758-96-3

Basic information

• Product Name: N,N-Dimethylpropionamide
• Synonyms: Dimethylamide of propionic acid;dimethylamideofpropionicacid;n,n-dimethyl-propanamid;N,N-Dimethylpropanamide;N,N-dimethyl-Propanamide;Propionamide, N,N-dimethyl-;propionamide,n,n-dimethyl;Propionic acid dimethylamide
• CAS NO: 758-96-3
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• EINECS: 212-064-9
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 758-96-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: -45 °C
• Boiling Point: 174-176 °C
• Flash Point: 63 °C
• Appearance: Colorless/Liquid
• Density: 0.93
• Vapor Pressure: 1.12mmHg at 25°C
• Refractive Index: 1.438-1.442
• Storage Temp.: Store below +30°C.
• PKA: -0.41±0.70(Predicted)
• Water Solubility: SOLUBLE
• Stability: Flammable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N,N-Dimethylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylpropionamide(758-96-3)
• EPA Substance Registry System: N,N-Dimethylpropionamide(758-96-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-24/25
• WGK Germany: 2
• RTECS: UE3810000
• TSCA: Yes
• Hazardous Substances Data: 758-96-3(Hazardous Substances Data)

Usage

Description

N,N-Dimethylpropionamide is a colorless liquid that acts as a strong donor solvent, coordinating with metal ions through the carbonyl oxygen atom. It is known for its ability to form solvation structures with metal ions, such as zinc (II), which has been studied using Raman spectroscopy.

Uses

Used in Chemical Synthesis:
N,N-Dimethylpropionamide is used as a solvent in the preparation of AST-type zeolite with a plate morphology. Its strong donor properties and ability to coordinate with metal ions make it a valuable component in the synthesis of specific zeolite structures.
Used in Solvation Studies:
N,N-Dimethylpropionamide is utilized in solvation studies, particularly with metal ions like zinc (II). Its coordination capabilities through the carbonyl oxygen atom allow for the investigation of solvation structures, which can provide insights into its potential applications in various chemical processes.

Purification Methods

Shake the amide over BaO for 1-2 days, then distil it under reduced pressure. [Beilstein 4 III 126.]

InChI:InChI=1/C5H11NO/c1-4-5(7)6(2)3/h4H2,1-3H3

Synthetic route

d'hydrazide de l'acide propionique (5818-15-5) + N,N-Dimethyl-N'-(dimethylamino-methoxymethyl)-formamidin → 1,2,4-Triazole (288-88-0) + N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
In methanol for 7h; Heating;	A 87% B 91%

triethylgermyllithium (6727-87-3) + N,N-dimethyl acetamide (127-19-5) → N,N-dimethyl-propanamide (758-96-3) + Triethylgerman (1188-14-3)

Conditions	Yield
With methyl iodide In tetrahydrofuran double excess of MeI; not isolated; GLC;	A 86% B 89%

1-hydroxy-2-butyl-dimethylamine (17199-17-6) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With potassium hydroxide; air In diethyl ether at 20℃; for 90h;	84%

propionyl chloride (79-03-8) + dimethyl amine (124-40-3) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
In benzene at 20℃;	80%
In diethyl ether at -30℃;	74%
With benzene
With diethyl ether
In tetrahydrofuran; dichloromethane at 20℃; Cooling with ice;

propionyl fluoride (430-71-7) + N,N-dimethyltriphenylgermylamine → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
In benzene Reflux; Schlenk technique;	63%

N,N-dimethyl acetamide (127-19-5) + Li{(CH2)(CH2)P(C6H5)2} (59983-62-9) + methyl iodide (74-88-4) → N,N-dimethyl-propanamide (758-96-3) + diphenylethylmethylphosphonium iodide (1661-08-1)

Conditions	Yield
at -50℃; for 5h; 1 equiv. of MeI;	A 60% B 60%

N,N-Dimethylacrylamide (2680-03-7) → N,N-dimethyl-propanamide (758-96-3) + bis(N,N-dimethyl)-γ-ketopimelamide (81733-98-4)

Conditions	Yield
With carbon monoxide; isopropyl alcohol; dodecacarbonyltetrarhodium(0) at 180℃; for 6h; Pressure (range begins): 75 ;	A 31 % Chromat. B 47%

N,N-Dimethylacrylamide (2680-03-7) + carbon monoxide (201230-82-2) → N,N-dimethyl-propanamide (758-96-3) + bis(N,N-dimethyl)-γ-ketopimelamide (81733-98-4)

Conditions	Yield
With isopropyl alcohol; dodecacarbonyltetrarhodium(0) at 180℃; for 6h; Pressure (range begins): 75 ;	A 31% B 47 % Chromat.

N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) + propionic acid (802294-64-0) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
under 100 Torr;

propionic acid (802294-64-0) + dimethyl amine (124-40-3) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With air at 155℃;

N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) + propionic acid anhydride (123-62-6) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
at 165℃;

propanoic acid methyl ester (554-12-1) + dimethyl amine (124-40-3) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With water

sodium proprionate (137-40-6) + N,N-Dimethylcarbamoyl chloride (79-44-7) → N,N-dimethyl-propanamide (758-96-3)

N,N-dimethyl acetamide (127-19-5) + methyl iodide (74-88-4) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
(i) NaNH2, liq. NH3, (ii) /BRN= 969135/; Multistep reaction;
With triethylgermyllithium 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C to r.t., 0.5 h; Yield given. Multistep reaction;
With (triethylgermyl)potassium 1.) THF, -20 deg C, 1 h, 2.) THF, RT, 1 h; Yield given. Multistep reaction;

N,N-dimethyl acetamide (127-19-5) → N,N-Dimethylamino acetonitrile (926-64-7) + N,N-dimethyl-propanamide (758-96-3) + acetone (67-64-1)

Conditions	Yield
under 0.008 - 0.8 Torr; radio-frequency discharge; Yield given. Yields of byproduct given;

propionic acid (802294-64-0) + diethylamine (109-89-7) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
aluminum oxide at 240℃; Kinetics; Rate constant; temperature range 200 - 320 deg C, energy of activation;

C120H120O24*C5H11NO → N,N-dimethyl-propanamide (758-96-3) + C120H120O24

Conditions	Yield
In various solvent(s) at 70 - 90℃; Kinetics; Activation energy; decomplexation;

W2(CH2CH3)2(N(CH3)2)4 (72286-65-8) + propionic acid anhydride (123-62-6) → W2(4+)*4C2H5COO(1-)=W2(O2CC2H5)4 + N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
In not given byproducts: C2H4, C2H6; react. hydrocarbon soln. 1,2-W2Et2(NMe2)4 with acid anhydride at room temp.; crystn. from benzene or hexane;

C2H7N*(x)C3H6O2 → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
at 260℃; under 22502.3 Torr; for 0.0125h; Microwave irradiation;

N,N-Dimethylacrylamide (2680-03-7) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With sodium tetrahydroborate; iron(III) trifluoromethanesulfonate; ethanol at 20℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;
With [Cp(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Ru(pyridine)2][PF6]; potassium tert-butylate; isopropyl alcohol at 70℃; for 8h; Glovebox; Schlenk technique; Inert atmosphere;	98 %Spectr.

propan-1-ol (71-23-8) + dimethyl amine (124-40-3) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With gold at 40℃; under 760.051 Torr; Green chemistry;

propionic acid (802294-64-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With dipotassium peroxodisulfate; (p-cymene)ruthenium(II) chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 160℃; for 6h;	93 %Chromat.

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + propionic acid (802294-64-0) → N,N-dimethyl-propanamide (758-96-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;

N,N-dimethyl-propanamide (758-96-3) + vinyltriphenylsilane (18666-68-7) → N,N,2-trimethyl-4-(triphenylsilyl)butanamide

Conditions	Yield
Stage #1: vinyltriphenylsilane With 18-crown-6 ether; potassium hexamethylsilazane at 25℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-propanamide at 25℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	100%

N,N-dimethyl-propanamide (758-96-3) + benzaldehyde (100-52-7) → 3-hydroxy-2,N,N-trimethyl-3-phenylpropionamide (20428-71-1)

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With n-butyllithium; polymer-bound N-isopropyl-5-(4-vinylphenyl)pentylamine In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; for 1.5h; Further stages.;	99%
(i) nBuLi, <1,3,5>trithiane, THF, (ii) /BRN= 471223/; Multistep reaction;

N,N-dimethyl-propanamide (758-96-3) + 1-[chloro(p-tolylsulfinyl)methylidene]cyclobutane (854139-13-2) → 2-(1-[chloro(p-tolylsulfinyl)methyl]cyclobutyl)-N,N-dimethylpropionamide (1150277-44-3)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;	99%
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: 1-[chloro(p-tolylsulfinyl)methylidene]cyclobutane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	99%

pyrrole (109-97-7) + N,N-dimethyl-propanamide (758-96-3) → 2-propionylpyrrole (1073-26-3)

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With trichlorophosphate at 0 - 20℃; for 0.25h; Stage #2: pyrrole In 1,2-dichloro-ethane at 0℃; for 0.5h; Heating / reflux; Stage #3: With sodium acetate In water; 1,2-dichloro-ethane for 0.5h; Heating / reflux;	98%
Stage #1: N,N-dimethyl-propanamide With bis(trichloromethyl) carbonate In tetrachloromethane at 0℃; Stage #2: pyrrole In tetrachloromethane at 40 - 50℃; for 1h; Vilsmeier-Haack reaction; Stage #3: With sodium hydroxide In tetrachloromethane	87%
With sodium hydroxide; water; trichlorophosphate 1) benzene, 18 h, 20 deg C, 2) 1 h, 20 deg C; Yield given. Multistep reaction;

N,N-dimethyl-propanamide (758-96-3) + dimethylaminobis(trifluoromethyl)borane (105224-90-6) → 1-dimethylaminocarbonylethyl-bis(trifluoromethyl)borane-dimethylamine (148298-50-4)

Conditions	Yield
In pentane dopwise addn. of (CF3)2BNMe2 to a stirred soln. of the carbonyl compound in dry pentane at 4°C; warmed to room temp. with stirring (1 h);; removal of solvent and volatile by-products in vac. at room temp., purifn. by sublimation in vac.; elem. anal.;;	98%

N,N-dimethyl-propanamide (758-96-3) + 1,3-diphenyl-1H-pyrazol-5-amine (5356-71-8) → N'-(1,3-diphenyl-1H-pyrazol-5-yl)-N,N-dimethylpropanimidamide (1257533-52-0)

Conditions	Yield
With trichlorophosphate at 30 - 40℃; Microwave irradiation;	95%

styrene (292638-84-7) + N,N-dimethyl-propanamide (758-96-3) → N,N,2-trimethyl-4-phenylbutanamide

Conditions	Yield
Stage #1: styrene With 18-crown-6 ether; potassium hexamethylsilazane at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-propanamide at 0℃; for 6h; Inert atmosphere;	95%
With potassium tert-butylate at 80℃; for 2h; Sealed tube;	93%

N,N-dimethyl-propanamide (758-96-3) + 1-methyl-2-vinyl-benzene (611-15-4) → N,N,2-trimethyl-4-(o-tolyl)butanamide

Conditions	Yield
Stage #1: 1-methyl-2-vinyl-benzene With 18-crown-6 ether; potassium hexamethylsilazane at 25℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-propanamide at 25℃; for 9h; Inert atmosphere;	95%

1,1-Diphenylethylene (530-48-3) + N,N-dimethyl-propanamide (758-96-3) → N,N,2-trimethyl-4,4-diphenylbutanamide

Conditions	Yield
Stage #1: 1,1-Diphenylethylene With 18-crown-6 ether; potassium hexamethylsilazane at 25℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-propanamide at 25℃; for 9h; Inert atmosphere;	95%

1-bromo-4-ethenyl-benzene (2039-82-9) + N,N-dimethyl-propanamide (758-96-3) → 4-(4-bromophenyl)-N,N,2-trimethylbutanamide

Conditions	Yield
Stage #1: 1-bromo-4-ethenyl-benzene With 18-crown-6 ether; 1,1,1,3,3,3-hexamethyl-disilazane at 25℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-propanamide at 25℃; for 6h; Inert atmosphere;	94%

N,N-dimethyl-propanamide (758-96-3) → N,N-dimethylpropane-1-amine hydrochloride (65845-57-0)

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With [κ2-{Ph2P(Se)NC9H6N}Al(Me)2]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Schlenk technique; Glovebox; Stage #2: With hydrogenchloride In water chemoselective reaction;	94%
Stage #1: N,N-dimethyl-propanamide With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;	87%

N,N-dimethyl-propanamide (758-96-3) + methyl 3-(benzyloxy)benzoate (79678-37-8) → 3-(3-(benzyloxy)phenyl)-N,N,2-trimethyl-3-oxopropanamide

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: methyl 3-(benzyloxy)benzoate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	94%

N,N-dimethyl-propanamide (758-96-3) + (phenylmethylene)bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane) → benzyl ethyl ketone (1007-32-5)

Conditions	Yield
With lithium tert-butoxide In tetrahydrofuran at 23℃; for 3h; Glovebox;	94%

N,N-dimethyl-propanamide (758-96-3) + 2-methoxybenzamide (2439-77-2) → N,N'-methylenebis(2-methoxybenzamide)

Conditions	Yield
With Selectfluor at 110℃; for 12h;	92%

N,N-dimethyl-propanamide (758-96-3) + 2-tert-butyldimethylsilyloxyethyl iodide (101166-65-8) → C13H29NO2Si (1070799-18-6)

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium chloride; lithium diisopropyl amide In tetrahydrofuran; hexanes at -78 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: 2-tert-butyldimethylsilyloxyethyl iodide In tetrahydrofuran; hexanes at 0℃; for 3.5h; Inert atmosphere;	91%
Stage #1: N,N-dimethyl-propanamide With n-butyllithium; diisopropylamine; lithium chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: 2-tert-butyldimethylsilyloxyethyl iodide In tetrahydrofuran; hexane at 0℃; for 3.5h; Inert atmosphere;	91%

phthalimide (136918-14-4) + N,N-dimethyl-propanamide (758-96-3) → N-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N-methylpropionamide (1401870-97-0)

Conditions	Yield
With tert.-butylhydroperoxide; potassium iodide In water at 90℃; for 1h;	91%

N,N-dimethyl-propanamide (758-96-3) + benzamide (55-21-0) → N,N'-methylenebisbenzamide (1575-94-6)

Conditions	Yield
With Selectfluor at 110℃; for 12h; Temperature; Reagent/catalyst;	91%

dimethyltitanocene (1271-66-5) + N,N-dimethyl-propanamide (758-96-3) → 1-Bromo-2-butanone (816-40-0)

Conditions	Yield
Stage #1: dimethyltitanocene; N,N-dimethyl-propanamide In toluene at 65℃; Schlenk technique; Inert atmosphere; Stage #2: With bromine In toluene at -78℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #3: With water In toluene at 20℃; for 1h; Solvent; Temperature; Reagent/catalyst; Schlenk technique; Inert atmosphere; regioselective reaction;	90%

2-chloro-1H-benzoimidazole (4857-06-1) + N,N-dimethyl-propanamide (758-96-3) → N-((2-chloro-1H-benzo[d]imidazol-1-yl)methyl)-N-methylpropionamide

Conditions	Yield
With dipotassium peroxodisulfate; potassium iodide at 80℃; for 6h; Schlenk technique;	90%

N,N-dimethyl-propanamide (758-96-3) + methyl 2-fluorobenzoate (394-35-4) → 3-(2-fluorophenyl)-N,N,2-trimethyl-3-oxopropanamide

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: methyl 2-fluorobenzoate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	90%

N-Methylpyrrole (96-54-8) + N,N-dimethyl-propanamide (758-96-3) → 1-(1-methyl-1H-pyrrol-2-yl)-1-propanone (17180-59-5)

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With bis(trichloromethyl) carbonate In tetrachloromethane at 0℃; Stage #2: N-Methylpyrrole In tetrachloromethane at 40 - 50℃; for 1h; Vilsmeier-Haack reaction; Stage #3: With sodium hydroxide In tetrachloromethane	88%

N,N-dimethyl-propanamide (758-96-3) + benzoic acid hydrazide (613-94-5) → 2-ethyl-5-phenyl-1,3,4-oxadiazole (73314-40-6)

Conditions	Yield
With trichlorophosphate at 80℃; for 0.666667h;	88%

N,N-dimethyl-propanamide (758-96-3) + 4-chlorobenzamide (619-56-7) → N,N'-methylenebis(4-chlorobenzamide) (22404-87-1)

Conditions	Yield
With Selectfluor at 110℃; for 12h;	88%

N,N-dimethyl-propanamide (758-96-3) + methyl 4-methoxybenzoate (121-98-2) → 3-(4-methoxyphenyl)-N,N,2-trimethyl-3-oxopropanamide

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: methyl 4-methoxybenzoate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	88%

N,N-dimethyl-propanamide (758-96-3) + 1-methoxycarbonyl-3-methylbenzene (99-36-5) → N,N,2-trimethyl-3-oxo-3-(m-tolyl)propanamide

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 1-methoxycarbonyl-3-methylbenzene In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	88%

N,N-dimethyl-propanamide (758-96-3) + anthranilic acid amide (28144-70-9) → 2-ethyl-3H-quinazolin-4-one (3137-64-2)

Conditions	Yield
With Imidazole hydrochloride at 150℃; for 13h;	88%

N,N-dimethyl-propanamide (758-96-3) + (Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-3-one (371778-06-2) → 3-tert-butyl-7,7,7-trifluoro-3-hydroxy-2,6-dimethyl-hept-4-enoic acid dimethylamide

Conditions	Yield
Stage #1: N,N-dimethyl-propanamide With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: (Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-3-one In tetrahydrofuran at -78℃; for 2h; Further stages.;	87.6%

benzophenone (119-61-9) + N,N-dimethyl-propanamide (758-96-3) → 3,3-diphenyl-2-methyl-3-hydroxy- N,N-dimethylpropionamide (20428-72-2, 72656-53-2)

Conditions	Yield
With samarium; copper(l) iodide; iodine at 80℃; for 2h;	87%
(i) nBuLi, <1,3,5>trithiane, THF, (ii) /BRN= 1238185/; Multistep reaction;
With cerium(III) chloride; lithium diisopropyl amide Yield given. Multistep reaction;

Upstream product

• 554-12-1 propanoic acid methyl ester 
• 124-40-3 dimethyl amine 
• 137-40-6 sodium proprionate 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 802294-64-0 propionic acid 
• 109-89-7 diethylamine 
• 5818-15-5 d'hydrazide de l'acide propionique 
• 71-23-8 propan-1-ol 
• 430-71-7 propionyl fluoride 
• 506-59-2 N,N-dimethylammonium chloride 
• 512-56-1 trimethyl phosphite 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 2680-03-7 N,N-Dimethylacrylamide 

Downstream Products

• 22582-68-9 1-(1H-indol-3-yl)propan-1-one 
• 38435-26-6 N,N'',N''-trimethyl-N-phenyl-propionamidrazone 
• 20428-71-1 3-hydroxy-3-phenyl-2,N,N-trimethylpropionamide 
• 36460-74-9 C₁₃H₂₁N₃ 
• 1073-26-3 2-propionylpyrrole 
• 90425-36-8 N,N-dimethyl 2,2-bisphenylthiopropionamide 
• 179473-61-1 7-bromo-3-propionylindole 
• 138201-37-3 (2SR,3SR)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide 
• 138201-37-3 (2RS,3SR)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide 
• 20595-82-8 α.N.N-Trimethyl-β.β-diphenyl-acrylamid 
• 117497-67-3 (E)-pentacarbonyl{1-(dimethylamino)-3-ethoxy-2-methyl-3-phenylpropenylidene}chromium 
• 117497-73-1 (E)-pentacarbonyl{1-(dimethylamino)-3-ethoxy-2-methyl-3-phenylpropenylidene}wolfram 
• 1174376-34-1 N'-[5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl]-N,N-dimethylpropionamidine 
• 1257533-52-0 N'-(1,3-diphenyl-1H-pyrazol-5-yl)-N,N-dimethylpropanimidamide 

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Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is

Direct amidation of acid fluorides using germanium amides

Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method for their preparation is presented where germanium amides Ph3GeNR2convert acid fluorides directly to amides. These germanium amides serve to abstract the fluorine atom of the acid fluoride and transfer their amide group -NR2to the carbonyl carbon, and so function as amidation reagents.

Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.