propionic acid
propionyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide at 70 - 75℃; | 97% |
With N,N-dimethyl-formamide; trichlorophosphate at 100℃; | 93.7% |
Stage #1: propionic acid With chloroform; oxygen; N,N-dimethyl-formamide at 30℃; for 3h; Irradiation; Stage #2: at 30℃; for 2h; | 86% |
Conditions | Yield |
---|---|
With phosphorus trichloride at 40 - 50℃; 4-5h; | A 57.9% B n/a |
With phosphorus trichloride at 40 - 50℃; 4-5h; | A 46.4% B 18% |
trimethylsilyl propionate
chlorosulfonate de trimethylsilyle
A
propionyl chloride
B
trimethylsilyl 1-<(trimethylsiloxy)carbonyl>ethanesulfonate
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane for 12h; Mechanism; Heating; course is discussed; further trimethylsilyl carboxylates, aldehydes and ketones; | A n/a B 41% |
In 1,2-dichloro-ethane for 12h; Heating; | A n/a B 41% |
3,4-dichloro-(E)-3-hexene
A
propionyl chloride
B
1,1-Dichlorpropylhydroperoxid
Conditions | Yield |
---|---|
With hydrogenchloride; ozone; formic acid ethyl ester at -10 - 0℃; |
Conditions | Yield |
---|---|
at 20℃; |
tetrachloromethane
chlorine
propionic acid anhydride
A
propionyl chloride
Conditions | Yield |
---|---|
at -15 - -5℃; unter Lichtausschluss; |
3,3-dichloro-1,2-diphenylcyclopropene
propionic acid
A
propionyl chloride
B
diphenylcyclopropenone
Conditions | Yield |
---|---|
In chloroform-d1 for 0.25h; Inert atmosphere; |
pentan-3-one
A
2-chloro-3-pentanone
B
1-chloro-3-pentanone
C
2,3-Pentanedione
D
propionyl chloride
E
acetaldehyde
Conditions | Yield |
---|---|
With oxygen; chlorine at 23.84℃; under 830 - 980 Torr; UV-irradiation; |
pentan-3-one
A
2-chloro-3-pentanone
B
1-chloro-3-pentanone
C
4-penten-3-one
D
propionyl chloride
E
acetaldehyde
Conditions | Yield |
---|---|
With oxygen; chlorine at 236.84℃; under 700 - 950 Torr; UV-irradiation; |
pentan-3-one
A
2-chloro-3-pentanone
B
1-chloro-3-pentanone
C
propionyl chloride
D
acetaldehyde
Conditions | Yield |
---|---|
With chlorine at 23.84℃; under 830 - 980 Torr; UV-irradiation; |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0℃; for 1.5h; Inert atmosphere; | 100% |
With aluminum (III) chloride In dichloromethane at 0℃; for 1.5h; Inert atmosphere; | 100% |
With zinc trifluoromethanesulfonate In nitromethane at 20℃; for 4h; Friedel-Crafts acylation; | 89% |
Conditions | Yield |
---|---|
for 8h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With Noccaea caerulescens extract supported in montmorillonite K10 at 60℃; for 6h; Friedel Crafts acylation; Inert atmosphere; regioselective reaction; | 100% |
With aluminum (III) chloride In dichloromethane at 5 - 20℃; for 2.5h; | 98% |
With benzyltributylammonium tetrachloroferrate at 50℃; for 0.1h; Friedel-Crafts reaction; | 93% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In acetone | 100% |
With triethylamine In benzene |
cortienic acid
propionyl chloride
11β-hydroxy-17α-propanoyloxy-3-oxo-androst-4-ene-17β-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
(i), (ii) Et2NH, acetone; Multistep reaction; |
Conditions | Yield |
---|---|
In pyridine for 3h; Ambient temperature; | 100% |
(-)-N-methylephedrine
propionyl chloride
(1R,2S)-(2-Dimethylamino-1-phenyl)propyl propanoate
Conditions | Yield |
---|---|
In dichloromethane | 100% |
In dichloromethane for 4h; Ambient temperature; | 99% |
In dichloromethane for 3h; Ambient temperature; | 99% |
In dichloromethane Yield given; |
(S)-4-Benzyl-2-oxazolidinone
propionyl chloride
(S)-4-benzyl-3-propionyl-2-oxazolidinone
Conditions | Yield |
---|---|
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: propionyl chloride In tetrahydrofuran at 0 - 20℃; | 100% |
With n-butyllithium In tetrahydrofuran | 100% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 99% |
propionyl chloride
2-phenylethyl chloride
4-(2-chloroethyl)propiophenone
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 0.416667h; Ambient temperature; | 100% |
aluminium trichloride In 1,2-dichloro-ethane | |
aluminium trichloride In 1,2-dichloro-ethane |
propionyl chloride
lithium 2,6-dimethylphenolate dimer
2,6-dimethylphenyl propionate
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; | 100% |
propionyl chloride
1-[(2R,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
Propionic acid (2R,3S,4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-phenylselanyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
100% |
propionyl chloride
(2S*,3S*)-1-<(tert-butyldimethylsilyl)oxy>-2-methyl-4-penten-3-ol
(2S*,3S*)-1-<(tert-butyldimethylsilyl)oxy>-2-methyl-4-penten-3-yl propanoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 2h; Ambient temperature; | 100% |
In dichloromethane | 73% |
propionyl chloride
2-(4-{2-[8-Fluoro-5-(4-fluoro-phenyl)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-ethyl}-piperazin-1-yl)-ethanol
Propionic acid 2-(4-{2-[8-fluoro-5-(4-fluoro-phenyl)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-ethyl}-piperazin-1-yl)-ethyl ester
Conditions | Yield |
---|---|
In chloroform for 1h; Heating; | 100% |
propionyl chloride
1-[8-Fluoro-5-(4-fluoro-phenyl)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-ethanone
Propionic acid 2-(4-{2-[8-fluoro-5-(4-fluoro-phenyl)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-2-oxo-ethyl}-piperazin-1-yl)-ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In chloroform for 1h; Heating; | 100% |
propionyl chloride
(S)-8-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride
(2S)-8-methoxy-2-(N-propylpropionamido)-1,2,3,4-tetrahydronaphthaline
Conditions | Yield |
---|---|
With triethylamine In diethyl ether Ambient temperature; | 100% |
propionyl chloride
(1S,2R)-N,N-dimethyl-2-hydroxy-1,2-diphenyl-ethylamine
Conditions | Yield |
---|---|
In dichloromethane | 100% |
propionyl chloride
(S)-(-)-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride
(S)-N-propionyl-7-methoxy-2-(propylamine)tetralin
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane for 0.5h; | 100% |
propionyl chloride
1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
N,N'-dipropanoyl-4,13-diaza-18-crown-6
Conditions | Yield |
---|---|
With sodium carbonate In benzene for 12h; Ambient temperature; | 100% |
propionyl chloride
cis-(1S,2S)-2-(3-methoxyphenyl)-N-propylcyclohexylamine
N-[(1S,2S)-2-(3-Methoxy-phenyl)-cyclohexyl]-N-propyl-propionamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1.5h; Ambient temperature; | 100% |
propionyl chloride
cis-(1R,2R)-2-(3-methoxyphenyl)-N-propylcyclohexylamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1.5h; Ambient temperature; | 100% |
propionyl chloride
cis-(1R,2R)-2-(3-methoxyphenyl)-N-propylcyclohexylamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1.5h; Ambient temperature; | 100% |
propionyl chloride
2-n-Propylamino-8-chloro-1,2,3,4-tetrahydronaphthalene
8-chloro-2-(N-n-propyl-N-propionyl-amino)-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.166667h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With diiodosilane; iodine In chloroform-d1 at 25℃; for 0.166667h; | 100% |
With trimethylsilyl iodide | 93% |
With sodium iodide In acetonitrile for 1h; Ambient temperature; | 53% |
With sodium iodide at 20℃; for 0.166667h; |
pentamethylbenzene,
propionyl chloride
1-(2,3,4,5,6-pentamethylphenyl)propan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0℃; for 0.583333h; | 100% |
aluminium trichloride In dichloromethane at 0℃; for 4h; | 92.1% |
propionyl chloride
(R)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-amino-4-oxo-4-(benzyloxy)butanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.5h; Ambient temperature; | 100% |
(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one
propionyl chloride
(4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Metallation; Stage #2: propionyl chloride In tetrahydrofuran; hexane at -78 - 0℃; for 1.5h; Acylation; | 100% |
Stage #1: (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: propionyl chloride In tetrahydrofuran at -78℃; for 2h; | 99.5% |
Stage #1: (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: propionyl chloride In tetrahydrofuran; hexane at -78 - 20℃; | 97% |
(R)-4-(phenylmethyl)-2-oxazolidinone
propionyl chloride
(3R)-3-propionyl-4-benzyloxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - -68℃; for 1h; Cooling with acetone-dry ice; Stage #2: propionyl chloride In tetrahydrofuran; hexane at -68 - 20℃; for 2.25h; | 100% |
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere; | 99% |
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 99% |
propionyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
propionyl chloride
(3aR,6S,6aR)-6-Isopropyl-3,3-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-c]isoxazole
1-[(3aR,6S,6aR)-6-Isopropyl-3,3-dimethyl-5-(toluene-4-sulfonyl)-hexahydro-pyrrolo[3,4-c]isoxazol-1-yl]-propan-1-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
Reported in EPA TSCA Inventory.
1. Introduction of Propionyl chloride
Propionyl chloride, its Synonyms are Propionic acid chloride; Propionic chloride; Propanoyl chloride.
2. Properties of Propionyl chloride
XLogP3-AA: 1.2
H-Bond Donor: 0
H-Bond Acceptor: 1
Index of Refraction: 1.396
Molar Refractivity: 20.82 cm3
Molar Volume: 86.5 cm3
Surface Tension: 25.7 dyne/cm
Density: 1.068 g/cm3
Flash Point: 11.7 °C
Enthalpy of Vaporization: 31.67 kJ/mol
Boiling Point: 75.5 °C at 760 mmHg
Vapour Pressure: 105 mmHg at 25 °C
Appearance: colorless liquid with a pungent odor
Melting Point: -94 °C
storage temp.: Flammables area
Water Solubility: REACTS
FreezingPoint: -94 °C
Sensitive: Moisture Sensitive
Product Categories: Organics; Acid Halides; Carbonyl Compounds; Organic Building Blocks
3. Structure Descriptors of Propionyl chloride
Canonical SMILES: CCC(=O)Cl
InChI: InChI=1S/C3H5ClO/c1-2-3(4)5/h2H2,1H3
InChIKey: RZWZRACFZGVKFM-UHFFFAOYSA-N
4. Safety Information of Propionyl chloride
A corrosive irritant to skin, eyes, and mucous membranes. Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Reacts with water or steam to produce toxic and corrosive fumes. Exothermic reaction with diisopropyl ether produces much gas. The reaction may be dangerous if confined. To fight fire, use CO2, dry chemical; do not use water. When heated to decomposition it emits highly toxic fumes of Cl−.
Hazard Codes: F,C
Risk Statements: 11-14-34
R11:Highly flammable.
R14 :Reacts violently with water.
R34:Causes burns.
Safety Statements: 9-16-26-45
S9:Keep container in a well-ventilated place.
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1815 3/PG 2
WGK Germany: 1
HazardClass: 3
PackingGroup: II
RTECS: UG6657000
5. Use of Propionyl chloride
In the pharmaceutical industry, Propionyl chloride is used for the production of anti-epileptic drugs , anti-adrenaline drug,etc.
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