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[ CAS No. 1218791-12-8 ] {[proInfo.proName]}

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Chemical Structure| 1218791-12-8
Chemical Structure| 1218791-12-8
Structure of 1218791-12-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1218791-12-8 ]

CAS No. :1218791-12-8 MDL No. :MFCD12546509
Formula : C13H17BClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BACIYPAZHNHGPX-UHFFFAOYSA-N
M.W : 281.54 Pubchem ID :46739587
Synonyms :

Calculated chemistry of [ 1218791-12-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.02
TPSA : 61.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 1.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.175 mg/ml ; 0.000623 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.127 mg/ml ; 0.000452 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.2
Solubility : 0.0178 mg/ml ; 0.0000632 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.67

Safety of [ 1218791-12-8 ]

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

Application In Synthesis of [ 1218791-12-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1218791-12-8 ]

[ 1218791-12-8 ] Synthesis Path-Downstream   1~11

YieldReaction ConditionsOperation in experiment
69%
69%
  • 2
  • [ 1218791-12-8 ]
  • [ 1459730-79-0 ]
  • [ 1459732-37-6 ]
YieldReaction ConditionsOperation in experiment
46% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 20℃; for 12h; Inert atmosphere; Reflux; 1004 Example 1004 2-chloro-4-(3-((2-oxo-l,2-dihydroquinolin-6-yl)methyl)-3H-[l,2,3]triazolo[4,5-b]pyridin- 5-yl)benzamide: Example 1004 2-chloro-4-(3-((2-oxo-l,2-dihydroquinolin-6-yl)methyl)-3H-[l,2,3]triazolo[4,5-b]pyridin- 5-yl)benzamide: [365] To a solution of Intermediate 32 (0.060 g, 0.202 mmol) and intermediate 9 (0.072 g, 0.253 mmol) in dioxane (1.8 ml), potassium carbonate (0.093 g, 0.675 mmol) was added and degassed for 30 min. To this tetrakis (triphenylphosphine)palladium(O) (0.018 g, 0.016 mmol) was added under nitrogen at RT and the reaction mixture was refluxed for 12h. The solvent was evaporated completely and water was added to the residue and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as an off-white solid (0.040 g, 46%). M.P.: >300°C. 'H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 11.74 (s 8.67 (d, J = 8.7 Hz, 1H), 8.31 (d, J = 1.5 Hz, 1H), 8.25 (dd, J = 8.0, 1.5 Hz, 1H), 8.20 (d, J = 8.8 Hz, 1H), 7.95 (s,lH), 7.89 (d, J = 9.5 Hz, 1H), 7.78 (s,lH), 7.68 (s,lH), 7.62 (d, J = 8.1 Hz, 2H), 7.28 (d, J = 8.4 Hz, 1H), 6.48 (d, J = 8.2 Hz, 1H), 6.03 (s, 2H).
46% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 12h; Inert atmosphere; Reflux; 1004 Example 1004 2-chloro-4-(3-((2-oxo-1,2-dihydroquinolin-6-yl)methyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-5-yl)benzamide Example 1004 2-chloro-4-(3-((2-oxo-1,2-dihydroquinolin-6-yl)methyl)-3H-[1,2,3]triazolo[4,5-b]pyridin-5-yl)benzamide [0715] To a solution of Intermediate 32 (0.060 g, 0.202 mmol) and intermediate 9 (0.072 g, 0.253 mmol) in dioxane (1.8 ml), potassium carbonate (0.093 g, 0.675 mmol) was added and degassed for 30 min. To this tetrakis (triphenylphosphine)palladium(0) (0.018 g, 0.016 mmol) was added under nitrogen at RT and the reaction mixture was refluxed for 12 h. The solvent was evaporated completely and water was added to the residue and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as an off-white solid (0.040 g, 46%). M.P.: >300° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 11.74 (s 8.67 (d, J=8.7 Hz, 1H), 8.31 (d, J=1.5 Hz, 1H), 8.25 (dd, J=8.0, 1.5 Hz, 1H), 8.20 (d, J=8.8 Hz, 1H), 7.95 (s, 1H), 7.89 (d, J=9.5 Hz, 1H), 7.78 (s, 1H), 7.68 (s, 1H), 7.62 (d, J=8.1 Hz, 2H), 7.28 (d, J=8.4 Hz, 1H), 6.48 (d, J=8.2 Hz, 1H), 6.03 (s, 2H).
  • 3
  • [ 1218791-12-8 ]
  • [ 1350426-10-6 ]
  • [ 1350428-31-7 ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 0.75h; Inert atmosphere; Microwave irradiation; 1008 Example 1008 2-Chloro-4-(3-(quinolin-6-ylmethyl)-3H-imidazo[4,5-b]pyridin-5-yl)benzamide: Example 1008 2-Chloro-4-(3-(quinolin-6-ylmethyl)-3H-imidazo[4,5-b]pyridin-5-yl)benzamide: To a solution of Intermediate 34 (0.150 g, 0.508 mmol) and intermediate 9 (0.179 g, 0.636 mmol), in dioxane (3 ml), potassium carbonate (1.276 g, 13.03 mmol), water (1 ml) and tetrakis (triphenylphosphine)palladium(O) (0.047 g, 0.040 mmol) was added under nitrogen at RT and the reaction mixture was kept under microwave irradiation (microwave power = 100W, temperature = 100 °C) for 45 min The solvent was evaporated completely and water was added to the residue and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as an off-white solid (0.095 g, 45%). M.P.: 212-214°C. 'H-NMR (δ ppm, DMSO-d6, 400 MHz ): δ 8.87 (dd, J = 4.1,2.8 Hz, 1H), 8.73 (s, 1H), 8.35 (d, J = 8.5 Hz, 1H), 8.20 (s, 1H), 8.18 (d, J = 7.6 Hz, 1H), 8.13 (d, J = 8.1 Hz, 1H), 8.01 (m, 3H), 7.90 (s, 1H), 7.83 (d, J = 8.7 Hz, 1H), 7.62(s, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.53 (dd, J = 8.6, 4.5 Hz, 1H), 5.78 (s, 2H).
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 0.75h; Inert atmosphere; Microwave irradiation; 1008 Example 1008 2-Chloro-4-(3-(quinolin-6-ylmethyl)-3H-imidazo[4,5-b]pyridin-5-yl)benzamide Example 1008 2-Chloro-4-(3-(quinolin-6-ylmethyl)-3H-imidazo[4,5-b]pyridin-5-yl)benzamide; To a solution of Intermediate 34 (0.150 g, 0.508 mmol) and intermediate 9 (0.179 g, 0.636 mmol), in dioxane (3 ml), potassium carbonate (1.276 g, 13.03 mmol), water (1 ml) and tetrakis (triphenylphosphine)palladium(0) (0.047 g, 0.040 mmol) was added under nitrogen at RT and the reaction mixture was kept under microwave irradiation (microwave power=100 W, temperature=100° C.) for 45 min. The solvent was evaporated completely and water was added to the residue and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as an off-white solid (0.095 g, 45%). M.P.: 212-214° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.87 (dd, J=4.1, 2.8 Hz, 1H), 8.73 (s, 1H), 8.35 (d, J=8.5 Hz, 1H), 8.20 (s, 1H), 8.18 (d, J=7.6 Hz, 1H), 8.13 (d, J=8.1 Hz, 1H), 8.01 (m, 3H), 7.90 (s, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.62 (s, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.6, 4.5 Hz, 1H), 5.78 (s, 2H).
  • 4
  • [ 426265-73-8 ]
  • [ 73183-34-3 ]
  • [ 1218791-12-8 ]
YieldReaction ConditionsOperation in experiment
72% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; Inert atmosphere; 29.1 Step 1. 2-chloro-4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)benzamide (2-68) A mixture of 2-67 (1.17 g, 5 mmol), (Pin)2B (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 ml) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-68 (yellow solid, 1.01 g, 72% yield). LCMS (m/z):282 [M+Hj .
69% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; 9 Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide: Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide: Potassium acetate (0.627 g, 6.39 mmol) and bis(pinacolato)diboron (0.595 g, 2.34 mmol) were added to a solution of 4-bromo-2-chlorobenzamide (0.500 g, 2.13 mmol) in dioxane 3.6 ml), and the solution was degassed for 30 min. To this solution [Ι, - bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (0.052 g, 0.063 mmol) was added under nitrogen atmosphere and heated to 80°C. After 12h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a brown solid (0.75 g, 69%). 'H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 7.91 (s, 1H), 7.89 (m, 1H), 7.61 (m, 2H), 7.44 (d, J = 7.6 Hz, 1H), 1.14 (s,12H).
69% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Potassium acetate (0.627 g, 6.39 mmol) and bis(pinacolato)diboron (0.595 g, 2.34 mmol) were added to a solution of 4-bromo-2-chlorobenzamide (0.500 g, 2.13 mmol) in dioxane 3.6 ml), and the solution was degassed for 30 min. To this solution [1,1'-bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (0.052 g, 0.063 mmol) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a brown solid (0.75 g, 69%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 7.91 (s, 1H), 7.89 (m, 1H), 7.61 (m, 2H), 7.44 (d, J=7.6 Hz, 1H), 1.14 (s, 12H).
  • 5
  • [ 1218791-12-8 ]
  • [ 1459732-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.75 h / 100 °C / Inert atmosphere; Microwave irradiation 2: hydrogenchloride / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C
  • 6
  • [ 1218791-12-8 ]
  • [ 1459732-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.75 h / 100 °C / Inert atmosphere; Microwave irradiation 2: water; acetonitrile / 0.33 h
  • 7
  • [ 1218791-12-8 ]
  • [ 1350426-10-6 ]
  • [ 1459732-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.75 h / 100 °C / Inert atmosphere; Microwave irradiation 2: hydrogenchloride / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C
  • 8
  • [ 1218791-12-8 ]
  • [ 700-36-7 ]
  • 4-(2-amino-5-bromopyridin-3-yl)-2-chlorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In N,N-dimethyl-formamide Inert atmosphere; 29.2 Step 2. 4-(2-amino-5-bromopyridin-3-yl)-2-chlorobenzamide (2-69) A mixture of 2-68 (1.01 g, 3.6 mmol), 2-3 (897 mg, 3 mmol), Pd(PPh3)2C12 (210 mg, 0.3 mmol), K3P04 (1.27 g, 6 mmol) and DMF (15 mL) was degassed with N2 and stirred at 45 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with PE/ethyl acetate from 2/1 to 1/2 to provide intermediate 2-69 (yellow solid, 381 mg, 39% yield). LCMS (m/z): 326 [M+Hj .
  • 9
  • [ 1218791-12-8 ]
  • 4-(2-amino-5-(2-fluoro-5-nitrophenyl)pyridin-3-yl)-2-chlorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / Inert atmosphere 2: potassium phosphate; bis-triphenylphosphine-palladium(II) chloride / water; tetrahydrofuran / 65 °C / Inert atmosphere
  • 10
  • [ 1218791-12-8 ]
  • 6-(tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine [ No CAS ]
  • 4-(6-(tert-butylsulfonyl)-7-methoxyimidazo[1,2-a]pyridin-3-yl)-2-chlorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; ethanol; water at 140℃; for 0.333333h; Inert atmosphere; Sealed tube; Microwave irradiation;
  • 11
  • [ 1218791-12-8 ]
  • tert-butyl ((3R,5R)-1-(2-(6-bromo-1-(cyclopropylmethyl)-1H-indol-2-yl)-4-methoxy-3-methylbenzofuran-6-carbonyl)-5-fluoropiperidin-3-yl)carbamate [ No CAS ]
  • tert-butyl ((3R,5R)-1-(2-(6-(4-carbamoyl-3-chlorophenyl)-1-(cyclopropylmethyl)-1H-indol-2-yl)-4-methoxy-3-methylbenzofuran-6-carbonyl)-5-fluoropiperidin-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; 162 Intermediate 162C tert-Butyl-((3R,5R)-1-(2-(6-(4-carbamoyl-3-chlorophenyl)-1-(cyclopropylmethyl)-1H- indol-2-yl)-4-methoxy-3-methylbenzofuran-6-carbonyl)-5-fluoropiperidin-3-yl)carbamate A solution of K2CO3 (95 mg, 0.687 mmol) in water (4.13 µl, 0.229 mmol) was added to a stirred and degasified solution of Intermediate 162B (150 mg, 0.229 mmol) and 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (97 mg, 0.344 mmol) in dioxane (2 ml), followed by addition of PdCl2(dppf)-CH2Cl2 adduct (14.04 mg, 0.017 mmol). The reaction mixture was heated to 80 and stirred for 16 hours, diluted with water (50 ml), and extracted with EtOAc (3×50 ml). The combined organic layers were dried over anhydrous sodium sulphate, filtered, and the filtrate was evaporated under reduced pressure concentrated to afford the crude material, which was purified using preparative HPLC to afford the product as brown oil (0.015 g, 8%). LC/MS m/z: 729 [M-H]+.
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