Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 23℃; | 100% |
With oxalyl dichloride In dichloromethane at 20℃; | 100% |
With oxalyl dichloride In dichloromethane for 24h; Inert atmosphere; | 100% |
tert-butyl 3-phenylpropanoate
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
With phosphorus trichloride In acetonitrile at 80℃; for 3h; Schlenk technique; | 57% |
With thionyl chloride; water at 20℃; for 0.5h; Reagent/catalyst; Sealed tube; |
4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine
B
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
A 3% B n/a |
Dichloromethyl methyl ether
3-Phenylpropionic acid
A
Methyl formate
B
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
With zinc(II) chloride at 100℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium / toluene / 4 h / Heating 1.2: 51 percent / toluene; benzene / 16 h / Heating 2.1: thionyl chloride / toluene / 2 h / 70 - 75 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / H2 / 5percent Pd-C / ethyl acetate / 10 h 2: thionyl chloride / CHCl3 / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 83 percent / H2 / platinum / ethanol 2: thionyl chloride / benzene View Scheme | |
Multi-step reaction with 2 steps 1: 5% Pd(OH)2/C; hydrogen / ethyl acetate / 22 h / 20 °C / 5171.62 Torr 2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 20 °C View Scheme |
2-methylpropyl 3-phenypropionate
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature 2: dicyclohexylcarbodiimide / CH2Cl2 3: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h 4: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature 2: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme |
3-phenyl-N-(pyridin-3-yl)propanamide
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h 2: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme |
N-(4-nitrophenyl)-3-phenylpropionamide
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) phosgene, 2.) pyridine / 1.) CH2Cl2, 0 deg C, 2.) CH2Cl2, rt, 30 min, 3.) CH2Cl2, 3 h 2: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature 3: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme |
3-Phenyl-N-pyridin-3-yl-thiopropionimidic acid pyridin-2-yl ester
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / water / dioxane / 12 h / Ambient temperature 2: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h 3: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / ethanol / 5 h / 20 °C / Inert atmosphere 2: oxalyl dichloride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal 2: oxalyl dichloride / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere; | |
With trichloroisocyanuric acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Irradiation; |
diazomethane
hydrocinnamic acid chloride
1-diazo-4-phenyl-2-butanone
Conditions | Yield |
---|---|
In diethyl ether 1.) ice-salt bath, 1 h, 2.) ice-salt bath -> room temperature, 1 h; | 100% |
With potassium hydroxide; ethoxyethoxyethanol; N-methyl-N-nitrosotoluene-p-sulfonamide In tetrahydrofuran; diethyl ether; water at 55℃; | 100% |
for 4h; Ambient temperature; | 93% |
diethylamine
hydrocinnamic acid chloride
N,N-diethyl-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 96% |
dimethyl amine
hydrocinnamic acid chloride
N,N-dimethyl-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 100% |
With triethylamine In diethyl ether | 93% |
With triethylamine In diethyl ether Inert atmosphere; | 93% |
1-amino-2-propene
hydrocinnamic acid chloride
N-(prop-2-enyl)-3-phenylpropanamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; | 100% |
hydrocinnamic acid chloride
(S)-5,5-Di(4'-tolyl)-4-isopropyl-1,3-oxazolidin-2-one
(S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With dmap; triethylamine | 100% |
With dmap; triethylamine In dichloromethane at 20℃; for 5h; | 100% |
hydrocinnamic acid chloride
dibenzylamine
(N,N)-dibenzyl-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 90% |
With triethylamine In dichloromethane at 0 - 23℃; for 16h; Inert atmosphere; | 80% |
With triethylamine In dichloromethane at 20℃; for 0.333333h; | 62% |
With triethylamine In dichloromethane at 23℃; for 1h; |
β-naphthol
hydrocinnamic acid chloride
naphthalen-2-yl 3-phenylpropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 23h; | 100% |
With triethylamine In dichloromethane for 23h; | 100% |
pyrrolidine
hydrocinnamic acid chloride
3-phenyl-1-pyrrolidin-1-yl-propane-1-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 99% |
In dichloromethane at 0 - 20℃; Inert atmosphere; | 78% |
With triethylamine In dichloromethane at 20℃; for 12h; | |
at 0 - 20℃; for 20h; Alkaline conditions; |
methyl pyrrolidine-2-carboxylate hydrochloride
hydrocinnamic acid chloride
methyl 1-(3-phenylpropanoyl)pyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 99% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 85% |
2,2-dimethoxyethylamine
hydrocinnamic acid chloride
N-(2,2-dimethoxyethyl)-3-phenylpropanamide
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide; ethyl acetate at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 99% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 86% |
In dichloromethane at 5 - 20℃; |
N-methylhydroxyamine hydrochloride
hydrocinnamic acid chloride
N-hydroxy-N-methyl-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane for 1h; Ambient temperature; | 88% |
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; Inert atmosphere; | 75% |
(3aS,7aS)-hexahydrobenzo[d]oxazol-2(3H)-one
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Stage #1: (4S,5S)-trans-hexahydrobenzoxazolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: hydrocinnamic acid chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; | 99% |
(3aR,7aS)-hexahydrobenzo[d]oxazol-2(3H)-one
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Stage #1: (3aR,7aS)-hexahydrobenzo[d]oxazol-2(3H)-one With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: hydrocinnamic acid chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; | 99% |
(3aS,7aR)-3a,4,5,6,7,7a-hexahydrobenzoxazolin-2-one
hydrocinnamic acid chloride
Conditions | Yield |
---|---|
Stage #1: (3aS,7aR)-3a,4,5,6,7,7a-hexahydrobenzoxazolin-2-one With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: hydrocinnamic acid chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; | 99% |
N,O-dimethylhydroxylamine*hydrochloride
hydrocinnamic acid chloride
N-methoxy-N-methyl-3-phenylpropionamide
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 99% |
With pyridine In dichloromethane at 0 - 20℃; | 93% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide; ethyl acetate at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 91% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 99% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide; ethyl acetate at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 97% |
(S)-1-phenyl-ethylamine
hydrocinnamic acid chloride
N-(3-phenylpropanoyl)-(S)-1-phenylethylamine
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 99% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 75% |
tert-butylamine
hydrocinnamic acid chloride
N-tert-butyl-3-phenylpropionamide
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 25℃; for 2h; | 99% |
With triethylamine In diethyl ether | 86% |
With triethylamine In diethyl ether Inert atmosphere; | 86% |
2,4-dichlorophenol
hydrocinnamic acid chloride
2,4-dichlorophenyl 3-phenylpropanoate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h; | 99% |
1-hydroxy-pyrrolidine-2,5-dione
hydrocinnamic acid chloride
2,5-dioxopyrrolidin-1-yl 3-phenylpropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | 99% |
2-(Methylthio)aniline
hydrocinnamic acid chloride
N-(hydrocinnamoyl)-2-methylthioaniline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 99% |
1-(3-phenylpropanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one
hydrocinnamic acid chloride
1-(3-phenylpropanoyl)-(3R,4R)-3-[1(R)-(3-phenylpropanoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 15h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Molecular sieve; | 99% |
2-(3,4-dimethoxyphenyl)-ethylamine
hydrocinnamic acid chloride
N-(3,4-dimethoxyphenethyl)-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; | 93% |
With sodium hydroxide In dichloromethane; water at 0℃; for 0.166667h; | 1920 mg |
5-(benzyloxy)-3,4,6-trimethylpyridine-2-amine
hydrocinnamic acid chloride
N-[5-(benzyloxy)-3,4,6-trimethylpyridin-2-yl]-3-phenylpropanamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 99% |
With triethylamine In dichloromethane at 20℃; for 8h; | 99% |
With triethylamine In dichloromethane at 20℃; for 8h; | 99% |
With triethylamine In dichloromethane at 20℃; | 99% |
Molecular Structure:
Molecular Formula: C9H9ClO
Molecular Weight: 168.6202
IUPAC Name: 3-Phenylpropanoyl chloride
Synonyms of Hydrocinnamoyl chloride (CAS NO.645-45-4): 3-Phenylpropanoyl chloride ; 3-Phenylpropionyl chloride ; 4-09-00-01762 (Beilstein Handbook Reference) ; AI3-18968 ; BRN 0742586 ; Benzenepropanoyl chloride ; CCRIS 8627 ; Dihydrocinnamoyl chloride ; EINECS 211-443-6 ; Hydrocinnamyl chloride ; NSC 2854 ; Propionyl chloride, 3-phenyl- ; beta-Phenylpropanoyl chloride ; beta-Phenylpropionyl chloride
CAS NO: 645-45-4
Classification Code: Drug / Therapeutic Agent
Melting point: −7-−5 °C
Index of Refraction: 1.527
Molar Refractivity: 45.31 cm3
Molar Volume: 147.2 cm3
Surface Tension: 38.6 dyne/cm
Density: 1.145 g/cm3
Flash Point: 108.3 °C
Enthalpy of Vaporization: 46.86 kJ/mol
Boiling Point: 232 °C at 760 mmHg
Vapour Pressure: 0.0606 mmHg at 25°C
Hydrocinnamoyl chloride (CAS NO.645-45-4) is used in the fields of medicine and organic synthesis.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | intraperitoneal | > 500mg/kg (500mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 221, 1954. | |
rat | LC50 | inhalation | 2750mg/m3/4H (2750mg/m3) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Toxicologist. Vol. 42, Pg. 254, 1998. |
Safety Information of Hydrocinnamoyl chloride (CAS NO.645-45-4):
Hazard Codes: C
Risk Statements: 20-34-29-14
20: Harmful by inhalation
34: Causes burns
29: Contact with water liberates toxic gas
14: Reacts violently with water
Safety Statements: 26-36/37/39-45-8-30-23
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
8: Keep container dry
30: Never add water to this product
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
RTECS: MW5652395
F: 10-21
HazardClass: 8
PackingGroup: II
HS Code: 29163900
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