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Cas Database

151-10-0

151-10-0

Identification

  • Product Name:1,3-Dimethoxybenzene

  • CAS Number: 151-10-0

  • EINECS:205-783-4

  • Molecular Weight:138.166

  • Molecular Formula: C8H10O2

  • HS Code:29093090

  • Mol File:151-10-0.mol

Synonyms:Benzene,m-dimethoxy- (8CI);3-Methoxyanisole;NSC 8699;Resorcinol dimethyl ether;m-Dimethoxybenzene;m-Methoxyanisole;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:1,3-Dimethoxybenzene
  • Packaging:10g
  • Price:$ 60
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  • Manufacture/Brand:TRC
  • Product Description:1,3-Dimethoxybenzene
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,3-Dimethoxybenzene >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,3-Dimethoxybenzene >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,3-Dimethoxybenzene >99.0%(GC)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1,3-Dimethoxybenzene 98%
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1,3-Dimethoxybenzene 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,3-Dimethoxybenzene ≥98%, FG
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Relevant articles and documentsAll total 146 Articles be found

Enantioselective total synthesis of (-)-blennolide A

Tietze, Lutz F.,Ma, Ling,Reiner, Johannes R.,Jackenkroll, Stefan,Heidemann, Sven

, p. 8610 - 8614 (2013)

Blennolide A can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7 a with 96 % ee and an enantioselective Wacker oxidation of 7 b with 89 % ee. Further transformations led to the α,β-unsaturated ester (E)-17, which was subjected to a highly selective Michael addition, introducing a methyl group to give 18 a. After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (-)-blennolide A (ent-1) in a few steps. Domino effect: An enantioselective domino-Wacker/carbonylation/methoxylation process and an enantioselective Wacker oxidation are the key steps in the first total synthesis of the fungal metabolite blennolide A (see scheme). Copyright

Facile C-S Bond Cleavage of Aryl Sulfoxides Promoted by Bronsted Acid

Brutiu, Bogdan R.,Klose, Immo,Maulide, Nuno

, p. 488 - 490 (2021)

A method for the Bronsted acid promoted desulfination of aryl sulfoxides is presented. In the presence of a thiol, electron-rich sulfoxides undergo C-S bond cleavage to give the corresponding protodesulfinated arenes and disulfides.

Carbon Kinetic Isotope Effects and the Mechanisms of Acid-Catalyzed Decarboxylation of 2,4-Dimethoxybenzoic Acid and CO2 Incorporation into 1,3-Dimethoxybenzene

Vandersteen, Adelle A.,Howe, Graeme W.,Sherwood Lollar, Barbara,Kluger, Ronald

, p. 15049 - 15053 (2017)

The rate of decarboxylation of 2,4-dimethoxybenzoic acid (1) is accelerated in parallel to the extent that the carboxyl group acquires a second proton (1H+). However, the conjugate acid would resist C-C bond breaking as that would lead to formation of doubly protonated CO2. An alternative via formation of a higher-energy protonated phenyl tautomer (2H+) prior to C-C bond breaking would produce protonated CO2, an energetically inaccessible species that can be avoided by transfer of the carboxyl proton to water in the same step. Headspace sampling of CO2 that evolves in the acid-catalyzed process and analysis by GC-IRMS gives a smaller than expected value of 1.022 for the carbon kinetic isotope (CKIE), k12/k13. While this value establishes that C-C cleavage is part of the rate-determining process, intrinsic CKIEs for decarboxylation reactions are typically greater than 1.03. Computational analysis of the C-C bond cleavage from 2H+ gives an intrinsic CKIE of 1.051 and suggests two partially rate-determining steps in the decarboxylation of 1: transfer of the second carboxyl proton to the adjacent phenyl carbon and C-C cleavage in which the carboxyl proton is also transferred to water. Applying the principle of microscopic reversibility to fixation of CO2 in acidic solutions reveals the importance of proton transfers to both carbon and oxygen in the overall fixation process.

Sakurai et al.

, p. 993 (1970)

-

Thoms,Siebeling

, p. 2135 (1911)

-

The molecular and electronic structure of octahedral tris(phenolato)iron(III) complexes and their phenoxyl radical analogues: A Mossbauer and resonance Raman spectroscopic study

Snodin, Michael D.,Ould-Moussa, Lynda,Wallmann, Ursula,Lecomte, Sophie,Bachler, Vinzenz,Bill, Eckhard,Hummel, Helga,Weyhermueller, Thomas,Hildebrandt, Peter,Wieghardt, Karl

, p. 2554 - 2565 (1999)

Hexadentate macrocyclic ligands containing a 1,4,7-triazacyclononane backbone and three N-bound pendent-arm phenolares form extremely stable neutral complexes with Fe(III)Cl3. The octahedral complexes [Fe(III)L] undergo three reversible one-electron oxidation processes to yield the mono- and dications, [FeL]+ and [FeL]2+, which are stable in solution for hours, whereas the trications, [FeL]3+, are only stable in solution on the time scale of a cyclic voltammetric experiment. These oxidations are shown to be ligand- rather than metal-centered. Three coordinated phenoxyl radicals are formed successively as shown conclusively by Mossbauer spectroscopy. The neutral, mono-, di-, and tricationic species each contain an octahedral, high-spin ferric ion (S(Fe) = 5/2), which is intramolecularly, antiferromagnetically coupled to the spin (S = 1/2 ) of the bound phenoxyl ligands to yield an S(t) = 2 ground state for the monocation, and an S(t) = 3/2 ground state for the dications as shown by EPR spectroscopy. The vibrations of the coordinated phenolate are observed by resonance Raman (RR) spectroscopy by excitation in resonance with the phenolate-to-iron charge- transfer (CT) transition above 500 nm or, alternatively, of the coordinated phenoxyl by excitation in resonance with the intraligand π → π* transition at about 410 nm. Use of 18O isotopomers selectively labeled at the phenolic oxygen allowed the identification of the C-O stretching and Fe-O stretching and bending modes. It is shown that the substitution pattern of phenolates and phenoxyls in their respective ortho and para positions and the charge of the complexes have a pronounced influence on the vibrational modes observed.

Polyfuryl(aryl)alkanes and their derivatives. 12. C-fur bond cleavage in the series of polyfuryl(aryl)alkanes

Butin,Stroganova,Kul'nevich

, p. 153 - 157 (1996)

Reactions taking place with cleavage of the C-Fur bond are examined. It was established that disproportionation in two directions, leading to the formation of tris(5-methyl-2-furyl)methane, takes place when 3,4-dimethoxyphenylbis(5-methyl-2-furyl)methane is boiled in an acidic medium. The acid-catalyzed reaction of 5-methylfurfural with ethylene glycol leads to the formation of either 2-(5-methyl-2-furyl)-1,3-dioxolane or tris(5-methyl-2-furyl)methane, depending on the catalyst. The treatment of 2-(5-methyl-2-furyl)-1,3-dioxolane or gemtris(5·methyl-2-furyl)ethane with trityl perchlorate leads to tris(5-methyl-2-furyl)carbenium or bis(5-methyl-2-furyl)methylcarbenium perchlorates respectively. 1996 Plenum Publishing Corporation.

Billek,Ziegler

, p. 1430 (1962)

Zweig et al.

, p. 4124,4125 (1964)

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Kang, Qi-Kai,Li, Ke,Li, Yuntong,Lin, Yunzhi,Shi, Hang,Xu, Lun

supporting information, p. 20391 - 20399 (2021/08/13)

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

K?nig, Burkhard,Wang, Hua,Wang, Shun

supporting information, p. 1653 - 1665 (2021/06/17)

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Method for synthesizing M-hydroxyanisole

-

Paragraph 0032-0033; 0052-0053; 0056-0057; 0060-0063, (2021/11/03)

The invention provides a method for synthesizing M-hydroxyanisole. Belong to organic synthesis technical field. The synthesis method comprises the following steps: a vapor phase mixture of resorcinol and methanol is subjected to alkylation reaction through a metal phosphate - alumina fixed phase catalyst to obtain m-hydroxyanisole. The method adopts the gas-solid phase alkylation method to synthesize the M-hydroxyanisole without separating the reaction product from the catalyst, has the characteristic of continuous reaction, and can realize continuous production in the industrial production process. The method utilizes the acid-base catalytic activity center on the surface of the stationary phase catalyst to catalyze the reaction of resorcinol and methanol, and has high resorcinol conversion rate. The method has the advantage of high selectivity of m-hydroxyanisole. Methanol is used as a methylation reagent, and the method is environmentally friendly, low in cost and high in economic benefit.

Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents

Matsuo, Kasumi,Kuriyama, Masami,Yamamoto, Kosuke,Demizu, Yosuke,Nishida, Koyo,Onomura, Osamu

, p. 4449 - 4460 (2021/08/25)

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

A highly stable all-in-one photocatalyst for aryl etherification: The NiIIembedded covalent organic framework

Chen, Hao,Dong, Wenbo,Hu, Jianxiang,Rao, Li,Wang, Pei,Wang, Shengyao,Xiang, Yonggang,Yang, Yi

, p. 5797 - 5805 (2021/08/23)

The efficient conversion of aryl bromides to the corresponding aryl alkyl ethers by dual nickel/photocatalysis has seen great progress, but difficulties of recycling the photosensitizer or nickel complexes cause problems of sustainability. Here, we report the design of a novel, highly stable vinyl bridge 2D covalent organic framework (COF) containing Ni, which combines the role of photosensitizer and reactive site. The as-prepared sp2c-COFdpy-Ni acts as an efficient heterogeneous photocatalyst for C-O cross coupling. The sp2c-COFdpy-Ni can be completely recovered and used repeatedly without loss of activity, overcoming the limitations of the prior methods. Preliminary studies reveal that strong interlayer electron transfer may facilitate the generation of the proposed intermediate sp2c-COFdpy-NiI in a bimolecular and self-sustained manner. This all-in-one heterogeneous photocatalyst exhibits good compatibility of substrates and tolerance of functional groups. The successful attempt to expand the 2D COFs with this new catalyst into photocatalytic organic transformation opens an avenue for photoredox/transition metal mediated coupling reactions.

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

2-(trimethylsilyl)-1,3-dimethoxybenzene
92669-93-7

2-(trimethylsilyl)-1,3-dimethoxybenzene

Trimethylmethoxysilane
1825-61-2

Trimethylmethoxysilane

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
Mechanism; Irradiation; other 2-trialkylsilyl-1,3-dimethoxybenzenes, var. solvents;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

recorcinol
108-46-3

recorcinol

methyl 2, 4-dimethoxybenzoate
2150-41-6

methyl 2, 4-dimethoxybenzoate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 170 ℃; for 0.666667h; Microwave irradiation; Green chemistry;
dibutyl(2,6-dimethoxyphenyl)phosphine hydrochloride
126590-46-3

dibutyl(2,6-dimethoxyphenyl)phosphine hydrochloride

di-n-butylphosphine
1732-72-5

di-n-butylphosphine

2-Dibutylphosphanyl-3-methoxy-phenol
141868-77-1

2-Dibutylphosphanyl-3-methoxy-phenol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 2h; Yield given. Title compound not separated from byproducts;
chloroform
67-66-3,8013-54-5

chloroform

1-iodo-2,4-dimethoxybenzene
20469-63-0

1-iodo-2,4-dimethoxybenzene

boron trifluoride
7637-07-2

boron trifluoride

2-Iodophenol
533-58-4

2-Iodophenol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
1-hydroxy-1-cyclohexanecarbonitrile
931-97-5

1-hydroxy-1-cyclohexanecarbonitrile

2,4 dimethoxybenzoic acid
91-52-1

2,4 dimethoxybenzoic acid

2,4-dimethoxybenzonitrile
4107-65-7

2,4-dimethoxybenzonitrile

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With bis(trifluoromethyl sulfate)palladium; silver carbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; for 0.0166667h;
47 %Chromat.
1-styryl-2,4-dimethoxybenzene

1-styryl-2,4-dimethoxybenzene

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With trifluoroacetic acid; In water; at 80 ℃; for 0.5h;
87%
methanol
67-56-1

methanol

recorcinol
108-46-3

recorcinol

O-methylresorcine
150-19-6

O-methylresorcine

4-methyl resorcinol
496-73-1,73073-80-0

4-methyl resorcinol

2-methylbenzene-1,3-diol
608-25-3

2-methylbenzene-1,3-diol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With lanthanum phosphate-alumina; at 290 ℃; Temperature; Reagent/catalyst; Inert atmosphere;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

recorcinol
108-46-3

recorcinol

O-methylresorcine
150-19-6

O-methylresorcine

4-methyl resorcinol
496-73-1,73073-80-0

4-methyl resorcinol

5-methoxy-2-methyl-phenol
20734-74-1

5-methoxy-2-methyl-phenol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With potassium; magnesium oxide; at 309.85 ℃; for 3h; Further Variations:; Temperatures; Reagents; Product distribution;
1-iodo-2,4-dimethoxybenzene
20469-63-0

1-iodo-2,4-dimethoxybenzene

methoxybenzene
100-66-3

methoxybenzene

trichloroacetic acid
76-03-9

trichloroacetic acid

4-iodoanisol
529-28-2

4-iodoanisol

para-iodoanisole
696-62-8

para-iodoanisole

1,5-diiodo-2,4-dimethoxy-benzene
51560-17-9

1,5-diiodo-2,4-dimethoxy-benzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
at 120 ℃;
1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

methyllithium
917-54-4

methyllithium

2,4-dimethoxytoluene
38064-90-3

2,4-dimethoxytoluene

2,4-Dimethoxybenzaldehyde
613-45-6

2,4-Dimethoxybenzaldehyde

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
Conditions Yield
With N,N-dimethyl-formamide; 1.) THF, ether, -65 deg C, 75 min, 2.) -65 deg C, 15 min;
31.2%
2.3%
33.2%

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