Phenylpropiolic acid supplier

Name
Phenylpropiolic acid
EINECS 211-285-8
CAS No. 637-44-5
Article Data243
CAS DataBase
Density 1.24 g/cm³
Solubility freely soluble
Melting Point 135-137 °C(lit.)
Formula C9H6 O2
Boiling Point 302.6 °C at 760 mmHg
Molecular Weight 146.145
Flash Point 151 °C
Transport Information
Appearance Slightly beige crystalline powder.
Safety 26-36
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms Propiolicacid, phenyl- (6CI,8CI); 3-Phenyl-2-propynoic acid; 3-Phenylpropargylic acid;3-Phenylpropiolic acid; 3-Phenylpropynoic acid; NSC 13669; Phenyl-2-propynoicacid; Phenylacetylenecarboxylic acid; Phenylacetylenemonocarboxylic acid;Phenylpropargylic acid; Phenylpropiolic acid; Phenylpropynoic acid; b-Phenylpropargylic acid
PSA 37.30000
LogP 1.12270

Synthetic route

: 124-38-9
carbon dioxide

: 536-74-3
phenylacetylene

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;	100%
With caesium carbonate In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube;	99%
With caesium carbonate In dimethyl sulfoxide at 50℃; under 750.075 Torr; for 12h; Reagent/catalyst; Time; Schlenk technique;	99.1%

: 1111-72-4
carbon dioxide

: 536-74-3
phenylacetylene

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
Stage #1: carbon dioxide; phenylacetylene With diethoxymethylane; potassium tert-butylate at 40℃; for 2h; Schlenk technique; Stage #2: With hydrogenchloride In water Reagent/catalyst; Schlenk technique;	98%

: 124-38-9
carbon dioxide

: diethoxy(methyl)(phenylethynyl)silane

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
Stage #1: carbon dioxide; diethoxy(methyl)(phenylethynyl)silane With potassium tert-butylate at 40℃; for 2h; Schlenk technique; Stage #2: With hydrogenchloride In water Reagent/catalyst; Schlenk technique;	98%

: 4-((tert-butyldimethylsilyl)oxy)benzyl 3-phenylpropiolate

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;	97%

: 591-50-4
iodobenzene

: 471-25-0
Propiolic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 50℃; for 5h; Sonogashira coupling; Sealed flask;	96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide for 5h; Sonogashira Cross-Coupling; Inert atmosphere;	65%
With cesium hydroxide In water at 60℃; for 12h; Sonogashira coupling; Inert atmosphere;	58%

: 124-38-9
carbon dioxide

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

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
Stage #1: carbon dioxide; 1-Phenyl-2-(trimethylsilyl)acetylene With cesium fluoride In dimethyl sulfoxide at 20℃; for 3h; Schlenk technique; Stage #2: With hydrogenchloride In water at 0℃; pH=> 1; Reagent/catalyst; Solvent;	96%
With 18-crown-6 ether; cesium fluoride In dimethyl sulfoxide at 30℃; under 760.051 Torr; for 20h; Schlenk technique;	94%

: Yb(2+)*2C6H5C2CO2(1-) = (C6H5C2CO2)2Yb

A: ytterbium hydroxide

B: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With water In pentane addn. of a mixture (1:3) of water and pentane under Ar at room temperature; removing solvent and volatile compound (PhCCCO2H) by vac. condensation;;	A 94.3% B 89.6%

: 108-86-1
bromobenzene

: 471-25-0
Propiolic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 35℃; for 24h; Sonogashira Cross-Coupling;	93%
With 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; tris-(dibenzylideneacetone)dipalladium(0); tetra-n-butylammoniumfluoride trihydrate In 1-methyl-pyrrolidin-2-one; water at 50℃; for 4h;	42%
With 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; bis(η3-allyl-μ-chloropalladium(II)); tetra-n-butylammoniumfluoride trihydrate In 1-methyl-pyrrolidin-2-one; water at 50℃; for 16h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide for 24h;

: tert-butyldimethylsilyl 3-phenylpropiolate

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
Stage #1: C15H20O2Si; carbon tetrabromide In methanol at 20℃; for 0.5h; Irradiation; Stage #2: In methanol at 20℃; for 5h;	92%

: (2-methoxyethoxy)methyl 3-phenylpropiolate

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With carbon tetrabromide In isopropyl alcohol for 1.5h; Heating;	91%

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

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In acetonitrile at 35℃; pH 6.7;	90%
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; pH=6.7; Green chemistry;	90%
Multi-step reaction with 2 steps 1: TEMPO; poly[4-(diacetoxyiodo)styrene] / acetone / 4 h / 20 °C 2: aq. TEMPO; poly[4-(diacetoxyiodo)styrene] / acetone / 24 h / 20 °C View Scheme
With sodium chlorite; Me-AZADO+Cl- In acetonitrile at 25℃; for 0.5h; pH=6.8; aq. phosphate buffer;

: tert-butyldiphenylsilyl 3-phenylpropiolate

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With water; N,N-dimethyl-formamide at 70℃; for 0.5h; Green chemistry; chemoselective reaction;	90%
Stage #1: C25H24O2Si; carbon tetrabromide In methanol at 20℃; for 0.5h; Irradiation; Stage #2: In methanol at 20℃; for 48h;	61%

: 2216-94-6
phenylpropynoic acid ethyl ester

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 1.5h;	84%
With aluminium(III) iodide In acetonitrile for 0.5h; Heating;	80%
With water; sodium hydroxide In ethanol at 50℃; for 1.5h;	56%

: 17763-67-6
Phenyl triflate

: 471-25-0
Propiolic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 35℃; for 24h; Sonogashira Cross-Coupling;	84%

: 21770-48-9, 52742-03-7, 52777-73-8, 113569-01-0, 113626-43-0
methyl 2,3-dibromo-3-phenylpropanoate

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	75.9%
With potassium hydroxide In ethanol at 85℃; for 36h;	73%

: 6738-06-3
phenylethynylmagnesium bromide

: 124-38-9
carbon dioxide

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
Stage #1: phenylethynylmagnesium bromide; carbon dioxide In tetrahydrofuran at 20℃; under 3000.3 Torr; gas-liquid flow reactor assembly; Stage #2: With polymer-supported sulfonic acid In tetrahydrofuran	75%

: 2579-22-8
Phenylpropargyl aldehyde

A: 65-85-0
benzoic acid

B: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h;	A 6% B 74%

: 2579-22-8
Phenylpropargyl aldehyde

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In acetone; acetonitrile at 0 - 2℃; for 3.5h; Oxidation;	73%
With poly[4-(diacetoxyiodo)styrene]; 2,2,6,6-tetramethyl-piperidine-N-oxyl In acetone at 20℃; for 24h;
Multi-step reaction with 2 steps 1: 70 percent / acetic acid; diethyl ether / 1 h / -10 °C 2: 27.4 percent / KOH, MnO2 / benzene / 3 h / Ambient temperature; other solvent, without MnO2 View Scheme
With potassium permanganate In water; acetonitrile

: 124-38-9
carbon dioxide

: 536-74-3
phenylacetylene

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

B: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With [tris(3,5-bis(trifluoromethyl)pyrazolate)tricopper(I)] In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 12h;	A 10% B 72%
Stage #1: carbon dioxide; phenylacetylene With sodium carbonate; N,N,N,N,-tetramethylethylenediamine; copper(l) chloride In acetonitrile at 20℃; for 24h; Stage #2: With hydrogenchloride In dichloromethane; water pH=1;	A 10% B 60%

...Expand

: N-methoxy-3-phenylpropiolamide

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With tert.-butylnitrite; water at 29℃; for 0.583333h;	72%

: 2-(3-phenyl-1-trifluoromethanesulfonyloxy-prop-2-ynylidene)-malonic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With water; sodium hydrogencarbonate at 20℃; for 12h; Elimination;	71%

: 4891-38-7
phenylpropynoic acid methyl ester

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With pyrographite; sodium hydroxide In water at 20℃; for 24h;	71%
With water; sodium hydroxide In ethanol Inert atmosphere;
With sodium hydroxide In methanol; water at 20℃; for 3h;

: 84452-21-1
2-hydroxy-4-phenyl-3-butynenitrile

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With manganese(IV) oxide In diethyl ether at 20 - 25℃; for 19h;	66.6%

: 124-38-9
carbon dioxide

: 159087-45-3
4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With copper(l) iodide; cesium fluoride; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2-methyltetrahydrofuran at 120℃; for 24h; Solvent; Sealed tube;	63%

: 67-66-3
chloroform

: 79069-32-2
phenyl(phenylethynyl)iodonium tosylate

A: 591-50-4
iodobenzene

B: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide at 50℃; for 1h; Carbonylation;	A n/a B 61%

...Expand

: 6286-30-2
2,3-dibromo-3-phenylpropanoic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating;	58.7%
Reaktion ueber mehrere Stufen;
Multi-step reaction with 2 steps 1: 56 percent / KOH / methanol / Heating 2: 57.5 percent / KOH / methanol / Heating View Scheme
Multi-step reaction with 2 steps 1: water 2: diethyl ether; sodium View Scheme
With potassium hydroxide for 2h; Reflux; Inert atmosphere; Schlenk technique;	5.7 g

: 15894-30-1
(E)-2-Bromo-3-phenyl-acrylic acid

: 637-44-5
phenylpropyolic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating;	57.5%

: 637-44-5
phenylpropyolic acid

: 7299-58-3
phenylpropiolyl chloride

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane for 12h; Inert atmosphere; Reflux;	100%
With thionyl chloride In dichloromethane at 40℃; for 16h;	80%
With thionyl chloride In tetrachloromethane at 30 - 40℃; for 2h;	73%

: 637-44-5
phenylpropyolic acid

: 1985-37-1
4-phenylnaphtho[2,3-c]furan-1,3-dione

Conditions

Conditions	Yield
Stage #1: phenylpropyolic acid With triethylamine In dichloromethane at 20℃; for 1.5h; Schlenk technique; Inert atmosphere; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; 1,2-dichloro-ethane at 0 - 20℃; Temperature; Time; Reagent/catalyst; Schlenk technique; Inert atmosphere;	100%
With 1-ethyl-piperidine; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride In dichloromethane at 20℃; for 0.75h;	97%
With palladium diacetate; caesium carbonate; triphenylphosphine In acetonitrile at 20℃; for 0.05h; Reagent/catalyst;	96%

: 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;

: 186581-53-3, 908094-01-9
diazomethane

: 637-44-5
phenylpropyolic acid

: 4891-38-7
phenylpropynoic acid methyl ester

Conditions

Conditions	Yield
In diethyl ether	100%
In diethyl ether	70%

: 868-84-8
S,S-dimethyl dithiocarbonate

: 637-44-5
phenylpropyolic acid

: 109480-88-8
(E)-3-Methylsulfanyl-3-phenyl-acrylic acid

Conditions

Conditions	Yield
With potassium hydroxide at 25 - 60℃; for 0.166667h;	100%

: 623-80-3
S,S-diethyl dithiocarbonate

: 637-44-5
phenylpropyolic acid

: 109480-89-9
(E)-3-Ethylsulfanyl-3-phenyl-acrylic acid

Conditions

Conditions	Yield
With potassium hydroxide at 25 - 60℃; for 0.166667h;	100%

: 55716-09-1
S,S'-di-n-butyl dithiocarbonate

: 637-44-5
phenylpropyolic acid

: 109480-90-2
(E)-3-Butylsulfanyl-3-phenyl-acrylic acid

Conditions

Conditions	Yield
With potassium hydroxide at 90℃; for 0.5h;	100%

: 75-03-6
ethyl iodide

: 637-44-5
phenylpropyolic acid

: 2216-94-6
phenylpropynoic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile for 1.5h; Heating;	100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;	68%

: 110-91-8
morpholine

: 637-44-5
phenylpropyolic acid

: 95969-89-4
1-(morpholin-4-yl)-3-phenylprop-2-yn-1-one

Conditions

Conditions	Yield
Stage #1: phenylpropyolic acid With (chloro-phenylthio-methylene)dimethylammonium chloride In dichloromethane at 0℃; for 0.5h; Stage #2: morpholine In dichloromethane at 20℃; for 12h;	100%
With oxalyl dichloride; triethylamine In dichloromethane at 0 - 20℃; for 5h; Schlenk technique; Inert atmosphere;	84%
Stage #1: phenylpropyolic acid With thionyl chloride In dichloromethane at 40℃; for 2h; Stage #2: morpholine In benzene at 10℃; for 1h;

: 7463-51-6
4-bromo-3,5-dimethylphenol

: 637-44-5
phenylpropyolic acid

: 267901-42-8
4-bromo-3,-5-dimethyl-phenyl 3-phenylpropiolate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 9h; Cooling with ice;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 9h; Cooling with ice;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 9h; Cooling with ice;	100%
With dmap; dicyclohexyl-carbodiimide at 20℃; Esterification;	80%

: 103-82-2
phenylacetic acid

: 917351-49-6
3-dimethylamino-1-(4-methylphenyl)propanamine

: 104-01-8
4-Methoxyphenylacetic acid

: 140-10-3
(E)-3-phenylacrylic acid

: 1929-29-9
3-(4-methoxyphenyl)propanoic acid

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

: 32857-62-8
4-Trifluoromethylphenylacetic acid

: 2062-26-2, 87212-84-8, 16642-92-5
3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid

: 53473-36-2
3-(4-trifluoromethylphenyl)propionic acid

: 637-44-5
phenylpropyolic acid

: 501-52-0
3-Phenylpropionic acid

A: N-[3-dimethylamino-1-(4-methylphenyl)propyl]cinnamic amide

B: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropiolic amide

C: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-phenylacetamide

D: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-trifluoromethylphenyl)acetamide

E: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-methoxyphenyl)acetamide

F: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropionamide

G: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-trifluoromethylphenyl)propionamide

H: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-methoxyphenyl)propionamide

I: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-(trifluoromethyl)cinnamamide

J: N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-methoxycinnamamide

Conditions

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 100% B 100% C 93% D 98% E 93% F 96% G 78% H 98% I 56% J 87%

...Expand

: 103-82-2
phenylacetic acid

: 917351-50-9
3-dimethylamino-1-(2-naphthyl)propanamine

: 104-01-8
4-Methoxyphenylacetic acid

: 140-10-3
(E)-3-phenylacrylic acid

: 1929-29-9
3-(4-methoxyphenyl)propanoic acid

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

: 32857-62-8
4-Trifluoromethylphenylacetic acid

: 2062-26-2, 87212-84-8, 16642-92-5
3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid

: 53473-36-2
3-(4-trifluoromethylphenyl)propionic acid

: 637-44-5
phenylpropyolic acid

: 501-52-0
3-Phenylpropionic acid

A: N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-trifluoromethylphenyl)acetamide

B: N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-methoxyphenyl)acetamide

C: N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-phenylacetamide

D: N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropionamide

E: N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-trifluoromethylphenyl)propionamide

F: N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-methoxyphenyl)propionamide

G: N-[3-dimethylamino-1-(2-naphthyl)propyl]cinnamamide

H: N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide

I: N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-methoxycinnamamide

J: N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropiolamide

Conditions

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 88% B 79% C 67% D 66% E 84% F 94% G 76% H 100% I 100% J 100%

...Expand

: 885672-69-5
1-(4-chlorophenyl)-N3,N3-dimethylpropane-1,3-diamine

: 103-82-2
phenylacetic acid

: 104-01-8
4-Methoxyphenylacetic acid

: 140-10-3
(E)-3-phenylacrylic acid

: 1929-29-9
3-(4-methoxyphenyl)propanoic acid

: 943-89-5
(E)-3-(4-methoxyphenyl)acrylic acid

: 32857-62-8
4-Trifluoromethylphenylacetic acid

: 2062-26-2, 87212-84-8, 16642-92-5
3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid

: 53473-36-2
3-(4-trifluoromethylphenyl)propionic acid

: 637-44-5
phenylpropyolic acid

: 501-52-0
3-Phenylpropionic acid

A: 885673-16-5
N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-phenylacetamide

B: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-(4-trifluoromethylphenyl)acetamide

C: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-2-(4-methoxyphenyl)acetamide

D: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-phenylpropionamide

E: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-(4-trifluoromethylphenyl)propionamide

F: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-(4-methoxyphenyl)propionamide

G: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]cinnamamide

H: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-4-(trifluoromethyl)cinnamamide

I: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-4-methoxycinnamamide

J: N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-3-phenylpropiolamide

Conditions

Conditions	Yield
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene;	A 92% B 96% C 96% D 92% E 83% F 81% G 83% H 97% I 83% J 100%

...Expand

: 637-44-5
phenylpropyolic acid

: 1033320-59-0
d-3-phenylpropiolic acid

Conditions

Conditions	Yield
With water-d2 at 20℃; for 0.5h;	100%
With d(4)-methanol at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;

: 637-44-5
phenylpropyolic acid

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

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 130℃; for 48h;	100%
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Reagent/catalyst;	97%
With tetrakis(triphenylphosphine) palladium(0); silver carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Sealed tube;	96%

: 26191-64-0
4'-methyl-biphenyl-4-ol

: 637-44-5
phenylpropyolic acid

: 4-(4-methylphenyl)phenyl 3-phenyl-propiolate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 11h; Cooling with ice;	100%

: 64-17-5
ethanol

: 637-44-5
phenylpropyolic acid

: 2216-94-6
phenylpropynoic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: phenylpropyolic acid With N-(methyl)-N-(p-toluenesulfonyl)ethynylamine In dichloromethane at 20℃; Stage #2: ethanol With N,N,N'N'-tetramethyl-1,3-propanediamine In acetonitrile at 20℃; for 24h;	99%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;	99%
With graphene oxide at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;	98%

: 637-44-5
phenylpropyolic acid

: 501-52-0
3-Phenylpropionic acid

Conditions

Conditions	Yield
With LaNi5 hydride In tetrahydrofuran; methanol 1) 0 deg C, 2 h, 2) r.t., 15 h;	99%
With ferrous ammonium sulphate hexahydrate; isopropyl β-D-thiogalactopyranoside In aq. phosphate buffer at 37℃; for 48h;	92%
With water; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere;	71%

: 637-44-5
phenylpropyolic acid

: 932-88-7
1-iodo-2-phenylethyne

Conditions

Conditions	Yield
With N-iodo-succinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane at 20℃; for 0.25h; iododecarboxylation;	99%
With N-iodo-succinimide; triethylamine In dichloromethane at 20℃; for 0.0833333h; Hunsdiecker reaction;	97%
With 1-iodo-3,5,5-trimethylhydantoin; triethylamine In dichloromethane at 20℃; for 0.0833333h; Concentration; Reagent/catalyst;	97%

: 100-39-0
benzyl bromide

: 637-44-5
phenylpropyolic acid

: 63888-21-1
benzyl 3-phenyl-2-propynoate

Conditions

Conditions	Yield
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 3h;	99%
With copper(l) iodide; caesium carbonate; acetonitrile at 60℃; for 24h;	99%
Stage #1: phenylpropyolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide for 66h;	93%

: 637-44-5
phenylpropyolic acid

: 71-43-2
benzene

: 55010-17-8
3,3-diphenyl-indan-1-one

Conditions

Conditions	Yield
trifluorormethanesulfonic acid	99%
With aluminum tri-bromide at 60℃; for 1h;	30%

: 78-39-7
Triethyl orthoacetate

: 637-44-5
phenylpropyolic acid

: 2216-94-6
phenylpropynoic acid ethyl ester

Conditions

Conditions	Yield
In various solvent(s) at 80℃; for 0.5h;	99%

: C20H16O2

: 637-44-5
phenylpropyolic acid

: C29H20O3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 0℃;	99%

: C20H16O2

: 637-44-5
phenylpropyolic acid

: C29H20O3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 0℃;	99%

: C21H15F3O2

: 637-44-5
phenylpropyolic acid

: C30H19F3O3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 0℃;	99%

: C23H22O2

: 637-44-5
phenylpropyolic acid

: C32H26O3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 0℃;	99%

: 3-(1-naphthyl)-1-phenylprop-2-yn-1-ol

: 637-44-5
phenylpropyolic acid

: C28H18O2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 0℃;	99%

: 4435-54-5
2-Methylene-1-butanol

: 637-44-5
phenylpropyolic acid

: 1130965-04-6
2-ethylallyl 3-phenylpropiolate

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 25℃; for 4h; Inert atmosphere;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 10h;

: 766-85-8
3-methoxy-1-iodobenzene

: 637-44-5
phenylpropyolic acid

: 37696-01-8
1-methoxy-3-(phenylethynyl)benzene

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	99%
With copper(l) iodide; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	99%
Stage #1: phenylpropyolic acid With silver(l) oxide In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-methoxy-1-iodobenzene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; lithium iodide In N,N-dimethyl-formamide at 70℃; for 2h; Sonogashira coupling; Inert atmosphere;	86%

Phenylpropiolic acid Chemical Properties

Molecule structure of Phenylpropiolic acid (CAS NO.637-44-5):

IUPAC Name: 3-Phenylprop-2-ynoic acid
Molecular Weight: 146.14274 [g/mol]
Molecular Formula: C₉H₆O₂
Index of Refraction: 1.602
Molar Refractivity: 40.3 cm³
Molar Volume: 117.3 cm³
Surface Tension: 57.5 dyne/cm
Density: 1.24 g/cm³
Melting Point: 135-137 °C(lit.)
Flash Point: 151 °C
Enthalpy of Vaporization: 57.32 kJ/mol
Boiling Point: 302.6 °C at 760 mmHg
Storage Temp.: 0-6 °C
Water Solubility: freely soluble
Vapour Pressure: 0.000433 mmHg at 25 °C
XLogP3-AA: 2
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 146.036779
MonoIsotopic Mass: 146.036779
Topological Polar Surface Area: 37.3
Heavy Atom Count: 11
Canonical SMILES: C1=CC=C(C=C1)C#CC(=O)O
InChI: InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
InChIKey: XNERWVPQCYSMLC-UHFFFAOYSA-N
EINECS: 211-285-8
Product Categories: Aromatic Propionic Acids; Acetylenes; Acetylenic Alcohols & Their Derivatives; Diyne Compounds (LB Films); Functional Materials; LB Films; Acetylenic Carboxylic Acids & Their Derivatives

Phenylpropiolic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
HazardClass: IRRITANT
HS Code: 29163900

Phenylpropiolic acid Specification

Phenylpropiolic acid (CAS NO.637-44-5) is also named as 2-Propynoic acid, 3-phenyl- ; 3-Phenylpropiolic acid ; 3-Phenylpropynoic acid ; AI3-17875 ; NSC 13669 ; Phenylacetylene monocarboxylic acid ; Phenylacetylenecarboxylic acid
; Phenylpropynoic acid ; Propiolic acid, 3-phenyl- ; Propiolic acid, phenyl- (8CI) . Phenylpropiolic acid (CAS NO.637-44-5) is white to slightly beige fine crystalline powder. When heated with water to 120 °C, it yields phenylacetylene (C₆H₅CCH).

Product Name

Phenylpropiolic acid

Synthetic route

Phenylpropiolic acid Chemical Properties

Phenylpropiolic acid Safety Profile

Phenylpropiolic acid Specification

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