17082-09-6

Basic information

• Product Name: CINNAMOYL CHLORIDE
• Synonyms: (E)-3-Phenylacrylyl chloride;(E)-3-Phenylpropenoyl chloride;(E)-Cinnamoyl chloride;trans-3-Phenylacrylyl chloride;(E)-3-Phenyl-2-propenoyl chloride;2-Propenoyl chloride, 3-phenyl-, (E)-;CINNAMOYL CHLORIDE FOR SYNTHESIS;CINNAMIC ACID CHLORIDE
• CAS NO: 17082-09-6
• Molecular Formula: C9H7ClO
• Molecular Weight: 166.6
• EINECS: 203-065-5
• Mol File: 17082-09-6.mol
• Article Data: 244

Chemical Properties

• Melting Point: 35-37 °C(lit.)
• Boiling Point: 256-258 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1,162 g/cm3
• Refractive Index: 1.5845
• Storage Temp.: 2-8°C
• Solubility: dioxane: 0.1 g/mL, clear
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• Merck: 14,2301
• BRN: 606265
• CAS DataBase Reference: CINNAMOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CINNAMOYL CHLORIDE(17082-09-6)
• EPA Substance Registry System: CINNAMOYL CHLORIDE(17082-09-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 17082-09-6(Hazardous Substances Data)

Usage

Uses

(E)-Cinnamoyl Chloride is used in the preparation of aminodihydroquinoline analogs displaying anticancer activity. It is also used in the preparation of lysergol and related derivatives for use as antibacterials.

InChI:InChI=1/C9H9Cl/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2/b7-4+

Upstream product

• 110-86-1 pyridine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 79-37-8 oxalyl dichloride 
• 18509-03-0 sodium trans-cinnamate 
• 140-10-3 cis-cinnamic acid 
• 621-82-9 Cinnamic acid 
• 91-66-7 N,N-diethylaniline 
• 71-43-2 benzene 
• 104-55-2 3-phenyl-propenal 
• 10026-13-8 phosphorus pentachloride 
• 766-51-8 2-Chloroanisole 
• 100-52-7 benzaldehyde 
• 538-56-7 cinnamic acid anhydride 

Downstream Products

• 24265-72-3 2-diazo-1-(4-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-ethanone 
• 300829-00-9 (2E)-3-phenyl-N-(1,3-thiazol-2-yl)prop-2-enamide 
• 102894-04-2 3,5-di-trans-2,6-dimethyl-pyran-4-one 
• 100622-76-2 N-(5-chloro-[2]pyridyl)-trans-cinnamamide 
• 54756-15-9 3-trans-cinnamoyl-6-methyl-pyran-2,4-dione 
• 101716-49-8 N-(quinolin-3-yl)cinnamamide 
• 100954-98-1 2-chloromethyl-5-trans-cinnamoyloxy-pyran-4-one 
• 102478-79-5 9-trans-cinnamoyl-1,2,3,4-tetrahydro-carbazole 
• 51528-61-1 7-trans-cinnamoyloxy-4-methyl-coumarin 
• 113061-08-8 (+/-)-1-(2-chloromethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl)-3t-phenyl-propenone 

Relevant articles and documents

AMIDE DERIVATIVES HAVING MULTIMODAL ACTIVITY AGAINST PAIN

The present invention relates to new compounds that show pharmacological activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially the α2δ-1 subunit of voltage-gated calcium channels or dual activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially the α2δ-1 subunit of voltage-gated calcium channels, and the μ-opiod receptor (MOR or mu-opioid). The invention is also related to the process for the preparation of said compounds as well as to compositions comprising them, and to their use as medicaments.

Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis

Piperlongumine (PL) has been showed to have multiple pharmacological activities. In this study, we reported the synthesis of three series of PL derivatives, and evaluation of their anti-inflammatory effects in both lipopolysaccharide (LPS)-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. Our results presented that two meta-substituent containing derivatives 1–3 and 1–6, in which γ-butyrolactam replaced α,β-unsaturated δ-valerolactam ring of PL, displayed low cytotoxicity and effective anti-inflammatory activity. Molecular docking also showed that the meta-substituted derivative, compared with the corresponding ortho- or para-substituted derivative, had significant interactions with the amino acid residues of CD14, which was the core receptors recognizing LPS. In vitro and in vivo studies, 1–3 and 1–6 could inhibit the expression of pro-inflammatory cytokines, and the excessive production of reactive nitrogen species and reactive oxygen species. Oral administration of 100 mg/kg/day of 1–3 or 1–6 alleviated the severity of clinical symptoms of colitis in mice, and significantly reduced the colonic tissue damage to protect the colonic tissue from the DSS-induced colitis. These results suggested that meta-substituted derivatives 1–3 and 1–6 were potential anti-inflammatory agents, which may lead to future pharmaceutical development.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.