21087-29-6

Basic information

• Product Name: Cinnamyl chloride
• Synonyms: trans-Cinnamylchloride;(3-Chloro-1-propenyl)benzene;3-Chloro-1-phenyl-1-propene;Cinnamyl chloride;[(E)-3-Chloroprop-1-enyl]benzene;(E)-3-Chloro-1-phenyl-1-propene;(E)-3-Phenylallyl chloride;[(E)-3-Chloro-1-propenyl]benzene
• CAS NO: 21087-29-6
• Molecular Formula: C₉H₉Cl
• Molecular Weight: 152.62
• EINECS: 220-246-4
• Mol File: 21087-29-6.mol
• Article Data: 49

Chemical Properties

• Melting Point: −19 °C(lit.)
• Boiling Point: 108 °C12 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0614mmHg at 25°C
• Refractive Index: n20/D 1.584(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: 200 mg/L (20 ºC)
• CAS DataBase Reference: Cinnamyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamyl chloride(21087-29-6)
• EPA Substance Registry System: Cinnamyl chloride(21087-29-6)

Safety Data

• Hazard Codes: T+,Xn
• Statements: 22-26-34-43-36/37/38
• Safety Statements: 26-28-36/37/39-45-37/39
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• RTECS: CZ0919905
• Hazardous Substances Data: 21087-29-6(Hazardous Substances Data)

Usage

Uses

(E)-Cinnamyl chloride synthesis of aryl and heterocyclic polyenes which exhibit antioxidant activity.

InChI:InChI=1/C9H9Cl/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2

Upstream product

• 100-42-5 styrene 
• 50-00-0 formaldehyd 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 4392-26-1 vinylbenzyl chloride 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 1476-11-5 Z-1,4-dichlorobutene 
• 7348-71-2 (E)-1-bromo-2-pentene 
• 33317-04-3 Methyl 4,5-dimethyl-3-formylpyrrole-2-carboxylate 
• 100-58-3 phenylmagnesium bromide 
• 107-02-8 acrolein 
• 768-03-6 Phenyl vinyl ketone 
• 100-52-7 benzaldehyde 

Downstream Products

• 108400-97-1 ethyl (4E)-2-acetyl-5-phenylpent-4-enoate 
• 99858-64-7 2-trans-cinnamylamino-ethanol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 117049-66-8 2-ethan-1-ol 
• 55089-14-0 2-(4t-phenyl-but-3-enyl)-4,5-dihydro-thiazole 
• 55552-40-4 (E)-2,3-Dimethyl-6-phenyl-hex-5-en-3-ol 
• 40596-08-5 2,3-dimethyl-4-phenyl-hex-5-en-3-ol 
• 104047-02-1 (3RS,4RS)-(E)-1,4-diphenylhexa-1,5-dien-3-ol 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 63158-17-8 methyl 4-phenyl 2-butenoate 
• 91083-82-8 (E)-methyl 4-phenylbut-3-enoate 
• 40395-23-1 3-phenyl-1-heptene 
• 10201-58-8 (E)-1-heptenylbenzene 
• 19752-23-9 cinnamyltrimethylsilane 

Relevant articles and documents

Geranyl-chlorid, ein einfaches Herstellungsverfahren

-

NMP-mediated chlorination of aliphatic alcohols with aryl sulfonyl chloride for the synthesis of alkyl chlorides

NMP-mediated chlorination of aliphatic alcohols has been developed for the synthesis of alkyl chlorides. This facile, efficient and practical approach used simple and readily available aryl sulfonyl chlorides as the chlorination reagent for the construction of C–Cl bond in good to excellent yields with mild conditions and broad substrate scope.

Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.