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[ CAS No. 122-85-0 ] {[proInfo.proName]}

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Chemical Structure| 122-85-0
Chemical Structure| 122-85-0
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Product Details of [ 122-85-0 ]

CAS No. :122-85-0 MDL No. :MFCD00003380
Formula : C9H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SKLUWKYNZNXSLX-UHFFFAOYSA-N
M.W : 163.17 Pubchem ID :73942
Synonyms :

Calculated chemistry of [ 122-85-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.14
TPSA : 46.17 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.25
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.52 mg/ml ; 0.0154 mol/l
Class : Very soluble
Log S (Ali) : -1.82
Solubility : 2.48 mg/ml ; 0.0152 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.308 mg/ml ; 0.00189 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 122-85-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 122-85-0 ]

* 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 [ 122-85-0 ]
  • Downstream synthetic route of [ 122-85-0 ]

[ 122-85-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 567 - 569
[2] ChemCatChem, 2018, vol. 10, # 6, p. 1253 - 1257
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10806 - 10810[4] Angew. Chem., 2016, vol. 128, p. 10964 - 10968,4
[5] Organometallics, 2017, vol. 36, # 21, p. 4095 - 4098
[6] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2319 - 2326
[7] Journal of Organic Chemistry, 1986, vol. 51, # 25, p. 4764 - 4767
[8] Journal of Chemical Research, Miniprint, 1988, # 1, p. 201 - 223
[9] Journal of Organic Chemistry, 1996, vol. 61, # 4, p. 1310 - 1314
[10] Journal of Chemical Research, Miniprint, 1999, # 8, p. 2052 - 2074
[11] International Journal of Chemical Kinetics, 2000, vol. 32, # 10, p. 615 - 622
[12] Journal of Physical Organic Chemistry, 2001, vol. 14, # 9, p. 650 - 656
[13] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 832 - 838
[14] Journal of Organic Chemistry, 2000, vol. 65, # 11, p. 3322 - 3325
[15] Journal of the Indian Chemical Society, 2007, vol. 84, # 6, p. 582 - 587
[16] Journal of the Indian Chemical Society, 2008, vol. 85, # 12, p. 1281 - 1288
[17] Journal of the Indian Chemical Society, 2009, vol. 86, # 9, p. 927 - 935
[18] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1173 - 1178
[19] Journal of the Indian Chemical Society, 2012, vol. 89, # 8, p. 1045 - 1052
  • 2
  • [ 64-19-7 ]
  • [ 103-89-9 ]
  • [ 66047-05-0 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Russian Journal of Applied Chemistry, 2008, vol. 81, # 7, p. 1198 - 1201
  • 3
  • [ 103-89-9 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Petroleum Chemistry, 2009, vol. 49, # 5, p. 397 - 400
  • 4
  • [ 103-89-9 ]
  • [ 66047-05-0 ]
  • [ 122-85-0 ]
  • [ 556-08-1 ]
Reference: [1] Petroleum Chemistry, 2009, vol. 49, # 5, p. 397 - 400
  • 5
  • [ 122-85-0 ]
  • [ 6393-40-4 ]
Reference: [1] New Journal of Chemistry, 2005, vol. 29, # 11, p. 1469 - 1474
  • 6
  • [ 122-85-0 ]
  • [ 16375-88-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium tetrahydroborate In methanol at 20℃; To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mL) was added sodium borohydride (800 mg) at room temperature in portions.
The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes: EtOAc as eluent.
Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap.
The residue was partitioned between water (25 mL) and ethyl acetate (4*50 mL) and the organic layer was washed with brine (25 mL).
The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85percent); 1H NMR (DMSO-d6): δ 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).
85% at 20℃; Preparation of 4-acetamidobenzyl alcohol. To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mE) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes:EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mE) and ethyl acetate (4x50 mE) and the organic layer was washed with brine (25 mE). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85percent); ‘H NMR (DMSO-d5): ö 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H) ppm.
61% With ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazole-(H))(PPh3); phenylsilane In tetrahydrofuran for 1.33333 h; Reflux General procedure: In a typical experiment, to a mixture of carbonyl compound (1.0mmol) and [ReOBr2(hmpbta)(PPh3)] (5molpercent) in THF (3mL) at reflux temperature was added PhSiH3 (2.0mmol). The reaction mixture was stirred under air atmosphere (the reaction times are indicated in the Table 4) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction was quenched with 1equiv of tetrabutylammonium fluoride (TBAF) (1.0M THF) during 1h. Then, the reaction mixture was evaporated and purified by silica gel column chromatography with the appropriate mixture of n-hexane and ethyl acetate to afford the alcohols, which are all known compounds.
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 676 - 681
[2] Chemical Communications, 2015, vol. 51, # 46, p. 9567 - 9570
[3] Organic Letters, 2017, vol. 19, # 13, p. 3656 - 3659
[4] Catalysis Science and Technology, 2013, vol. 3, # 1, p. 81 - 84
[5] Patent: US2007/149462, 2007, A1, . Location in patent: Page/Page column 22
[6] Patent: US9138442, 2015, B2, . Location in patent: Page/Page column 37
[7] ChemCatChem, 2017, vol. 9, # 1, p. 80 - 83
[8] Tetrahedron, 1981, vol. 37, p. 2165 - 2172
[9] Journal of the Chemical Society, Chemical Communications, 1981, # 3, p. 121 - 122
[10] Tetrahedron Letters, 2015, vol. 56, # 2, p. 414 - 418
[11] Tetrahedron, 2006, vol. 62, # 34, p. 8164 - 8168
[12] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 15935 - 15939
[13] Angewandte Chemie - International Edition, 2013, vol. 52, # 19, p. 5120 - 5124[14] Angew. Chem., 2013, vol. 125, # 19, p. 5224 - 5228
  • 7
  • [ 122-85-0 ]
  • [ 62-53-3 ]
  • [ 16375-88-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 24, p. 5725 - 5734
  • 8
  • [ 18699-02-0 ]
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
  • [ 103-84-4 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 4, p. 182 - 187
  • 9
  • [ 18699-02-0 ]
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 4, p. 182 - 187
  • 10
  • [ 122-85-0 ]
  • [ 51818-99-6 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 39, p. 7093 - 7096
[2] New Journal of Chemistry, 2005, vol. 29, # 11, p. 1469 - 1474
[3] Journal of the American Chemical Society, 2004, vol. 126, # 10, p. 3357 - 3367
[4] Journal of the Chemical Society, 1927, p. 25
  • 11
  • [ 122-85-0 ]
  • [ 178265-65-1 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 343, p. 511/193 - 516/198
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