Home Cart 0 Sign in  

[ CAS No. 172975-69-8 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 172975-69-8
Chemical Structure| 172975-69-8
Structure of 172975-69-8 * Storage: {[proInfo.prStorage]}

Quality Control of [ 172975-69-8 ]

Related Doc. of [ 172975-69-8 ]

SDS
Alternatived Products of [ 172975-69-8 ]
Alternatived Products of [ 172975-69-8 ]

Product Details of [ 172975-69-8 ]

CAS No. :172975-69-8 MDL No. :MFCD00185689
Formula : C8H11BO2 Boiling Point : 312.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :149.98 g/mol Pubchem ID :2734349
Synonyms :

Safety of [ 172975-69-8 ]

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 [ 172975-69-8 ]

  • Upstream synthesis route of [ 172975-69-8 ]
  • Downstream synthetic route of [ 172975-69-8 ]

[ 172975-69-8 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 172975-69-8 ]
  • [ 461-97-2 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[2] Organic Letters, 2013, vol. 15, # 19, p. 5134 - 5137
  • 2
  • [ 172975-69-8 ]
  • [ 556-96-7 ]
YieldReaction ConditionsOperation in experiment
71% With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
  • 3
  • [ 172975-69-8 ]
  • [ 22445-41-6 ]
YieldReaction ConditionsOperation in experiment
77% With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
  • 4
  • [ 67-56-1 ]
  • [ 55124-35-1 ]
  • [ 556-96-7 ]
  • [ 172975-69-8 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667 h;
Stage #2: at 70℃;
General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H2O.
Reference: [1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171
  • 5
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 34696-73-6 ]
  • [ 172975-69-8 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
A solution of 3,5-dimethylphenylmagnesium bromide obtained from a solution of190.3 g (1.03 mol) of 1-bromo-3,5-dimethylbenzene in 1000 ml ofTHF and 32 g(1.32 mol, 28percent excess) of magnesium turnings was cooled to -78°C, and 104 g (1.0 mol) of trimethylborate was added in one portion. The resulting heterogeneousmixture was stirred overnight at room temperature. The boronic ester washydrolyzed by careful addition of 1200 ml of2 M HCl. 500 ml of diethyl ether wasadded, the organic layer was separated, and the aqueous layer was additionallyextracted with 2 x 500 ml of diethyl ether. The combined organic extract was dried over Na2S04 and then evaporated to dryness to give white mass. The latter wastriturated with 200 ml of hexane, filtered through glass frit (G3), and the precipitatewas dried in vacuo. This procedure gave 114.6 g (74percent) of(3,5-dimethylphenyl)boronic acid.Anal. calc. for C8H11B02: C, 64.06; H, 7.39. Found: C, 64.38; H, 7.72. 1H NMR (DMSO-d6): 8 7.38 (s, 2H), 7.00 (s, 1H), 3.44(very br.s, 2H), 2.24 (s, 6H).
Reference: [1] Patent: WO2018/91684, 2018, A1, . Location in patent: Page/Page column 66; 67
  • 6
  • [ 556-96-7 ]
  • [ 172975-69-8 ]
Reference: [1] Chemical Communications, 2005, # 25, p. 3213 - 3214
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118
[3] Journal of the American Chemical Society, 2009, vol. 131, # 6, p. 2159 - 2171
[4] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
  • 7
  • [ 5419-55-6 ]
  • [ 556-96-7 ]
  • [ 172975-69-8 ]
YieldReaction ConditionsOperation in experiment
29.7% With N2 In tetrahydrofuran B.
3,5-dimethylphenyl boronic acid
Mg turnings (1.44 g, 59.43 mmol) were covered with dry THF (18.8 ml) in a dried, N2 filled flask fitted with an addition funnel and reflux condenser.
To this was added 5-bromo-m-xylene (10 g, 54.03 mmol) in THF (15 ml) after initiation of the Grignard reaction.
The addition was carried out over several minutes and the reaction mixture was heated at reflux for 1-2 h until most of the Mg had reacted.
The reaction mixture was then cooled and transferred to an addition funnel fitted to a N2 filled flask containing triisopropyl borate (24.9 ml) at -70° C.
The dropwise addition was carried out over several minutes and the mixture warmed to room temperature and stirred overnight.
The grey solution was poured onto 2 M HCl and immediately turned yellow.
The solution was extracted into Et2 O and the Et2 O fractions were combined, dried over MgSO4 and the solvent was removed in vacuo to yield 2.41 g (29.7percent).
mp 249-251° C.; 1 H NMR (CDCl3) 2.44 (6H, s), 7.23 (1H, s), 7.84 (2H, s); 13 C NMR (CD3 OD) 21.36, 133.28, 134.39, 137.48.
29.7% With N2 In tetrahydrofuran 3,5-dimethylphenyl boronic acid
Mg turnings (1.44 g, 59.43 mmol) were covered with dry THF (18.8 ml) in a dried, N2 filled flask fitted with an addition funnel and reflux condenser.
To this was added 5-bromo-m-xylene (10 g, 54.03 mmol) in THF (15 ml) after initiation of the Grignard reaction.
The addition was carried out over several minutes and the reaction mixture was heated at reflux for 1-2 h until most of the Mg had reacted.
The reaction mixture was then cooled and transferred to an addition funnel fitted to a N2 filled flask containing triisopropyl borate (24.9 ml) at -70° C.
The dropwise addition was carried out over several minutes and the mixture warmed to room temperature and stirred overnight.
The grey solution was poured onto 2M HCl and immediately turned yellow.
The solution was extracted into Et2 O and the Et2 O fractions were combined, dried over MgSO4 and the solvent was removed in vacuo to yield 2.41 g (29.7percent).
mp 249-251° C.; 1 H NMR (CDCl3) 2.44 (6 H, s), 7.23 (1 H, s), 7.84 (2 H, s); 13 C NMR (CD3 OD) 21.36, 133.28, 134.39, 137.48.
Reference: [1] Patent: US5965539, 1999, A,
[2] Patent: US5834434, 1998, A,
[3] Patent: US5756507, 1998, A,
[4] Patent: US6197975, 2001, B1,
[5] Organic Letters, 2015, vol. 17, # 2, p. 346 - 349
  • 8
  • [ 121-43-7 ]
  • [ 556-96-7 ]
  • [ 172975-69-8 ]
Reference: [1] Organometallics, 2001, vol. 20, # 11, p. 2321 - 2330
[2] Journal of the American Chemical Society, 2009, vol. 131, # 6, p. 2159 - 2171
  • 9
  • [ 325142-93-6 ]
  • [ 172975-69-8 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 757 - 760
[2] Organic Letters, 2007, vol. 9, # 5, p. 761 - 764
  • 10
  • [ 108-38-3 ]
  • [ 172975-69-8 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 757 - 760
[2] Organic Letters, 2007, vol. 9, # 5, p. 761 - 764
  • 11
  • [ 34696-73-6 ]
  • [ 172975-69-8 ]
Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 450 - 451
  • 12
  • [ 95070-94-3 ]
  • [ 172975-69-8 ]
Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 450 - 451
  • 13
  • [ 34907-38-5 ]
  • [ 172975-69-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 14
  • [ 1016971-57-5 ]
  • [ 301699-39-8 ]
  • [ 172975-69-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 15
  • [ 1016971-59-7 ]
  • [ 301699-39-8 ]
  • [ 172975-69-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 16
  • [ 1016971-63-3 ]
  • [ 172975-69-8 ]
  • [ 233584-42-4 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 17
  • [ 1016971-64-4 ]
  • [ 172975-69-8 ]
  • [ 233584-42-4 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 18
  • [ 1016971-54-2 ]
  • [ 172975-69-8 ]
  • [ 182163-96-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 19
  • [ 1016971-55-3 ]
  • [ 172975-69-8 ]
  • [ 182163-96-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 20
  • [ 1016971-54-2 ]
  • [ 172975-69-8 ]
  • [ 182163-96-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 21
  • [ 1016971-55-3 ]
  • [ 172975-69-8 ]
  • [ 182163-96-8 ]
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 219 - 223
  • 22
  • [ 67-56-1 ]
  • [ 172975-69-8 ]
  • [ 177735-55-6 ]
Reference: [1] CrystEngComm, 2018, vol. 20, # 13, p. 1874 - 1881
Historical Records

Related Functional Groups of
[ 172975-69-8 ]

Organoboron

Chemical Structure| 17933-03-8

[ 17933-03-8 ]

m-Tolylboronic acid

Similarity: 0.97

Chemical Structure| 55499-44-0

[ 55499-44-0 ]

2,4-Dimethylphenylboronic acid

Similarity: 0.95

Chemical Structure| 2156-04-9

[ 2156-04-9 ]

4-Vinylbenzeneboronic acid

Similarity: 0.95

Chemical Structure| 16419-60-6

[ 16419-60-6 ]

2-Methylphenylboronic acid

Similarity: 0.95

Chemical Structure| 55499-43-9

[ 55499-43-9 ]

3,4-Dimethylphenylboronic acid

Similarity: 0.95

Aryls

Chemical Structure| 17933-03-8

[ 17933-03-8 ]

m-Tolylboronic acid

Similarity: 0.97

Chemical Structure| 55499-44-0

[ 55499-44-0 ]

2,4-Dimethylphenylboronic acid

Similarity: 0.95

Chemical Structure| 2156-04-9

[ 2156-04-9 ]

4-Vinylbenzeneboronic acid

Similarity: 0.95

Chemical Structure| 16419-60-6

[ 16419-60-6 ]

2-Methylphenylboronic acid

Similarity: 0.95

Chemical Structure| 55499-43-9

[ 55499-43-9 ]

3,4-Dimethylphenylboronic acid

Similarity: 0.95

Organoboron

Chemical Structure| 17933-03-8

[ 17933-03-8 ]

m-Tolylboronic acid

Similarity: 0.97

Chemical Structure| 55499-44-0

[ 55499-44-0 ]

2,4-Dimethylphenylboronic acid

Similarity: 0.95

Chemical Structure| 2156-04-9

[ 2156-04-9 ]

4-Vinylbenzeneboronic acid

Similarity: 0.95

Chemical Structure| 16419-60-6

[ 16419-60-6 ]

2-Methylphenylboronic acid

Similarity: 0.95

Chemical Structure| 55499-43-9

[ 55499-43-9 ]

3,4-Dimethylphenylboronic acid

Similarity: 0.95