52378-69-5

Basic information

• Product Name: DIETHYL TRANS-CINNAMYLPHOSPHONATE 98
• Synonyms: DIETHYL TRANS-CINNAMYLPHOSPHONATE 98;Diethyl cinnamylphosphonate (E)
• CAS NO: 52378-69-5
• Molecular Formula: C₁₃H₁₉O₃P
• Molecular Weight: 254.261921
• Product Categories: Horner-Wadsworth-Emmons ReagentsPolymer Science;C-C Bond Formation;Monomers;Olefination;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
• Mol File: 52378-69-5.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 368.2°C at 760 mmHg
• Flash Point: 228 °F
• Appearance: /
• Density: 1.093 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.74E-05mmHg at 25°C
• Refractive Index: n20/D 1.5280(lit.)
• CAS DataBase Reference: DIETHYL TRANS-CINNAMYLPHOSPHONATE 98(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL TRANS-CINNAMYLPHOSPHONATE 98(52378-69-5)
• EPA Substance Registry System: DIETHYL TRANS-CINNAMYLPHOSPHONATE 98(52378-69-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 52378-69-5(Hazardous Substances Data)

Usage

General Description

DIETHYL TRANS-CINNAMYLPHOSPHONATE 98 is a chemical compound commonly used in the fragrance and flavor industry. It is a synthetic aroma chemical that imparts a sweet, balsamic, and powdery scent reminiscent of cinnamon and honey. DIETHYL TRANS-CINNAMYLPHOSPHONATE 98 is widely utilized in the production of perfumes, personal care products, and scented household items. Additionally, it also finds application in the food industry as a flavoring agent for baked goods, confectionery, and beverages. With a purity of 98%, it is a high-quality and versatile ingredient with a wide range of uses in the manufacturing of scented products.

InChI:InChI=1/C13H19O3P/c1-3-15-17(14,16-4-2)12-8-11-13-9-6-5-7-10-13/h5-11H,3-4,12H2,1-2H3/b11-8+

Upstream product

• 7318-33-4 cinnamaldehyde tosylhydrazone 
• 762-04-9 phosphonic acid diethyl ester 
• 104-55-2 3-phenyl-propenal 
• 591-50-4 iodobenzene 
• 1067-87-4 Diethyl allylphosphonate 
• 135760-95-1 (E)-(3-phenyl-1-propenyl)phosphonic acid diethyl ester 
• 98-88-4 benzoyl chloride 
• 52378-69-5 diethyl cinnamylphosphonate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 103-26-4 Methyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 122-52-1 triethyl phosphite 
• 100-52-7 benzaldehyde 

Downstream Products

• 283169-69-7 2-(diethoxy-phosphoryl)-4-phenyl-but-3-enoic acid tert-butyl ester 
• 52221-91-7 diethyl 3-phenylpropyl-1-phosphonate 
• 27331-25-5 1-(4-chlorophenyl)-4-phenyl-1,3-butadiene 
• 164930-14-7 trimethyl((6E,8E)-9-phenylnona-6,8-dien-1-yn-1-yl)silane 

Relevant articles and documents

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.

Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation

The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.

TRIARYLAMINE HYDRAZONE DERIVATIVE AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound that improves the electric characteristics of electrophotographic photoreceptors. SOLUTION: A triarylamine hydrazone compound is represented by formula (1) or a specific structure (R1 and R2 are halogen, an alkyl group, an alkoxy group, or an aryl group). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT