7341-96-0

Basic information

• Product Name: PROPYNOIC ACID AMIDE
• Synonyms: PROPYNOIC ACID AMIDE;2-Propynamide;HCequivCCONH2;Propynamide;Propiolamide;PropynoicAcidAmide,Propynamide;prop-2-ynaMide;Propiolic acid amide
• CAS NO: 7341-96-0
• Molecular Formula: C₃H₃NO
• Molecular Weight: 69.06
• Product Categories: Miscellaneous Reagents
• Mol File: 7341-96-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 61-62°C
• Boiling Point: 134.6 °C at 760 mmHg
• Flash Point: 35.2 °C
• Appearance: Waxy Yellow Solid
• Density: 1.102 g/cm³
• Vapor Pressure: 8.03mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Methanol
• PKA: 13.48±0.50(Predicted)
• CAS DataBase Reference: PROPYNOIC ACID AMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPYNOIC ACID AMIDE(7341-96-0)
• EPA Substance Registry System: PROPYNOIC ACID AMIDE(7341-96-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 7341-96-0(Hazardous Substances Data)

Usage

Uses

Propiolamide (cas# 7341-96-0) is a compound useful in organic synthesis.

InChI:InChI=1/C3H3NO/c1-2-3(4)5/h1H,(H2,4,5)

Synthetic route

propynoic acid methyl ester (922-67-8) → 2-propynamide (7341-96-0)

Conditions	Yield
With ammonia In water for 0.166667h; Cooling with isopropanol-dry ice;	100%
With ammonia In water	99%
With ammonia In water at -30 - 30℃; for 0.333333h;	95.4%

propynoic acid ethyl ester (623-47-2) → 2-propynamide (7341-96-0)

Conditions	Yield
With ammonia at -78 - 20℃; for 5h;	100%
With ammonia at -55℃; for 9h;	83%
With ammonium hydroxide at -10℃; for 1h; Inert atmosphere;	74%

3-(trimethylsilyl)prop-2-ynamide → 2-propynamide (7341-96-0)

Conditions	Yield
With KF-Al2O3 (5 mol percent) In methanol at 25℃; for 0.333333h;	82%

propargyl alcohol (107-19-7) → 2-propynamide (7341-96-0)

Conditions	Yield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; hydroxylamine hydrochloride; iodine; potassium carbonate In 1,2-dichloro-ethane at 90℃; for 19h;	75%

propiolic acid anhydride (4672-74-6) → 2-propynamide (7341-96-0)

Conditions	Yield
With diethyl ether; ammonia

propiolonitrile (1070-71-9) → 2-propynamide (7341-96-0)

Conditions	Yield
With sulfuric acid at 35 - 40℃;

2-propynamide (7341-96-0) → (Z)-3-Chloropropenamide (78708-26-6)

Conditions	Yield
With acetic acid; lithium chloride at 90℃; for 22h;	98%

2-propynamide (7341-96-0) → (Z)-3-Iodopropenamide (137627-61-3)

Conditions	Yield
With acetic acid; lithium iodide at 90℃; for 22h;	98%
With lithium iodide In acetic acid at 90℃; for 8h;	85%

2-propynamide (7341-96-0) + pivalaldehyde (630-19-3) → C8H14INO2

Conditions	Yield
Stage #1: pivalaldehyde With magnesium iodide In dichloromethane at 0 - 20℃; Morita-Baylis-Hillman reaction; Inert atmosphere; Stage #2: 2-propynamide In dichloromethane at 20℃; for 30h; Morita-Baylis-Hillman reaction; Inert atmosphere;	98%

2-propynamide (7341-96-0) + 1-selenonaphthol (16645-11-7) → β-(1-naphthylseleno)acrylamide (94848-98-3)

Conditions	Yield
In ethanol at 40 - 50℃; for 0.5h;	95.3%

2-propynamide (7341-96-0) + indole-2,3-dione (91-56-5) + L-proline (147-85-3) → 2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxamide (1453811-29-4)

Conditions	Yield
With copper(l) iodide In acetonitrile at 80℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;	92%

piperidine (110-89-4) + 2-propynamide (7341-96-0) → (E)-3-(piperidin-1-yl)acrylamide (64164-01-8)

Conditions	Yield
In diethyl ether for 1h;	91%

2-propynamide (7341-96-0) + 5,7-dinitro-1H-indole-2,3-dione (5453-79-2) + L-proline (147-85-3) → 5,7-dinitro-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxamide (1453811-35-2)

Conditions	Yield
With copper(l) iodide In acetonitrile at 80℃; for 2h; Inert atmosphere;	90%

2-propynamide (7341-96-0) + 2-(benzylideneamino)phenol (1624-53-9, 3230-45-3, 137838-23-4) + methyl 2-diazo-2-(3-methoxyphenyl)acetate (384365-49-5) → C26H24N2O5

Conditions	Yield
Stage #1: 2-(benzylideneamino)phenol In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Stage #2: 2-propynamide; methyl 2-diazo-2-(3-methoxyphenyl)acetate With dirhodium tetraacetate In dichloromethane at 20℃; for 1h; Molecular sieve;	90%

2-propynamide (7341-96-0) + 3',6'-bis(dimethylamino)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid (150322-05-7) → C28H25N3O4

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃;	90%

2-propynamide (7341-96-0) → 3-iodopropiolamide

Conditions	Yield
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;	89%
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve;	89%
With iodine; sodium hydroxide In water

2-propynamide (7341-96-0) + 2-((naphthalen-2-ylmethylene)amino)phenol (78685-68-4) + Methyl phenyldiazoacetate (22979-35-7) → methyl 3-((2-hydroxyphenyl)amino)-3-(naphthalen-2-yl)-2-phenyl-2-propiolamidopropanoate

Conditions	Yield
With rhodium(II) acetate dimer In dichloromethane at 20 - 25℃; for 6h; Molecular sieve; Inert atmosphere; diastereoselective reaction;	89%

2-propynamide (7341-96-0) + 2-(4-bromo-benzylidenamino)-phenol (117649-27-1, 3230-46-4) + Methyl phenyldiazoacetate (22979-35-7) → methyl 3-(4-bromophenyl)-3-((2-hydroxyphenyl)amino)-2-phenyl-2-propiolamidopropanoate + methyl 3-(4-bromophenyl)-3-((2-hydroxyphenyl)amino)-2-phenyl-2-propiolamidopropanoate

Conditions	Yield
Stage #1: 2-(4-bromo-benzylidenamino)-phenol In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Stage #2: 2-propynamide; Methyl phenyldiazoacetate With dirhodium tetraacetate In dichloromethane at 20℃; for 1h; Molecular sieve;	A 89% B n/a

2-propynamide (7341-96-0) + 2-((naphthalen-1-ylmethylene)amino)phenol (5932-25-2) + Methyl phenyldiazoacetate (22979-35-7) → C29H24N2O4 + C29H24N2O4

Conditions	Yield
Stage #1: 2-((naphthalen-1-ylmethylene)amino)phenol In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Stage #2: 2-propynamide; Methyl phenyldiazoacetate With dirhodium tetraacetate In dichloromethane at 20℃; for 1h; Molecular sieve;	A n/a B 89%

2-propynamide (7341-96-0) + (+)-pinanediol (1R)-2-azido-1-[(2-thienylacetyl)amino]ethaneboronate → (+)-pinanediol (1R)-2-(4-carboxamido[1,2,3]triazol-1-yl)-1-(2-thienylacetylamino)ethaneboronate

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 60℃; for 0.5h; Inert atmosphere; Sealed tube;	89%

2-propynamide (7341-96-0) + 1-(azidomethyl)-3,5-dimethylbenzene (222716-36-1) → 1-(3,5-dimethylbenzyl)-1H-1,2,3-triazole-4-carboxamide

Conditions	Yield
With sodium chloride In water for 5h; Irradiation; regioselective reaction;	89%

morpholine (110-91-8) + 2-propynamide (7341-96-0) → trans-β-(morpholino)acrylic acid amide (118091-04-6)

Conditions	Yield
In diethyl ether at 20℃; for 18h;	88%
In dichloromethane for 1h;	83%

2-propynamide (7341-96-0) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9) → methyl 1-(3-amino-3-oxoprop-1-enyl)-2-oxocyclopentanecarboxylate (1199941-88-2)

Conditions	Yield
With sodium carbonate In water at 0 - 20℃; for 2h; Michael addition;	88%

2-propynamide (7341-96-0) + 4',4''-O,O-dimethylcurcumin (160096-59-3) → (2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide (1118765-37-9)

Conditions	Yield
Stage #1: 4',4''-O,O-dimethylcurcumin With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: 2-propynamide In tetrahydrofuran; mineral oil at 20℃; for 24.1667h;	88%

2-propynamide (7341-96-0) + N-4-chlorobenzylidene-2-hydroxyaniline (117909-29-2, 5348-11-8) + methyl 3-chlorophenyldiazoacetate (264882-01-1) → methyl 2-(3-chlorophenyl)-3-(4-chlorophenyl)-3-[(2-hydroxyphenyl)amino]-2-(prop-2-ynamido)propanoate

Conditions	Yield
With rhodium(II) acetate dimer In dichloromethane at 20 - 25℃; for 6h; Molecular sieve; Inert atmosphere; diastereoselective reaction;	88%

Upstream product

• 623-47-2 propynoic acid ethyl ester 
• 107-19-7 propargyl alcohol 
• 1070-71-9 propiolonitrile 
• 922-67-8 propynoic acid methyl ester 
• 4672-74-6 propiolic acid anhydride 

Downstream Products

• 109650-86-4 4-hydroxy-4-(4-methoxy-phenyl)-4-phenyl-but-2-ynoic acid amide 
• 544-44-5 agrocybin 
• 63462-41-9 β-(p-tolylseleno)acrylamide 
• 94848-97-2 β-(p-chlorophenylseleno)acrylamide 
• 54670-85-8 2-Phenyl-5-benzyl-4-oxo-3,4-dihydropyridine 
• 142334-75-6 (Z)-5-Phenyl-pent-2-en-4-ynoic acid amide 
• 888034-79-5 3-(2,4,6-trimethylphenyl)isoxazole-4-carboxamide 
• 1118765-37-9 (2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide 
• 1453811-40-9 1-(3-chlorobenzyl)-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxamide 
• 80819-65-4 1-benzyl-1H-1,2,3-triazole-4-carboxamide 

Relevant articles and documents

Synthesis of propiolamide and 1H, 13C and 15N NMR spectra of formamide, acetamide and propiolamide

A high-yield synthesis and purification of propiolamide is described. The structure and purity of the compound were confirmed by 1H, 13C and 15N NMR studies. Natural abundance 13C and 15N chemical shift measurements in 3.0 M acetonitrile solutions are reported along with 1H-1H, 1H-15N and 1H-13C spin coupling constants. Polarization transfer techniques were used for the 15N and 13C measurements. The propiolamide NMR parameters were compared with those for 3.0 M solutions of formamide and acetamide in acetonitrile solution. Measurements at 298 and 278 K indicated that for all three compounds there is still significant rotation about the carbon-nitrogen bond at room temperature.

Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction

The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.

Samarium-mediated intramolecular cross-couplings of an α,β-unsaturated N-acylpyrrole

The first example of an α,β-unsaturated N-acylpyrrole undergoing a SmI2-mediated cyclization is reported. In contrast to other unsaturated units, the intermediate samarium enolate readily engages in aldol-type reactions, necessitating careful control of the reaction conditions.