13321-74-9

Basic information

• Product Name: 4-BROMO-2,5-DIMETHOXYTOLUENE
• Synonyms: 4-BROMO-2,5-DIMETHOXYTOLUENE;1-BROMO-2,5-DIMETHOXY-4-METHYLBENZENE;Benzene,1-broMo-2,5-diMethoxy-4-Methyl-
• CAS NO: 13321-74-9
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 13321-74-9.mol

Chemical Properties

• Melting Point: 77-78
• Boiling Point: 270.408 °C at 760 mmHg
• Flash Point: 114.151 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BROMO-2,5-DIMETHOXYTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2,5-DIMETHOXYTOLUENE(13321-74-9)
• EPA Substance Registry System: 4-BROMO-2,5-DIMETHOXYTOLUENE(13321-74-9)

Safety Data

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 13321-74-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research and Experimentation:
4-Bromo-2,5-dimethoxytoluene is used as a research chemical for its unique properties and reactivity. Its functional groups and stable aromatic ring make it a valuable compound for studying chemical reactions and mechanisms.
Used in Organic Synthesis:
In the field of organic synthesis, 4-bromo-2,5-dimethoxytoluene is used as a building block or intermediate for the synthesis of more complex molecules. Its bromo and methoxy groups can be further modified or used as starting points for the creation of various organic compounds.
Used in Pharmaceutical Development:
4-Bromo-2,5-dimethoxytoluene may be used as a precursor in the development of pharmaceutical compounds. Its unique structure and reactivity can be harnessed to create new drugs with potential therapeutic applications.
Used in Material Science:
In material science, 4-bromo-2,5-dimethoxytoluene could be used to develop new materials with specific properties, such as improved solubility or reactivity, which can be beneficial in various applications, including coatings, adhesives, or polymers.

InChI:InChI=1/C9H11BrO2/c1-6-4-9(12-3)7(10)5-8(6)11-2/h4-5H,1-3H3

Upstream product

• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 24599-58-4 2,5-dimethoxy toluene 
• 95-71-6 2-methylbenzene-1,4-diol 
• 74-88-4 methyl iodide 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 553-97-9 2-Methyl-1,4-benzoquinone 

Downstream Products

• 68409-21-2 2-(2,5-Dimethoxy-4-methylbenzoyl)-3-methoxybenzoesaeure-methylester 
• 68409-20-1 6-(2,5-Dimethoxy-4-methylbenzoyl)-2-methoxybenzoesaeure-methylester 
• 68409-19-8 3-(2,5-Dimethoxy-4-methylphenyl)-3-hydroxy-7-methoxy-1(3H)-isobenzofuranon 
• 203579-44-6 1,4-dimethoxy-2-methyl-5-trideuteriomethylbenzene 
• 180578-98-7 2,5-dimethoxy-4-methylphenylmagnesium bromide 
• 13070-25-2 2-bromo-5-methyl-[1,4]benzoquinone 
• 78920-00-0 1-(2,5-dimethoxy-4-methylphenyl)ethyl diisopropylcarbamate 
• 100108-66-5 murrayaquinone A 

Relevant articles and documents

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A

A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).

Synthesis of murrayaquinone A and analogues via ring-closing C-H arylation

A compact synthesis of Murrayaquinone A is reported, based on sequential Buchwald-Hartwig amination/annulative C-H activation followed by oxidation of the intermediate carbazole. The methodology can be readily extended to other analogues with electron-rich quinone rings.

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to the selection of distinct compounds for antimalarial versus antischistosomal action. The AgII-assisted oxidative radical decarboxylation of the phenyl acetic acids using AgNO3 and ammonium peroxodisulfate was modified to generate the 3-picolinyl-menadione with improved pharmacokinetic parameters, high antimalarial effects and capacity to inhibit the formation of β-hematin. The Royal Society of Chemistry 2012.

A short synthesis of bisabolane sesquiterpenes

A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials.

Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene

The enantioselective total syntheses of enokipodins A and B, α-cuparenone-type sesquiterpenoids with antimicrobial activity, have been achieved. The key step is the enantiospecific construction of the quaternary carbon center using a palladium-catalyzed a

Factors influencing prenylation of an aromatic organolithium

An apparently routine metal-halogen exchange (MHE) reaction gave variable low yields under typical conditions. 13C and 7Li NMR studies suggested a diversity of organolithiums were formed in the MHE reaction leading to a plethora of p

Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus

Two triprenylated toluquinone and toluhydroquinone marine fungal metabolites, 5-methyl-2-[(2′E,6′E)-3′,7′,11′-trimethyl-2′,6′,10′-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione and 5-methyl-2-[(2′E,6′E)-3,7,11-trimethyl-2′,6′,10′-dodecatrienyl]-1,4-benzenediol, were synthesized in four and five steps, respectively, from 2-methyl-1,4-benzoquinone. The synthesis extends the applicability of the oxidative ether cleavage of hydroquinone dimethyl ethers with argentic oxide under acidic conditions to include the oxidative demethylation of polyprenylated-1,4-dimethoxy-toluhydroquinones with a quantitative survival of the oxidation- and acid-sensitive polyprenyl side chain.

Synthesis of hipposudoric and norhipposudoric acids: The pigments responsible for the color reaction of the red sweat of Hippopotamus amphibius

Highly unstable pigments, hipposudoric acid and norhipposudoric acid, isolated from the red sweat of hippopotamus were synthesized using the Pschorr reaction for the construction of the fluorene nucleus as the key step and the careful oxidation in the las

Stereospecific synthesis of amphetamines

Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine.