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[ CAS No. 4101-32-0 ] {[proInfo.proName]}

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Chemical Structure| 4101-32-0
Chemical Structure| 4101-32-0
Structure of 4101-32-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4101-32-0 ]

CAS No. :4101-32-0 MDL No. :MFCD00130048
Formula : C10H11NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :ZVLFGESHYMKNQP-UHFFFAOYSA-N
M.W : 225.20 Pubchem ID :77737
Synonyms :

Calculated chemistry of [ 4101-32-0 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.44
TPSA : 81.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.38
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 0.1
Log Po/w (SILICOS-IT) : 0.09
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.12
Solubility : 1.71 mg/ml ; 0.0076 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.458 mg/ml ; 0.00203 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.38
Solubility : 0.945 mg/ml ; 0.0042 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.3

Safety of [ 4101-32-0 ]

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

Application In Synthesis of [ 4101-32-0 ]

* 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 [ 4101-32-0 ]
  • Downstream synthetic route of [ 4101-32-0 ]

[ 4101-32-0 ] Synthesis Path-Upstream   1~7

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  • [ 4101-32-0 ]
  • [ 35654-56-9 ]
Reference: [1] Heterocycles, 2016, vol. 92, # 10, p. 1882 - 1887
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  • [ 13425-93-9 ]
Reference: [1] Heterocycles, 2016, vol. 92, # 10, p. 1882 - 1887
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  • [ 1131-62-0 ]
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YieldReaction ConditionsOperation in experiment
87.9% With nitric acid; sodium nitrite In water at 5 - 10℃; for 3 - 5 h; (1)
Step of nitration:
3,4-Dimethoxyacetophenone (1500 g) was dissolved in 17percent nitric acid (1400 g) at 5 to 10°C to prepare a solution which was then slowly added dropwise to a mixed solution composed of 67percent nitric acid (8430 g) and sodium nitrite (18 g) at 5 to 10°C over a period of 2 to 3 hr.
After the completion of the dropwise addition, the reaction solution was stirred at 5 to 10°C for 1 to 2 hr.
Cold water (7.5 L) was added thereto, and the mixture was stirred for 30 min.
The reaction solution was then filtered and was washed with water (30 L).
The filtered product was added to water (7.5 L), and the mixture was neutralized with an aqueous sodium bicarbonate solution, was then filtered, and was washed with water (7 L).
The filtered product was dried under the reduced pressure to give 3,4-dimethoxy-6-nitroacetophenone (2164 g, yield 87.9percent).
1H-NMR (400 MHz, CDCl3/ppm); δ 2.50 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 6.76 (s, 1H), 7.62 (s, 1H)
86% at 60℃; for 3.5 h; A mixture of 1-(3,4-dimethoxyphenyl)ethan-1-one 11 (180 g, 1.0 mol), HOAc (1.5 L) was stirred and heated to 60°C. When the solid dissolved, 65percent HNO3 (110 mL, 1.5 mol) was added over 30 min and the mixture was stirred for another 3 h to give a yellow solution. The reaction mixture was poured slowly into ice-water (5 L) while stirring constantly. The yellow solid formed was filtered off and washed with cold water (600 mL × 2), dried at 60°C for 4 h to give crude product 12 (210 g). The crude 12 (210 g) was stirred and heated with EtOAc : petroleum ether= 1:1 (v:v) (800 mL) at reflux for 2 h then cooled to room temperature, the resulting solid was filtered off and washed with EtOAc : petroleum ether = 1:1 (v:v) (100 mL × 2), dried at 50°C for 4 h to afford 12(193.7 g, 86percent) as a yellow solid; mp 131.3−133.1° C (Lit.10 130−132°C). 1H NMR (400 MHz,DMSO-d6): δ 2.52 (s, 3H), 3.90 (s, 3H), 3.93(s, 3H), 7.23 (s, 1H), 7.64 (s, 1H). MS (ESI): m/z = 226.1 [M+ H]+, 473.2 [2M + Na]+.
67% at 0℃; for 4 h; Inert atmosphere 1-(3, 4-dimethoxyphenyl)ethan-1-one (10 g) was added to acetic anhydride (30 mL). After the solution was cooled to 0 °C, a mixture of nitric acid (200 mL) and acetic anhydride (10 mL) were added dropwise. Upon completion of the addition, the reaction solution was stirred for 4 hours, poured into 1 L of ice water, filtered, washed with water and dried to obtain 1-(4,5-dimethoxy-2-nitrophenyl)ethan-1-one (8 g, 67percent).
60% With nitric acid In diethyl ether at 0℃; for 5 h; General procedure: To a solution of 3,4-di(1H,1H,2H,2H,3H,3H-perfluoroheptyloxy)acetophenone (2.14 g, 3.18 mmol) in diethyl ether (10 mL), HNO3 (15 mL) was carefully added dropwise at 0 °C. The solution was subsequently stirred at 0 °C for 5 h. The solution was added to ice water (100 mL) and the solution was extracted with ethyl acetate (40 mL x 2). The organic layer was washed with 5percent NaHCO3 (50 mL x 3) and dried over MgSO4. After concentrating the solution using a rotary evaporator, the residue was purified by recrystallization with ethanol to yield 1.38 g (1.92 mmol, 60percent) of 4g as yellow needle crystals.
50.7% for 2 h; Cooling with ice 3,4-dimethoxyacetophenone (15 g; 83.2 mmol) was added in small amounts to well stirred, ice-cooled nitric acid (sp gr 1.42; 90 ml) over a period of 1 hr. The final mixture was stirred for one further hour and then poured onto 400 g of crushed ice. When the ice had melted the resulting yellow solid was filtered off, air-dried and recrystallized from ethanol (9.5 g; 50.7percent yield).

Reference: [1] Patent: EP1559715, 2005, A1, . Location in patent: Page/Page column 17
[2] Heterocycles, 2016, vol. 92, # 10, p. 1882 - 1887
[3] Chemistry Letters, 2000, # 7, p. 712 - 713
[4] Patent: EP3205650, 2017, A1, . Location in patent: Paragraph 0106; 0354; 0355
[5] Journal of Organic Chemistry, 1999, vol. 64, # 21, p. 7988 - 7995
[6] Journal of Materials Chemistry B, 2014, vol. 2, # 21, p. 3333 - 3339
[7] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 1, p. 125 - 134
[8] Organic Letters, 2017, vol. 19, # 7, p. 1618 - 1621
[9] Tetrahedron, 2007, vol. 63, # 2, p. 474 - 491
[10] Journal of Fluorine Chemistry, 2010, vol. 131, # 5, p. 597 - 605
[11] Patent: US6384264, 2002, B1, . Location in patent: Page column 9
[12] Journal of Organic Chemistry, 1990, vol. 55, # 5, p. 1585 - 1589
[13] Journal of the Chemical Society, 1946, p. 96
[14] Journal of the Chemical Society, 1924, vol. 125, p. 653
[15] Patent: US4490374, 1984, A,
[16] Journal of the American Chemical Society, 2015, vol. 137, # 6, p. 2155 - 2158
  • 4
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Reference: [1] Tetrahedron, 2007, vol. 63, # 2, p. 474 - 491
[2] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 1, p. 125 - 134
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Reference: [1] Journal of the Chemical Society, 1946, p. 96
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  • [ 7697-37-2 ]
  • [ 1131-62-0 ]
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Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 653
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  • [ 475108-18-0 ]
Reference: [1] Heterocycles, 2016, vol. 92, # 10, p. 1882 - 1887
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