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

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

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

Method for preparing 2-chloro-5-substituted pyridine

The invention belongs to the technical field of chemical synthesis of pesticides, and particularly relates to a method for preparing 2-chloro-5-substituted pyridine, in particular to a method for preparing 2-chloro-5-methylpyridine. The method comprises the following steps: reacting amide as shown in a formula C which is used as a raw material in the presence of a chlorinating agent and N, N-dimethylformamide, and distilling after the reaction is finished to obtain the 5-substituted 2-chloropyridine as shown in a formula I which is described in the specification. When the 5-substituted 2-chloropyridine is prepared from the compound with the structure shown in the formula C, the by-product is allyl chloride (or homologues thereof) with small molecular weight, the boiling point of the by-product is obviously different from that of the product, the reaction conversion rate and the yield are higher than those of the prior art, the by-product is easy to separate from the product, and the by-product is more beneficial to recovery; therefore, according to the preparation method, the equipment investment can be greatly saved, the production cost is reduced, and the operation procedure is simplified; and in the route, the amine with lower price is used as a starting raw material, so that the production cost is reduced.

PdII/Novel Chiral Cinchona Alkaloid Oxazoline-Catalyzed Enantioselective Oxidative Cyclization of Aromatic Alkenyl Amides

A highly enantioselective PdII-catalyzed aza-Wacker oxidation tandem cyclization of aromatic nitrogen-containing dienes has been achieved in the presence of novel chiral cinchona alkaloid oxazoline ligands for the first time, affording chiral dihydroindole nitrogen-containing polycyclic compounds with good yields (up to 83 %), high diastereoselectivities (> 95:5 dr), and excellent enantioselectivities (up to 97 % ee).

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.).

SNAr catalysis enhanced by an aromatic donor-acceptor interaction; Facile access to chlorinated polyfluoroarenes

Selective catalytic SNAr reaction of polyfluoroaryl C-F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor-acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility.

Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

Formononetin derivatives and preparation methods and medical application thereof

The invention relates to the field of pharmaceutical chemistry, and relates to formononetin derivatives and preparation methods and medical application thereof, in particular to formononetin derivatives with the general formula as shown in (I), preparation methods thereof, pharmaceutical compositions containing the compounds and medical application of the derivatives and the pharmaceutical compositions, particularly, application of the derivatives and the pharmaceutical compositions serving as drugs for preventing or treating hyperlipidaemia or obesity or type-II diabetes. Please see the formula in the description.

Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.

Synthetic study of kosinostatin aglycone: Synthesis of BCDE rings using alkoxycarbonylmethylation of diazonaphthoquinone

A synthetic study of kosinostatin aglycone is reported. Synthesis of key intermediate lactone 3, which corresponds to the BCDE ring fragment, was accomplished, and the precursor BCD ring fragment 5 was synthesized via two routes. First, 5 was synthesized from 2,5-dimethoxybenzaldehyde 16 by the combination of typical known transformations including efficient application of non-aqueous OsO4 oxidation in the presence of PhB(OH)2. However the synthesis required 15 long steps, and its main difficulty was ortho-alkoxycarbonylmethylation of 1-naphthol. Next we attempted to apply our recently developed alkoxycarbonylmethylation of diazonaphthoquinone for the synthesis of 5, and 5 was successfully synthesized in 9 steps from the same starting compound 16. Finally, 5 was stereoselectively converted to lactone 3 via trifluoroacetic acid-mediated cyclization of the 3,4- epoxycylohexanecarboxylic acid derivative.

One-pot synthesis of functionalized p-terphenyl derivatives

A one-pot synthetic route for preparing functionalized p-terphenyl derivatives 1 and 4 is developed. The route is easily carried from the treatment of cinnamyl aldehydes 2 with substituted allylsulfones 3 in good yields via the tandem intermolecular aldol condensation/intramolecular electrocyclization/ oxidative dehydrogenation.