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Chemical Structure| 6232-11-7
Chemical Structure| 6232-11-7
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Product Details of [ 6232-11-7 ]

CAS No. :6232-11-7 MDL No. :MFCD00182671
Formula : C9H12ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GIZCKBSSWNIUMZ-UHFFFAOYSA-N
M.W :201.65 Pubchem ID :2729253
Synonyms :

Calculated chemistry of [ 6232-11-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.36
TPSA : 52.32 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) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 1.58
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.656 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.389 mg/ml ; 0.00193 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.622 mg/ml ; 0.00308 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 6232-11-7 ]

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 [ 6232-11-7 ]

* 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 [ 6232-11-7 ]
  • Downstream synthetic route of [ 6232-11-7 ]

[ 6232-11-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 6232-11-7 ]
  • [ 18469-52-8 ]
Reference: [1] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 276 - 279[2] Angewandte Chemie, 2015, vol. 127, # 1, p. 278 - 281,4
  • 2
  • [ 6232-11-7 ]
  • [ 39895-56-2 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4786 - 4797
[2] Patent: EP1550657, 2005, A1, . Location in patent: Page/Page column 48
[3] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 16
  • 3
  • [ 1129-35-7 ]
  • [ 6232-11-7 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8781 - 8788
[2] ACS Catalysis, 2018, vol. 8, # 10, p. 9125 - 9130
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5944 - 5948
[4] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12808 - 12814
[5] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4991 - 5002
[6] ChemCatChem, 2016, vol. 8, # 7, p. 1329 - 1334
[7] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13554 - 13561
  • 4
  • [ 56-91-7 ]
  • [ 6232-11-7 ]
YieldReaction ConditionsOperation in experiment
97% With thionyl chloride In methanol at 20℃; for 16 h; 4-(Aminomethyl)benzoic acid (302 mg, 2.00 mmol) was dissolved in MeOH (30 mL) and thionyl chloride (1.16 mL, 16.0 mmol) was carefully added dropwise at rt. The reaction mixture was stirred overnight at rt. Afterwards the solvent was removed under reduced pressure to yield 15d. Colorless solid, mp 234 °C, yield 390 mg (97 percent). C9H12ClNO2 (201.7). Rf = 0.22 (ethyl acetate/1percent diethylmethylamine, detection: 254 nm). 1H NMR (400 MHz, DMSO-D6): δ [ppm] = 3.86 (s, 3H, CO2CH3), 4.10 (s, 2H, H3NCH2), 7.63-7.67 (m, 2H, 3-HB, 5-HB), 7.96-8.01 (m, 2H, 2-HB, 6-HB), 8.61 (br s, 3H, NH3). 13C NMR (101 MHz, DMSO-D6): δ [ppm] = 41.7 (1C, H3NCH2), 52.2 (1C, CO2CH3), 129.2 (2C, C-3B, C-5B), 129.3 (2C, C-2B, C-6B), 129.5 (1C, C-1B), 139.4 (1C, C-4B), 165.9 (1C, CO2CH3). FT-IR: ν [cm-1] = 2963 (NH3+), 2878 (C-Haliph.), 2573 (NH3+), 1678 (C=O), 1597, 1578, 1477 (C=CAr), 864 (Ar-Hout of plane). HRMS (APCI): m/z = 166.0865 (calcd. 166.0863 for C9H12NO2 [M+H]+). HPLC: tR = 6.4 min, purity 99.9 percent.
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 21, p. 4872 - 4875
[2] European Journal of Medicinal Chemistry, 2017, vol. 129, p. 124 - 134
[3] Patent: US5585381, 1996, A,
  • 5
  • [ 67-56-1 ]
  • [ 56-91-7 ]
  • [ 6232-11-7 ]
YieldReaction ConditionsOperation in experiment
99% at 0℃; for 24 h; Reflux Example 1: Preparation of N-(2-aminophenyl)-4-((4-bromo-5,6-dimethoxy-l- oxoisoindolin-2-yl) methyl)benzamideStep 1 : Preparation of methyl 4-(aminomethyl)benzoate hydrochloride4-Aminomethylbenzoic acid (2.0 g, 13 mmol) was dissolved in MeOH(5.0 mL), thionylchloride (2.9 mL, 3 equiv.) was slowly added thereto at 0 °C and fluxed for 24 hrs. The mixture thus obtained was distilled under a reduced pressure to remove the solvent and thionyl chloride, and dried under vacuum to obtain the title compound (2.7 g, 99 percent).1H NMR (300 MHz, D2O): δ 7.93 (d, 2H, J = 8.4 Hz), 7.41 (d, 2H, J = 8.4Hz), 4.12(s, 2H), 3.79 (s, 3H).
93% at 0 - 75℃; for 5 h; Compound 5 (1.5 g, 10 mmol) was dissolved in 200 mL MeOH, thenacetyl chloride (2.4 g, 30 mmol) was added dropwise at 0 °C; themixed solution was refluxed at 75 °C for 5 h. The solvent wasevaporated under vacuum, the product was washed by diethylether to give compound 6, a white solid powder (1.7 g, 93percent).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6516 - 6532
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 19, p. 4189 - 4206
[3] Patent: WO2010/131922, 2010, A2, . Location in patent: Page/Page column 28
[4] Organic Letters, 2017, vol. 19, # 7, p. 1768 - 1771
[5] Journal of Medicinal Chemistry, 1994, vol. 37, # 12, p. 1810 - 1822
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8948 - 8952
[7] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 276 - 279[8] Angewandte Chemie, 2015, vol. 127, # 1, p. 278 - 281,4
[9] Molecules, 2008, vol. 13, # 5, p. 1111 - 1119
[10] Journal of the American Chemical Society, 2015, vol. 137, # 5, p. 1983 - 1992
[11] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 185 - 206
[12] Journal of Organic Chemistry, 1995, vol. 60, # 21, p. 6970 - 6979
[13] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4455 - 4458
[14] Chemical Communications, 2014, vol. 50, # 97, p. 15341 - 15344
[15] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9942 - 9959
[16] Patent: JP5871223, 2016, B2, . Location in patent: Paragraph 0039
[17] Patent: WO2018/71740, 2018, A1, . Location in patent: Page/Page column 27
  • 6
  • [ 94341-53-4 ]
  • [ 6232-11-7 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 19, p. 4418 - 4422
  • 7
  • [ 120157-96-2 ]
  • [ 6232-11-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 5, p. 1199 - 1212
  • 8
  • [ 18469-52-8 ]
  • [ 6232-11-7 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5944 - 5948
[2] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13554 - 13561
  • 9
  • [ 33233-67-9 ]
  • [ 6232-11-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 5, p. 1199 - 1212
  • 10
  • [ 2417-72-3 ]
  • [ 6232-11-7 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 19, p. 4418 - 4422
  • 11
  • [ 6232-11-7 ]
  • [ 123986-64-1 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 15, p. 3043 - 3046
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