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Product Details of [ 34801-09-7 ]

CAS No. :34801-09-7 MDL No. :MFCD00210388
Formula : C8H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :MPXAYYWSDIKNTP-UHFFFAOYSA-N
M.W : 150.18 Pubchem ID :11149
Synonyms :

Calculated chemistry of [ 34801-09-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.16
TPSA : 55.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 0.25
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.2
Solubility : 9.47 mg/ml ; 0.0631 mol/l
Class : Very soluble
Log S (Ali) : -0.97
Solubility : 16.2 mg/ml ; 0.108 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.588 mg/ml ; 0.00392 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 34801-09-7 ]

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

Application In Synthesis of [ 34801-09-7 ]

* 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.

  • Upstream synthesis route of [ 34801-09-7 ]
  • Downstream synthetic route of [ 34801-09-7 ]

[ 34801-09-7 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 34801-09-7 ]
  • [ 29043-48-9 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 174
[2] Journal of the Chemical Society, 1928, p. 174
[3] Journal of the Chemical Society, 1928, p. 174
  • 2
  • [ 552-32-9 ]
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YieldReaction ConditionsOperation in experiment
96% With hydrogen In ethanol for 2 h; A solution of 2-nitroacetanilide (1.0 g, 5.6 mmol) in EtOH was purged with nitrogen, treated with Pd(OH)2 (20percent by wt. on C, 200 mg, cat.), and shaken for 2 h under H2 (20 psi). The catalyst was removed by filtration through a 0.22 um cellulose acetate membrane (Corning), and the filtrate was concentrated in vacuo to afford the white crystalline solid product (800 mg, 96percent). 1H NMR (300 MHz, d6-DMSO) δ: 9.12 (s, 1H), 7.14 (dd, J=7.8, 1.3 Hz, 1H), 6.88 (dt, J=7.6, 1.5 Hz, 1H), 6.70 (dd, J=8.0, 1.3 Hz, 1H), 6.52 (dt, J=7.5, 1.4 Hz, 1H), 4.85 (br s, 2H), 2.03 (s, 3H). LRMS (ES pos.) m/z=151 (M+1).
78% at 80℃; for 8 h; General procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 °C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.
72% With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 50℃; for 24 h; General procedure: Nitrobenzene (0.6mmol), 5wtpercent Pd/C (0.5mmol percent, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99percent).
62% With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24 h; Schlenk technique General procedure: A 20 mL Schlenk tube was charged with 8-nitroquinoline (1k; 87 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4(135 mg, 1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 80 °C for 24 h, then cooled to room temperature and concentrated under reduced pressure. Similar workup to 2a gave a brown solid (4a: 63 mg, 87percent yield).

Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9235 - 9244
[2] Patent: US6667300, 2003, B2, . Location in patent: Page column 98
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
[4] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677
[5] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677
[6] Petroleum Chemistry, 2002, vol. 42, # 1, p. 30 - 33
[7] Tetrahedron, 2001, vol. 57, # 9, p. 1793 - 1799
[8] Canadian Journal of Chemistry, 2003, vol. 81, # 3, p. 197 - 198
[9] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 709 - 711
[10] Supramolecular Chemistry, 2010, vol. 22, # 10, p. 586 - 597
[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 501 - 506
[12] Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 115, p. 217 - 226
[13] Synlett, 2018, vol. 29, # 13, p. 1765 - 1768
[14] Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904
[15] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
[16] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 7, p. 1019 - 1023
[17] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 7, p. 1019 - 1023
[18] Tetrahedron, 2018, vol. 74, # 17, p. 2121 - 2129
[19] Journal of Chemical Research, 2006, # 4, p. 223 - 224
[20] Chemical & Pharmaceutical Bulletin, 1989, vol. 37, # 3, p. 615 - 617
[21] Journal of Organic Chemistry, 1941, vol. 6, p. 25,28
[22] Journal of the Chemical Society, 1954, p. 3586,3593
[23] Journal of Organic Chemistry, 1954, vol. 19, p. 1594,1597
[24] Journal of the Chemical Society, 1928, p. 174
[25] Journal of the Chemical Society, 1926, p. 954
[26] Chemische Berichte, 1907, vol. 40, p. 1086
[27] Journal of the Indian Chemical Society, 1983, vol. 60, p. 737 - 740
[28] Chemistry of Heterocyclic Compounds, 2013, vol. 49, # 9, p. 1264 - 1273[29] Khim. Geterotsikl. Soedin., 2013, vol. 49, # 9, p. 1356 - 1366,11
  • 3
  • [ 551-93-9 ]
  • [ 34801-09-7 ]
YieldReaction ConditionsOperation in experiment
60% With hydroxylamine hydrochloride In acetonitrileReflux General procedure: Ketones (1 mmol) and hydroxylamine hydrochloride (0.0694g,1 mmol) were dissolved in CH3CN (10 mL) and stirred for 10 - 15 min. The complex (CS-SalBr-Zn-L) (10 molpercent) were added tothe reaction flask. The reaction mixture was heated under reflux for specific time (3e7 h). After completion, the reaction mixture was cooled to room temperature and the catalyst was removed by filtration. The filtrate was treated with ethyl acetate (3 10 mL).The combined organic layers were treated with saturated brine solution and dried over anhydrous sodium sulphate. The removal of solvent yields crude product, which after purification by column chromatography over Silica gel (100e200 mesh), afforded the desired products.
Reference: [1] Synthetic Communications, 2003, vol. 33, # 17, p. 2971 - 2978
[2] Journal of Molecular Structure, 2017, vol. 1130, p. 368 - 373
[3] Annali di Chimica (Rome, Italy), 1958, vol. 48, p. 1329,1332, 1333
  • 4
  • [ 614-76-6 ]
  • [ 34801-09-7 ]
Reference: [1] Chemical Communications, 2008, # 46, p. 6200 - 6202
[2] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3311 - 3316
  • 5
  • [ 108-24-7 ]
  • [ 95-54-5 ]
  • [ 34801-09-7 ]
YieldReaction ConditionsOperation in experiment
18% at 0℃; for 14 h; To a solution of benzene-1 ,2-diamine (100 g, 0.93 moi) in dichloromethane (1 L) at 0 °C was added acetic anhydride (87 mi_, 0.92 mo.). After stirring at 0 °C for 2 hours, the mixture was stand at 0 °C for 12 hours and the precipitate was coilected by filtration, washed by dichloromethane and ether, dried in air to afford the product A/-(2-aminopheny.)acetamide (25 g, yield 18 percent). 1H NMR (400 MHz, CDCI3) δ ppm 7.14-7.28 (rrs, 2H), 7.04-7.08 (m, 1 H), 8.78-8.81 (m, 2H), 3.88 (br s, 2H), 2.20 (s, 3H).
Reference: [1] European Journal of Organic Chemistry, 2004, # 6, p. 1254 - 1260
[2] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4742 - 4749
[3] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3286 - 3292
[4] Russian Journal of Organic Chemistry, 1999, vol. 35, # 10, p. 1476 - 1479
[5] Journal of the Chemical Society, Dalton Transactions, 2002, # 8, p. 1714 - 1720
[6] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 6, p. 3651 - 3660
[7] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9826 - 9834
[8] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 67
[9] Journal of the Society of Chemical Industry, London, 1923, vol. 42, p. 469 T.[10] Chem. Zentralbl., 1924, vol. 95, # I, p. 1024
  • 6
  • [ 75-36-5 ]
  • [ 95-54-5 ]
  • [ 34801-09-7 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 21, p. 4185 - 4187
[2] Monatshefte fur Chemie, 2006, vol. 137, # 2, p. 175 - 179
[3] Tetrahedron Letters, 2010, vol. 51, # 6, p. 912 - 916
  • 7
  • [ 88-74-4 ]
  • [ 507-09-5 ]
  • [ 34801-09-7 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3221 - 3223
  • 8
  • [ 95635-45-3 ]
  • [ 7439-89-6 ]
  • [ 95635-47-5 ]
  • [ 34801-09-7 ]
Reference: [1] Patent: US4684397, 1987, A,
[2] Patent: US4709049, 1987, A,
  • 9
  • [ 88-74-4 ]
  • [ 34801-09-7 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 115, p. 217 - 226
[2] Journal of the American Chemical Society, 1935, vol. 57, p. 1835,1838
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
  • 10
  • [ 88-74-4 ]
  • [ 34801-09-7 ]
  • [ 552-32-9 ]
Reference: [1] Patent: US4415572, 1983, A,
  • 11
  • [ 103-84-4 ]
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  • [ 122-80-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 12
  • [ 103-84-4 ]
  • [ 34801-09-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
  • 13
  • [ 62-53-3 ]
  • [ 34801-09-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
  • 14
  • [ 2050-85-3 ]
  • [ 34801-09-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1901, vol. 31 I, p. 22
  • 15
  • [ 71-43-2 ]
  • [ 34801-09-7 ]
  • [ 122-80-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 16
  • [ 19165-25-4 ]
  • [ 95-54-5 ]
  • [ 34801-09-7 ]
  • [ 5794-88-7 ]
Reference: [1] Monatshefte fur Chemie, 1996, vol. 127, # 1, p. 103 - 110
  • 17
  • [ 2050-85-3 ]
  • [ 144-62-7 ]
  • [ 615-15-6 ]
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Reference: [1] Gazzetta Chimica Italiana, 1901, vol. 31 I, p. 22
  • 18
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  • [ 108-24-7 ]
  • [ 2050-85-3 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 174
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