2687-12-9

Basic information

• Product Name: Cinnamyl chloride
• Synonyms: beta-chloromethylstyrene;Propene, 3-chloro-1-phenyl-;r-Chloropropenylbenzene;β-Chloromethylstylene;3-PHENYLALLYL CHLORIDE;3-PHENYL-2-PROPENYL CHLORIDE;(3-CHLOROPROPENYL)BENZENE;3-CHLORO-1-PHENYLPROPENE
• CAS NO: 2687-12-9
• Molecular Formula: C₉H₉Cl
• Molecular Weight: 152.62
• EINECS: 220-246-4
• Product Categories: Pharmaceutical Intermediates
• Mol File: 2687-12-9.mol
• Article Data: 33

Chemical Properties

• Melting Point: −19 °C(lit.)
• Boiling Point: 108 °C12 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Yellow to yellow-brown/Liquid
• 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.: Refrigerator (+4°C)
• Water Solubility: 0.2 g/L (20 ºC)
• Sensitive: Lachrymatory
• BRN: 741974
• CAS DataBase Reference: Cinnamyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamyl chloride(2687-12-9)
• EPA Substance Registry System: Cinnamyl chloride(2687-12-9)

Safety Data

• Hazard Codes: T+,C
• Statements: 22-26-34-43-36
• Safety Statements: 26-28-36/37/39-45-28A-23-27
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• RTECS: CZ0919905
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2687-12-9(Hazardous Substances Data)

Usage

Description

Cinnamyl chloride is a yellow to yellow-brown liquid that reacts regioselectively with aryl and alkenylgold(I) phosphanes in the presence of a palladium catalyst in THF, resulting in the formation of the α-substitution product. It is a versatile chemical intermediate with various applications in different industries.

Uses

Used in Pharmaceutical Industry:
Cinnamyl chloride is used as a key intermediate for the enantioselective total synthesis of helioporins C and E, which are bioactive marine diterpenes. These compounds have potential applications in the development of new drugs and therapies due to their unique chemical structures and biological activities.
Used in Chemical Synthesis:
Cinnamyl chloride is utilized as a valuable building block in the synthesis of various organic compounds, taking advantage of its reactivity with aryl and alkenylgold(I) phosphanes in the presence of a palladium catalyst. This allows for the creation of a wide range of chemical products with diverse applications.
Used in Research and Development:
Due to its unique chemical properties and reactivity, cinnamyl chloride is also employed in research and development settings to explore new reaction pathways, develop novel synthetic methods, and investigate its potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.

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

Upstream product

• 104-54-1 3-Phenylpropenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 60-29-7 diethyl ether 
• 122-04-3 4-nitro-benzoyl chloride 
• 18776-14-2 1-Phenyl-1-aethoxy-propanol-⁽³⁾ 
• 772-00-9 4-phenyl-1,3-dioxane 
• 67-66-3 chloroform 
• 4392-26-1 vinylbenzyl chloride 
• 100-42-5 styrene 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 7732-18-5 water 
• 13898-47-0 hypochloric acid 
• 5586-89-0 3-phenylprop-2-en-1-amine hydrochloride 

Downstream Products

• 85620-82-2 (E)-4-cinnamylmorpholine 
• 33962-90-2 N,N-dimethylcinnamylamine 
• 97526-50-6 triethyl-cinnamyl-ammonium; chloride 
• 1142-24-1 N-cinnamylbenzenamine 
• 22774-39-6 N,N-bis-cinnamylaniline 
• 60960-88-5 N-methyl-3-phenylprop-2-en-1-amine 
• 74394-96-0 3-phenyl-2-propenyl thiocyanate 
• 16170-45-9 4-phenylbut-3-enenitrile 
• 1476-07-9 cinnamyl ethyl ether 
• 4360-51-4 cinnamylamine 
• 17480-07-8 2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 90149-90-9 2-hydroxy-3-(3-phenylallyl)-1,4-naphthoquinone 
• 96654-82-9 trimethyl-trans-cinnamyl-ammonium; chloride 
• 96654-82-9 cinnamyl-trimethyl-ammonium; chloride 

Relevant articles and documents

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A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones

A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.

Intermolecular Halogenation/Esterification of Alkenes with N-Halosuccinimide and Acetic Acid Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

1,4-Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N-chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans-chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N-bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Br?nsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems. (Figure presented.).