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[ CAS No. 22162-15-8 ] {[proInfo.proName]}

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Chemical Structure| 22162-15-8
Chemical Structure| 22162-15-8
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Product Details of [ 22162-15-8 ]

CAS No. :22162-15-8 MDL No. :MFCD12755934
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PXSWIWNWHAUARP-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :21345674
Synonyms :

Calculated chemistry of [ 22162-15-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.36
TPSA : 66.05 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) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 1.24
Log Po/w (MLOGP) : 0.68
Log Po/w (SILICOS-IT) : -0.03
Consensus Log Po/w : 1.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.16 mg/ml ; 0.00692 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.365 mg/ml ; 0.00218 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.99
Solubility : 1.72 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 22162-15-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22162-15-8 ]

* 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 [ 22162-15-8 ]
  • Downstream synthetic route of [ 22162-15-8 ]

[ 22162-15-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 22162-15-8 ]
  • [ 72005-84-6 ]
YieldReaction ConditionsOperation in experiment
90% With manganese(IV) oxide In dichloromethane at 20℃; General procedure: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35-36), commercial activated manganese(IV) oxide (MnO2) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite® 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized
2-Methyl-4-nitro-benzaldehyde (2b)
Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro-benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (1a) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (MnO2) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90percent yield) of the target compound (7b) as a yellow solid.
The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf: ˜0.58 (EtOAc/Hxn=1:2 v/v).
1H NMR (300 MHz, CDCl3): δ 10.39 (s, 1H), 8.20 (dd, J=8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J=8.1 Hz, 1H), 2.79 (s, 3H) ppm.
The spectroscopic data correspond to the data provided in the literature.
The compound is also commercially available.
90% With manganese(IV) oxide In dichloromethane at 20℃; General procedure: Variant B: Adapting literature known protocol (Aoyama, et al., Synlett, 1998, 35- 36), commercial activated manganese(IV) oxide (Mn02) (250-275 mmol) is added at room temperature to a solution of the benzylic alcohol (25 mmol) in dichloromethane (DCM) (100 mL). The reaction mixture is stirred for 12-24 h. The reaction is monitored by TLC and/or LCMS to completion. The reaction mixture is filtered over a short path of Celite® 545 and the filtrate is concentrated under reduced pressure. The material is often of sufficient purity to be used directly in the next step without further isolation and purification. If needed, the crude material is purified by silica gel column chromatography or is re-crystallized. Following the General Procedure of Description 2 (Variant B), 2-methyl-4-nitro- benzaldehyde (2b) was prepared from 2-methyl-4-nitro-phenyl)methanol (la) (8.4 g, 50.3 mmol) in the presence of manganese dioxide (Mn02) (48.1 g, 553 mmol). Work-up afforded 7.5 g (90percent yield) of the target compound (2b) as a yellow solid. The material was of sufficient purity to be used directly in the next step without further isolation and purification. Rf. -0.58 (EtOAc/Hxn = 1 :2 v/v). 1H MR (300 MHz, CDC13): δ 10.39 (s, 1H), 8.20 (dd, J = 8.4, 2.1 Hz, 1H), 8.14 (br. s, 1H), 7.98 (d, J= 8.1 Hz, 1H), 2.79 (s, 3H) ppm. The spectroscopic data correspond to the data provided in the literature. The compound is also commercially available
13 g With manganese(IV) oxide In dichloromethane at 40℃; for 2 h; A flask was charged with (2-methyl-4-nitro-phenyl)-methanol (16.7 g, 0.100 mol) (334 mL), to manganese(IV) oxide (5 μm, 102.3 g, 1.00 mol), and CH2Cl2 (334 mL). The stirred mixture was heated at 40° C. for at least 2 h or until in-process HPLC analysis showed that conversion was greater than 95percent. The cooled mixture was filtered through a celite cake (8 g) loaded onto a fritted funnel and the filter cake was rinsed with CH2Cl2 (340 mL). The filtrate and wash were concentrated under reduced pressure to dryness to afford the title compound as an amorphous solid (13.0 g, 78percent yield).
Reference: [1] Patent: US2015/218086, 2015, A1, . Location in patent: Paragraph 0527; 0528; 0582
[2] Patent: WO2017/24009, 2017, A1, . Location in patent: Paragraph 0559; 0602
[3] Journal of the American Chemical Society, 2008, vol. 130, # 44, p. 14533 - 14543
[4] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 7, p. 818 - 829
[5] Patent: US2013/310394, 2013, A1, . Location in patent: Paragraph 0167-0168
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