Home Cart 0 Sign in  
X

[ CAS No. 16375-88-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 16375-88-5
Chemical Structure| 16375-88-5
Chemical Structure| 16375-88-5
Structure of 16375-88-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 16375-88-5 ]

Related Doc. of [ 16375-88-5 ]

Alternatived Products of [ 16375-88-5 ]
Product Citations

Product Details of [ 16375-88-5 ]

CAS No. :16375-88-5 MDL No. :MFCD00016868
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XEYORFKUJZEQCH-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :152141
Synonyms :

Calculated chemistry of [ 16375-88-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.88
TPSA : 49.33 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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 0.79
Log Po/w (MLOGP) : 0.96
Log Po/w (SILICOS-IT) : 1.23
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) : -1.32
Solubility : 7.91 mg/ml ; 0.0479 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 14.6 mg/ml ; 0.0883 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.61
Solubility : 0.409 mg/ml ; 0.00248 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 16375-88-5 ]

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 [ 16375-88-5 ]

* 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 [ 16375-88-5 ]
  • Downstream synthetic route of [ 16375-88-5 ]

[ 16375-88-5 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 88867-64-5 ]
  • [ 23438-23-5 ]
  • [ 16375-90-9 ]
  • [ 16375-88-5 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
  • 2
  • [ 88867-64-5 ]
  • [ 23438-23-5 ]
  • [ 18931-78-7 ]
  • [ 16375-90-9 ]
  • [ 16375-88-5 ]
  • [ 98922-96-4 ]
  • [ 98922-97-5 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
  • 3
  • [ 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
  • 4
  • [ 623-04-1 ]
  • [ 108-24-7 ]
  • [ 16375-88-5 ]
YieldReaction ConditionsOperation in experiment
98% at 20℃; for 0.2 h; Green chemistry General procedure: In a round-bottomed flask (25 mL) equipped with a magnetic stirrer, a mixture of aniline (0.093 g, 1 mmol) and Co3O4 (0.006 g) was prepared. Acetic anhydride (0.102, 1 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 3 min. The progress of the reaction was followed by TLC. After the reaction completion, the products was extracted with EtOAc and filtered to remove Co3O4. The organic solvent was then washed with H2O (2 x 10 mL) and saturated NaHCO3 solution and then dried over anhydrous Na2SO4. The solvent was removed under vacuum to afford the pure product.
91% at 20℃; for 0.1 h; General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 °C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC‐MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10percent solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC‐MS, FT‐IR, and 1H‐NMR spectral data by comparing thesespectra with those of standard samples or literature data.
91% at 50℃; for 0.15 h; General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of PhNH2(1 mmol, 0.093 g) and H2O(3 mL) in oil bath (50 °C) was prepared. Magnetically recyclable nanoparticles of Fe3O4/Cu (0.05 mmol) was then added, and the mixture was stirred for 1 min under oil bath conditions. Addition of Ac2O(1 mmol, 0.102 g) to the prepared mixture was followed by stirring for 3 min at 50 °C. After completion of the reaction, the copper nanocatalyst was separated by an external magnet and the mixture was extracted with EtOAc (3 × 8 mL). Organic layers were then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure affords the pure acetanilide in 95percent yield (0.128 g, Table 2, entry 1).
Reference: [1] Research on Chemical Intermediates, 2017, vol. 43, # 1, p. 413 - 422
[2] Chinese Journal of Catalysis, 2014, vol. 35, # 3, p. 368 - 375
[3] Journal of the Iranian Chemical Society, 2017, vol. 14, # 11, p. 2467 - 2474
[4] Applied Catalysis A: General, 2010, vol. 382, # 2, p. 293 - 302
[5] Journal of the Iranian Chemical Society, 2014, vol. 11, # 4, p. 1103 - 1112
[6] Journal of Organic Chemistry, 2001, vol. 66, # 26, p. 8815 - 8830
[7] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9553 - 9561
[8] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2542 - 2553
[9] Chemistry of Materials, 2011, vol. 23, # 21, p. 4844 - 4856
[10] Journal of the American Chemical Society, 2016, vol. 138, # 17, p. 5568 - 5575
  • 5
  • [ 623-04-1 ]
  • [ 10387-40-3 ]
  • [ 16375-88-5 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 3, p. 1732 - 1736
  • 6
  • [ 17012-22-5 ]
  • [ 16375-88-5 ]
  • [ 79663-14-2 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 6, p. 3665 - 3669
  • 7
  • [ 1402073-35-1 ]
  • [ 16375-88-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 34, p. 8564 - 8567
  • 8
  • [ 122-85-0 ]
  • [ 62-53-3 ]
  • [ 16375-88-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 24, p. 5725 - 5734
  • 9
  • [ 108-24-7 ]
  • [ 24173-36-2 ]
  • [ 16375-88-5 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 23, p. 3625 - 3628
  • 10
  • [ 16331-48-9 ]
  • [ 16375-88-5 ]
Reference: [1] Journal of Natural Products, 2003, vol. 66, # 1, p. 62 - 66
  • 11
  • [ 556-08-1 ]
  • [ 16375-88-5 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 22, p. 4133 - 4136
[2] Journal of Natural Products, 2003, vol. 66, # 1, p. 62 - 66
  • 12
  • [ 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
  • 13
  • [ 18699-02-0 ]
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 4, p. 182 - 187
  • 14
  • [ 88867-64-5 ]
  • [ 23438-23-5 ]
  • [ 16375-90-9 ]
  • [ 16375-88-5 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
  • 15
  • [ 88867-64-5 ]
  • [ 23438-23-5 ]
  • [ 18931-78-7 ]
  • [ 16375-90-9 ]
  • [ 16375-88-5 ]
  • [ 98922-96-4 ]
  • [ 98922-97-5 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
  • 16
  • [ 16375-88-5 ]
  • [ 25027-73-0 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 19, p. 4418 - 4422
  • 17
  • [ 16375-88-5 ]
  • [ 131230-76-7 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 84, p. 12623 - 12625
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 16375-88-5 ]

Aryls

Chemical Structure| 103-89-9

[ 103-89-9 ]

4'-Methylacetanilide

Similarity: 0.87

Chemical Structure| 16375-90-9

[ 16375-90-9 ]

N-(4-hydroxy-3-methylphenyl)acetamide

Similarity: 0.86

Chemical Structure| 556-08-1

[ 556-08-1 ]

4-Acetamidobenzoic acid

Similarity: 0.85

Chemical Structure| 1459-50-3

[ 1459-50-3 ]

N-(4-(Adamantan-1-yl)phenyl)acetamide

Similarity: 0.82

Chemical Structure| 25412-53-7

[ 25412-53-7 ]

4-Acetamidobenzylamine

Similarity: 0.81

Alcohols

Chemical Structure| 127838-58-8

[ 127838-58-8 ]

4-(Hydroxymethyl)pyridin-2(1H)-one

Similarity: 0.80

Chemical Structure| 31570-97-5

[ 31570-97-5 ]

5-Hydroxyquinolin-2(1H)-one

Similarity: 0.79

Chemical Structure| 19315-93-6

[ 19315-93-6 ]

6-Hydroxyquinolin-2(1H)-one

Similarity: 0.77

Chemical Structure| 86-95-3

[ 86-95-3 ]

4-Hydroxyquinolin-2(1H)-one

Similarity: 0.76

Chemical Structure| 109205-68-7

[ 109205-68-7 ]

5-(Hydroxymethyl)pyridin-2(1H)-one

Similarity: 0.76

Amides

Chemical Structure| 103-89-9

[ 103-89-9 ]

4'-Methylacetanilide

Similarity: 0.87

Chemical Structure| 16375-90-9

[ 16375-90-9 ]

N-(4-hydroxy-3-methylphenyl)acetamide

Similarity: 0.86

Chemical Structure| 556-08-1

[ 556-08-1 ]

4-Acetamidobenzoic acid

Similarity: 0.85

Chemical Structure| 1459-50-3

[ 1459-50-3 ]

N-(4-(Adamantan-1-yl)phenyl)acetamide

Similarity: 0.82

Chemical Structure| 25412-53-7

[ 25412-53-7 ]

4-Acetamidobenzylamine

Similarity: 0.81

Amines

Chemical Structure| 103-89-9

[ 103-89-9 ]

4'-Methylacetanilide

Similarity: 0.87

Chemical Structure| 16375-90-9

[ 16375-90-9 ]

N-(4-hydroxy-3-methylphenyl)acetamide

Similarity: 0.86

Chemical Structure| 556-08-1

[ 556-08-1 ]

4-Acetamidobenzoic acid

Similarity: 0.85

Chemical Structure| 1459-50-3

[ 1459-50-3 ]

N-(4-(Adamantan-1-yl)phenyl)acetamide

Similarity: 0.82

Chemical Structure| 25412-53-7

[ 25412-53-7 ]

4-Acetamidobenzylamine

Similarity: 0.81