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| CAS No.: | 621-82-9 |
|---|---|
| Name: | 2-Propenoicacid, 3-phenyl- |
| Article Data: | 643 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C9H8O2 |
| Molecular Weight: | 148.161 |
| Synonyms: | Cinnamicacid (7CI,8CI);3-Phenyl-2-propenoic acid;3-Phenylacrylic acid;NSC 623441;NSC 9189;Phenylacrylic acid;b-Phenylacrylicacid;Cinnamic acid; |
| EINECS: | 210-708-3 |
| Density: | 1.184 g/cm3 |
| Melting Point: | 133 °C(lit.) |
| Boiling Point: | 265 °C at 760 mmHg |
| Flash Point: | 189.5 °C |
| Solubility: | 0.4 g/L (20℃) |
| Appearance: | monoclinic crystal |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| Transport Information: | N/A |
| PSA: | 37.30000 |
| LogP: | 1.78440 |
allyl cinnamate
Cinnamic acid
| Conditions | Yield |
|---|---|
| With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere; | 100% |
| Stage #1: allyl cinnamate With sodium tetrahydroborate In dimethyl sulfoxide at 20℃; Stage #2: With hydrogenchloride; water In dimethyl sulfoxide for 0.5h; chemoselective reaction; | 87% |
C23H18O3
Cinnamic acid
| Conditions | Yield |
|---|---|
| With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 1h; Irradiation; | 100% |
| With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 90℃; for 12h; chemoselective reaction; | 71% |
Cinnamic acid
| Conditions | Yield |
|---|---|
| With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Irradiation; | 100% |
| Conditions | Yield |
|---|---|
| With PNODAM-5 catalyst; triethylamine In n-heptane; N,N-dimethyl acetamide at 100℃; for 22h; Heck reaction; | 99% |
| With tetrabutyl ammonium fluoride; palladium diacetate; potassium carbonate at 70℃; for 18h; Heck reaction; air; | 99% |
| With potassium carbonate In water at 90℃; for 2h; Heck Reaction; Green chemistry; | 98% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; acetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid at 90℃; for 27h; Heck reaction; | 99% |
| With dihydrogen hexachloroplatinate; trifluoroacetic acid for 6h; Heating; | 6.5% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; potassium carbonate In PEG-400 at 60℃; for 18h; Heck type coupling reaction; under air; | 99% |
| Conditions | Yield |
|---|---|
| With iodine; aluminium In acetonitrile at 80℃; for 18h; | 98% |
| With potassium hydroxide In methanol at 35℃; for 0.416667h; | 96% |
| With Dowex-50 In water for 12h; Heating; | 88% |
| Conditions | Yield |
|---|---|
| With NAD; alcohol dehydrogenase HeADH-II from Halomonas elongata; NADH-oxidase from Lactobacillu spentosus; flavin-adenin dinucleotide, disodium salt In dimethyl sulfoxide for 4h; pH=8; Enzymatic reaction; | 98% |
| With C30H24AgBr4N8(1+)*AgBr2(1-); potassium hydroxide In 1,2-dimethoxyethane at 60℃; for 24h; Molecular sieve; Schlenk technique; | 95% |
| With potassium pyrosulfate; potassium aquapentachlororuthenate(III); potassium hydroxide at 20℃; for 0.5h; Catalytic behavior; Sonication; | 94% |
| Conditions | Yield |
|---|---|
| Stage #1: acrylic acid With potassium tert-butylate In water at 20℃; for 0.166667h; Inert atmosphere; Stage #2: bromobenzene With C16H21Br2N3Pd In water at 120℃; for 24h; Mizoroki-Heck reaction; Inert atmosphere; Sealed tube; | 98% |
| With potassium carbonate In water at 90℃; for 1.5h; Heck Reaction; Green chemistry; | 98% |
| With potassium carbonate In water for 2.5h; Heck Reaction; Reflux; Green chemistry; | 98% |
| Conditions | Yield |
|---|---|
| With 2-carbamoylhydrazine-1-sulfonic acid In neat (no solvent) at 110℃; for 0.416667h; Reagent/catalyst; Temperature; Solvent; Green chemistry; | 98% |
| With lemon juice In water at 20℃; for 0.25h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry; | 98% |
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The Cinnamic acid is an organic compound with the formula C9H8O2. The IUPAC name of this chemical is (E)-3-phenylprop-2-enoic acid. With the CAS registry number 621-82-9, it is also named as 3c-phenyl-acrylic acid. The product's classification codes are Drug / Therapeutic Agent; Skin / Eye Irritant. Besides, it is a monoclinic crystal, which should be stored in a closed cool and dry place. It is mainly used for making esters of cinnamic acid.
Physical properties about Cinnamic acid are: (1)ACD/LogP: 2.41; (2)ACD/LogD (pH 5.5): 0.79; (3)ACD/LogD (pH 7.4): -0.91; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 11.54; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 26.3Å2; (12)Index of Refraction: 1.616; (13)Molar Refractivity: 43.7 cm3; (14)Molar Volume: 125 cm3; (15)Polarizability: 17.32×10-24cm3; (16)Surface Tension: 49.7 dyne/cm; (17)Density: 1.184 g/cm3; (18)Flash Point: 189.5 °C; (19)Enthalpy of Vaporization: 53.13 kJ/mol; (20)Boiling Point: 265 °C at 760 mmHg; (21)Vapour Pressure: 0.00471 mmHg at 25°C.
Preparation: this chemical can be prepared by acrylic acid and iodobenzene. This reaction will need reagent Na2CO3, catalyst PdCl2 and solvent H2O. The reaction temperature is 100 °C.
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Uses of Cinnamic acid: it can be used to produce 3-phenyl-acrylic acid methyl ester by heating. It will need reagent silica chloride with reaction time of 5 hours. The yield is about 94%.
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When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C=C\c1ccccc1
(2)InChI: InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
(3)InChIKey: WBYWAXJHAXSJNI-VOTSOKGWBT
(4)Std. InChI: InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
(5)Std. InChIKey: WBYWAXJHAXSJNI-VOTSOKGWSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LDLo | oral | > 5gm/kg (5000mg/kg) | Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974. | |
| mouse | LD50 | intraperitoneal | 160mg/kg (160mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 687, 1978. | |
| mouse | LD50 | intravenous | 380mg/kg (380mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 617, 1969. | |
| mouse | LD50 | oral | 5gm/kg (5000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(1), Pg. 94, 1981. | |
| rat | LD50 | intraperitoneal | 1600mg/kg (1600mg/kg) | Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973. | |
| rat | LD50 | oral | 2500mg/kg (2500mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 687, 1978. |
