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[ CAS No. 179942-55-3 ] {[proInfo.proName]}

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Chemical Structure| 179942-55-3
Chemical Structure| 179942-55-3
Structure of 179942-55-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 179942-55-3 ]

CAS No. :179942-55-3 MDL No. :MFCD06739099
Formula : C7H7BN4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DXUPJOQUAAVAGV-UHFFFAOYSA-N
M.W : 189.97 Pubchem ID :46737995
Synonyms :

Calculated chemistry of [ 179942-55-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 49.44
TPSA : 94.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.04
Log Po/w (WLOGP) : -1.45
Log Po/w (MLOGP) : -0.26
Log Po/w (SILICOS-IT) : -1.03
Consensus Log Po/w : -0.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.49
Solubility : 6.11 mg/ml ; 0.0322 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 4.93 mg/ml ; 0.0259 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.9
Solubility : 2.39 mg/ml ; 0.0126 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 179942-55-3 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H315-H319-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 179942-55-3 ]

* 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 [ 179942-55-3 ]

[ 179942-55-3 ] Synthesis Path-Downstream   1~22

  • 2
  • [ 3934-20-1 ]
  • [ 179942-55-3 ]
  • [ 1026029-40-2 ]
  • 3
  • [ 179942-55-3 ]
  • [ 1168720-53-3 ]
  • [ 1168723-11-2 ]
YieldReaction ConditionsOperation in experiment
38% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 125℃; for 4h;Microwave irradiation; A mixture of 3-iodo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-indazole-6- carbaldehyde (100 mg, 0.25 mmol), <strong>[179942-55-3]3-(tetrazol-5-yl)phenylboronic acid</strong> (57 mg, 0.30 mmol), Pd(PPh3)4 (18 mg, 0.025 mmol) and 2M Na2CO3 (0.13 mL, 0.25 mmol) in DMEZH2OZEtOH (2.8 mLZ0.8 mLZ0.4 mL) was degassed by evacuation and blanketed with Ar. The reaction mixture was sealed and heated with stirring <n="210"/>under microwave irradiation at 125 0C for 4 hours. The crude reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using MeOH (5% to 10 %) in DCM as the eluent to provide a white solid (40 mg, 38 %). 1H NMR (400 MHz, CD3OD) delta ppm 10.10 (s, 1 H), 8.59 (s, 1 H), 8.25 (s, 1 H), 8.21 (d, J= 8.5 Hz, 1 H), 8.11 (d, J= 7.9 Hz, 1 H), 8.04 (d, J= 8.3 Hz, 1 H), 7.77 (d, J= 8.4 Hz, 1 H), 7.67 (t, J= 7.8 Hz, 1 H), 5.88 (s, 2 H), 3.66 (t, J = 8.1 Hz, 2 H), 0.89 (t, J = 8.0 Hz, 2 H), -0.10 (s, 9 H); MS ESI 421.1 (100) [M + H]+, calcd for [C21H24N6O2Si + H]+ 421.2.
  • 4
  • [ 890839-39-1 ]
  • [ 179942-55-3 ]
  • [ 890842-77-0 ]
  • 5
  • [ 179942-55-3 ]
  • 5-(3-(4-bromophenyl)-3-(4-fluoro-2-methylphenyl)-1-(hydroxyimino)propyl)-1-methylpyridin-2(1H)-one [ No CAS ]
  • [ 1354812-91-1 ]
  • 5-{3-(4-fluoro-2-methyl-phenyl)-1-[(Z)-hydroxyimino]-3-[4'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-propyl}-1-methyl-1H-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 23h; Example 2605-{3-(4-Fluoro-2-methyl-phenyl)-l-[(E)-hydroxyimino]-3-[4'-(lH-tetrazol-5-yl)-biphenyl-4- yl]-propyl}-l-methyl-lH-pyridin-2-oneTo a solution of (E)-5-(3-(4-bromophenyl)-3-(4-fluoro-2-methylphenyl)- l-(hydroxyimino)propyl)-l-methylpyridin-2(lH)-one (0.1 g, example 224) in dioxane (1 mL) was added [l,l'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane adduct (CAS RN: [95464-05-4]) (9.21 mg), 4-(lH-tetrazol-5-yl)phenylboronic acid (64.3 mg, CAS RN:[179942-55-3]), water (0.65 mL) and aqueous 2M sodium carbonate solution (338 mu) and the reaction mixture was heated for 23 hours at 80C. The reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography using a MPLC system (20 g silica gel column, CombiFlash Companion, Isco Inc.) eluting with a gradient of dichloromethane : methanol (100 : 0 to 75 : 25). The product was purified a second time by preparative HPLC (phenomenex gemini column) with a gradient of acetonitrile : water (containing 0.5% formic acid) (10: 90 to 98 : 2) to yield the title compound containing 10% of the corresponding Z isomer as as a white foam, MS (ESI+): m/z = 509.21 [M+H]+.
  • 6
  • [ 179942-55-3 ]
  • [ 123990-76-1 ]
  • [ 1371588-17-8 ]
YieldReaction ConditionsOperation in experiment
84% To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(lH-tetrazol-5-yl)phenylboronic acid (91.2 mg, 0.482 mmol), K2C03 (199 mg, 1.45 mmol), and PdCl2(dppf) (17.6 mg, 0.024 mmol) was added 7 mL of DEGME and 3 mL of H20 under argon. The mixture was stirred at 150 C in a microwave reactor for 1.5 hours. The crude mixture was diluted with IN NaOH (10 mL) and slowly acidified to a pH of 4.0 using cone. HC1. The solids were filtered to yield 128 mg (84% yield) of desired product.
84% With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DEGME; water; at 150℃; for 1.5h;Inert atmosphere; microwave reactor; To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, mmol), 4-(lH-tetrazol-5-yl)phenylboronic acid (91.2 mg, 0.482 mmol), K2C03 (199 mg, 1.45 mmol), and PdCl2(dppf) (17.6 mg, 0.024 mmol) was added 7 rriL of DEGME and 3 rriL of H20 under argon. The mixture was stirred at 150 C in a microwave reactor for 1.5 hours. The crude mixture was diluted with IN NaOH (10 rriL) and slowly acidified to a pH of 4.0 using cone. HCl. The solids were filtered to yield 128 mg (84% yield) of the desired product.
  • 7
  • [ 179942-55-3 ]
  • [ 123990-76-1 ]
  • [ 1371587-45-9 ]
  • 8
  • [ 179942-55-3 ]
  • [ 1454558-14-5 ]
  • [ 1454555-19-1 ]
YieldReaction ConditionsOperation in experiment
96.3 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate monohydrate; In 1,2-dimethoxyethane; water; for 4h;Inert atmosphere; Heating; Part C. (2-Methoxy-ethyl)-f3-r4-(lH-tetrazol-5-yl)-Dhenyl1-Dyrazo To a mixture of (3-bromo-pyrazolo[l,5-a]pyrimidin-5-yl)-(2-methoxy-ethyl)-amine (307.7 mg, 1.1 mmol), (4-(lH-tetrazol-5-yl)phenyl)boronic acid [179942-55-3] (259.6 mg, 1.4 mmol), potassium phosphate tribasic monohydrate [27176-10-9] (522.4 mg, 2.3 mmol), and [Iota, - bis(diphenylphosphino)ferrocene] dichloro- palladium(ll), complex with dichloromethane [95464-05- 4] (106.3 mg, 0.1 mmol) contained in a 50 ml_ round bottomed flask was added a solution of 30% (v/v) water in 1,2-dimethoxyethane (12 ml_) and a magnetic stir bar. The reaction pot was fitted to a reflux condenser, lowered into an ambient temperature oil bath, and the system taken through 10 evacuation / N2 blanket cycles while being rapidly stirred. The rapidly stirred, N2 blanketed, reaction was heated to an oil bath temperature of 85 C for 4 h then cooled, diluted with methanol, and gravity filtered. The filtrate was preabsorbed on silica gel and flash chromatographed (silica gel eluted with 1% NH4OH in 10% (v/v) methanol / ethyl acetate). Desired chromatography fractions were combined, evaporated, redissolved in 2-propanol and gravity filtered into stirring heptane to precipitate purified product. (2-Methoxy-ethyl)-[3-[4-(lH-tetrazol-5-yl)-phenyl]-pyrazolo[l,5-a]pyrimidin- 5-yl}-amine was isolated by filtration as 96.3 mg of solid material, mp. 264-265C (dec). ^ NMR (400 MHz, DMSO-de) delta ppm 3.63 (t, J=4.29 Hz, 5 H) 6.41 (d, J=7.58 Hz, 1 H) 7.88 (br. s., 1 H) 8.04 (m, J=8.59 Hz, 2 H) 8.31 (m, J=8.34 Hz, 2 H) 8.47 (s, 1 H) 8.53 (d, J=7.58 Hz, 1 H). NMR (100 MHz, DMSO-de) delta ppm 40.69, 58.48, 70.48, 100.86, 103.75, 119.86, 125.23, 127.61, 135.97, 137.08, 142.42, 145.63, 156.60, LRMS (ESI) m/z 337.2 [(M+H)]+, calc'd for CisHieNsO: 336.36.
  • 9
  • [ 179942-55-3 ]
  • 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine [ No CAS ]
  • butyl-{3-[4-(1H-tetrazol-5-yl)-phenyl]-imidazo[1,2-b]pyridazin-6-yl}-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
101.7 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate monohydrate; In 1,2-dimethoxyethane; water; for 17h;Reflux; Inert atmosphere; To a mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine (327.5 mg, 1.2 mmol), [<strong>[179942-55-3][4-(2H-tetrazol-5-yl)phenyl]boronic acid</strong> [179942-55-3] (287.2 mg, 1.5 mmol), potassium phosphatetribasic monohydrate [27176-10-9] (564.7 mg, 2.5 mmol), and [1,1'-bis(diphenylphosphino)20 ferrocene] dichloropalladium(ll), complex with dichloromethane [95464-05-4] (103.7 mg, 0.1 mmol)contained in a 50 ml round bottomed flask was added a solution of 30% (vlv) water in 1,2-dimethoxyethane (20 ml) and a magnetic stir bar. The reaction pot was fitted to a reflux condenser,lowered into an ambient temperature oil bath, and the system taken through 10 evacuation 1 N2blanket cycles while being rapidly stirred. The rapidly stirred, N2 blanketed, reaction was heated to an25 oil bath temperature of 85C for 17 h then cooled, diluted with methanol, filtered, and flashchromatographed (silica gel, eluted with 1% acetic acid in 10% (vlv) methanol 1 ethyl acetate) toisolate a tan solid which was recrystallized from boiling 2-propanol to yield 101.7 mg of butyi-{3-[4-(1H-tetrazol-5-yl)-phenyl]-imidazo[1,2-b]pyridazin-6-yl}-mine as an off white powder, mp. 270-271C.1H NMR (400 MHz, DMSO-d6) 8 ppm 0.98 (t, J=7.06 Hz, 3 H) 1.38 -1.53 (m, 2 H) 1.59- 1.73 (m, 230 H) 3.34 (d, J=5.51 Hz, 2 H) 6.75 (d, J=9.48 Hz, 1 H) 7.17 (br. s., 1 H) 7.79 (d, J=9.04 Hz, 1 H) 8.06(br. s., 1 H) 8.12 (m, J=7.72 Hz, 2 H) 8.47 (m, J=7.72 Hz, 2 H).13C NMR (100 MHz, DMSO-d6) 8 ppmm 13.63, 19.77, 30.02, 40.66, 112.49, 122.39, 125.43, 125.65, 126.80, 130.59, 131.70, 153.44.LRMS (ESI) mjz 335.1 [(M+H)]+, calc'd for C11H1sNs: 334.39.
  • 10
  • [ 179942-55-3 ]
  • [ 4774-14-5 ]
  • C11H7ClN6 [ No CAS ]
  • 11
  • [ 179942-55-3 ]
  • C22H22N8 [ No CAS ]
  • 12
  • [ 179942-55-3 ]
  • 3-bromo-6-(3-(cyclopropylsulfonyl)phenyl)imidazo[1,2-b]pyridazine [ No CAS ]
  • 3-(4-(1H-tetrazol-5-yl)phenyl)-6-(3-(cyclopropylsulfonyl)phenyl)imidazo[1,2-b]pyridazine [ No CAS ]
  • 13
  • [ 179942-55-3 ]
  • 3-bromo-6-(3-(methylsulfonyl)phenyl)imidazo[1,2-b]pyridazine [ No CAS ]
  • C20H15N7O2S [ No CAS ]
  • 14
  • [ 179942-55-3 ]
  • 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridine [ No CAS ]
  • 3-(4-(1H-tetrazol-5-yl)phenyl)-5-(1-methyl-1H-pyrazol-4-yl)furo[3,2-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; butan-1-ol; for 2.5h;Inert atmosphere; Reflux; Degassed 1-butanol (2.0 mL) and H20 (0.4 mL) were placed into a 10 mL round bottom flask. Then, the product from Preparative Example 58 (23.8 mg, 85.6 muetaiotaomicron), (4-(1Eta- tetrazol-5-yl)phenyl)boronic acid (19.5 mg, 0.103 mmol), Pd(PPh3)4 (5.0 mg, 4.3 muiotatauiotaomicron) and K3P04 (54.5 mg, 0.257 mmol) were added. The mixture was refluxed under N2 for 150 min. The solvent was evaporated and the residue purified by column chromatography on silica gel (EtOAc/MeOH; from 3:1 to 2:1) and then by preparative TLC (THF/MeOH; 2:1). The product was obtained as a colorless semi-solid (12 mg; 41 %). NMR (300 MHz, CD3OD) delta 8.44 (s, 1H), 8.37 - 8.30 (m, 2H), 8.20 - 8.13 (m, 3H), 8.05 (d, J= 0.7 Hz, 1H), 7.83 (d, J- 8.7 Hz, 1H), 7.57 (d, J= 8.7 Hz, 1H), 3.96 (s, 3H). 13C NMR (75 MHz, CD3OD) delta 149.9, 148.9, 147.3, 146.6, 138.4, 132.7, 130.7, 130.0, 128.2, 127.9, 126.5, 125.4, 122.0, 120.3, 116.9, 39.1. HRMS (APCI): calcd. for C18Hi3N70 [M+H]+ = 344.1254; found [M+H]+ = 344.1252.
  • 15
  • [ 875639-15-9 ]
  • [ 179942-55-3 ]
  • C21H15BrN6O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 110℃;Inert atmosphere; General procedure: 5-Bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1 equiv.), Ar1 boronic acidderivate (1 equiv.) and K2CO3 (3 equiv.) in a mixture of dioxane/water (3/1, 0.1 mol/L) were degazedwith argon. Then Pd(dppf)Cl2 (0.02 equiv.) was added and the mixture was stirred at 110C for 5 h.Ar2 boronic acid derivate (1 to 1.5 equiv.) and K2CO3 (3 equiv.) were added and the mixture wasdegazed with argon. Pd(dppf)Cl2 (0.02 equiv.) was added and the mixture was stirred at 110Covernight. The solvent was removed under reduced pressure; then the mixture was dissolved in EtOAcand washed with a saturated aqueous NaHCO3 solution. The combined organic layers were dried overNa2SO4 and evaporated. The crude product and Cs2CO3 (3 equiv.) in a mixture of THF/MeOH (1/1,0.05 mol/L) were stirred at room temperature overnight. The solvents were evaporated under reducedpressure; then the mixture was dissolved in EtOAc and washed with a saturated aqueous NaHCO3solution. The combined organic layers were dried over Na2SO4 and evaporated. and the crude productwas purified by flash reverse phase chromatography with eluents: H2O + 1%TFA and ACN + 1%TFA(80/20 to 0/100).
  • 16
  • [ 179942-55-3 ]
  • [ 890842-77-0 ]
  • 17
  • [ 179942-55-3 ]
  • 5-phenyl-3-[4-(1H-tetrazol-5-yl)phenyl]-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 19
  • [ 179942-55-3 ]
  • 3-(6-bromo-4-chloroquinolin-3-yl)acrylate [ No CAS ]
  • [ 98-16-8 ]
  • 9-(4-(1H-tetrazol-5-yl)phenyl)-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one [ No CAS ]
  • 20
  • [ 179942-55-3 ]
  • C14H14ClN5 [ No CAS ]
  • C21H19N9 [ No CAS ]
  • 21
  • [ 179942-55-3 ]
  • N-[3-(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)-2,6-difluorophenyl]methanesulfonamide [ No CAS ]
  • N-[2,6-difluoro-3-[5-[4-(1H-tetrazol-5-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With methanesulfonic acid(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 1h;Inert atmosphere; Microwave irradiation; A microwave vessel was charged with N-[3-(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)- 2,6-difluorophenyl]methanesulfonamide (60.0 mg, 0.139 mmol), XPhos Pd G3 (3.53 mg, 0.00417 mmol) and <strong>[179942-55-3][4-(1H-tetrazol-5-yl)phenyl]boronic acid</strong> (31.7 mg, 0.167 mmol) and purged with argon. Degassed 1,4-dioxane (0.464 mL) and degassed aqueous 1.5 M (1012) Potassium Carbonate (0.325 mL, 0.487 mmol) were added and the mixture was heated to 110 C under microwave irradiation for 60 minutes. After cooling, the mixture was diluted with EtOAc and neutralized with sat. NH4Cl solution. The organic phase was concentrated under reduced pressure and the product isolated by flash chromatography (DCM + MeOH (+1% formic acid) 5% to 15%), triturated with MeOH and dried at 100 C in a vacuum oven to yield N-[2,6-difluoro-3-[5-[4-(1H-tetrazol-5-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-3- carbonyl]phenyl]methanesulfonamide (21.0 mg, 0,0423 mmol, 30% yield). Analytical data: (1013) 1H NMR (200 MHz, DMSO) delta 14.85 (s, 1H), 9.75 (s, 1H), 9.10 (d, J = 2.1 Hz, 1H), 8.86 (d, J = 2.2 Hz, 1H), 8.25- 8.00 (m, 4H), 7.97- 7.81 (m, 1H), 7.41 (td, J = 8.9, 1.3 Hz, 1H), 3.12 (s, 3H); (1014) MS: [M-1]- = 495.2.
  • 22
  • [ 179942-55-3 ]
  • 4-(benzyloxy)-6-bromo-3-hydroxypicolinonitrile [ No CAS ]
  • 6-(4-(1H-tetrazol-5-yl)phenyl)-4-(benzyloxy)-3-hydroxypicolinonitrile [ No CAS ]
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