| Identification | More | [Name]
Hydrocinnamoyl chloride | [CAS]
645-45-4 | [Synonyms]
3-PHENYLPROPANOYL CHLORIDE
3-PHENYLPROPIONIC ACID CHLORIDE
3-PHENYLPROPIONYL CHLORIDE
BENZENEPROPANOYL CHLORIDE
BETA-PHENYLPROPIONYL CHLORIDE
B-PHENYLPROPIONYL CHLORIDE
DIHYDROCINNAMIC ACIDCHLORIDE
HCC
HYDROCINNAMONYL CHLORIDE
HYDROCINNAMOYL CHLORIDE
LABOTEST-BB LTBB000490
PHENYLPROPIONYLCHLORIDE
beta-Phenylpropanoyl chloride
beta-phenylpropanoylchloride
dihydrocinnamoylchloride
Propionyl chloride, 3-phenyl-
2-Ethoxybenzyl Chloride
3-Phenylpropionyl Chloride beta-Phenylpropionyl Chloride
3-PHENYL PROPANOYL CHLOVIDE
3-Phenylpropionylchloride,98% | [EINECS(EC#)]
211-443-6 | [Molecular Formula]
C9H9ClO | [MDL Number]
MFCD00000748 | [Molecular Weight]
168.62 | [MOL File]
645-45-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to light yellow liquid | [Melting point ]
−7-−5 °C(lit.)
| [Boiling point ]
107 °C11 mm Hg(lit.)
| [density ]
1.135 g/mL at 25 °C(lit.)
| [vapor pressure ]
6.893Pa@25°C | [refractive index ]
n20/D 1.5265(lit.)
| [Fp ]
227 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly) | [form ]
Liquid | [color ]
deep greenish-yellow
| [Water Solubility ]
Soluble in water (reacts), and ether. | [Sensitive ]
Moisture Sensitive | [Detection Methods]
GC | [BRN ]
742586 | [InChI]
1S/C9H9ClO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2 | [InChIKey]
MFEILWXBDBCWKF-UHFFFAOYSA-N | [SMILES]
ClC(=O)CCc1ccccc1 | [LogP]
1.73 | [CAS DataBase Reference]
645-45-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzenepropanoyl chloride(645-45-4) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
645-45-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H315-H331-H412 | [Precautionary statements ]
P261-P264-P271-P273-P302+P352-P304+P340+P311 | [Hazard Codes ]
C | [Risk Statements ]
R20:Harmful by inhalation.
R34:Causes burns.
R29:Contact with water liberates toxic gas.
R14:Reacts violently with water. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S8:Keep container dry .
S30:Never add water to this product .
S23: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 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29163900 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Inhalation
Aquatic Chronic 3
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to light yellow liquid | [Uses]
Hydrocinnamoyl chloride is a derivative of phenylpropionic acid used in the preparation of a wide range of pharmaceutical compounds such as antivirals and antitumor agents.
| [General Description]
Reduction of hydrocinnamoyl chloride at mercury cathodes in acetonitrile containing tetraalkylammonium perchlorates has been investigated by cyclic voltammetry. | [Flammability and Explosibility]
Notclassified(100%) | [Synthesis]
General procedure for the synthesis of hydrocinnamoyl chloride from hydrogenated cinnamic acid: To a 200 mL flask equipped with a stir bar and an argon inlet septum were added hydrogenated cinnamic acid (5.00 g, 33.3 mmol), N,N-dimethylformamide (DMF, 0.1 mL), and dichloromethane (CH2Cl2, 30 mL). Oxalyl chloride ((COCl)2, 2 M in CH2Cl2, 20.0 mL, 40.0 mmol) was slowly added to the resulting solution over 30 min. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by vacuum concentration to afford 3-phenylpropionyl chloride (74, 5.9 g, yellow oil) in 100% yield. The purity of the product was confirmed to be 99% by high performance liquid chromatography (HPLC) analysis (mobile phase ratio: water:acetonitrile:methanol = 15:10:75) with a retention time of 5.3 min. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2899 - 2903
[2] Patent: WO2013/101911, 2013, A2. Location in patent: Page/Page column 57
[3] Arkivoc, 2018, vol. 2018, # 5, p. 334 - 347
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830
[5] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6311 - 6314 |
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