3923-52-2

Basic information

• Product Name: 1,1-DIPHENYL-2-PROPYN-1-OL
• Synonyms: 1,1-diphenyl-2-propyn-1-o;1,1-Diphenylpropargyl alcohol;1,1-diphenylpropargylalcohol;2-Propyn-1-ol, 1,1-diphenyl-;3,3-Diphenyl-3-hydroxy-1-propyne;alpha-ethynyl-alpha-phenyl-benzenemethano;Diphenylethinylcarbinol;TIMTEC-BB SBB008737
• CAS NO: 3923-52-2
• Molecular Formula: C₁₅H₁₂O
• Molecular Weight: 208.26
• EINECS: 213-658-0
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 3923-52-2.mol
• Article Data: 57

Chemical Properties

• Melting Point: 47-49 °C(lit.)
• Boiling Point: 183 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to pale yellow/Powder or Crystals
• Density: 1.0459 (rough estimate)
• Vapor Pressure: 7.37E-05mmHg at 25°C
• Refractive Index: 1.5361 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.58±0.29(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 514549
• CAS DataBase Reference: 1,1-DIPHENYL-2-PROPYN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DIPHENYL-2-PROPYN-1-OL(3923-52-2)
• EPA Substance Registry System: 1,1-DIPHENYL-2-PROPYN-1-OL(3923-52-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DA4796050
• F: 10-23
• Hazardous Substances Data: 3923-52-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

Different sources of media describe the Uses of 3923-52-2 differently. You can refer to the following data:
1. 1,1-Diphenyl-2-propyn-1-ol is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is used in medicine.
2. 1,1-Diphenyl-2-propyn-1-ol may be used in the synthesis of:(PCy3)2Cl2Ru(3-phenylinden-1-ylidene) (Cy=cyclohexyl)thieno-2H-chromenes{Ru(Cp*)(CO)[=C(OMe)CH=CPh2][Ph2PCH2C(=O)tBu]}[PF6] (Cp=cyclopentadienyl)

General Description

1,1-Diphenyl-2-propyn-1-ol is an alkynol.

InChI:InChI=1/C15H12O/c1-2-15(16,13-9-5-3-6-10-13)14-11-7-4-8-12-14/h1,3-12,16H

Synthetic route

benzophenone (119-61-9) + trimethylsilylacetylene (1066-54-2) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone at -10 - 20℃; for 4h; Stage #3: With potassium hydroxide In methanol for 0.5h;	100%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -10 - 0℃; for 3h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; hexane at 0 - 20℃; Inert atmosphere;	96%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane for 4h; Inert atmosphere; Stage #3: With potassium hydroxide In tetrahydrofuran; methanol; hexane at 20℃; for 0.5h;	92%

benzophenone (119-61-9) + acetylene (74-86-2) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With sodium ethanolate In ethanol at 0 - 5℃; for 0.5h; Inert atmosphere; Large scale;	99.2%
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃;	96%
With sodium hydroxide; tetrabutylammomium bromide In toluene for 2h; Ambient temperature;	90%

1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol (73502-43-9) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 2h; Inert atmosphere;	99%
With methanol; potassium carbonate In tetrahydrofuran	80%
With potassium carbonate In methanol for 12h; Yield given;

benzophenone (119-61-9) + acetylenemagnesium bromide (4301-14-8) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
In tetrahydrofuran at 23 - 25℃; for 4h; Inert atmosphere;	94%
In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere;	93%
In tetrahydrofuran Heating;	75%

benzophenone (119-61-9) + sodium acetylide (1066-26-8) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
In tetrahydrofuran; xylene at -10 - 20℃;	88%
With ammonia
In ammonia

benzophenone (119-61-9) + calcium carbide (75-20-7) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With tetrabutyl ammonium fluoride; water In dimethyl sulfoxide at 20℃; for 5h; Inert atmosphere;	53%

benzophenone (119-61-9) + calcium carbide → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Stage #1: calcium carbide With potassium hydroxide for 0.5h; Favorskii Rearrangement; Milling; Sealed tube; Stage #2: benzophenone for 3h; Reagent/catalyst; Favorskii Rearrangement; Milling; Sealed tube;	A 41% B 25%

ethynyldimagnesium dibromide (4301-15-9) + benzophenone (119-61-9) + diethyl ether (60-29-7) → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
at -10℃;

benzophenone (119-61-9) → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With potassium hydroxide; diethyl ether Einleiten von Acetylen;

1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With potassium carbonate at 170℃; unter vermindertem Druck;

benzophenone (119-61-9) + lithium acetylide-ethylenediamine complex (1216963-74-4) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With acetylene In N,N-dimethyl acetamide at 25℃; for 1.75h;

Carbamidsaeure-<1,1-diphenyl-propin-(2)-ylester> (10473-72-0) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With sodium hydroxide In ethanol

benzophenone (119-61-9) + lithium acetylide (70277-75-7) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

benzophenone (119-61-9) + etheric ethynylene-bis magnesium bromide → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
anschliessendes Behandeln mit Aethanol;

benzophenone (119-61-9) + ammonia (7664-41-7) + sodium acetylide (1066-26-8) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

benzophenone (119-61-9) + ammonia (7664-41-7) + potassium acetylide (1111-63-3, 115570-71-3) → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + K2CO3 → benzophenone (119-61-9) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
at 170℃; unter vermindertem Druck;

benzophenone (119-61-9) + 1.1.1-triphenyl-propanone-(2) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 5 min, 2.) reflux, 12 h 2: K2CO3 / methanol / 12 h View Scheme

C33H26OSi (1158955-17-9) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 3h;

benzophenone (119-61-9) + lithium trimethylsilylacetylenide (54655-07-1) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Stage #1: benzophenone; lithium trimethylsilylacetylenide In tetrahydrofuran at -78 - -20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran

benzophenone (119-61-9) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 °C / Inert atmosphere 1.2: 1 h / -70 - 20 °C / Inert atmosphere 2.1: methanol; potassium carbonate / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 10 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; methanol; hexane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / Inert atmosphere 2: potassium hydroxide / methanol / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1.2 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: potassium carbonate / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether / -10 °C / Inert atmosphere 1.2: -10 - 20 °C 2.1: potassium carbonate / methanol; tetrahydrofuran View Scheme

benzoyl chloride (98-88-4) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / Inert atmosphere 2: n-butyllithium / tetrahydrofuran / Inert atmosphere 3: potassium hydroxide / methanol / Inert atmosphere View Scheme

O-(trimethylsilyl)-1,1-diphenyl-2-propyn-1-ol (121284-44-4) → 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 2h;

benzophenone (119-61-9) + calcium carbide (75-20-7) → 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (1483-74-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2)

Conditions	Yield
In neat (no solvent) for 0.666667h; Milling; Sealed tube; Overall yield = 75 percent;

1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 3,3-diphenyl-2-propenal (1210-39-5)

Conditions	Yield
With sulfuric acid In 1,4-dioxane; water for 0.0833333h; Meyer-Schuster rearrangement; Heating;	100%
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate In water; ethyl acetate at 80℃; for 24h; Meyer-Schuster Rearrangement; Sealed tube; Green chemistry; chemoselective reaction;	97%
With ReOCl3(SMe2)(OPPh3) In 1,2-dimethoxyethane at 80℃; for 20h; Meyer-Schuster rearrangement;	96%

Triethylgerman (1188-14-3) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → (E)-Et3GeCH=CHC(OH)Ph2 (226706-64-5)

Conditions	Yield
Rh(acac)(cyclooctene)(PCy3) In benzene-d6 Ar-atmosphere; 48 h at room temp.;	100%

1,1-diphenyl-2-propyn-1-ol (3923-52-2) + para-nitrophenyl bromide (586-78-7) → 3-(4-nitrophenyl)-1,1-diphenylprop-2-yn-1-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 12h; Sonogashira Cross-Coupling; Inert atmosphere; Reflux;	100%

(1,1-dimethylethyl)(3-iodophenoxy)dimethylsilane (133910-12-0) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 3-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1,1-diphenyl-prop-2-yn-1-ol (188957-25-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In dichloromethane for 18h; Heating;	99.7%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → O-(trimethylsilyl)-1,1-diphenyl-2-propyn-1-ol (121284-44-4)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.416667h;	99%

silver(I) hexafluorophosphate (26042-63-7) + [RuCl(1,1'-bis(diphenylphosphino)ferrocene)(HB(C3H3N2)3)] + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → Ru(CCC(C6H5)2)(((C6H5)2PC5H4)2Fe)(HB(C3H3N2)3)(1+)*PF6(1-)=[Ru(CCC(C6H5)2)(((C6H5)2PC5H4)2Fe)(HB(C3H3N2)3)]PF6

Conditions	Yield
In tetrahydrofuran stirring (40 min), evapn.; extg. (CH2Cl2), filtering, concg., pptn. on hexane addn., filtering, washing (hexane), drying (vac.); elem. anal.;	99%

1-Azidoadamantane (24886-73-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → (1-adamantyl-1H-1,2,3-triazol-4-yl)diphenylmethanol (1262782-79-5)

Conditions	Yield
With 2,6-dimethylpyridine In water at 20℃; for 24h; Huisgen 1,3-dipolar cycloaddition; regioselective reaction;	99%

(E)-5-trifluoromethanesulfonyloxymethylidene-1-cyclopenten-1-yl trifluoromethanesulfonate (134267-79-1) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 1,1-diphenyl-3-<(E)-5-(4,4-diphenyl-4-hydroxy-2-butynylidene)-1-cyclopenten-1-yl>-2-propyn-1-ol (135748-59-3)

Conditions	Yield
With diethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide Ambient temperature;	98%
With copper(l) iodide; Pd2Cl(PPh3)2; diethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;	96%

1,1-diphenyl-2-propyn-1-ol (3923-52-2) + β-naphthol (135-19-3) → 3,3-diphenyl-3H-naphtho[2,1-b]pyran (4222-20-2)

Conditions	Yield
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%

C5(CH3)5Ru(Cl)(SC3H7)2RuC5(CH3)5(1+)*OSO2CF3(1-)={C5(CH3)5Ru(Cl)(SC3H7)2RuC5(CH3)5}{OSO2CF3} + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → C5(CH3)5Ru(Cl)(SC3H7)2Ru(C3(C6H5)2)C5(CH3)5(1+)*OSO2CF3(1-)={C5(CH3)5Ru(Cl)(SC3H7)2Ru(C3(C6H5)2)C5(CH3)5}{OSO2CF3}

Conditions	Yield
In tetrahydrofuran addn. of the alkyne in THF to a THF soln. of the Ru-compd., stirring overnight at room temp.; removal of solvent, washing of resultant solid with hexane, chromy. on silica gel with THF, evapn. of solvent;	98%

dichlorotris(triphenylphosphine)osmium(II) (56586-93-7, 40802-32-2) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → OsCl2(CCC(C6H5)2)(P(C6H5)3)2*1.5C7H8

Conditions	Yield
In toluene (N2); stirring (reflux, 3 h); solvent removal (reduced pressure), redissoln. (CH2Cl2), slow addn. of hexane, filtration, washing (hexane), drying (vac.); elem. anal.;	98%

1,1-diphenyl-2-propyn-1-ol (3923-52-2) + methyl iodide (74-88-4) → 1,1-diphenyl-1-methoxybut-2-yne (839-23-6)

Conditions	Yield
Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: methyl iodide With dimethyl sulfoxide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	98%

sodium hexaflorophosphate + chloro(hydridotris(pyrazolyl)borate-N,N',N'')(1,3,5-triaza-7-phosphaadamantane)(triphenylphosphine)ruthenium + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → [(hydridotris(pyrazolyl)borate)Ru(CCCPh2)(1,3,5-triaza-7-phosphaadamantane)(triphenylphosphine)]PF6

Conditions	Yield
In methanol under Ar; Ru complex dissolved in MeOH; Ph2C(OH)CCH (excess) added; stirred for 1 min; NaPF6 added; refluxed for 24 h; filtered; solvent removed in vac.; treated with Et2O and n-hexane; ppt. collected; elem. anal.;	98%

benzyl bromide (100-39-0) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → (1-benzyl-1H-[1,2,3]triazol-4-yl)-diphenyl-methanol

Conditions	Yield
With sodium azide; sodium L-ascorbate In water at 90℃; for 0.5h; Huisgen Cycloaddition; Green chemistry; regioselective reaction;	98%
With sodium azide; [CuI(3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane)3] In water; acetonitrile at 125℃; for 0.25h; Catalytic behavior; Huisgen Cycloaddition; Sealed tube; Microwave irradiation;	81%
With sodium azide; [(tris(3,5-dimethyl-1-pyrazolyl)methane)2Cu](BF4)2 In methanol; water at 125℃; for 0.5h; Catalytic behavior; Microwave irradiation;	78%

1-azidohexane (6926-45-0) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → C21H25N3O (1396338-35-4)

Conditions	Yield
With copper(ll) sulfate pentahydrate In dichloromethane at 20℃; for 24h;	98%

1,1-diphenyl-2-propyn-1-ol (3923-52-2) + thieno[3,2-b]pyridin-3(2H)-one (58327-79-0) → 2-(3,3-diphenylprop-2-en-1-ylidene)thieno[2,3-b]pyridin-3(2H)-one

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile for 1h; Inert atmosphere; Reflux;	98%

4-chloro-1-(cyclobutylidene(phenyl)-methyl)-2-iodobenzene + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 3-(5-chloro-2-(cyclobutylidene(phenyl)methyl)phenyl)-1,1-diphenylprop-2-yn-1-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 80℃; for 8h; Inert atmosphere;	98%

(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) (157072-60-1, 61521-25-3, 166941-05-5, 16971-33-8) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → RuCl(CO)(CHCHC(C6H5)2OH)(P(C6H5)3)2 (229955-66-2, 241465-39-4)

Conditions	Yield
	97%

Ru(2+)*Cl(1-)*2(CH3)2SO*P(C6H11)3*O3SCF3(1-)=[RuCl(OS(CH3)2)2(P(C6H11)3)]O3SCF3 + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → Ru(2+)*Cl(1-)*2(CH3)2SO*CCC(C6H5)2*P(C6H11)3*O3SCF3(1-)=[RuCl(OS(CH3)2)2(P(C6H11)3)(C3(C6H5)2)]O3SCF3

Conditions	Yield
In dichloromethane Ar; stirred at room temp. for 4 h; solvent distilled (vac.);	97%

sodium azide + benzyl bromide (100-39-0) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → (1-benzyl-1H-[1,2,3]triazol-4-yl)-diphenyl-methanol

Conditions	Yield
With 2,6-dimethylpyridine; C21H26N4O4P2S*F6P(1-)*Cu(1+) In water at 20℃; for 7h;	97%

diazoacetic acid ethyl ester (623-73-4) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → ethyl 5-hydroxy-5,5-diphenylpenta-2,3-dienoate

Conditions	Yield
Stage #1: diazoacetic acid ethyl ester; 1,1-diphenyl-2-propyn-1-ol With copper(l) iodide In acetonitrile at 25℃; Stage #2: With triethylamine In dichloromethane at 0℃; for 1h;	97%

1-(azidomethyl)-4-methoxybenzene (70978-37-9) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → (1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)diphenylmethanol

Conditions	Yield
With copper(II) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 5h;	97%

ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate (675125-42-5) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 2,2-diphenyl-5-ethoxycarbonyl-6-phenyl-[2H]-naphtho[1,2-b]pyran

Conditions	Yield
With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Heating;	96%
With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Reflux;	24%

chloridogold(I)[tri[1,3,5-triaza-7-phosphaadamantane]phosphane] (159283-71-3) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → [Au(C2CPh2OH)(1,3,5-triaza-7-phosphaadamantane)] (876069-41-9)

Conditions	Yield
With NaOC2H5 In ethanol to a soln. of NaOC2H5 in ethanol was added Au-complex and alkyne, the mixt. was allowed to stir at room temp. overnight; filtered, ppt. was wasehd with water, ethanol and pentane; elem. anal.;	96%

2-iodobenzonitrile (4387-36-4) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)benzonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 50℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere;	96%

acetic anhydride (108-24-7) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 1,1-diphenyl-2-propyn-1-yl acetate (3848-49-5)

Conditions	Yield
With triethylamine In dichloromethane for 16h; Reflux; Inert atmosphere;	95%
With dmap; triethylamine	72%
With sodium hydroxide; diethyl ether

Phenylselenyl chloride (5707-04-0) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → E-2-chloro-3-phenylseleno-1,1-diphenyl-2-propen-1-ol (77955-91-0)

Conditions	Yield
In dichloromethane Ambient temperature;	95%

Upstream product

• 4301-15-9 ethynyldimagnesium dibromide 
• 119-61-9 benzophenone 
• 60-29-7 diethyl ether 
• 1066-26-8 sodium acetylide 
• 1483-74-5 1,1,4,4-tetraphenyl-2-butyne-1,4-diol 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 10473-72-0 Carbamidsaeure-<1,1-diphenyl-propin-(2)-ylester> 
• 74-86-2 acetylene 
• 70277-75-7 lithium acetylide 
• 4301-14-8 acetylenemagnesium bromide 
• 73502-43-9 1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol 
• 7664-41-7 ammonia 
• 1111-63-3 potassium acetylide 
• 1158955-17-9 C₃₃H₂₆OSi 

Downstream Products

• 134406-41-0 2-(1,1-diphenyl-prop-2-ynyloxy)-tetrahydro-pyran 
• 13294-67-2 acetic acid 2-oxo-1,1-diphenyl-propyl ester 
• 3848-49-5 1,1-diphenyl-2-propyn-1-yl acetate 
• 1674-16-4 1,1,6,6-tetraphenyl-1,2,3,4,5-hexapentaene 
• 110474-97-0 benzoic acid-(1,1-diphenyl-prop-2-ynyl ester) 
• 122315-03-1 1,1-bis-(4-methoxy-phenyl)-4,4-diphenyl-butatriene 
• 94802-88-7 1,1-diphenyl-hexa-2,4-diyne-1,6-diol 
• 1483-74-5 1,1,4,4-tetraphenyl-2-butyne-1,4-diol 
• 101875-27-8 6-hydroxy-6,6-diphenyl-hexa-2,4-diynoic acid 
• 101736-41-8 1,1-diphenyl-hexa-2,4-diyn-1-ol 
• 13667-78-2 fluoren-9-ylidene-diphenyl-allene 
• 103161-63-3 9-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-fluoren-9-ol 
• 15880-45-2 1,4-bis-triphenylbutatrienyl-benzene 
• 124119-99-9 1,1,4-triphenyl-4-p-tolyl-but-2-yne-1,4-diol 

Relevant articles and documents

Syntheses and characterizations of Zn (Ⅱ) Phthalocyanines & Naphthopyrans based polymers for improved nonlinear optical properties

In this paper, four organic polymers of poly [(MMA)x-co-(NPMA)y-co-(CPMA)z] and four zinc phthalocyanine (ZnPc) polymers of poly [(MMA)x-co-(NPMA)y-co-(ZnPc)z] have been successfully synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization, where MMA is methyl methacrylate, NPMA is 3,3-diphenyl-8-methacryloxy-3H-naphtho [2,1-b]pyran, and CPMA is 3,4-dicyanophenyl methacrylate. The components of these polymers have been fully characterized by 1H and 13C NMR, FT-IR, Raman, XPS, UV–Vis, and photoluminescence (PL) spectroscopy. From PL spectra, poly [(MMA)x-co-(NPMA)y-co-(ZnPc)z] polymers display strong fluorescence quenching by the energy transfer (ET) process between NPMA and ZnPc moieties. The third-order nonlinear optical (NLO) properties of poly [(MMA)x-co-(NPMA)y-co-(ZnPc)z] polymers have been investigated by the Z-scan technique, and poly [(MMA)168-co-(NPMA)5.2-co-(ZnPc)1.2] (Q4) showed the best NLO properties owing to the much stronger ET between NP and ZnPc units. Furthermore, it is essential to obtain doped poly (methyl methacrylate) (PMMA) films for practical application. The poly [(MMA)168-co-(NPMA)5.2-co-(ZnPc)1.2]/PMMA film exhibited a higher nonlinear absorption coefficient of 61 × 10?11 m/W and a lower limiting threshold of 0.19 J/cm2. The significantly enhanced NLO properties of poly [(MMA)168-co-(NPMA)5.2-co-(ZnPc)1.2]/PMMA film compared with solution are attributed to the weaker aggregation effect in PMMA film. This research provides a promising molecular design strategy for high performance NLO materials.

Calcium-Catalyzed Intramolecular Hydroamination-Deacylation Reaction of in situ formed β-Amino Allenes

We have developed a simple, One-Pot, three-component reaction of tert-propargyl alcohols, primary amines and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives in good to excellent yields with large substrate diversity. An eco-friendly calcium catalyst catalyzes the reaction to form the key intermediate β-amino allene that undergoes subsequent Thorpe-Ingold effect assisted hydroamination and aromaticity driven deacylation reaction to yield fully substituted five and six-membered azacyclic compounds. (Figure presented.).

Development of Axially Chiral Styrene-Type Carboxylic Acid Ligands via Palladium-Catalyzed Asymmetric C-H Alkynylation

A weakly coordinated carboxylate-directed palladium-catalyzed atroposelective C-H alkynylation method for the development of novel axially chiral styrene-type carboxylic acids is disclosed. This transformation exhibits good yields (up to 85%), excellent enantiocontrol (up to 99% ee), and mild conditions. Notably, the synthetic utility of the resulting alkynyl carboxylic acid derivatives was demonstrated by various derivatizations as well as their potential as chiral ligands in asymmetric C-H activations.