28446-69-7

Basic information

• Product Name: 3-METHOXYCINNAMONITRILE
• Synonyms: 3-(3-methoxyphenyl)-2-propenenitril;m-methoxy-cinnamonitril
• CAS NO: 28446-69-7
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• Mol File: 28446-69-7.mol

Chemical Properties

• Boiling Point: 299.6°Cat760mmHg
• Flash Point: 126.2°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: 3-METHOXYCINNAMONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXYCINNAMONITRILE(28446-69-7)
• EPA Substance Registry System: 3-METHOXYCINNAMONITRILE(28446-69-7)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 28446-69-7(Hazardous Substances Data)

Usage

Physical State

Pale yellow liquid

Odor

Sweet, floral, slightly spicy

Uses

Flavoring ingredient in food and beverage industry, production of perfumes and fragrances, synthesis of pharmaceuticals and organic compounds

Properties

Potential antioxidant and antibacterial properties

Applications

Ingredient in cosmetic and personal care products

InChI:InChI=1/C10H9NO/c1-12-10-6-2-4-9(8-10)5-3-7-11/h2-6,8H,1H3/b5-3+

Upstream product

• 18826-43-2 3-(m-Methoxy-phenyl)-2-chlor-propionitril 
• 372-09-8 cyanoacetic acid 
• 591-31-1 3-methoxy-benzaldehyde 
• 536-90-3 m-Anisidine 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

Downstream Products

• 18655-52-2 3-(3-methoxyphenyl)propan-1-amine 
• 1129-59-5 3-(3-methoxyphenyl)propanenitrile 
• 1027279-47-5 2-Formyl-3-(3-methoxy-phenyl)-propionitrile 
• 146385-97-9 3-Amino-4-(3-methoxy-benzyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 1026731-04-3 3-Amino-4-(3-methoxy-benzyl)-pyrrole-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester 
• 146386-25-6 3-(3-Benzoyl-2-methyl-isothioureido)-4-(3-methoxy-benzyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 146386-11-0 3-(3-Benzoyl-thioureido)-4-(3-methoxy-benzyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 108010-35-1 2-(2-Hydroxyethyl)-N-<3-(3-methoxyphenyl)propyl>benzamid 
• 108010-38-4 2-<2-(Ethoxycarbonyloxy)ethyl>-N-<3-(3-methoxyphenyl)propyl>benzamid 
• 1415684-34-2 C₃₀H₃₇N₃O₄ 
• 1049696-27-6 3-(3-methoxyphenyl)propan-1-amine hydrochloride 
• 1454706-72-9 C₁₉H₂₆N₂O₅ 

Relevant articles and documents

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

A Route to the C,D,E Ring System of the Aspidosperma Alkaloids

A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the

Modular Approach to 9-Monosubstituted Fluorene Derivatives Using MoV Reagents

Oxidative coupling using molybdenum(V) reagents provides fast access to highly functionalized 9-monosubstituted fluorenes. This synthetic approach is highly modular, is high yielding, and tolerates a variety of labile moieties, e.g. amides or iodo groups. The established protocol leads to promising precursors for pharmacologically important analogues of melatonin.

Method for producing compounds comprising nitrile functions

The present invention concerns the production of compounds comprising nitrite functions and cyclic imide compounds. More specifically, the invention relates to the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, advantageously of natural and renewable origin, and from methyl-2 glutaronitrile (MGN) or a mixture N of dinitriles comprising methyl-2 glutaronitrile (MGN), ethyl-2 succinonitrile (ESN) and adiponitrile (AdN).

Diverse alkaloid-like structures from a common building block

A wealth of unique enantiopure polycyclic alkaloid-like scaffolds can be prepared on a multigram scale in only a few steps from a common, commercially available intermediate. The attached nitromethyl group can then be used to construct highly diverse func

SYNTHESIS OF POLYCYCLIC ALKALOIDS

Disclosed embodiments concern polycyclic alkaloid compounds and methods for their use and synthesis. Particular embodiments concern polycyclic alkaloids having a fused, six-membered ring, while other embodiments concern polycyclic alkaloids having a fused

Structure-based design of inhibitors of purine nucleoside phosphorylase. 1. 9-(Arylmethyl) derivatives of 9-deazaguanine

Purine nucleoside phosphorylase (PNP, EC 2.4.2.1) is a salvage enzyme important to the T-cell-mediated part of the immune system and as such is an important therapeutic target. This paper describes the design, synthesis, and enzymatic evaluation of potent, competitive inhibitors of PNP. Potential inhibitors were designed using the three-dimensional structure of the enzyme in an iterative process that involved interactive computer graphics to model the native enzyme and complexes of it with the inhibitors, Monte Carlo-based conformational searching, and energy minimization. Studies of the enzyme/inhibitor complexes were used to determine priorities of the synthetic efforts. The resulting compounds were then evaluated by determination of their IC50 values and by X-ray diffraction analysis using difference Fourier maps. In this manner, we have developed a series of 9-(arylmethyl)- 9-deazapurines (2-amino-7-(arylmethyl)-4H-pyrrolo[3,2-d]-pyrimidin-4-ones) that are potent, membrane-permeable inhibitors of the enzyme. The IC50 values of these compounds range from 17 to 270 nM (in 1 mM phosphate), with 9-(3,4-dichlorobenzyl)-9-deazaguanine being the most potent inhibitor. X-ray analysis explained the role of the aryl groups and revealed the rearrangement of hydrogen bonds in the binding of the 9-deazaguanines in the active site of PNP relative to the binding of the 8-aminoguanines that results in more potent inhibition of the enzyme.