Conditions | Yield |
---|---|
With piperidine; pyridine at 22℃; for 3h; ultrasound; | 99% |
With piperidine In pyridine for 5h; Reflux; | 99% |
With aluminum oxide; lithium chloride for 0.1h; Doebner condensation; microwave irradiation; | 97% |
methyl 3-(4-chlorophenyl)propenoate
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 2h; | 98% |
(2RS,3SR)-2,3-dibromo-3-(4-chlorophenyl)propanoic acid
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With zinc In acetic acid for 0.0166667h; microwave irradiation; | 97% |
Conditions | Yield |
---|---|
With calcium carbonate; palladium diacetate In tetrahydrofuran at 60℃; for 4.5h; Heck arylation; | 96% |
Conditions | Yield |
---|---|
With potassium hydroxide; PS-PEG-NH-C(O)C6H4PPh2-PdCl(η3-C3H5) at 25℃; Heck reaction; | 95% |
With tributyl-amine; silica-supported bidentate arsine palladium(0) In para-xylene at 100℃; for 6h; Heck arylation; | 95% |
With tributyl-amine; Si-SH-Pd(0) In xylene at 100℃; for 6h; | 94% |
carbon tetrabromide
1-nitro-2-(4-chlorophenyl)ethylene
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With tris(2,2'-bipyridyl)ruthenium dichloride; water; diisopropylamine In acetonitrile at 20℃; for 10h; Inert atmosphere; Irradiation; stereoselective reaction; | 94% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 0.416667h; Heck Reaction; | 91% |
With tributyl-amine; silica-supported bidentate arsine palladium(0); triphenylphosphine In para-xylene at 140℃; for 12h; Heck arylation; | 55% |
malonic acid
sodium (4-chlorophenyl)(hydroxy)methanesulfonate
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With piperazine In ethylene glycol for 0.108333h; Knoevenagel condensation; microwave irradiation; | 90% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube; | 89% |
Conditions | Yield |
---|---|
With pyridine; dmap; sodium tetraborate decahydrate; N-benzyl-N,N,N-triethylammonium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 8h; | 86% |
With pyridine; dmap; lithium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 10h; | 83% |
maleic anhydride
1-Chloro-4-iodobenzene
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane at 125℃; chemoselective reaction; | 85% |
ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 24h; | 81% |
With potassium hydroxide In ethanol at 20℃; for 2h; | |
With water; lithium hydroxide In methanol at 20℃; for 16h; | |
With sodium hydroxide In ethanol; water at 60℃; | |
With lithium hydroxide In tetrahydrofuran; ethanol; water at 20℃; for 4h; |
carbon dioxide
(E)-4-chlorostyrylboronic acid
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With potassium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 70℃; under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 80% |
(E)-3-(p-chlorophenyl)prop-2-en-1-ol
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With potassium phosphate; carbon dioxide; CrH6Mo6O24(3-)*3H3N*3H(1+) In dimethyl sulfoxide at 80℃; under 750.075 Torr; for 24h; Green chemistry; | 80% |
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran for 2h; Ambient temperature; | 77% |
carbon monoxide
1-(2-bromovinyl)-4-chlorobenzene
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With [bmim]PF6; triethylamine; bis-triphenylphosphine-palladium(II) chloride In water at 100℃; under 15001.2 Torr; for 20h; | 76% |
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane at 130℃; chemoselective reaction; | 74% |
(trimethylsilyl)ketene bis(trimethylsilyl) acetal
4-chlorobenzaldehyde
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With sodium fluoride In N,N-dimethyl-formamide for 5.5h; | 73% |
Conditions | Yield |
---|---|
Stage #1: 3-(4-chlorophenyl)propanoic acid With Zn(2,2,6,6-tetramethylpiperidine)2*2LiCl In tetrahydrofuran at -40℃; for 1.5h; Inert atmosphere; Sealed tube; Stage #2: With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate In tetrahydrofuran at -40 - 60℃; for 3h; Inert atmosphere; Sealed tube; diastereoselective reaction; | 66% |
Conditions | Yield |
---|---|
Stage #1: malonic acid; 4-chlorobenzaldehyde With ammonium acetate In ethanol for 7h; Heating; Stage #2: With hydrogenchloride | A n/a B 65% |
4-vinylbenzyl chloride
carbon tetrabromide
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With Eosin Y; dimethyl sulfoxide; cobalt(II) iodide at 50℃; for 15h; Inert atmosphere; UV-irradiation; | 60% |
(3E)-4-(4-chlorophenyl)-3-buten-2-one
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h; | 51% |
ethyl acetoacetate
4-chlorobenzaldehyde
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
Stage #1: 4-chlorobenzaldehyde With hydrogenchloride; sodium azide; sodium nitrite In water at 0 - 20℃; for 2h; Stage #2: ethyl acetoacetate With triethylamine In N,N-dimethyl-formamide at 20℃; Stage #3: With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 2h; | 51% |
diethylphosphonoacetic acid
4-chlorobenzaldehyde
A
3-(4-chlorophenyl)prop-2-enoic acid
B
(E)-diethyl (4-chlorostyryl)phosphonate
Conditions | Yield |
---|---|
With piperidine; pyridine for 3h; Heating; | A 21% B 48% |
p-chlorobenzylidenepropane-1,3-dioic acid
3-(4-chlorophenyl)prop-2-enoic acid
acetic anhydride
4-chlorobenzaldehyde
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With potassium acetate at 150 - 190℃; | |
With sodium acetate at 180 - 200℃; |
Conditions | Yield |
---|---|
With sodium acetate; acetic anhydride | |
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: water; lithium hydroxide / methanol / 16 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 60 °C 2: sodium hydroxide / ethanol; water / 60 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride Diazotization.Eintragen in ein Gemisch von Maleinsaeure (oder Acrylsaeure), Kupfer(II)-chlorid, Natriumacetat und Wasser; |
(E)-5-(4-chlorostyryl)-3-methyl-4-nitroisoxazole
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 6h; Heating; | 67 % Turnov. |
-α-<<3-(4-chlorophenyl)-1-oxo-2-propenyl>oxy>benzenepropanoic acid
A
3-(4-chlorophenyl)prop-2-enoic acid
B
L-3-phenyllactic acid
Conditions | Yield |
---|---|
carboxypeptidase A In water at 25℃; Rate constant; Equilibrium constant; pH 7.5, ionic strength 0.55; |
3-(4-chlorophenyl)prop-2-enoic acid
cinnamoyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With thionyl chloride In N,N-dimethyl-formamide for 4h; Reflux; | 100% |
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide Reflux; Inert atmosphere; | 100% |
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With aluminum oxide; rhodium(III) chloride; potassium deuteroformate for 0.05h; microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine In tetrahydrofuran; dichloromethane at 60℃; for 6h; Inert atmosphere; | 99% |
diazomethane
3-(4-chlorophenyl)prop-2-enoic acid
methyl 3-(4-chlorophenyl)propenoate
Conditions | Yield |
---|---|
In methanol; diethyl ether at 20℃; for 0.25h; Inert atmosphere; | 98% |
In diethyl ether |
Conditions | Yield |
---|---|
With triethylamine In toluene at 80 - 110℃; for 18h; | 98% |
ethanol
3-(4-chlorophenyl)prop-2-enoic acid
ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 24h; Fischer esterification; Heating; | 97% |
With sulfuric acid for 30h; Reflux; | 70% |
With sulfuric acid for 5h; Heating; | 64% |
3-(4-chlorophenyl)prop-2-enoic acid
α,β-dibromo-p-chlorohydrocinnamic acid
Conditions | Yield |
---|---|
With bromine In acetic acid at 0 - 20℃; for 3.5h; | 97% |
With bromine In tetrachloromethane | 94% |
With bromine In various solvent(s) at 95℃; for 2h; | 77% |
3-(4-chlorophenyl)prop-2-enoic acid
1-nitro-2-(4-chlorophenyl)ethylene
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; copper(II) nitrate trihydrate In acetonitrile at 100℃; for 2h; stereoselective reaction; | 97% |
With ferric nitrate for 1h; Milling; | 86% |
With quinoline; dipotassium peroxodisulfate; tert.-butylnitrite In acetonitrile at 85℃; for 5h; | 85% |
3-(4-chlorophenyl)prop-2-enoic acid
ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; benzene | 97% |
3-(4-chlorophenyl)prop-2-enoic acid
disodium ethylenediaminetetraacetic acid
trans-β-(p-Chlorophenyl)glycidic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate In water; ethyl acetate; acetone | 97% |
methanol
3-(4-chlorophenyl)prop-2-enoic acid
methyl 3-(4-chlorophenyl)propenoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Reflux; | 96% |
Dowex H+ resin Heating; | 95% |
With Dowex-WX4 In various solvent(s) Heating; | 95% |
3-(4-chlorophenyl)prop-2-enoic acid
o-phenylenediamine sulphate
(E)-2-(4-chlorostyryl)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
In ethylene glycol for 3h; Heating; | 96% |
Conditions | Yield |
---|---|
Stage #1: NH-pyrazole With thionyl chloride In dichloromethane at 0 - 25℃; for 1h; Stage #2: 3-(4-chlorophenyl)prop-2-enoic acid In dichloromethane for 3h; | 96% |
Stage #1: NH-pyrazole With thionyl chloride In dichloromethane at 0 - 20℃; for 1h; Stage #2: 3-(4-chlorophenyl)prop-2-enoic acid In dichloromethane for 3h; | 96% |
3-(4-chlorophenyl)prop-2-enoic acid
N,O-dimethylhydroxylamine*hydrochloride
(E)-3-(4-chlorophenyl)-N-methoxy-N-methylacrylamide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 96% |
3-(4-chlorophenyl)prop-2-enoic acid
methyl 3-(4-chlorophenyl)propenoate
Conditions | Yield |
---|---|
With sulfuric acid In methanol | 95% |
With hydrogenchloride; methanol | |
Multi-step reaction with 2 steps 1: SOCl2 2: methanol View Scheme | |
With sulfuric acid In methanol | |
Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / 20 °C 2: dichloromethane / 0.5 h / 20 °C View Scheme |
3-(4-chlorophenyl)prop-2-enoic acid
(2RS,3SR)-2,3-dibromo-3-(4-chlorophenyl)propanoic acid
Conditions | Yield |
---|---|
With copper(II) nitrate trihydrate; trimethylsilyl bromide In acetonitrile at 50℃; for 2h; | 95% |
With selenium(IV) oxide; hydrogen bromide In diethyl ether Ambient temperature; | 35% |
With chloroform; bromine at 20℃; |
3-(4-chlorophenyl)prop-2-enoic acid
(E)-3-(4-Chloro-phenyl)-acryloyl azide
Conditions | Yield |
---|---|
With sodium azide; N,N-dimethyl-formamide; trichlorophosphate at 10 - 15℃; for 3h; | 95% |
With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; Inert atmosphere; | 80% |
With thionyl chloride; sodium azide 1) 1 h, reflux, 2) 1 h, acetone, water; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: triethylamine / acetone / 1 h / 0 °C 2: sodium azide / acetone; H2O / 16 h / 20 °C View Scheme | |
With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 3h; Cooling with ice; |
(3S,5S)-3-(2-tert-butoxycarbonylaminoethyl)-5-(aminomethyl)-1-(2-ethylbutyl)-1,4-diazepan-2-one
3-(4-chlorophenyl)prop-2-enoic acid
(E)-N-(((3S,5S)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl)methyl)-3-(4-chlorophenyl)acrylamide
Conditions | Yield |
---|---|
Stage #1: (3S,5S)-3-(2-tert-butoxycarbonylaminoethyl)-5-(aminomethyl)-1-(2-ethylbutyl)-1,4-diazepan-2-one; 3-(4-chlorophenyl)prop-2-enoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h; | 95% |
Stage #1: (3S,5S)-3-(2-tert-butoxycarbonylaminoethyl)-5-(aminomethyl)-1-(2-ethylbutyl)-1,4-diazepan-2-one; 3-(4-chlorophenyl)prop-2-enoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h; | 95% |
3-(4-chlorophenyl)prop-2-enoic acid
methoxybenzene
4'-methoxy-4-chlorochalcone
Conditions | Yield |
---|---|
With phosphoric acid; trifluoroacetic acid at 20℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 125℃; for 3h; | 94% |
3-(4-chlorophenyl)prop-2-enoic acid
N-isocyaniminotriphenylphosphorane
dimethylglyoxal
3-{5-[(E)-2-(4-chlorophenyl)-1-ethenyl]-1,3,4-oxadiazol-2-yl}-3-hydroxy-2-butanone
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.333333h; Aza-Wittig Reaction; Sonication; | 94% |
In water at 20 - 26℃; for 12h; Green chemistry; | 90% |
In dichloromethane at 20℃; for 12h; Aza-Wittig Reaction; Neutral conditions; | 88% |
cyclohexyl-N-tosyl aziridine
3-(4-chlorophenyl)prop-2-enoic acid
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 48h; Inert atmosphere; | 94% |
3-(4-chlorophenyl)prop-2-enoic acid
(R)-4-(phenylmethyl)-2-oxazolidinone
(4R)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 3-(4-chlorophenyl)prop-2-enoic acid; (R)-4-(phenylmethyl)-2-oxazolidinone With pivaloyl chloride; triethylamine In tetrahydrofuran at -20℃; for 2h; Stage #2: With lithium chloride In tetrahydrofuran at -20℃; for 16h; Further stages.; | 93% |
1. Introduction of 4-Chlorocinnamic acid
4-Chlorocinnamic acid , its cas register number is 1615-02-7. It also can be called p-Chlorocinnamic acid; 3-(p-Chlorophenyl)acrylic acid; trans-3-(4-Chlorophenyl)propenoic acid; and 3-(4-Chlorophenyl)-2-propenoic acid. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, 4-Chlorocinnamic acid could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Hydrogen chloride, carbon monoxide, carbon dioxide.
2. Properties of 4-Chlorocinnamic acid
Melting point: 248-250 °C(lit.)
Index of Refraction: 1.627
Molar Refractivity: 48.6 cm3
Molar Volume: 136.9 cm3
Surface Tension: 52 dyne/cm
Density: 1.332 g/cm3
Flash Point: 150.5 °C
Enthalpy of Vaporization: 59.9 kJ/mol
Boiling Point: 325.3 °C at 760 mmHg
Vapour Pressure: 9.47E-05 mmHg at 25 °C
Appearance: White to light yellow crystal powder
3. Structure Descriptors of 4-Chlorocinnamic acid
InChI
InChI=1/C9H7ClO2/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6H,(H,11,12)/b6-3+
Smiles
c1(ccc(Cl)cc1)\C=C\C(O)=O
Product Categories: Benzene series;Cinnamic acid;Aromatics Compounds;Acids & Esters;Chlorine Compounds
4. Toxicity of 4-Chlorocinnamic acid
4-Chlorocinnamic acid hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | intraperitoneal | > 350mg/kg (350mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA BEHAVIORAL: REGIDITY | Indian Journal of Pharmaceutical Sciences. Vol. 49, Pg. 77, 1987. |
mouse | LD50 | oral | 1622mg/kg (1622mg/kg) | Pharmazie. Vol. 23, Pg. 714, 1968. |
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36-28A-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36:Wear suitable protective clothing.
WGK Germany 3
RTECS GD8490000
Hazard Note Irritant
6. Preparation of 4-Chlorocinnamic acid
4-Chlorocinnamic acid can be derived by the reaction of right-Chlorobenzaldehyde with Acetic anhydride . Taking Chlorobenzaldehyde , Acetic anhydride and Sodium acetate together at 180 ° C for the reaction 13h.
7. Use of 4-Chlorocinnamic acid
4-Chlorocinnamic acid is used as organic synthesis intermediate for the synthesis of aromatic acid, production of herbicide Mr enemy scattered.
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