Home Cart 0 Sign in  

[ CAS No. 886853-93-6 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 886853-93-6
Chemical Structure| 886853-93-6
Structure of 886853-93-6 * Storage: {[proInfo.prStorage]}

Quality Control of [ 886853-93-6 ]

Related Doc. of [ 886853-93-6 ]

SDS
Alternatived Products of [ 886853-93-6 ]
Alternatived Products of [ 886853-93-6 ]

Product Details of [ 886853-93-6 ]

CAS No. :886853-93-6 MDL No. :MFCD09800894
Formula : C10H10BNO3 Boiling Point : 414.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :203.00 g/mol Pubchem ID :16106577
Synonyms :

Safety of [ 886853-93-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886853-93-6 ]

  • Upstream synthesis route of [ 886853-93-6 ]
  • Downstream synthetic route of [ 886853-93-6 ]

[ 886853-93-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 6931-16-4 ]
  • [ 5419-55-6 ]
  • [ 886853-93-6 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran
Stage #3: With hydrogenchloride In tetrahydrofuran; water
[00235] To a solution of to 2-methoxyquinoline (10.0 g, 62.8 mmol) and triisiopropylborate (17.86 g, 95.1 mmol) in THF (140 mL) at -78 0C was added LDA solution (75.4 mmol, prepared from Pr'2NH and n-BuLi). The mixture was stirred at -78 0C for over 4 hours and slowly warmed to rt overnight. The mixture was quenched with saturated NH4Cl (68 mL) and acidified to a pH=5 with 3M HCl. The organic solvent THF and hexanes were evaporated under vacuum and EPO <DP n="133"/>boronic acid was precipitated as a white solid. The mixture was filtered through a Buchner funnel and the solid was washed thoroughly with H2O to afford the product after dried under high vacuum (12.11 g, 95 percent). 1H NMR (400 MHz, CDCl3) δ 8.64 (IH, s), 7.85 (IH, d, J= 8.3 Hz), 7.80 (IH, dJ= 7.9 Hz), 7.68 (IH, dd, 7=14.1, 1.1 Hz), 7.41 (IH, J= 7.5 Hz), 5.91 (2H, s, br), 4.18 (3H, s). 13C NMR (400 MHz, CDCl3) δ 164.9, 149.8, 148.I5 131.1, 128.6, 127.4, 125.5, 124.7, 53.9. HRMS (EI) calc'd for C10H10BNO3 ([M]+) 203.0754. Found: 203.0758.
77% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 9 h; 2-methoxy-quinoline (20.0g, 126mmol), triisopropoxy borane(59.1g, 314mmol,Mixture of tetrahydrofuran (dehydrated) (200mL) and cooled to -78 .There was added n- butyllithium (in hexanes 1.6M, 86mL, 138mmol), stirred for 4 hours at -78 ,The temperature was raised to room temperature over 5 hours.After the reaction, the addition of saturated NH4Cl solution (100mL), and was added until the pH of HCl (3M) solution be 5. Then, the suspended solids obtained by concentration of the organic layer was washed with water, and filtered to give the number of 2-methoxy-3-boronic acid (19.7g, 97.0mmol) (yield 77percent).
Reference: [1] Patent: WO2006/47888, 2006, A1, . Location in patent: Page/Page column 73; 131-132
[2] Patent: KR2016/18458, 2016, A, . Location in patent: Paragraph 0309; 0312; 0313
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1657 - 1662
  • 2
  • [ 6931-16-4 ]
  • [ 886853-93-6 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1341 - 1346
  • 3
  • [ 612-62-4 ]
  • [ 886853-93-6 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1341 - 1346
  • 4
  • [ 939-16-2 ]
  • [ 886853-93-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 40, p. 9622 - 9628
  • 5
  • [ 101870-60-4 ]
  • [ 886853-93-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 40, p. 9622 - 9628
Historical Records

Related Functional Groups of
[ 886853-93-6 ]

Organoboron

Chemical Structure| 163105-90-6

[ 163105-90-6 ]

2-Methoxy-3-pyridineboronic acid

Similarity: 0.78

Chemical Structure| 854373-97-0

[ 854373-97-0 ]

(2-Ethoxypyridin-3-yl)boronic acid

Similarity: 0.76

Chemical Structure| 1150114-42-3

[ 1150114-42-3 ]

(2-Isopropoxypyridin-3-yl)boronic acid

Similarity: 0.75

Chemical Structure| 1245898-82-1

[ 1245898-82-1 ]

(2-(tert-Butoxy)pyridin-3-yl)boronic acid

Similarity: 0.74

Chemical Structure| 1300750-50-8

[ 1300750-50-8 ]

(2-(Difluoromethoxy)pyridin-3-yl)boronic acid

Similarity: 0.72

Ethers

Chemical Structure| 163105-90-6

[ 163105-90-6 ]

2-Methoxy-3-pyridineboronic acid

Similarity: 0.78

Chemical Structure| 854373-97-0

[ 854373-97-0 ]

(2-Ethoxypyridin-3-yl)boronic acid

Similarity: 0.76

Chemical Structure| 1150114-42-3

[ 1150114-42-3 ]

(2-Isopropoxypyridin-3-yl)boronic acid

Similarity: 0.75

Chemical Structure| 1245898-82-1

[ 1245898-82-1 ]

(2-(tert-Butoxy)pyridin-3-yl)boronic acid

Similarity: 0.74

Chemical Structure| 1300750-50-8

[ 1300750-50-8 ]

(2-(Difluoromethoxy)pyridin-3-yl)boronic acid

Similarity: 0.72

Organoboron

Chemical Structure| 163105-90-6

[ 163105-90-6 ]

2-Methoxy-3-pyridineboronic acid

Similarity: 0.78

Chemical Structure| 854373-97-0

[ 854373-97-0 ]

(2-Ethoxypyridin-3-yl)boronic acid

Similarity: 0.76

Chemical Structure| 1150114-42-3

[ 1150114-42-3 ]

(2-Isopropoxypyridin-3-yl)boronic acid

Similarity: 0.75

Chemical Structure| 1245898-82-1

[ 1245898-82-1 ]

(2-(tert-Butoxy)pyridin-3-yl)boronic acid

Similarity: 0.74

Chemical Structure| 1300750-50-8

[ 1300750-50-8 ]

(2-(Difluoromethoxy)pyridin-3-yl)boronic acid

Similarity: 0.72

Related Parent Nucleus of
[ 886853-93-6 ]

Quinolines

Chemical Structure| 70254-42-1

[ 70254-42-1 ]

Quinolin-2-ol

Similarity: 0.63

Chemical Structure| 376581-24-7

[ 376581-24-7 ]

Quinolin-6-ylboronic acid

Similarity: 0.62

Chemical Structure| 6931-16-4

[ 6931-16-4 ]

2-Methoxyquinoline

Similarity: 0.62

Chemical Structure| 86-58-8

[ 86-58-8 ]

Quinolin-8-ylboronic acid

Similarity: 0.62

Chemical Structure| 355386-94-6

[ 355386-94-6 ]

Quinolin-5-ylboronic acid

Similarity: 0.61