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1171891-31-8

1171891-31-8

Identification

  • Product Name:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

  • CAS Number: 1171891-31-8

  • EINECS:

  • Molecular Weight:219.091

  • Molecular Formula: C

  • HS Code:2934999090

  • Mol File:1171891-31-8.mol

Synonyms:4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • 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:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
  • Packaging:100mg
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
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  • Manufacture/Brand:Synthonix
  • Product Description:4-Methylpyridine-3-boronicacidpinacolester 95+%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-Methylpyridine-3-boronicacidpinacolester 95+%
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  • Manufacture/Brand:Crysdot
  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 98%
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  • Manufacture/Brand:ChemScene
  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine ≥98.0%
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  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine ≥98.0%
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  • Manufacture/Brand:ChemScene
  • Product Description:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine ≥98.0%
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Relevant articles and documentsAll total 5 Articles be found

Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

Yang, Lichen,Uemura, Nao,Nakao, Yoshiaki

supporting information, p. 7972 - 7979 (2019/05/22)

We report herein the iridium-catalyzed meta-selective C-H borylation of benzamides by using a newly designed 2,2′-bipyridine (bpy) ligand bearing an alkylaluminum biphenoxide moiety. We also demonstrate the iridium-catalyzed C3-selective C-H borylation of pyridine with a 1,10-phenanthroline (Phen) ligand bearing an alkylborane moiety. It is proposed that the Lewis acid-base interaction between the Lewis acid moiety and the aminocarbonyl group or the sp2-hybridized nitrogen atom accelerates the reaction and controls the site-selectivity.

Iridium-catalyzed C-H borylation of heteroarenes: Scope, regioselectivity, application to late-stage functionalization, and mechanism

Larsen, Matthew A.,Hartwig, John F.

supporting information, p. 4287 - 4299 (2014/04/03)

A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were found to be amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodology for the synthesis of complex heteroaryl structures. Application of this methodology to the synthesis and late-stage functionalization of biologically active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.

Synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle

Wang, Lianhui,Cui, Xiuling,Li, Jingya,Wu, Yusheng,Zhu, Zhiwu,Wu, Yangjie

experimental part, p. 595 - 603 (2012/03/09)

The tricyclohexylphosphane adduct of cyclopalladated ferrocenylimine I exhibited high catalytic activity in the one-pot borylation/Suzuki-Miyaura coupling (BSC) reaction with low catalyst loading (2 mol-%). Various biaryls were obtained in good to excellent yields for 37 examples. This process was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups and did not require an excess amount of phosphane ligand and the addition of the palladium catalyst in the second step. Cyclopalladated ferrocenylimine I exhibited high catalytic activity in the borylation/Suzuki- Miyaura coupling (BSC) reaction with low catalyst loading. Various unsymmetrical biaryls were obtained ingood to excellent yields in one pot. This protocol was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups without adding catalyst in the second step. Copyright

Pyrrolopyrimidines and Pyrrolopyridines

-

Page/Page column 50-52, (2009/07/25)

Compounds of formula I in free or salt or solvate form, wherein X, T1, T3 and T4 have the meanings as indicated in the specification, are useful for treating diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

5-Thioxylopyranose Compounds

-

Page/Page column 11, (2009/07/25)

Compounds of 5-thioxylopyranose, preferably derivatives of the 5-thioxilopyranose type, a method for preparing such compounds, and the use of such compounds as an active ingredient in pharmaceutical compositions which are useful, in particular, for treati

Process route upstream and downstream products

Process route

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3-Bromo-4-methylpyridin
3430-22-6

3-Bromo-4-methylpyridin

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions
Conditions Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 120 ℃; for 1h; Microwave irradiation;
With (C5H5FeC5H3C(CH3)NC6H4CH3)PdCl(tricyclohexylphosphine); potassium acetate; In 1,4-dioxane; at 100 ℃; for 6h; Inert atmosphere;
picoline
108-89-4

picoline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions
Conditions Yield
With C44H72B3IrN2O6; In tetrahydrofuran; at 80 ℃; for 7h; Inert atmosphere; Glovebox;
Ca. 10 %Spectr.
picoline
108-89-4

picoline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

4-methyl-3,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

4-methyl-3,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions
Conditions Yield
bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3-(2-(2-(dicyclohexylboraneyl)ethyl)phenyl)-1,10-phenanthroline; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In 1,4-dioxane; at 25 ℃; for 0.166667h; Inert atmosphere; Glovebox;
picoline; In hexane; at 25 ℃; for 18h; Overall yield = 35 %; Overall yield = 100.8 mg; regioselective reaction; Inert atmosphere; Glovebox;
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions
Conditions Yield
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

1-[8-[bis[(2,4-dimethoxybenzyl)]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-(1-methylpyrazol-4-yl)urea

1-[8-[bis[(2,4-dimethoxybenzyl)]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-(1-methylpyrazol-4-yl)urea

1-[8-[bis[(2,4-dimethoxybenzyl)]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-(1-methyl pyrazol-4-yl)urea

1-[8-[bis[(2,4-dimethoxybenzyl)]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-(1-methyl pyrazol-4-yl)urea

Conditions
Conditions Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate; XPhos; In 1,4-dioxane; water; at 100 ℃; for 1.5h; Inert atmosphere;
89%
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

tert-butyl 3-[[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]carbamoylamino]azetidine-1-carboxylate

tert-butyl 3-[[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]carbamoylamino]azetidine-1-carboxylate

tert-butyl 3-[[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]carbamoylamino]azetidine-1-carboxylate

tert-butyl 3-[[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]carbamoylamino]azetidine-1-carboxylate

Conditions
Conditions Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos; In 1,4-dioxane; water; at 100 ℃; for 2h; Inert atmosphere;
88%
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-[1-(1-cyanoethyl)pyrazol-4-yl]urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-[1-(1-cyanoethyl)pyrazol-4-yl]urea

(+/-)-1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-[1-(1-cyanoethyl)pyrazol-4-yl]urea

(+/-)-1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-[1-(1-cyanoethyl)pyrazol-4-yl]urea

Conditions
Conditions Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate; XPhos; In 1,4-dioxane; water; at 100 ℃; for 2h;
92.1%
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

C<sub>11</sub>H<sub>10</sub>BrN<sub>3</sub>O<sub>3</sub>

C11H10BrN3O3

C<sub>17</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub>

C17H16N4O3

Conditions
Conditions Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100 ℃; for 20h; Inert atmosphere;
60%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100 ℃; for 20h; Inert atmosphere;
60%
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-(2-hydroxy-1-methylethyl)urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-(2-hydroxy-1-methylethyl)urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-(2-hydroxy-1-methylethyl)urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-(2-hydroxy-1-methylethyl)urea

Conditions
Conditions Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos; In 1,4-dioxane; water; at 100 ℃; for 2h; Inert atmosphere;
78%
4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1171891-31-8

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-[1-(2-methoxyethyl)azetidin-3-yl]urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-chloro-2,7-naphthyridin-3-yl]-3-[1-(2-methoxyethyl)azetidin-3-yl]urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-[1-(2-methoxyethyl)azetidin-3-yl]urea

1-[8-[bis[(2,4-dimethoxyphenyl)methyl]amino]-6-(4-methyl-3-pyridyl)-2,7-naphthyridin-3-yl]-3-[1-(2-methoxyethyl)azetidin-3-yl]urea

Conditions
Conditions Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 105 ℃; for 3h;
75%

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