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Cas Database

5720-06-9

5720-06-9

Identification

  • Product Name:Boronic acid,B-(2-methoxyphenyl)-

  • CAS Number: 5720-06-9

  • EINECS:611-481-7

  • Molecular Weight:151.958

  • Molecular Formula: C7H9BO3

  • HS Code:29163990

  • Mol File:5720-06-9.mol

Synonyms:Benzeneboronicacid, o-methoxy- (6CI,7CI,8CI);Boronic acid, (2-methoxyphenyl)- (9CI);(2-Methoxyphenyl)boric acid;2-Methoxybenzeneboronic acid;[2-(Methyloxy)phenyl]boronic acid;o-Anisylboronicacid;o-Methoxybenzeneboronic acid;o-Methoxyphenylboronic acid;

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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:Usbiological
  • Product Description:2-Methoxyphenylboronic acid
  • Packaging:25g
  • Price:$ 459
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:2-MethoxylphenylboronicAcid(containsvaryingamountsofAnhydride)
  • Packaging:10g
  • Price:$ 140
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  • Manufacture/Brand:TRC
  • Product Description:2-MethoxylphenylboronicAcid(containsvaryingamountsofAnhydride)
  • Packaging:1g
  • Price:$ 110
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Methoxyphenylboronic Acid (contains varying amounts of Anhydride)
  • Packaging:1g
  • Price:$ 14
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Methoxyphenylboronic Acid (contains varying amounts of Anhydride)
  • Packaging:5g
  • Price:$ 19
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Methoxyphenylboronic Acid (contains varying amounts of Anhydride)
  • Packaging:25g
  • Price:$ 62
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  • Manufacture/Brand:Synthonix
  • Product Description:2-Methoxyphenylboronic acid 97%
  • Packaging:100g
  • Price:$ 280
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  • Manufacture/Brand:Synthonix
  • Product Description:2-Methoxyphenylboronic acid 97%
  • Packaging:25g
  • Price:$ 80
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  • Manufacture/Brand:Synthonix
  • Product Description:2-Methoxyphenylboronic acid 97%
  • Packaging:5g
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  • Manufacture/Brand:Synthonix
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Relevant articles and documentsAll total 48 Articles be found

Aryl boronic acid preparation method

-

Paragraph 0033-0040, (2020/01/25)

The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.

Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions

Varni, Anthony J.,Bautista, Michael V.,Noonan, Kevin J.T.

, p. 6770 - 6777 (2020/07/21)

A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.

Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems

Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū

supporting information, p. 353 - 359 (2019/12/15)

Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).

Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes

Sweetman, Brian A.,Guiry, Patrick J.

, p. 5567 - 5581 (2018/08/09)

The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yl]phenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%).

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong

, p. 4253 - 4257 (2018/09/18)

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Process route upstream and downstream products

Process route

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

2-bromoanisole
578-57-4

2-bromoanisole

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
2-bromoanisole; With n-butyllithium; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;
Trimethyl borate; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;
With hydrogenchloride; In diethyl ether; hexane; water; for 1h;
69%
With n-BuLi; HCl; In tetrahydrofuran; hexane; all manipulations under N2; soln. of BuLi in hexane added to soln. of org. compd. in THF at -78°C, stirred for 1 h, mixt. added to soln.of B compd. in THF at -78°C, warmed to room temp., stirred overnight, aq. HCl added, stirred 10 min; org. phase sepd., aq. phase extd. with Et2O, org. phase washed with brine, dried over Na2SO4, solvent removed, added NaOH in EtOH, stirred for 20 min at room temp., water added, washed, dried with Na2SO4, solvent evapd., recrystd. from ether/hexane;
61%
2-bromoanisole; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 1h;
Trimethyl borate; In tetrahydrofuran; at -78 ℃; for 1h;
With n-butyllithium; In tetrahydrofuran; N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;
2-bromoanisole; With magnesium; In diethyl ether;
Trimethyl borate; In tetrahydrofuran; diethyl ether;
Trimethyl borate; 2-bromoanisole; With n-butyllithium; at -78 ℃; Inert atmosphere;
With hydrogenchloride; In water; Inert atmosphere;
With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;
With n-butyllithium;
2-bromoanisole; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;
Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;
2-bromoanisole
578-57-4

2-bromoanisole

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
2-bromoanisole; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;
With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
87%
2-bromoanisole; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h;
With Trimethyl borate; In diethyl ether; hexane; at 20 ℃;
86%
2-bromoanisole; With magnesium; In tetrahydrofuran; Reflux;
With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;
80%
With hydrogenchloride; n-butyllithium; Triisopropyl borate; 1.) hexane, Et2O, -78 deg C, 30 min; 2.) hexane, Et2O, -78 deg C, 30 min, then room temp.;
68%
2-bromoanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -90 ℃; for 0.25h;
With Trimethyl borate; In tetrahydrofuran; hexane; at -90 - 20 ℃; for 2h;
With hydrogenchloride; pH=5 - 6; cooling;
67%
2-bromoanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
With Trimethyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 3h;
42%
2-bromoanisole; With magnesium; In tetrahydrofuran; for 3h; Heating;
With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;
With hydrogenchloride; In tetrahydrofuran; water;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; pentane / 1.42 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 - 20 °C / Inert atmosphere
2.1: hydrogenchloride; water / Inert atmosphere
With hydrogenchloride; n-butyllithium; water; In tetrahydrofuran; pentane;
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos; In ethanol; at 80 ℃; for 1.5h; Inert atmosphere;
With tetrahydroxydiboron; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine; In ethanol; at 80 ℃; for 2h; Inert atmosphere; Sealed tube;
2-bromoanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
With triisopropyl borate;
With hydrogenchloride; In water; ethyl acetate;
Multi-step reaction with 2 steps
1.1: magnesium; lithium chloride / Inert atmosphere; Schlenk technique
1.2: Inert atmosphere; Schlenk technique
2.1: copper(I) iodide-lithium chloride / tetrahydrofuran / 20 °C / Schlenk technique; Inert atmosphere
With copper(I) iodide-lithium chloride; magnesium; lithium chloride; In tetrahydrofuran;
Triisopropyl borate
5419-55-6

Triisopropyl borate

2-bromoanisole
578-57-4

2-bromoanisole

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
2-bromoanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -10 ℃;
Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;
69%
2-bromoanisole; With magnesium; In tetrahydrofuran; at 20 ℃; for 1h; Heating;
Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 18h;
With water; In tetrahydrofuran; for 1h;
69%
With n-butyllithium; In diethyl ether; hexane; addn. of hexane soln. of n-BuLi to Et2O soln. of bromoanisole at -78°C, stirring (-78°C, 30 min), addn. of the mixture to a Et2O soln. of borate under N2 atmosphere, stirring (-78°C, 30 min), stirring (room temp.); aq. HCl (10%), extn. (Et2O), washing of extracts (water), drying (Na2SO4), crystn. (refrigerator, 24 h), washing (cold pentane), drying (vacuum);
68%
water
7732-18-5

water

potassium (2-methoxyphenyl)trifluoroborate

potassium (2-methoxyphenyl)trifluoroborate

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
With montmorillonite K10; at 25 ℃; for 3h;
80%
pinacol 2-anisylboronate
190788-60-4

pinacol 2-anisylboronate

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
With hydrogenchloride; polystyrene boronic acid; In acetonitrile; at 20 ℃; for 18h;
95%
pinacol 2-anisylboronate; With potassium hydrogen difluoride; In methanol; at 20 ℃; for 0.25h;
With chloro-trimethyl-silane; water; In acetonitrile; for 1h;
70%
methoxybenzene
100-66-3

methoxybenzene

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
methoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 5h;
With Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;
With hydrogenchloride; In tetrahydrofuran; hexane;
64%
Multi-step reaction with 2 steps
1: nBuLi / tetrahydrofuran / 10 h / 20 °C
2: 8.87 g / HCl / tetrahydrofuran / 1 h / pH 3
With hydrogenchloride; n-butyllithium; In tetrahydrofuran;
Triisopropyl borate
5419-55-6

Triisopropyl borate

4-iodoanisol
529-28-2

4-iodoanisol

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;
n-butyllithium
109-72-8,29786-93-4

n-butyllithium

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
With hydrogenchloride; In tetrahydrofuran; methoxybenzene;
1.32 g (87%)
2-methoxyphenylmagnesium bromide
16750-63-3

2-methoxyphenylmagnesium bromide

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
2-methoxyphenylmagnesium bromide; With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;
With hydrogenchloride; In water;
45%
potassium (2-methoxyphenyl)trifluoroborate

potassium (2-methoxyphenyl)trifluoroborate

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

Conditions
Conditions Yield
With water; silica gel; at 20 ℃; for 1h; Inert atmosphere;
67%

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