17598-02-6

Basic information

• Product Name: 7-METHOXY-2,2-DIMETHYL-3-CHROMENE
• Synonyms: 2,2-Dimethyl-2H-chromen-7-yl methyl ether;2,2-dimethyl-7-methoxy-2h-1-benzopyra;2,2-Dimethyl-7-methoxy-2H-1-benzopyran;2H-1-Benzopyran, 2,2-dimethyl-7-methoxy-;2H-1-Benzopyran, 7-methoxy-2,2-dimethyl-;6-Demethoxyageratochromene;Demethoxyageratochromene;PRICOCENE I
• CAS NO: 17598-02-6
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 241-566-0
• Mol File: 17598-02-6.mol

Chemical Properties

• Boiling Point: 68 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.052 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00315mmHg at 25°C
• Refractive Index: n20/D 1.56(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-METHOXY-2,2-DIMETHYL-3-CHROMENE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXY-2,2-DIMETHYL-3-CHROMENE(17598-02-6)
• EPA Substance Registry System: 7-METHOXY-2,2-DIMETHYL-3-CHROMENE(17598-02-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 61
• WGK Germany: 3
• RTECS: DJ2529000
• Hazardous Substances Data: 17598-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-METHOXY-2,2-DIMETHYL-3-CHROMENE is used as a pharmaceutical compound for its potential therapeutic effects. The specific application reason is due to its unique chemical structure, which may allow it to interact with biological targets and exhibit beneficial properties for human health.
Used in Chemical Research:
In the field of chemical research, 7-METHOXY-2,2-DIMETHYL-3-CHROMENE is used as a research compound to study its properties, reactivity, and potential applications in the synthesis of other compounds. The reason for its use in this context is to gain a deeper understanding of its chemical behavior and to explore its potential in creating new molecules with desired characteristics.
Used in Material Science:
7-METHOXY-2,2-DIMETHYL-3-CHROMENE may also be used in material science as a component in the development of new materials with specific properties. The application reason is based on its unique molecular structure, which could contribute to the creation of materials with improved characteristics, such as enhanced stability, reactivity, or other desirable traits.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 803, 1979 DOI: 10.1021/jo01319a030

InChI:InChI=1/C12H14O2/c1-12(2)7-6-9-4-5-10(13-3)8-11(9)14-12/h4-8H,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 531-59-9 7-methoxycoumarin 
• 917-54-4 methyllithium 
• 20321-73-7 7-methoxy-2,2-dimethyl-4-chromanone 
• 25974-59-8 2-hydroxy-4-methoxy-2',2'-dimethylallylbenzene 
• 93097-55-3 3-hydroxy-7-methoxy-2,2-dimethylchroman 
• 676-58-4 methylmagnesium chloride 
• 34191-90-7 1-methoxy-3-(2-methylbut-3-yn-2-yloxy)benzene 
• 150-19-6 O-methylresorcine 
• 73509-11-2 1-(2'-hydroxy-4'-methoxyphenyl)-3-hydroxy-3-methylbutan-1-one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 108-46-3 recorcinol 
• 99323-00-9 1-(2',4'-dihydroxyphenyl)-3-methyl-but-2-en-1-one 
• 541-47-9 3-Methylbutenoic acid 

Downstream Products

• 109397-34-4 7-methoxy-2,2-dimethyl-chroman-4-one-(2,4-dinitro-phenylhydrazone) 
• 82864-23-1 (+)-(3R,4R)-cis-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 82864-24-2 (-)-(3S,4S)-cis-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 74094-51-2 6-hydroxy-7-methoxy-2,2-dimethylchromen 
• 62291-19-4 7-methoxy-2,2-dimethyl-2H-chromen-6-carbaldehyde 
• 17771-33-4 7-hydroxy-2,2-dimethyl-chroman-4-one 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4S)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 83686-07-1 C₃₀H₃₄N₂O₆ 
• 83686-06-0 C₃₀H₃₄N₂O₆ 
• 82833-93-0 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4S)-3-bromo-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-93-0 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4S)-3-bromo-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 19013-03-7 6-acetyl-7-hydroxy-2,2-dimethyl-1H-chromene 

Relevant articles and documents

Phenylboronic acid-mediated synthesis of 2H-Chromenes

Condensation of phenols with but-2-enal and 3-methyl-but-2-enal in the presence of phenylboronic acid in acetic acid-toluene solution leads to substituted and condensed 2H-chromenes, constituting a mild and advantageous complement to classical routes for this class of heterocycles.

Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications

The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and σ-insertion reactions to produce structurally novel substituted chromenes and chromanes. The excellent regioselectivity of the reaction is facilitated by the oxygen-containing guiding groups at the ortho-position of the triple bond, which can be removed or switched to other functional groups including alkenyl, aryl, heteroaryl, and arylamino groups.

Synthesis of new (±) pterocarpans by Heck oxyarylation

Among a wide variety of synthetic routes to pterocarpan prototypes, a mild approach uses a reaction known as Heck oxyarylation. This method involves a reaction between 2H-chromenes and 2-chloromercuriophenols in the presence of Li2PdCl4. 2005 Springer Science+Business Media, Inc.

THE SYNTHESIS OF CYCLOPROPYL ANALOGUES OF PRECOCENE I

A new, short synthesis of precocene I is described together with the synthesis of two cyclopropyl analogues.One of these compounds showed interesting biological activity against the bean aphid, Aphis fabae.

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Boronic acid/Br?nsted acid co-catalyst systems for the synthesis of 2: H -chromenes from phenols and α,β-unsaturated carbonyls

Protocols for the synthesis of substituted 2H-chromenes from α,β-unsaturated carbonyls and phenols are described. Optimal combinations of arylboronic acids and Br?nsted acids have been identified, such that both can be employed in catalytic quantities to accelerate these condensations. The method has been used to synthesize a variety of substituted 2H-chromenes, as well as photochromic naphthopyrans. The use of pentafluorophenylboronic acid and diphenylphosphinic acid enabled an expansion of the electrophile scope to include α,β-unsaturated ketones. Hall's 'phase-switching' of boronic acids has been exploited to achieve the separation of the two co-catalysts from unpurified reaction mixtures by a simple liquid-liquid extraction.

USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS

The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

Enantioselective reduction of 4-chromanone and its derivatives by selected filamentous fungi

Biotransformation of 4-chromanone and its derivatives in the cultures of three biocatalysts: Didymosphaeria igniaria, Coryneum betulinum and Chaetomium sp. is presented. The biocatalysts were chosen due to their capability of enantiospecific reduction of low-molecular-weight ketones (acetophenone and its derivatives and α- and β-tetralone). The substrates were reduced to the respective S-alcohols with high enantiomeric excesses, according to the Prelog's rule. In the culture of Chaetomium sp. after longer biotransformation time an inversion of configuration of the formed alcohols was also observed. The highest yield of transformation was observed for 6-methyl-4-chromanone. In all the tested cultures, the higher was the molecular weight of a chromanone, the lower conversion percent was observed.

Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: Application to the concise synthesis of benzopyran natural products

Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7% relative yield. The Ph 3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans seselin, xanthyletin, precocenes I and II, 8-(3′,3′- dimethylallyl)wenteria chromene, and 2,2-dimethyl-8-prenylchromene-6-propenoic acid. Ph3PAuNTf2 is a general, highly efficient, and product-selective catalyst for the clean synthesis of 2H-chromenes from the cycloisomerization of aryl propargyl ethers.The Ph3PAuNTf 2-catalyzed cyclization was applied as a key step in the synthesis of several benzopyran-bearing naturally occurring substances. Copyright

Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II

Herein is reported an efficient method for the synthesis of 2,2-dimethyl-2H-chromenes in a single step from the corresponding phenol and 3-methyl-2-butenal via microwave irradiation in CDCl3. This protocol features a mild reaction environment (neutral, no added catalyst) which yields regioselective formation of the chromene and displays tolerance toward acid- and base-sensitive protecting groups.