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

Description

Cinnamyl chloride, also known as 3-phenylprop-2-enyl chloride or cinnamyl chloride, is an organic compound with the chemical formula C9H9Cl. It is a colorless to pale yellow liquid with a characteristic odor. Cinnamyl chloride is derived from the cinnamic acid and is used as a building block in the synthesis of various organic compounds.

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 
• 75-36-5 acetyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1986-47-6 tranylcypromine hydrochloride 
• 64-19-7 acetic acid 
• 4392-26-1 vinylbenzyl chloride 
• 1476-11-5 Z-1,4-dichlorobutene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 75-62-7 Bromotrichloromethane 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 
• 4192-77-2 ethyl cinnamate 
• 4510-34-3 (Z)-cinnamyl alcohol 

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

Geranyl-chlorid, ein einfaches Herstellungsverfahren

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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.