276884-47-0

Basic information

• Product Name: 2-Pyridinemethanol,alpha-ethynyl-(9CI)
• Synonyms: 2-Pyridinemethanol,alpha-ethynyl-(9CI)
• CAS NO: 276884-47-0
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.14728
• Product Categories: PYRIDINE
• Mol File: 276884-47-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 224.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.167±0.06 g/cm3(Predicted)
• PKA: 11.52±0.20(Predicted)
• CAS DataBase Reference: 2-Pyridinemethanol,alpha-ethynyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinemethanol,alpha-ethynyl-(9CI)(276884-47-0)
• EPA Substance Registry System: 2-Pyridinemethanol,alpha-ethynyl-(9CI)(276884-47-0)

Safety Data

• Hazardous Substances Data: 276884-47-0(Hazardous Substances Data)

Synthetic route

pyridine-2-carbaldehyde (1121-60-4) + acetylenemagnesium bromide (4301-14-8) → 3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;	92%
In tetrahydrofuran at -78 - 20℃;	86%
In tetrahydrofuran at 0℃; for 1h;	86%

pyridine-2-carbaldehyde (1121-60-4) + acetylene (74-86-2) → 3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0)

Conditions	Yield
Stage #1: acetylene With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: pyridine-2-carbaldehyde In tetrahydrofuran at 0℃; for 1h; Further stages.;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (2-(1-(tert-butyldimethyl)silanyloxy)prop-2-ynyl)pyridine (912964-92-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 1h;	97%
With 1H-imidazole In dichloromethane at 20℃; for 1h;	97%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + pivaloyl chloride (3282-30-2) → 1-(pyridin-2-yl)prop-2-ynyl pivalate (934399-66-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 3h;	84%
With dmap; triethylamine In dichloromethane for 3h;	1.46 g

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + tris(triphenylphosphine)ruthenium(II) chloride (15529-49-4, 41756-81-4) → [Ru(CHC(PPh3))C(OH)(2-Py)Cl(PPh3)2]Cl (1443430-76-9)

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; for 7h; Inert atmosphere; Schlenk technique;	75%

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → 1-(pyridin-2-yl)prop-2-yn-1-one (72839-09-9)

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;	48%

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + tris(triphenylphosphine)ruthenium(II) chloride (15529-49-4, 41756-81-4) + 4-phenyl-3-butyne-2-one (1817-57-8) → C36H29NOP(1+)*BF4(1-) (1443430-74-7)

Conditions	Yield
With tetrafluoroboric acid; triphenylphosphine In dichloromethane; chloroform at 20℃; for 24h; Inert atmosphere; Schlenk technique;	10%

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + diethyl chlorophosphate (814-49-3) → C12H16NO4P

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + acetyl chloride (75-36-5) → acetic acid 1-(pyridin-2-yl)prop-2-ynyl ester (949101-30-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + acetic anhydride (108-24-7) → acetic acid 1-(pyridin-2-yl)prop-2-ynyl ester (949101-30-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 0.5h;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → 1-(diethylphosphatoxy)indolizine

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; DMAP / CH2Cl2 / 20 °C 2: 64 percent / AgBF4 / toluene / 20 °C View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → acetic acid indolizin-1-yl ester (949101-41-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; DMAP / CH2Cl2 / 20 °C 2: 87 percent / AgBF4 / toluene / 20 °C View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → 1-((tert-butyldimethyl)silanyloxy)indolizine (912964-79-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide / 12 h / 20 °C 2: 57 percent / 2-(dicyclohexylphosphino)biphenyl / platinum(II) chloride / benzene / 16 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 97 percent / imidazole / CH2Cl2 / 1 h / 20 °C 2: 62 percent / AuBr3 / toluene View Scheme
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 1 h / 20 °C 2: gold(I) chloride / toluene / 65 °C / Inert atmosphere View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → indolizin-1-yl pivalate

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 20 °C 2: 79 percent / 2-(dicyclohexylphosphino)biphenyl / platinum(II) chloride / benzene / 8 h / 70 °C View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → 2-[1-(tert-butyldimethyl-silanyloxy)prop-2-ynyl]pyridine-d1 (912964-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 97 percent / imidazole / CH2Cl2 / 1 h / 20 °C 2.1: n-BuLi / hexane / 0.17 h 2.2: 89 percent / methanol-d4 / hexane / 0.33 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: 1H-imidazole / dichloromethane / 1 h / 20 °C 2.1: n-butyllithium / hexane / -78 - 20 °C / Inert atmosphere 2.2: Inert atmosphere View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → C14H19(2)H2NOSi

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 97 percent / imidazole / CH2Cl2 / 1 h / 20 °C 2.1: n-BuLi / hexane / 0.17 h 2.2: 89 percent / methanol-d4 / hexane / 0.33 h / -78 °C 3.1: 73 percent / AuBr3 / toluene / 2.5 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1.1: 1H-imidazole / dichloromethane / 1 h / 20 °C 2.1: n-butyllithium / hexane / -78 - 20 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: gold(I) chloride / toluene / 65 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane / 1 h / 20 °C 2: gold(I) chloride / toluene / 65 °C / Inert atmosphere View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (275386-73-7) → rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(2-pyridinyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Conditions	Yield
CuI; (Ph3P)2PdCl2 In triethylamine; N,N-dimethyl-formamide

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) + methyl 4-(azidomethyl)benzoate (94341-53-4) → C17H16N4O3 (1422453-85-7)

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol 1,3-dipolar cycloaddition;

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → C20H28N2ORuS4(2+)*2ClO4(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: methanol / 16 h / Inert atmosphere; Schlenk technique; Reflux 2.2: Inert atmosphere; Schlenk technique 3.1: 16 h / 20 °C / Inert atmosphere; Schlenk technique View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → C24H25N3ORuS3(2+)*2ClO4(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique 2: tetrahydrofuran / 16 h / 120 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

3-hydroxy-3-(2-pyridinyl)-1-propyne (276884-47-0) → C18H25ClNORuS4(1+)*ClO4(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: methanol / 16 h / Inert atmosphere; Schlenk technique; Reflux 2.2: Inert atmosphere; Schlenk technique View Scheme

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 74-86-2 acetylene 

Downstream Products

• 1422453-85-7 C₁₇H₁₆N₄O₃ 
• 1443430-74-7 C₃₆H₂₉NOP⁽¹⁺⁾*BF₄^(1-) 
• 1443430-76-9 [Ru(CHC(PPh₃))C(OH)(2-Py)Cl(PPh₃)₂]Cl 

Relevant articles and documents

On the validity of au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines

A mechanism of the Au-catalyzed cycloisomerization of propargylpyridines has been investigated. Both DFT computational and experimental results strongly support generation of a Au-carbene via a cyclization/proton transfer sequence over the previously proposed path involving a Au-vinylidene intermediate. For the β-Si-substituted Au-carbene (G = SiR3), a 1,2-Si migration was shown to be kinetically favored over a 1,2-H shift. This study highlights the importance of alternative pathways that could explain reactivities commonly attributed to an alkyne-vinylidene isomerization in Au catalysis.

Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones

A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.

Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones

Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles.