Conditions | Yield |
---|---|
Stage #1: propionic acid With niobium pentachloride In dichloromethane Stage #2: diethylamine In dichloromethane at 45 - 50℃; for 2.5h; | 84% |
With tetrachlorosilane; benzene | |
(i) 4-dimethylamino-but-3-yn-2-one, THF, (ii) /BRN= 605268/; Multistep reaction; |
methyl(diethylamino)acetylene
N,N-dibenzylhydroxylamine
A
N,N-diethylpropanamide
B
benzaldehyde
C
benzylamine
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; Ambient temperature; | A 80% B 10% C 7% |
propionyl chloride
N,N-diethyl-1,1,1-trimethylsilanamine
N,N-diethylpropanamide
Conditions | Yield |
---|---|
In hexane for 5h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 2h; | 58% |
isocyanatoethene
methyl(diethylamino)acetylene
A
N,N-diethylpropanamide
B
4-(diethylamino)-3-methyl-2-pyridinone
C
2-(diethylamino)-3-methyl-4-pyridinone
D
N-(ethenylcarbamoyl)-4-(diethylamino)-3-methyl-2-pyridinone
Conditions | Yield |
---|---|
In diethyl ether Mechanism; Product distribution; Ambient temperature; vinyl isothiocyanate, var. mol. ratio of Educts; | A 15.5% B 15.5% C 42% D 28.5% |
In diethyl ether 1.) reflux, 2.) room temp., overnight; | A 15.5% B 42% C 3.7% D 28.5% |
Conditions | Yield |
---|---|
With benzene |
ethyl N,N-diethylcarbamate
ethylmagnesium bromide
N,N-diethylpropanamide
Conditions | Yield |
---|---|
In tetrahydrofuran |
diethyl-amidosulfurous acid methyl ester
propionic acid
N,N-diethylpropanamide
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With cobalt(II) formate at 250 - 380℃; |
1-(3,5-dimethyl-1H-pyrazol-1-yl)propan-1-one
diethylamine
A
3,5-dimethyl-1H-pyrazole
B
N,N-diethylpropanamide
Conditions | Yield |
---|---|
In benzene at 29.5℃; Rate constant; other pyrazol, other amines; |
1-diethylamino-1-(2-hydroxyethoxy)-1-propene
N,N-diethylpropanamide
Conditions | Yield |
---|---|
With sodium hydroxide at 80℃; for 2h; |
1,1-dichloroethane
carbon monoxide
diethylamine
A
N,N-diethylpropanamide
B
N,N-diethyl-2-diethylaminopropionamide
Conditions | Yield |
---|---|
With triethylamine; dicobalt octacarbonyl at 100℃; under 38000 Torr; for 48h; Yield given. Yields of byproduct given; |
1,1-Dibromoethane
carbon monoxide
diethylamine
A
N-formyldiethylamine
B
N,N-diethylpropanamide
C
N,N,N',N'-tetraethylurea
D
N,N,N',N'-tetraethyloxamide
E
N,N-diethyl-2-diethylaminopropionamide
F
N,N,N',N'-tetraethyl-methylmalonamide
Conditions | Yield |
---|---|
With triethylamine; dicobalt octacarbonyl In hexane at 100℃; under 38000 Torr; for 48h; Product distribution; K2CO3, other solvents; other catalysts; other geminal dihaloalkanes; |
1,1-Dibromoethane
carbon monoxide
diethylamine
A
N,N-diethylpropanamide
B
N,N-diethyl-2-diethylaminopropionamide
C
N,N,N',N'-tetraethyl-methylmalonamide
Conditions | Yield |
---|---|
With triethylamine; dicobalt octacarbonyl In tetrahydrofuran at 100℃; under 38000 Torr; for 48h; K2CO3, other catalysts and solvents; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With ruthenium trichloride; triethylamine at 100℃; for 10h; |
2-((E)-1-Diethylamino-propenyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one
A
N,N-diethylpropanamide
B
saccharin
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 20.2 percent / H2SO4 / 4 h / 50 - 60 °C 2: 20percent aq. NaOH / 2 h / 80 °C View Scheme |
Conditions | Yield |
---|---|
In water |
Conditions | Yield |
---|---|
With CO |
carbon monoxide
triethylamine
A
diethylacetamide
B
N-Ethyl,N-methylacetamide
C
N,N-diethylpropanamide
Conditions | Yield |
---|---|
With tertamethylammonium iodide; palladium dichloride In 1-methyl-pyrrolidin-2-one at 20 - 240℃; under 7500.75 - 48754.9 Torr; for 2.33333h; Autoclave; | A 43 %Chromat. B 12 %Chromat. C 37 %Chromat. |
N,N-diethylpropanamide
2-chloro-N,N-diethylpropionamide
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-methylphenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 98% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromo-phenol With {[P(t-Bu3)]PdBr}2; potassium hydride In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 95% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 1-bromo-4-methoxy-benzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 94% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 3-Bromothiophene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 70℃; for 24h; | 92% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-bromoprop-1-ene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 92% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-Bromo-6-methoxynaphthalene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 92% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: (4-bromophenyl)thioanisole With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromobenzenecarbonitrile With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: p-trifluoromethylphenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 90% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromo-aniline With {[P(t-Bu3)]PdBr}2; potassium hydride In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 90% |
Conditions | Yield |
---|---|
Stage #1: dimethyltitanocene; N,N-diethylpropanamide 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; Schlenk technique; Inert atmosphere; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-bromoanisole With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 88% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: bromochlorobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 87% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: para-nitrophenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 87% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 3-Bromopyridine With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 70℃; for 24h; | 86% |
Conditions | Yield |
---|---|
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: o-fluorobromobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h; | 86% |
Conditions | Yield |
---|---|
In dichloromethane addn. of a large excess of ligand in CH2Cl2 to a suspn. of UBr4 in CH2Cl2; stirring for ca 1 h; evapn., dark green oil solidified with toluene; washed with toluene, n-pentane; dried in vac. for 10 h; elem. anal.; | 84% |
N,N-diethylpropanamide
2,4-dimethoxy-N-(phenylmethylene)benzeneamine
Conditions | Yield |
---|---|
With potassium hexamethylsilazane; bis[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]methane In tetrahydrofuran at -78℃; for 24h; Mannich Aminomethylation; Inert atmosphere; stereoselective reaction; | 81% |
N,N-diethylpropanamide
thorium tetrabromide
{ThBr3(C2H5CON(C2H5)2)3}(1+)*Br(1-)={ThBr3(C2H5CON(C2H5)2)3}Br
Conditions | Yield |
---|---|
In tetrahydrofuran an excess of C2H5CON(C2H5)2 was added to a filtered soln. of ThBr4;; after 30 min the product was separated, washed twice with THF, and once with n-pentane, and dried for 8 h in vac.; elem.anal.;; | 80% |
N,N-diethylpropanamide
5-Fluor-2-(4-fluorphenyl)-4-(trifluormethyl)oxazol
2-<2-(4-Fluorphenyl)-4-(trifluormethyl)oxazol-5-yl>propansaeure-diethylamid
Conditions | Yield |
---|---|
In hexane Heating; | 75% |
N,N-diethylpropanamide
Conditions | Yield |
---|---|
In ethanol addn. of large excess of the ligand (in abs. ethanol) to stirred soln. (abs. ethanol); stirring (1 h);; evapn. (colorless oil); dissolving (CH2Cl2); filtrate: evapn. to dryness; solidification overnight under pentane; washing (3 times/n-pentane); drying (vac./8 h); elem. anal.;; | 72% |
N,N-diethylpropanamide
methyloxirane
4-hydroxy-2-methyl-pentanoic acid diethylamide
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran | 71% |
N,N-diethylpropanamide
propargyl bromide
N,N-diethyl-2-methylpent-4-ynamide
Conditions | Yield |
---|---|
With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane; toluene at -75 - 20℃; Inert atmosphere; | 71% |
N,N-diethylpropanamide
uranium(IV) chloride
{UCl3(N,N'-diethylpropionamide)4}{UCl5(N,N'-diethylpropionamide)}
Conditions | Yield |
---|---|
In tetrahydrofuran under N2, large excess of ligand added to soln. of UCl4 in THF, stirredfor 24 h; evapd. slowly in vac.; elem. anal.; | 70% |
Conditions | Yield |
---|---|
at 120℃; for 24h; | 65% |
Conditions | Yield |
---|---|
With hydrogen; hexarhodium hexadecacarbonyl; decacarbonyldirhenium(0) In 1,2-dimethoxyethane at 160℃; under 76000 Torr; for 36h; | 62% |
With dodecacarbonyl-triangulo-triruthenium; hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 16h; Inert atmosphere; | |
With hydrogen In 1,2-dimethoxyethane at 160℃; under 22502.3 Torr; for 20h; Inert atmosphere; Autoclave; Molecular sieve; | |
With [(SIMes)PFMe2][B(C6F5)4]2; phenylsilane at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox; |
Reported in EPA TSCA Inventory.
The N,N-Diethylpropionamide is an organic compound with the formula C7H15NO. The IUPAC name of this chemical is N,N-diethylpropanamide. With the CAS registry number 1114-51-8, it is also named as Diethylamide of propionic acid. The product's categories are Amides; Carbonyl Compounds; Organic Building Blocks. Besides, it should be stored in a closed cool and dry place.
Physical properties about N,N-Diethylpropionamide are: (1)ACD/LogP: 0.85; (2)ACD/LogD (pH 5.5): 0.85; (3)ACD/LogD (pH 7.4): 0.85; (4)ACD/BCF (pH 5.5): 2.6; (5)ACD/BCF (pH 7.4): 2.6; (6)ACD/KOC (pH 5.5): 68.89; (7)ACD/KOC (pH 7.4): 68.89; (8)#H bond acceptors: 2 ; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 20.31 Å2; (11)Index of Refraction: 1.428; (12)Molar Refractivity: 38.22 cm3; (13)Molar Volume: 148.4 cm3; (14)Polarizability: 15.15×10-24cm3; (15)Surface Tension: 27.9 dyne/cm; (16)Density: 0.87 g/cm3; (17)Flash Point: 73.6 °C; (18)Enthalpy of Vaporization: 43.05 kJ/mol; (19)Boiling Point: 194.3 °C at 760 mmHg; (20)Vapour Pressure: 0.444 mmHg at 25°C.
Preparation: this chemical can be prepared by propionyl chloride and diethyl-trimethylsilanyl-amine. This reaction will need solvent hexane. The reaction time is 5 hours at ambient temperature. The yield is about 71%.
Uses of N,N-Diethylpropionamide: it can be used to produce diethyl-propyl-amine at temperature of 160 °C. It will need reagent H2, catalyst Rh6(CO)16, Re2(CO)10 and solvent 1,2-dimethoxy-ethane with reaction time of 36 hours. The yield is about 62%.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. When you are using it, wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N(CC)CC)CC
(2)InChI: InChI=1/C7H15NO/c1-4-7(9)8(5-2)6-3/h4-6H2,1-3H3
(3)InChIKey: YKOQQFDCCBKROY-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C7H15NO/c1-4-7(9)8(5-2)6-3/h4-6H2,1-3H3
(5)Std. InChIKey: YKOQQFDCCBKROY-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 770mg/kg (770mg/kg) | VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 18, Pg. 245, 1966. |
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