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

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

Used in Pharmaceutical Industry:
Cinnamyl chloride is used as a key intermediate in the synthesis of aryl and heterocyclic polyenes, which exhibit antioxidant activity. These antioxidants are essential in the pharmaceutical industry for the development of drugs that can combat oxidative stress and related diseases.
Used in Chemical Synthesis:
Cinnamyl chloride is used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional group compatibility make it a valuable component in the development of new molecules with potential applications in various industries.

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 
• 104-54-1 3-Phenylpropenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 58844-31-8 (Z)-1-Phenyl-2-trimethylsilyl-3-chlor-1-propen 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 1986-47-6 tranylcypromine hydrochloride 
• 96233-07-7 3-phenyl-allyl diphenyl phosphate 
• 109391-77-7 C₁₅H₁₅Cl₃Se 
• 109391-76-6 C₁₅H₁₅Cl₃Se 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 

Downstream Products

• 14593-45-4 3-phenyl-(E)-2-propenyl n-propyl ether 
• 58463-02-8 (1E,5E)-1,6-diphenyl-1,5-hexadiene 
• 101583-20-4 trans-cinnamyl-formylamino-malonic acid diethyl ester 
• 90-86-8 (1R,2S)-2-{methyl-[(E)-3-phenyl-2-propenyl]amino}-1-phenylpropan-1-ol 
• 90-86-8 D-erythro-2-(methyl-trans-cinnamyl-amino)-1-phenyl-propanol-⁽¹⁾ 
• 291309-97-2 9-cinnamyl-9H-fluorene 
• 60607-24-1 (+/-)-trans-cinnamyl-methyl-(2-phenyl-propyl)-amine 
• 90-86-8 (1RS:2SR)-2-(methyl-trans-cinnamyl-amino)-1-phenyl-propanol-⁽¹⁾ 
• 40132-64-7 (E)-(4,4-dimethylpent-1-en-1-yl)benzene 
• 59117-56-5 E-(3-phenylallyl) methyl sulfide 
• 21040-45-9 Cinnamyl acetate 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 17480-07-8 2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 108400-97-1 ethyl (4E)-2-acetyl-5-phenylpent-4-enoate 

Relevant articles and documents

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

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.

Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl-Amides: Bypassing the Inherent Regioselectivity of the Cyclization

A selective and efficient methodology for the construction of either oxazolines or dihydrooxazines from the corresponding allyl-amides is reported. Bypassing the inherent selectivity of the cyclization and depending on the substitution pattern of the substrate, a selective epoxidation-cyclization was developed leading to either the five-membered or the six-membered ring, upon simple and complementary reaction conditions. The cyclization products were obtained in good to excellent yields and high selectivities. (Figure presented.).

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.

Method for preparing naftifine hydrochloride

The invention provides a method for preparing naftifine hydrochloride. The finished naftifine hydrochloride is obtained through subjecting relatively-cheap cinnamyl alcohol, which serves as a raw material, to chlorinating-reagent chlorinating, methyl-amination and 1-chloromethyl naphthalene substitution sequentially, and finally, carrying out acidification salt-forming and crystallization refining. According to the method provided by the invention, all intermediates in first three steps of reactions are subjected to a reaction without purification, process flows are continuous and non-intermittent, the operation is simplified, the yield and production efficiency of the product are increased, and meanwhile, the purity of the product is ensured, so that the method is applicable to industrialization; and meanwhile, the method has the advantages of simple reaction conditions, low cost and environment-friendliness.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols

Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.

Method for preparing chlorohydrocarbons from alcohols by using aryl sulfonyl chloride as chlorination agent

The invention provides a method for preparing chlorohydrocarbons from alcohols by using aryl sulfonyl chloride as a chlorination agent. The method comprises the following steps: heating alcohols and aryl sulfonyl chloride in N,N-dialkyl substituted amide to react for 30 minutes, cooling the reaction product to room temperature, adding dichloromethane and water, carrying out extraction and skimming, washing the organic layer with saturated saline water, drying with anhydrous sodium sulfate, steaming to remove the solvent, and carrying out further separation and purification to obtain the chlorohydrocarbons. The method has the characteristics of cheap and accessible chlorination agent, simple technical process, short reaction time and the like, can obtain high reaction under the condition that the aryl sulfonyl chloride consumption is approximate to the stoichiometric quality, and can remove the reaction byproduct aryl sulfonic acid from the reaction mixture.