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
• Article Data: 10

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

Description

3-Hydroxyphenylacetylene is a clear yellow liquid that possesses unique chemical properties, making it a versatile compound with various applications across different industries.

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

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

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 
• 918483-34-8 1-(cyclopropylmethoxy)-3-ethynylbenzene 
• 128133-59-5 1-ethynyl-3-(phenylmethoxy)benzene 
• 931430-26-1 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol 
• 10401-12-4 3-acetoxyphenylacetylene 
• 1268853-78-6 (R)-N-isopropyl-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxamide 
• 1268853-79-7 ethyl (R)-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxylate 
• 1318024-55-3 3-[1-((4-chlorophenyl)imino)ethyl]phenol 
• 1318024-44-0 3-[1-(phenylimino)ethyl]phenol 
• 1318024-70-2 3-(1-(mesitylimino)ethyl)phenol 

Relevant articles and documents

Acid-catalysed Aromatisation of Benzene cis-1,2-dihydrodiols: a Carbocation Transition State poorly stabilised by Resonance

Acid-catalysed dehydration of 3-substituted benzene cis-1,2-dihydrodiols exhibits a Hammett plot with ρ=-8.2, consistent with reaction via a benzenonium ion-like intermediate; however, correlation of +M resonance substituents such as Me and MeO by ?p rather than ?+ constants indicates a marked imbalance between resonance and inductive stabilisation of the transition state.

BTK Inhibitors and uses thereof

The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.

HETEROCYCLIC DERIVATIVES MODULATING ACTIVITY OF CERTAIN PROTEIN KINASES

The present invention relates to novel heterocyclic derivatives having general formula (I) and their therapeutic use for diseases such as cancer, inflammation, pain, autoimmune diseases or neurodegenerative diseases like Alzheimer's or Parkinson's disease that can be treated by modulation of certain protein kinases. Compounds of formula (I) can be used for treatment of patients who do not respond to kinase inhibition therapy that comprises currently available medications.