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Cas Database

1798-09-0

1798-09-0

Identification

  • Product Name:3-Methoxyphenylacetic acid

  • CAS Number: 1798-09-0

  • EINECS:217-282-8

  • Molecular Weight:166.177

  • Molecular Formula: C9H10O3

  • HS Code:29189090

  • Mol File:1798-09-0.mol

Synonyms:(3-Methoxyphenyl)acetic acid;2-(3-methoxyphenyl)acetic acid;4-10-00-00541 (Beilstein Handbook Reference);Benzeneacetic acid, 3-methoxy- (9CI);m-Methoxyphenylacetic acid;2-(3-methoxyphenyl)acetate;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • 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

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:3-Methoxyphenylacetic acid
  • Packaging:25 g
  • Price:$ 85
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Methoxyphenylacetic Acid >98.0%(T)
  • Packaging:25g
  • Price:$ 72
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Methoxyphenylacetic acid 98%
  • Packaging:5 g
  • Price:$ 16
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Methoxyphenylacetic acid 98%
  • Packaging:25 g
  • Price:$ 32
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Methoxyphenylacetic acid ≥99%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Methoxyphenylacetic acid ≥99%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Methoxyphenylacetic acid ≥99%
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  • Manufacture/Brand:Matrix Scientific
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  • Manufacture/Brand:Heterocyclics
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Relevant articles and documentsAll total 25 Articles be found

An Efficient and Remarkably Regioselective Synthesis of Benzocyclobutenones from Benzynes and 1,1-Dimethoxyethylene

Stevens, Robert V.,Bisacchi, Gregory S.

, p. 2393 - 2396 (1982)

New efficient methodology for the synthesis of substituted benzocyclobutenones is presented that involves the cycloaddition of various substituted benzynes to 1,1-dimethoxyethylene followed by hydrolysis to the corresponding ketone.In most cases studied a high degree of regioselectivity was observed.These observations are consistent with a nonsynchronous mechanism wherein steric and inductive considerations can be used to account for the products observed.

-

Kornfeld

, p. 1373,1375, 1376 (1948)

-

Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst

Iwasawa, Nobuharu,Jin, Yushu,Toriumi, Naoyuki

, (2021/12/14)

A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

Bo, Zhi-Yu,Chen, Lin,Gao, Tian-Yu,Jing, Ke,Lan, Yu,Liu, Shi-Han,Luo, Shu-Ping,Yan, Si-Shun,Yu, Bo,Yu, Da-Gang

supporting information, p. 3099 - 3113 (2021/11/16)

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Goh, Jeffrey,Loh, Teck-Peng,Maraswami, Manikantha

supporting information, p. 9724 - 9728 (2020/12/21)

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Carboxylation of benzylic and aliphatic C-H bonds with CO2 induced by light/ketone/nickel

Ishida, Naoki,Masuda, Yusuke,Imamura, Yuuya,Yamazaki, Katsushi,Murakami, Masahiro

supporting information, p. 19611 - 19615 (2019/12/24)

A photoinduced carboxylation reaction of benzylic and aliphatic C-H bonds with CO2 is developed. Toluene derivatives capture gaseous CO2 at the benzylic position to produce phenylacetic acid derivatives when irradiated with UV light in the presence of an aromatic ketone, a nickel complex, and potassium tert-butoxide. Cyclohexane reacts with CO2 to furnish cyclohexanecar-boxylic acid under analogous reaction conditions. The present photoinduced carboxylation reaction provides a direct access from readily available hydrocarbons to the corresponding carboxylic acids with one carbon extension.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Liao, Li-Li,Cao, Guang-Mei,Ye, Jian-Heng,Sun, Guo-Quan,Zhou, Wen-Jun,Gui, Yong-Yuan,Yan, Si-Shun,Shen, Guo,Yu, Da-Gang

, p. 17338 - 17342 (2019/01/04)

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.

Process route upstream and downstream products

Process route

2-<3-methoxyphenyl>-1-tetrahydro-2H-1,4-oxazin-4-yl-1-ethanethione
221354-48-9

2-<3-methoxyphenyl>-1-tetrahydro-2H-1,4-oxazin-4-yl-1-ethanethione

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With sulfuric acid; acetic acid; Erhitzen des Reaktionsprodukts mit Raney-Nickel und wss. NaOH;
4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one
82301-50-6,82301-53-9,113697-03-3

4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
Behandeln des Reaktionsprodukts mit alkal. Wasserstoffperoxyd-Loesung;
potassium cyanide
151-50-8

potassium cyanide

m-methoxybenzyl chloride
824-98-6

m-methoxybenzyl chloride

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With ethanol; Verseifung mit waessrig-alkoholischer Kalilauge;
3-methoxyphenylacetonitrile
19924-43-7

3-methoxyphenylacetonitrile

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With potassium hydroxide;
methanol
67-56-1

methanol

1-Naphthylmethyl 3-methoxyphenylacetate
143659-24-9

1-Naphthylmethyl 3-methoxyphenylacetate

1-(methoxymethyl)naphthalene
5903-23-1

1-(methoxymethyl)naphthalene

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

1-[2-(3-Methoxy-phenyl)-ethyl]-naphthalene

1-[2-(3-Methoxy-phenyl)-ethyl]-naphthalene

Conditions
Conditions Yield
Irradiation;
16 % Chromat.
71 % Chromat.
Rate constant; Quantum yield; Irradiation; rate of decarboxylation k(CO2);
16 % Chromat.
71 % Chromat.
2-(3-methoxyphenyl)-ethanol
5020-41-7

2-(3-methoxyphenyl)-ethanol

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In acetonitrile; at 35 ℃; pH 6.7;
96%
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; water; acetonitrile; at 35 ℃; pH=6.7; Reagent/catalyst; Green chemistry;
96%
With sodium hydroxide; oxygen; lead acetate; palladium on activated charcoal; In water; at 90 ℃; for 3h; under 3800 Torr;
82.8%
5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one
66947-60-2

5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With sodium hydroxide; at 60 ℃; for 2h;
100%
methyl (3-methoxyphenyl)acetate
18927-05-4

methyl (3-methoxyphenyl)acetate

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With sodium hydroxide; for 2h; Heating;
96%
With sodium hydroxide; In methanol; for 4h; Yield given; Ambient temperature;
With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 70 ℃; for 3h;
m-hydroxyphenylacetic acid
621-37-4

m-hydroxyphenylacetic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
With hydrogenchloride; sodium hydroxide; Yield given. Multistep reaction; 1.) 55 deg C, 70 min., 2.) 0 deg C, 1 h.;
carbon monoxide
201230-82-2

carbon monoxide

m-methoxybenzyl chloride
824-98-6

m-methoxybenzyl chloride

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

Conditions
Conditions Yield
iron pentacarbonyl; tetrabutylammonium sulfate; In sodium hydroxide; toluene; at 50 ℃; for 51h; under 45600 Torr;
35%

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