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[ CAS No. 18640-60-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 18640-60-3
Chemical Structure| 18640-60-3
Chemical Structure| 18640-60-3
Structure of 18640-60-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 18640-60-3 ]

CAS No. :18640-60-3 MDL No. :MFCD03787322
Formula : C8H6ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HVXQVXNQKCPSLH-UHFFFAOYSA-N
M.W : 199.59 Pubchem ID :255582
Synonyms :

Calculated chemistry of [ 18640-60-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.47
TPSA : 62.89 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.18
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.645 mg/ml ; 0.00323 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.279 mg/ml ; 0.0014 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.367 mg/ml ; 0.00184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 18640-60-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18640-60-3 ]

* 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 [ 18640-60-3 ]
  • Downstream synthetic route of [ 18640-60-3 ]

[ 18640-60-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 18640-60-3 ]
  • [ 4104-35-2 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 19, p. 4990 - 4993
  • 2
  • [ 18640-60-3 ]
  • [ 1685-19-4 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogen In ethanol at 20℃; for 4.5 h; b) A mixture of 1-(5-chloro-2-nitrophenyl)ethanone (4.40 g, 22.05 mmol), PtO2 (40 mg) and charcoal (400 mg) in EtOH (80 mL) was rapidly stirred at RT for 4.5 h under one atmosphere of hydrogen. The reaction mixture was filtered through a pad of celite (the residues washed with CH2Cl2) and concentrated under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 4:1) to afford a pale green oil which was recrystallized from Et2O/PE to give 1-(2-amino-5-chlorophenyl)ethanone (3.30 g, 88percent), as pale green crystals.
88% With hydrogen In ethanol at 20℃; for 4.5 h; b) A mixture of 1-(5-chloro-2-nitrophenyl)ethanone 17 (4.40 g, 22.05 mmol), PtO2 (40 mg) and charcoal (400 mg) in EtOH (80 mL) was rapidly stirred at RT for 4.5 h under one atmosphere of hydrogen. The reaction mixture was filtered through a pad of celite (the residues washed with CH2Cl2) and concentrated under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 4:1) to afford a pale green oil which was recrystallized from Et2O/PE to give 1-(2-amino-5-chlorophenyl)ethanone 18 (3.30 g, 88percent), as pale green crystals.
84% With iron; ammonium chloride In methanol; water at 60℃; 2-nitro-5-chloroacetophenone was dissolved in 1 L of H2O / MeOH (1: 1) mixed solution, 75 g of iron powder and 380 g of ammonium chloride were added and stirred at 60 ° C overnight. After filtration, the mixture was extracted with ethyl acetate, dried and recrystallized from EA / PE to give 79 g of 4-amino-5-chloroacetophenone as a yellow solid in 84percent yield.
Reference: [1] Patent: US2007/238700, 2007, A1, . Location in patent: Page/Page column 26
[2] Patent: US2006/63841, 2006, A1, . Location in patent: Page/Page column 24; 4/12
[3] Patent: CN102898374, 2016, B, . Location in patent: Paragraph 0039; 0040
[4] Journal of Fluorine Chemistry, 2010, vol. 131, # 5, p. 597 - 605
[5] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6873 - 6877
[6] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3400 - 3407
  • 3
  • [ 99-02-5 ]
  • [ 18640-60-3 ]
YieldReaction ConditionsOperation in experiment
85% at -18℃; 100 g of m-chloroacetophenone was slowly added dropwise to 500 ml of sulfuric acid nitric acid mixture (volume ratio 1: 6.5, minus 18 degrees), and the temperature was stirred overnight. Was added to ice water and filtered to give 110 g of 2-nitro-5-chloroacetophenone as a yellow solid in 85percent yield.
84% at -20 - -10℃; for 5.25 h; Example 1; Preparation of N-(2-acetyl-4-chlorophenyl)-trifluoromethanesulfonamide; The following compounds were prepared according to the reaction scheme illustrated by FIG. 1. a) To a rapidly stirred solution of fuming HNO3 (17 mL) and concentrated H2SO4 (2.5 mL) at -20° C. was added portionwise 3-chloroacetophenone (5.0 g, 32.34 mmol) over 15 min. The reaction mixture was allowed to warm to -10° C. and stirred for 5 h at this temperature after which ice-water (75 mL) was added and the reaction mixture extracted twice with CH2Cl2. The organic layers were combined, washed five times with water, dried over MgSO4 and concentrated under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 4:1) to afford a pale green oil which was recrystallized from Et2O/PE to give 1-(5-chloro-2-nitrophenyl)ethanone (5.45 g, 84percent), as pale yellow crystals.
84% at -20 - -10℃; for 5.25 h; Example 1 Preparation of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide (Formula 19) The following compounds were prepared according to the reaction scheme illustrated by FIG. 4. a) To a rapidly stirred solution of fuming HNO3 (17 mL) and concentrated H2SO4 (2.5 mL) at -20° C. was added portionwise 3-chloroacetophenone (5.0 g, 32.34 mmol) over 15 min. The reaction mixture was allowed to warm to -10° C. and stirred for 5 h at this temperature after which ice-water (75 mL) was added and the reaction mixture extracted twice with CH2Cl2. The organic layers were combined, washed five times with water, dried over MgSO4 and concentrated under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 4:1) to afford a pale green oil which was recrystallized from Et2O/PE to give 1-(5-chloro-2-nitrophenyl)ethanone 17 (5.45 g, 84percent), as pale yellow crystals.
83.69% at -10 - -5℃; for 0.5 h; KNO3 (13.50 g, 0.133 mol) was crushed and added with stirring into concentrate H2SO4. The mixture was cooled to below -10 °C and 3-chloroacetophenone (20 g/16.8 mL, 0.13 mol) was added at -10 to -5 °C. After a further 30 min at -10 to -5 °C, the mixture was poured into ice-water (500 g). The precipitate was collected by filteration and recrystallized in 95percent ethanol to give (2) as a colorless crystal (21.60 g, 83.69percent): mp 60-62 °C (litrefPreviewPlaceHolder18 63-65 °C).

Reference: [1] Patent: CN102898374, 2016, B, . Location in patent: Paragraph 0035-0038
[2] Patent: US2007/238700, 2007, A1, . Location in patent: Page/Page column 26
[3] Patent: US2006/63841, 2006, A1, . Location in patent: Page/Page column 23-24; 4/12
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5612 - 5627
[5] Journal of Fluorine Chemistry, 2010, vol. 131, # 5, p. 597 - 605
[6] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3400 - 3407
[7] Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3932 - 3936
[8] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6873 - 6877
[9] Patent: US2007/72833, 2007, A1, . Location in patent: Page/Page column 20
  • 4
  • [ 99-02-5 ]
  • [ 18640-60-3 ]
  • [ 116686-84-1 ]
YieldReaction ConditionsOperation in experiment
55.8% With sulfuric acid; nitric acid In water at -5℃; for 3 h; 65percent HNO3 (80 ml) was stirred at -5° C.±1° C. and 98percent H2SO4 (10 mix 10) was added dropwise.
To the stirring solution of HNO3/H2SO4 was added 3-chloroacetophenone (54) (12.0 g, 77.6 mmol).
The mixture was stirred at -5°±1° for 3 h and poured into crushed ice, and extracted with CH2Cl2.
The extract was dried over MgSO4 and evaporated.
The crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1) to give 55 as yellow solid (9.3 g, 46.6 mmol). Yield: 55.8percent; mp 47-49° C.; 1H-NMR (CDCl3, 200 MHz): δ 2.48 (s, 3H), 7.32 (d, J=2.4 Hz, 1H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 198.27, 143.78, 141.05, 139.44, 130.55, 127.36, 125.91, 30.06; Anal. Calcd for C8H6ClNO3: C, 48.14; H, 3.03; N, 7.02.
Reference: [1] Patent: US2012/15908, 2012, A1, . Location in patent: Page/Page column 24
  • 5
  • [ 7463-31-2 ]
  • [ 18640-60-3 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 646,655
  • 6
  • [ 6637-18-9 ]
  • [ 18640-60-3 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 646,655
  • 7
  • [ 41994-44-9 ]
  • [ 105-53-3 ]
  • [ 18640-60-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1969, vol. 17, p. 596 - 604
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