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[ CAS No. 948592-80-1 ] {[proInfo.proName]}

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Chemical Structure| 948592-80-1
Chemical Structure| 948592-80-1
Structure of 948592-80-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 948592-80-1 ]

CAS No. :948592-80-1 MDL No. :MFCD06795664
Formula : C13H20BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LOOBNTHIWCHTCR-UHFFFAOYSA-N
M.W : 233.11 Pubchem ID :17750208
Synonyms :

Calculated chemistry of [ 948592-80-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.29
TPSA : 44.48 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 : Yes
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 1.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.18 mg/ml ; 0.000772 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.157 mg/ml ; 0.000672 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.03
Solubility : 0.0217 mg/ml ; 0.0000929 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.84

Safety of [ 948592-80-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 948592-80-1 ]

* 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 [ 948592-80-1 ]

[ 948592-80-1 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 478620-86-9 ]
  • [ 948592-80-1 ]
  • 2'-(1-ethyl-1-methoxymethoxymethyl-propyl)-5-methyl-biphenyl-2-ylamine [ No CAS ]
  • 3
  • [ 948592-80-1 ]
  • 2-(2'-amino-5'-methyl-biphenyl-2-yl)-2-ethyl-butan-1-ol [ No CAS ]
  • 4
  • [ 948592-80-1 ]
  • 9,9-diethyl-2-methyl-8,9-dihydro-5<i>H</i>-7-oxa-5-aza-dibenzo[<i>a</i>,<i>c</i>]cyclononen-6-one [ No CAS ]
  • 5
  • [ 1058062-42-2 ]
  • [ 948592-80-1 ]
  • [ 1058062-78-4 ]
  • 6
  • [ 94-41-7 ]
  • [ 948592-80-1 ]
  • [ 73402-92-3 ]
  • 7
  • [ 856850-57-2 ]
  • [ 948592-80-1 ]
  • [ 1208348-10-0 ]
  • 8
  • [ 40473-07-2 ]
  • [ 948592-80-1 ]
  • [ 1208348-06-4 ]
  • 9
  • [ 583-68-6 ]
  • [ 73183-34-3 ]
  • [ 948592-80-1 ]
YieldReaction ConditionsOperation in experiment
94% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere; 2-Bromo-4-methylaniline (3 g, 16.12 mmol), bis(pinacolato)diboron (6.14 g,24.19 mmol), KOAc (4.07 g, 41.4 mmol) were added to DMSO (9 mL) under N2 atm and then degassed for 10 mm. Pd(dppf)C12.CH2Cl2Adduct (0.395 g, 0.484 mmol) was added and the resulting suspension was stirred overnight at 80 C. The reaction mixture was partitioned between DCM and water. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated then purified normal phase chromatography usinghexane and EtOAc as eluents to give 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.52 g, 94% yield) as a clear oil which solidified into a white solid upon standing. MS(ESI) m/z: 152.3 (M-C6H,o+H). ?H NMR (400MHz, CDC13-d) oe 7.43 (d, J=1.8 Hz, 1H), 7.04 (dd, J=8.3, 2.3 Hz, 1H), 6.55 (d, J=8.1 Hz, 1H), 4.60 (br. s., 2H), 2.23- 2.20 (m, 3H), 1.38 - 1.32 (m, 12H).
85.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux; Add 2-bromo-4-methylaniline (15 g, 80.62 mmol) to a two-neck flask and dissolve in dioxane (300 mL). Potassium acetate (32 g, 322.48 mmol) and Pd (dppf)Cl2 4.03 mmol). After 5 minutes, add Bis(pinacolato)diboron (26.6 g, 104.8 mmol) and reflux for 10 hours. When the reaction is complete, extract with CH2Cl2. Purification by silica gel column (yield: 85.1%)
  • 10
  • [ 112575-13-0 ]
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  • [ 1208348-08-6 ]
  • 11
  • [ 52488-36-5 ]
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  • [ 1253410-39-7 ]
  • 12
  • [ 948592-80-1 ]
  • [ 348640-06-2 ]
  • [ 1253410-44-4 ]
  • 13
  • [ 75-36-5 ]
  • [ 948592-80-1 ]
  • [ 1352874-36-2 ]
YieldReaction ConditionsOperation in experiment
68% With pyridine; In dichloromethane; at 20℃; for 1h; Intermediate X: N-[4-Methyl-2-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenyl]- acetamideTo a solution of 4-Methyl-2-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenylamine (2.0 g, 8.58 mmol) in CH2CI2 (28.6 ml) were added acetyl chloride (1.219 ml, 17.16 mmol) and pyridine (1 .388 ml, 17.16 mmol). The reaction mixture was stirred for an hour at rt. The reaction mixture was then diluted with CH2CI2 (200 ml.) and washed with 1 N aqueous sodium hydroxide solution (100 ml_). The aqueous layer was extracted with CH2CI2 (2 x 100 ml_). The organic layers were combined and dried over Na2S04, filtered and concentrated under reduced pressure to give the title product, 1 .6 g (68%), which was used without purification. HPLC/MS (method A) tR0.47 minute, ion detected at 176.0 amu in positive ionisation mode (100%). 1 H NMR (Dimethylsulfoxyde-d6) Ppm 1.17 (s, 12 H) 2.20 - 2.31 (m, 6 H) 6.91 (d, 1 H) 7.04 (dd, 1 H) 7.20 (d, 1 H) 1 1 .68 (br. s., 1 H).
  • 14
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  • 15
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  • [ 1352874-37-3 ]
  • 17
  • [ 916244-47-8 ]
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  • [ 1361550-23-3 ]
  • 18
  • [ 1361550-29-9 ]
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  • [ 1361550-22-2 ]
  • 19
  • [ 275361-65-4 ]
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  • [ 1361550-21-1 ]
  • 21
  • [ 948592-80-1 ]
  • [ 1373751-99-5 ]
  • 22
  • [ 948592-80-1 ]
  • C18H25NO2 [ No CAS ]
  • 24
  • [ 109-04-6 ]
  • [ 948592-80-1 ]
  • [ 1342131-12-7 ]
  • 25
  • [ 948592-80-1 ]
  • [ 1393605-74-7 ]
  • 26
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  • [ 1393605-87-2 ]
  • 27
  • [ 948592-80-1 ]
  • [ 1393606-33-1 ]
  • 28
  • [ 948592-80-1 ]
  • [ 1393606-80-8 ]
  • 29
  • [ 30414-53-0 ]
  • [ 948592-80-1 ]
  • [ 1423076-84-9 ]
  • 30
  • [ 30414-57-4 ]
  • [ 948592-80-1 ]
  • [ 1423076-85-0 ]
  • 31
  • [ 105-45-3 ]
  • [ 948592-80-1 ]
  • methyl 2,5-dimethyl-1H-indole-3-carboxylate [ No CAS ]
  • 32
  • [ 948592-80-1 ]
  • [ 1422193-35-8 ]
  • 33
  • [ 948592-80-1 ]
  • [ 1422192-34-4 ]
  • 34
  • [ 948592-80-1 ]
  • C14H18N4 [ No CAS ]
  • 35
  • [ 948592-80-1 ]
  • [ 1422192-43-5 ]
  • 36
  • C13H20F3NO5S [ No CAS ]
  • [ 948592-80-1 ]
  • [ 1422193-28-9 ]
  • 38
  • [ 948592-80-1 ]
  • [ 1579291-53-4 ]
  • 39
  • [ 948592-80-1 ]
  • [ 1579291-63-6 ]
  • 40
  • [ 873-32-5 ]
  • [ 948592-80-1 ]
  • 6-amino-2-methylphenanthridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere; General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration.
  • 41
  • [ 948592-80-1 ]
  • 2-azido-5-methylphenyllead acetate [ No CAS ]
  • 42
  • [ 948592-80-1 ]
  • [ 1611447-07-4 ]
  • 43
  • [ 948592-80-1 ]
  • [ 1611447-14-3 ]
  • 44
  • [ 14309-57-0 ]
  • [ 948592-80-1 ]
  • (2RS,4SR)-2,6-dimethyl-4-pentyl-1,2,3,4-tetrahydroquinoline [ No CAS ]
  • C16H25N [ No CAS ]
  • 45
  • [ 14309-57-0 ]
  • [ 948592-80-1 ]
  • C16H23N [ No CAS ]
  • 46
  • [ 948592-80-1 ]
  • methyl-2-(2-azido-5-methylphenyl)cyclohex-1-enecarboxylate [ No CAS ]
  • 47
  • [ 948592-80-1 ]
  • methyl-6-methyl-2,3,4,4a-tetrahydro-1H-carbazole-4a-carboxylate [ No CAS ]
  • 48
  • [ 762-42-5 ]
  • [ 948592-80-1 ]
  • C13H14BNO5 [ No CAS ]
  • 49
  • [ 26452-81-3 ]
  • [ 948592-80-1 ]
  • 2-(6-methoxypyrimidin-4-yl)-4-methylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 90℃; for 2h;Reflux; Inert atmosphere; To a RBF equipped with a reflux condenser containing DME (42.9 mL), EtOH(5.36 mL) was added <strong>[26452-81-3]4-chloro-6-methoxypyrimidine</strong> (1.55 g, 10.72 mmol), 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.5 g, 10.72 mmol) and 2 M aqNa2CO3 (5.36 mL, 10.72 mmol). The mixture was purged with Ar for 10 mm thenPdC12(dppf)-CH2Cl2Adduct (0.876 g, 1.072 mmol) was added and the reaction mixtureheated at 90 °C. After 2 h, the reaction was diluted with water and extracted with EtOAc. The organic layer washed with brine and concentrated to give a brown oil. The crude product was purified by normal phase chromatography using heptane and EtOAc as eluents to give 2-(6-methoxypyrimidin-4-yl)-4-methylaniline (670 mg, 29percent) as a solid.MS(ESI)m/z: 216.1 (M+H). ?HNMR(500MHz, CDC13-d) oe 8.79 (d, J1.1 Hz, 1H),7.33 (d, J1.4 Hz, 1H), 7.08 - 7.01 (m, 2H), 6.67 (d, J8.3 Hz, 1H), 5.68 (br. s., 2H), 4.03 (s, 3H), 2.29 (s, 3H).
  • 50
  • [ 948592-80-1 ]
  • 4-methoxy-6-(5-methyl-2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)phenyl)pyrimidine [ No CAS ]
  • 51
  • [ 948592-80-1 ]
  • 6-(5-methyl-2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)phenyl)pyrimidin-4-ol [ No CAS ]
  • 52
  • [ 948592-80-1 ]
  • C14H15N3O2 [ No CAS ]
  • 53
  • [ 948592-80-1 ]
  • C18H24N4O [ No CAS ]
  • 54
  • [ 948592-80-1 ]
  • C17H17N3 [ No CAS ]
  • 55
  • [ 948592-80-1 ]
  • C15H17NO2 [ No CAS ]
  • 56
  • [ 948592-80-1 ]
  • C17H17N [ No CAS ]
  • C17H17N [ No CAS ]
  • 57
  • 8-chloro-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
  • [ 948592-80-1 ]
  • 8-(2-amino-5-methylphenyl)-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 110℃;Inert atmosphere; A 5-mL microwave vial is charged with sodium carbonate (1 15 mg; 1.09 mmol; 5 eq.), 4-methyl-2-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- phenylamine (56 mg; 0.24 mmol; 1.10 eq.), chloro-A/-(4- methanesulfonylpyridin-3-yl)quinoxalin-6-amine (Intermediate 3B, 75 mg; 0.22 mmol; 1 eq.), followed by water (0.5 mL), ethanol (0.50 mL) and toluene (1 mL). The mixture is sparged with argon under sonication, and tetrakis(triphenylphosphine)palladium(0) (13 mg; 0.01 mmol; 0.05 eq.) is added. The vial is sealed and the mixture is stirred at 10 C overnight. After coming back to room temperature, the reaction mixture is filtered through a pad of celite, eluting with DCM. The filtrate is washed with water, dried over sodium sulfate, filtered through a 1-cm high pad of neutral alumina (rinsing the filter cake with EtOAc), and evaporated in vacuo. The residue is purified by FCC (100% EtOAc) to afford 8-(2-amino-5-methylphenyl)-A/-(4- methanesulfonylpyridin-3-yl)quinoxalin-6-amine (38 mg; 0.09 mmol; 43%; yellow powder; HPLC purity: 99.7%).
  • 58
  • [ 63069-48-7 ]
  • [ 948592-80-1 ]
  • C13H13ClN2 [ No CAS ]
  • 59
  • [ 63069-48-7 ]
  • [ 948592-80-1 ]
  • 3-chloro-6-methyl-9H-carbazole [ No CAS ]
  • 60
  • C17H10Br2O2 [ No CAS ]
  • [ 948592-80-1 ]
  • C31H22N2 [ No CAS ]
  • 61
  • C13H7ClF3NO2 [ No CAS ]
  • [ 948592-80-1 ]
  • N-[4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-[4-(trifluoromethyl)phenoxy]pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h; General procedure: Step A: To a solution of 4 (1.1 g, 4.0 mmol) in CH2Cl2 (24 mL)was added oxalyl chloride (1.0 mL, 12 mmol) followed by DMF (4drops) at room temperature. The reaction mixture was stirred atroom temperature for 1 h and concentrated in vacuo to give crude4-[5-(trifluoromethyl)pyridin-2-yl]oxy}benzoyl chloride, whichwas used directly in the next step. Step B: Crude 4-[5-(trifluoromethyl)pyridin-2-yl]oxy}benzoyl chloride was dissolved inCH2Cl2 (24mL) at 0 C. To the solution was added DIPEA (0.75mL,4.4 mmol) and 5a (0.88 g, 4.4 mmol). After stirring at room temperaturefor 1 h, the mixture was diluted with H2O and extractedwith AcOEt. The organic layer was washed with brine, dried overNa2SO4 and concentrated in vacuo. The resulting residue was purifiedby silica gel chromatography (hexane-AcOEt) to give 6a
  • 62
  • 3-chloro-5-(trifluoromethyl)-2-vinylpyridine [ No CAS ]
  • [ 948592-80-1 ]
  • 8-methyl-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido-[2,3-f]azepine [ No CAS ]
  • 63
  • [ 948592-80-1 ]
  • 3-(2-iodo-5-methylphenyl)-1H-indole [ No CAS ]
  • 64
  • [ 948592-80-1 ]
  • 7-methyl-2-phenyl-4,5-dihydro-3H-spiro[acenaphthylene-1,3'-indole] [ No CAS ]
  • 65
  • [ 948592-80-1 ]
  • C22H18INO2S [ No CAS ]
  • 66
  • [ 170456-80-1 ]
  • [ 948592-80-1 ]
  • C22H20N2O2S [ No CAS ]
  • 67
  • [ 577-19-5 ]
  • [ 948592-80-1 ]
  • 5-methyl-2'-nitro-[1,1'-biphenyl]-2-amine [ No CAS ]
  • 68
  • [ 948592-80-1 ]
  • C28H21IN2O [ No CAS ]
  • 69
  • [ 948592-80-1 ]
  • C30H25IN2O3 [ No CAS ]
  • 70
  • [ 948592-80-1 ]
  • 2-iodo-5-methyl-2'-nitro-1,1'-biphenyl [ No CAS ]
  • 71
  • [ 948592-80-1 ]
  • 2-iodo-2'-methoxy-5-methyl-6'-nitro-1,1'-biphenyl [ No CAS ]
  • 72
  • [ 948592-80-1 ]
  • 2'-iodo-5'-methyl-[1,1'-biphenyl]-2-amine [ No CAS ]
  • 73
  • [ 948592-80-1 ]
  • 2'-iodo-6-methoxy-5'-methyl-[1,1'-biphenyl]-2-amine [ No CAS ]
  • 74
  • [ 948592-80-1 ]
  • 2-iodo-2'-isocyano-5-methyl-1,1'-biphenyl [ No CAS ]
  • 75
  • [ 948592-80-1 ]
  • 2-iodo-2'-isocyano-6'-methoxy-5-methyl-1,1'-biphenyl [ No CAS ]
  • 76
  • [ 948592-80-1 ]
  • (3-methyl-9H-carbazol-9-yl)(9-methylphenanthridin-6-yl)methanone [ No CAS ]
  • 77
  • [ 948592-80-1 ]
  • (5-methoxy-3-methyl-9H-carbazol-9-yl)(1-methoxy-9-methylphenanthridin-6-yl)methanone [ No CAS ]
  • 78
  • [ 67853-37-6 ]
  • [ 948592-80-1 ]
  • 2'-methoxy-5-methyl-6'-nitro-[1,1'-biphenyl]-2-amine [ No CAS ]
  • 79
  • [ 948592-80-1 ]
  • 3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridine [ No CAS ]
  • 80
  • [ 948592-80-1 ]
  • C72H57IrN6 [ No CAS ]
  • 81
  • [ 948592-80-1 ]
  • 2,9-dimethylphenanthridin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In ethanol; water; toluene; for 24h; 4-methyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline is dissolved in toluene and placed in a two-neck flask. Add Tripotassium phosphate, Pd (PPh3) 2Cl2 and Ethanol (10 mL) dissolved in water (15 mL). After 5 minutes, add 2-bromo-4-methylbenzonitrile. Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by a silica gel column (yield: 68%)
  • 82
  • [ 948592-80-1 ]
  • 3-(2,6-dimethylphenyl)-7,10-dimethylimidazo[1,2-f]phenanthridine [ No CAS ]
  • 83
  • [ 2042-37-7 ]
  • [ 948592-80-1 ]
  • 6-amino-2-methylphenanthridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In ethanol; water; toluene; for 24h;Reflux; 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (5 g, 21.45 mmol) was dissolved in toluene (300 mL) and added to a two-neck Put it in the flask. Tripotassium phosphate (13.7 g, 64.35 mmol), Pd (PPh3) 2Cl2 (0.75 g, 1.07 mmol) and ethanol (10 mL) dissolved in water (30 mL) After 5 minutes, add 2-bromobenzonitrile (3.9 g, 21.45 mmol). Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by a silica gel column (yield: 70%)
  • 84
  • [ 948592-80-1 ]
  • (±)-cis-4a-hydroxy-6-methyl-2-(pyrrolidin-1-yl)-4,4a,9,9a-tetrahydro-1H-carbazole-3-carbonitrile [ No CAS ]
  • 85
  • [ 948592-80-1 ]
  • C16H20N2O [ No CAS ]
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5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

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Chemical Structure| 1315350-04-9

[ 1315350-04-9 ]

4-Amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

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Chemical Structure| 191171-55-8

[ 191171-55-8 ]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

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Chemical Structure| 393877-09-3

[ 393877-09-3 ]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride

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Chemical Structure| 631909-35-8

[ 631909-35-8 ]

3-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

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