Phenylacetylene supplier | CasNO.536-74-3

Name
Phenylacetylene
EINECS 208-645-1
CAS No. 536-74-3
Article Data489
CAS DataBase
Density 0.951 g/cm³
Solubility insoluble in water
Melting Point - 44.8 °C
Formula C₈H₆
Boiling Point 142.4 °C at 760 mmHg
Molecular Weight 102.136
Flash Point 31.111 °C
Transport Information UN 3295 3/PG 3
Appearance colourless liquid
Safety 16-26-36/37/39-45
Risk Codes 10-36/37/38-40-65
Molecular Structure
Hazard Symbols Xn
Synonyms 1-Phenylethyne;Ethyne, phenyl-;NSC 4957;Ethynylbenzene;Phenylethyne;
PSA 0.00000
LogP 1.66790

Synthetic route

: 103-64-0
bromostyrene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With potassium tert-butylate	100%
With sodium hexamethyldisilazane In 1,2-dimethoxyethane at 20℃; for 1h;	92%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 50℃; for 0.166667h; Schlenk technique; Inert atmosphere;	86%

: 637-44-5
phenylpropyolic acid

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0)	100%
With [Au(DPB)SbF6]2(cod) In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;	24%
With water at 120℃; im geschlossenen Rohr;

: 2,2-diphenylethenyl(phenyl)iodonium tetrafluoroborate

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With triphenyl-arsane; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.5h; Rearrangement; reductive elimination;	100%

: 591-51-5
phenyllithium

: diphenyl(phenylethynyl)selenium trifluoromethanesulfonate

A: 886-66-8
1,4-diphenyl-1,3-butadiyne

B: 1132-39-4
diphenylselenide

C: 10271-65-5
2-(phenylethynyl)-1,1'-biphenyl

D: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 3h; Substitution; Further byproducts given;	A 2% B 100% C 4% D 60%

...Expand

: (C5H5)2V(C2C6H5)2

A: 12083-48-6
bis(cyclopentadienyl)vanadium dichloride

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With HCl In diethyl ether -28°C;	A 99% B 61%
With HCl In diethyl ether -50°C;	A 99% B 68%
With HCl In diethyl ether 20°C;	A 94% B 50%

: 102921-26-6, 93-52-7
(1,2-dibromoethyl)benzene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 80℃; for 1h;	98%
With sodium methylate In tetrahydrofuran Solvent; Reagent/catalyst; Reflux;	97.5%
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 25℃; for 0.5h;	95%

: 588-73-8
(Z)-β-bromostyrene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 60℃; for 1h;	98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 1h; microwave irradiation;	88%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0166667h; microwave irradiation;
With potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 12h; Solvent;

: bis(phenylethynyl) ytterbium tetrahydrofuranate

: 7732-18-5
water

A: ytterbium hydroxide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran hydrolysis;	A 97.5% B 86.9%

...Expand

: 2170-06-1
1-Phenyl-2-(trimethylsilyl)acetylene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;	97%
With potassium hydroxide	95%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h;	93%

: 100-52-7
benzaldehyde

: 145397-30-4
C8H21N4PSi

A: α-trimethylsilyloxybenzyl-N,N,N',N'-tetramethylphosphondiamide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In pentane at 20℃; for 0.166667h;	A 97% B n/a

...Expand

: tris(phenylethynyl)ytterbium tetrahydrofuranate

: 7732-18-5
water

A: ytterbium hydroxide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: benzene; hydrolysis;	A 95.5% B 20%

...Expand

: tris(phenylacetylene)thulium(III) tetrahydrofuranate

: 7732-18-5
water

A: thulium(III) hydroxide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: benzene; hydrolysis;	A 95.5% B 20%

...Expand

: tris(phenylethynyl)holmium(III) tetrahydrofuranate

: 7732-18-5
water

A: holmium(III) hydroxide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: benzene; hydrolysis;	A 95.5% B 20%

...Expand

: 42599-24-6
E-styryl iodide

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With palladium bromide; P(p-CH3OC6H4)3; silver benzoate In 1,4-dioxane at 125℃; for 16h; Inert atmosphere;	95%

: 931-48-6
2-cyclohexylacetylene

: 40032-57-3
N-(3-phenylprop-2-ynyl)benzenemethanamine

A: N-benzyl-3-cyclohexylprop-2-yn-1-amine

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A 95% B n/a

...Expand

: 127072-73-5
1-(phenylethynyltelluriomethyl)silatrane

: 108-98-5
thiophenol

A: 536-74-3
phenylacetylene

B: 1-(phenylthiotelluriomethyl)silatrane

Conditions

Conditions	Yield
In chloroform for 2h; Irradiation;	A n/a B 94%

...Expand

: 591-50-4
iodobenzene

: 994-89-8
tributylethynyltin

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) Stille reaction;	93%
With copper(l) iodide; triphenyl-arsane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 60℃; for 6h;	58 % Chromat.

: 994-89-8
tributylethynyltin

: diphenyliodonium tetrafluoroborate

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With palladium on activated charcoal In water; acetonitrile for 4h; Ambient temperature;	93%

: 1074-11-9
1-(1,2-dichloroethyl)benzene

A: 618-34-8
1-chlorostyrene

B: 622-25-3
1-(2-chlorovinyl)benzene

C: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With potassium hydroxide; cetyltrimethylammonim bromide In toluene at 80℃; Product distribution; Further Variations:; Catalysts;	A 93% B 0.9% C 0.5%

...Expand

: 137436-78-3
(2,2'-bipyridine)(phenylacetylene)copper(I) hexafluoroantimonate

A: 137436-83-0
(phenylacetylene)bis{(2,2'-bipyridine)copper(I)} hexafluoroantimonate

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In acetone dissolving of (Cu(bpy)(HCCPh))SbF6 in acetone; addn. of hexane, pptn., filtration, two addnl. repptn., washing (hexane, 3 times), drying (vac., overnight); elem. anal.;	A 93% B n/a

: 6286-30-2, 31357-31-0, 54624-38-3, 91649-50-2, 99145-28-5, 113569-00-9, 113626-42-9
erythro-2,3-dibromo-3-phenylpropanoic acid

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 115℃; for 12h;	93%

: {C6H5C2B9H11}(1-)

A: 292638-84-7
styrene

B: 100-41-4
ethylbenzene

C: 100-52-7
benzaldehyde

D: 536-74-3
phenylacetylene

E: 108-88-3
toluene

Conditions

Conditions	Yield
With chromic sulfuric acid oxidative decompn. by chromic sulfuric acid, at 100°C; only by steam distn. isolated products;	A 0.2% B 0.3% C 92.5% D 1.5% E 2.1%

...Expand

: 698-88-4
(2,2-dichlorovinyl)benzene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Dehalogenation;	92%
	92%
With hydrogenchloride; n-butyllithium 1.) THF, from -78 deg C to 0 deg C, 2.) THF; Yield given. Multistep reaction;

: 246023-21-2
α-(dichloromethyl)benzenemethanol 4-methylbenzenesulfonate

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Elimination;	92%

: 16029-98-4
trimethylsilyl iodide

: hexa(tetrahydrofuranate)dipraseodymium tris(triphenylethynylcuprate)

A: 13146-23-1
copper(I) phenylacetylide

B: 1373445-38-5
(THF)3-phenylethynylpraseodymium(III) iodide

C: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With Me3SiCCPh In tetrahydrofuran using Schlenk techniques; Me3SiI added to soln. of Pr complex (molar ratio 6:1) in THF; kept at room temp. for 10 d; PhC2Cu ppt. sepd.; solvent distd. off from filtrate, hexane added, residue washed with hexane, dried in vac. (PhC2PrI2(THF)3); elem. anal.;	A 91% B 92% C 5%

...Expand

: 109-99-9
tetrahydrofuran

: bis(tetrahydrofuran)ytterbium tris(phenylethynyl)cuprate

: 76-83-5
trityl chloride

A: 13146-23-1
copper(I) phenylacetylenide

B: 2216-49-1
triphenylmethyl radical

C: 18909-18-7
1-diphenylmethylene-4-trityl-2,5-cyclohexadiene

D: YbCl2*4C4H8O

E: C8H5(1-)*Cl(1-)*Yb(2+)*C4H8O*C19H15Cl

F: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
at 20℃; for 72h; Schlenk technique;	A 91% B n/a C 62.5% D 18.5% E 70.5% F 7 %Chromat.

...Expand

: 932-87-6
1-Bromo-2-phenylacetylene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With water; caesium carbonate; dimethyl sulfoxide at 115℃; for 12h; Mechanism; Reagent/catalyst;	90%
With ethyleneimine In diethyl ether 1. -30 deg C; 2. 20 deg C, 1 h;	67%

: 100-52-7
benzaldehyde

: 714276-40-1
2-(diazo-trimethylsilanyl-methyl)-1,3-diisopropyl-[1,3,2]diazaphospholidine

A: α-trimethylsilyloxybenzyl-N,N'-ethylene-N,N'-diisopropylphosphonamide

B: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	A 90% B n/a

...Expand

: 7436-90-0
2,2-dibromostyrene

: 536-74-3
phenylacetylene

Conditions

Conditions	Yield
With caesium carbonate; dimethyl sulfoxide at 115℃; for 12h;	89%
With n-butyllithium In hexane at -78 - 20℃; for 5h;
With hydrogenchloride; caesium carbonate In dimethyl sulfoxide at 20 - 125℃; for 12h; pH=7;
With sodiumsulfide nonahydrate In dimethyl sulfoxide at 40℃; for 14h;
beim Ueberleiten ueber Kupfer unter vermindertem Druck;

: 108-98-5
thiophenol

: 536-74-3
phenylacetylene

: 7214-53-1
(E)-[2-(phenylsulfanyl)vinyl]benzene

Conditions

Conditions	Yield
In i-AmOH; ethylene glycol at 40℃; for 6h; stereoselective reaction;	100%
With RhCl(PPh3)3 In ethanol at 40℃; for 20h;	97%
β‐cyclodextrin In water; acetone at 20℃; for 4h; anti-Markonikov addition reaction;	96%

: 50-00-0
formaldehyd

: 109-89-7
diethylamine

: 536-74-3
phenylacetylene

: 22396-72-1
diethyl-(3-phenyl-prop-2-ynyl)-amine

Conditions

Conditions	Yield
With copper dichloride at 80℃; under 150.015 Torr; for 3h; Mannich reaction;	100%
With silver nitrate at 105℃; for 0.133333h; microwave irradiation;	99%
copper(l) iodide In water; dimethyl sulfoxide at 30℃; for 10h;	98%

...Expand

: 536-74-3
phenylacetylene

: 622-79-7
benzyl azide

: 108717-96-0
1-benzyl-4-phenyl-1H-[1,2,3]triazole

Conditions

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In methanol; water at 24℃; for 0.2h;	100%
tris[1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]methanol*CuCl In water at 20℃; for 24h; Product distribution / selectivity;	100%
With C48H40ClCu2N8(1+)*Cl(1-) In acetonitrile at 20℃; for 5h; Schlenk technique;	100%

: 536-74-3
phenylacetylene

: 67-64-1
acetone

: 1719-19-3
2-Methyl-4-phenyl-3-butyn-2-ol

Conditions

Conditions	Yield
phosphazene base-P4-tert-butyl In hexane; dimethyl sulfoxide at 120℃; for 24h;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: acetone In tetrahydrofuran; hexane at -78 - 20℃;	100%
With Nd(3+)8Na(1+)10C4H9O(1-)*HO(1-) In dimethyl sulfoxide at 30℃; for 24h; Catalytic behavior; Concentration; Solvent; Reagent/catalyst; Inert atmosphere;	100%

: 536-74-3
phenylacetylene

: 74-88-4
methyl iodide

: 673-32-5
1-Phenylprop-1-yne

Conditions

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -20 - 20℃;	100%
Stage #1: phenylacetylene With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: methyl iodide	89%
With potassium hydroxide In dimethyl sulfoxide at 18℃; for 1.5h;	80%

: 536-74-3
phenylacetylene

: 292638-84-7
styrene

Conditions

Conditions	Yield
With hydrogen; (Ph2PCH2PPh2CHC(O)Ph)>I In dichloromethane at 65℃; for 18h; Pressure (range begins): 120 ;	100%
With samarium diiodide; N,N,N',N'',N''-pentamethylethylene triamine; water In tetrahydrofuran at 20℃; for 0.00277778h;	100%
With formic acid; nickel dibromide; zinc In tetrahydrofuran at 80℃; for 16h; Sealed tube;	100%

: 536-74-3
phenylacetylene

: 100-41-4
ethylbenzene

Conditions

Conditions	Yield
With hydrogen; palladium on C60 In methanol under 760 Torr; for 0.216667h; Ambient temperature; other substrates: cyclohexene, hex-1-ene, other catalysts: palladium on activated charcoal, C60, other reaction time;	100%
silver tetrafluoroborate; (Ph2PCH2PPh2CHC(O)Ph)>I In dichloromethane at 65℃; for 18h; Pressure (range begins): 120 ;	100%
With hydrogen; N,N′-bis(salicylidene)-ethylenediamino‑palladium In methanol for 0.85h;	100%

: 536-74-3
phenylacetylene

: 886-66-8
1,4-diphenyl-1,3-butadiyne

Conditions

Conditions	Yield
With sodium acetate; copper dichloride In methanol; carbon dioxide at 40℃; under 105008 Torr; for 3h; Glaser coupling;	100%
With triethylamine; copper(l) iodide; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 at 90℃; for 4h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; air; palladium diacetate; copper(l) iodide In acetonitrile at 20℃; for 2h;	100%

: 536-74-3
phenylacetylene

: 98-81-7
1-bromovinylbenzene

Conditions

Conditions	Yield
With hydrogen bromide In solid at -145.1 - -123.1℃; Product distribution; HBr (and HCl) - phenylacetylene complexes at lower temperatures; cis-stereospecific with DBr;	100%
With hydrogen bromide In solid at -145.1 - -123.1℃;	100%
With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II); camphor-10-sulfonic acid; benzyltriethylammonium bromide; triphenylphosphine In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;	95%

: 536-74-3
phenylacetylene

: 98-86-2
acetophenone

Conditions

Conditions	Yield
With mercuric triflate; water; tetramethylurea In dichloromethane; acetonitrile at 20℃; for 12h;	100%
With Au nanoparticles covalently bonded to HS/SO3H functionalized periodic mesoporous organosilica (Et) at 70℃; for 1.5h; neat (no solvent);	100%
With water at 59.84℃; for 24h; Ionic liquid;	100%

: 108-94-1
cyclohexanone

: 536-74-3
phenylacetylene

: 20109-09-5
1-(phenylethynyl)-1-cyclohexanol

Conditions

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: cyclohexanone In tetrahydrofuran; hexane at -78℃; for 2h; Further stages.;	100%
With In(hexamethyldisilazide)2F In 1,2-dimethoxyethane at 40℃; for 48h;	100%
With n-butyllithium; cerium(III) chloride In tetrahydrofuran at -78℃; stereoselective reaction;	97%

: 100-52-7
benzaldehyde

: 536-74-3
phenylacetylene

: 1817-49-8
1,3-diphenyl-1-propyn-3-ol

Conditions

Conditions	Yield
With diethylzinc; Ti(2,3-dihydro-2,2-dimethyl-7-benzofuran-O)4 In hexane; toluene at 25℃; for 24h; Product distribution; Further Variations:; Temperatures;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	100%
With zinc(II) iodide; triethylamine In toluene at -30℃; for 60h;	99%

: 75-07-0
acetaldehyde

: 536-74-3
phenylacetylene

: 73922-81-3, 81555-86-4, 104597-03-7, 5876-76-6
4-phenyl-but-3-yn-2-ol

Conditions

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;	100%
Stage #1: phenylacetylene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: acetaldehyde In diethyl ether; hexane at -78 - 20℃; for 1h; Inert atmosphere; Schlenk technique;	98%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Cooling with ice; Stage #2: acetaldehyde In tetrahydrofuran; hexane	87%

: 141-78-6
ethyl acetate

: 536-74-3
phenylacetylene

: 1817-57-8
4-phenyl-3-butyne-2-one

Conditions

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: ethyl acetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl acetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane at -78 - 20℃;	96%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Stage #2: ethyl acetate With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 20℃; for 1h;	89%

: 1122-91-4
4-bromo-benzaldehyde

: 536-74-3
phenylacetylene

: 57341-98-7
4-(phenylethynyl)benzaldehyde

Conditions

Conditions	Yield
Stage #1: 4-bromo-benzaldehyde With 5% Pd/C; triethylamine; triphenylphosphine for 0.0833333h; Sonogashira Cross-Coupling; Sealed tube; Sonication; Stage #2: phenylacetylene for 3h; Sealed tube;	100%
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Sonogashira Cross-Coupling;	99%
With C19H16ClNPdS; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; Solvent; Reagent/catalyst; Sonogashira Cross-Coupling;	99%

: 106-95-6
allyl bromide

: 536-74-3
phenylacetylene

: 4289-20-7
1-phenyl-4-penten-1-yne

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; further reagents, further solvent, further temperature;	100%
With copper(l) iodide; potassium carbonate; sodium sulfite In dimethyl sulfoxide at 30℃; for 4h;	100%
With copper(l) iodide; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	91%

: 14371-10-9
(E)-3-phenylpropenal

: 536-74-3
phenylacetylene

: 63124-66-3, 128812-14-6
(1E)-1,5-diphenylpent-1-en-4-yn-3-ol

Conditions

Conditions	Yield
Stage #1: phenylacetylene With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran at 23 - 25℃; for 3h; Further stages.;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	97%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; pentane at -78℃; Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; pentane at -78℃;	89%

: 50-00-0
formaldehyd

: 536-74-3
phenylacetylene

: 1504-58-1
3-Phenyl-2-propyn-1-ol

Conditions

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at 20℃; for 24h; Inert atmosphere;	97%
With n-butyllithium In tetrahydrofuran at 20℃; for 3h;	92%

: 75-77-4
chloro-trimethyl-silane

: 536-74-3
phenylacetylene

: 2170-06-1
1-Phenyl-2-(trimethylsilyl)acetylene

Conditions

Conditions	Yield
With lithium iodide at 80℃; for 24h; Reagent/catalyst; Solvent;	100%
Stage #1: phenylacetylene With ethylmagnesium bromide In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%
With diethylzinc In hexane; acetonitrile at 80℃; for 20h; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere;	99%

: 123-73-9
trans-Crotonaldehyde

: 536-74-3
phenylacetylene

: 63124-67-4
(E)-1-phenylhex-4-en-1-yn-3-ol

Conditions

Conditions	Yield
Stage #1: phenylacetylene With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h; Stage #2: trans-Crotonaldehyde In tetrahydrofuran at 23 - 25℃; for 3h; Further stages.;	100%
Stage #1: phenylacetylene With lithium In tetrahydrofuran at 15 - 20℃; sonication; Stage #2: trans-Crotonaldehyde In tetrahydrofuran at 15 - 20℃; for 0.5h;	53%
(i) EtMgBr, Et2O, (ii) /BRN= 1209254/; Multistep reaction;

: 79-24-3
Nitroethane

: 536-74-3
phenylacetylene

: 1008-75-9
3-methyl-5-phenylisoxazole

Conditions

Conditions	Yield
With dmap; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In acetonitrile at 80℃; for 0.05h; microwave irradiation;	100%
With dmap; di-tert-butyl dicarbonate In acetonitrile at 20℃; for 3h;	37%
With sodium methylate; acetyl chloride In N,N-dimethyl acetamide for 16h; Ambient temperature;	36%
(i) NaOMe, AcNMe2, MeOH, (ii) /BRN= 605461/, AcCl; Multistep reaction;

: 998-30-1
Triethoxysilane

: 536-74-3
phenylacetylene

: 65119-09-7
(E)-styryl(triethoxy)silane

Conditions

Conditions	Yield
With C34H39N3O2Rh(1+)*BF4(1-) In dichloromethane-d2 at 60℃; for 4h; Inert atmosphere; Glovebox; stereoselective reaction;	100%
With 2-dicyclohexyl-phosphino-2',4',6'-triisopropylbiphenyl; platinum(IV) oxide In tetrahydrofuran at 60℃; for 1h;	72%
With C24H23ClCrIrNO3 In 1,1,2,2-tetrachloroethane at 100℃; for 24h; Catalytic behavior; Inert atmosphere; Schlenk technique; regioselective reaction;	63%

: 588-72-7
[(E)-2-bromoethenyl]benzene

: 536-74-3
phenylacetylene

: 13343-79-8
(E)-1,4-Diphenylbut-1-en-3-yne

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 135℃; for 24h; Inert atmosphere;	100%
With copper(l) iodide; iodophenylbis(triphenylphosphine)palladium; triethylamine In chloroform at 20℃; for 1h;	94%
With C38H36Cl2Fe2N2Pd2; caesium carbonate; copper(I) bromide at 40℃; for 24h; Sonogashira coupling; Inert atmosphere; diastereospecific reaction;	91%

: 624-38-4
para-diiodobenzene

: 536-74-3
phenylacetylene

: 1849-27-0
1,4-bis(2-phenylethynyl)benzene

Conditions

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 89℃; for 0.05h;	100%
With bis-triphenylphosphine-palladium(II) chloride; SEC-BUTYLAMINE In water at 25℃; for 1.5h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 20℃; for 12h; Sonogashira Cross-Coupling; Inert atmosphere;	99%

: 536-74-3
phenylacetylene

: 450-95-3
2-fluoroacetophenone

Conditions

Conditions	Yield
With methanol; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor at 70℃; for 17h;	100%
With 8-methylquinoline 1-oxide; [(1,1′-biphenyl-2-yl)di-tert-butylphosphine]gold(I) bis(trifluoromethanesulfonyl)imide; pyridine hydrogenfluoride In dichloromethane at 20℃; under 760.051 Torr; for 24h; Reagent/catalyst;	90%
With fluoro alcohol
Multi-step reaction with 2 steps 1: silver carbonate; trimethylsilylazide / water; dimethyl sulfoxide 2: Selectfluor; sodium hydrogencarbonate; water / acetonitrile View Scheme

: 536-74-3
phenylacetylene

: 13343-79-8
(E)-1,4-Diphenylbut-1-en-3-yne

Conditions

Conditions	Yield
With C40H36Cl2N2O4Ru2; sodium carbonate In tetrahydrofuran; isopropyl alcohol at 80℃; for 15h; Inert atmosphere;	100%
With (N,N’-bis-(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)Pd(cinnamyl)Cl; potassium hydroxide In n-heptane; water Catalytic behavior; Reagent/catalyst; Solvent; Reflux; regioselective reaction;	100%
With [{Pd(μ-OH)Cl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)}2]; potassium hydroxide In ethanol at 22℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; stereoselective reaction;	99%

: 536-74-3
phenylacetylene

: 71955-87-8, 72903-51-6, 86195-27-9
trichloro[(Z)-2-chloro-2-phenylethenyl]-λ4-tellane

Conditions

Conditions	Yield
With tellurium tetrachloride In tetrachloromethane; benzene Reflux; stereoselective reaction;	100%
With tellurium tetrachloride In tetrachloromethane; benzene for 10h; Reflux; Inert atmosphere; diastereoselective reaction;	100%
With tellurium tetrachloride In tetrachloromethane
With tellurium tetrachloride In benzene at 20℃;

: 536-74-3
phenylacetylene

: 4440-01-1
lithium phenylacetylide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	100%
With n-butyllithium In hexane at -78 - 20℃;	98%
With bromobenzene; lithium

Phenylacetylene Chemical Properties

Ethynylbenzene (CAS NO.536-74-3) is also named as 1-Phenylethyne ; Acetylene, phenyl- ; acetylene,phenyl- ; Benzene, ethynyl- ; Benzene,ethynyl- ; Ethinylbenzene ; Ethyne, phenyl- ; ethyne,phenyl- ; Phenylacethylene ; Styrene trimer,and so on. Phenylacetylene(CAS NO.536-74-3) is colourless liquid.
CAS: 536-74-3
Molecular Formula: C₈H₆
Molecular Weight: 102.13
Molecular structure:
EINECS: 208-645-1
Melting point: -44.8 °C
Boiling point: 142-144 °C(lit.)
Density: 0.93 g/mL at 25 °C(lit.)
Vapor pressure: 17.6 mm Hg ( 37.7 °C)
Refractive index: n20/D 1.549(lit.)
Flash point: 88 °F
Storage temp.: 2-8°C
Water Solubility: Insoluble
Sensitive: Light Sensitive
BRN: 605461

Phenylacetylene Uses

Ethynylbenzene (CAS NO.536-74-3) is mainly used as pharmaceutical intermediates.

Phenylacetylene Toxicity Data With Reference

ivn-mus LD₅₀:100 mg/kg

CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04866 .

Phenylacetylene Consensus Reports

Reported in EPA TSCA Inventory.

Phenylacetylene Safety Profile

Poison by intravenous route. Explosive reaction with perchloric acid above −78°C. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xn Harmful
Risk Statements: 10-36/37/38-40-65 (10: Flammable 36/37/38: Irritating to eyes, respiratory system and skin 40: Limited evidence of a carcinogenic effect 65: Harmful: May cause lung damage if swallowed)
Safety Statements: 16-26-36/37/39-45 (16: Keep away from sources of ignition - No smoking 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 36/37/39: Wear suitable protective clothing, gloves and eye/face protection 45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible))
RIDADR: UN 3295 3/PG 3
WGK Germany: 1
F: 8-19
HazardClass: 3
PackingGroup: III

Product Name

Phenylacetylene

Synthetic route

Phenylacetylene Chemical Properties

Phenylacetylene Uses

Phenylacetylene Toxicity Data With Reference

Phenylacetylene Consensus Reports

Phenylacetylene Safety Profile

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