15-[3-(4-m-hydroxyphenyl-[1,2,3]triazol-1-yl)-propyl]-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one ethylene glycol acetal 
• 847258-23-5 (Z)-3-hydroxystyryl 2-hydroxyphenyl sulfide 
• 933463-49-1 3-(2'-deoxy-β-D-ribofuranosyl)-6-(3-hydroxyphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2(3H)-one 
• 868861-66-9 3-(4-methanesulfonyl-phenylethynyl)-phenol 
• 868861-78-3 3-(2-methanesulfonyl-phenylethynyl)-phenol 
• 868861-72-7 3-(3-methanesulfonyl-phenylethynyl)-phenol 

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