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[ CAS No. 635-93-8 ] {[proInfo.proName]}

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Chemical Structure| 635-93-8
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Product Details of [ 635-93-8 ]

CAS No. :635-93-8 MDL No. :MFCD00003331
Formula : C7H5ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FUGKCSRLAQKUHG-UHFFFAOYSA-N
M.W : 156.57 Pubchem ID :12481
Synonyms :

Calculated chemistry of [ 635-93-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.86
TPSA : 37.3 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.12 mg/ml ; 0.00714 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.92 mg/ml ; 0.0123 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.663 mg/ml ; 0.00424 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 635-93-8 ]

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 [ 635-93-8 ]

* 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 [ 635-93-8 ]
  • Downstream synthetic route of [ 635-93-8 ]

[ 635-93-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 685-87-0 ]
  • [ 635-93-8 ]
  • [ 10242-10-1 ]
YieldReaction ConditionsOperation in experiment
55.5% With potassium hydroxide; potassium carbonate In ethanol; water; butanone Preparation 5
5-Chlorobenzofuran-2-carboxylic acid.
A suspension of 5-chlorosalicyl aldehyde (10.62 g, 67.8 mmol), ethyl bromomalonate (25.3 g, 105.8 mmol) and anhydrous potassium carbonate (9.37 g, 67.8 mmol) in ethylmethylketone (50 ml) was refluxed for 5 hours, then kept under stirring at RT overnight.
The solvent was evaporated and the residue was diluted with water (500 ml), then the pH was neutralized with 1N HCl.
The suspension was extracted with Et2 O, then the organic phase was dried (MgSO4) and concentrated.
The oily residue was dissolved in absolute EtOH (50 ml) and added to a 10percent ethanolic solution of KOH.
The thick suspension was refluxed under vigorous stirring overnight then after cooling to RT the solvent was taken off and water was added.
The aqueous phase was washed with Et2 O, then the pH adjusted to 2 with 1N HCl.
The aqueous suspension was extracted with EtOAc and the organic phase after drying (MgSO4) and concentration produced pure title compound (7.4 g, 37.6 mmol, yield 55.5percent) as a yellow oil.
Reference: [1] Patent: US6025390, 2000, A,
[2] Gazzetta Chimica Italiana, 1955, vol. 85, p. 381,388
[3] Patent: US4332952, 1982, A,
[4] Patent: US4342771, 1982, A,
  • 2
  • [ 635-93-8 ]
  • [ 10242-10-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 1, p. 71 - 74
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 4093 - 4103
  • 3
  • [ 90-02-8 ]
  • [ 1927-94-2 ]
  • [ 635-93-8 ]
  • [ 90-60-8 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
  • 4
  • [ 635-93-8 ]
  • [ 74-88-4 ]
  • [ 7035-09-8 ]
YieldReaction ConditionsOperation in experiment
82.58%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 5 - 10℃; for 0.333333 h;
Stage #2: at 5 - 20℃; for 2 h;
A solution of 5-chloro-2-hydroxybenzaldehyde (20g, 128mmol) in DMF (70mL) was cooled to a temperature between 5-10 C. Sodium hydride (7.69g, 192mmol) was added to the above solution in small portions over a period of 20 minutes. Methyl iodide (23.8ml, 384mmol) was then added drop wise to the above reaction mixture whilst maintaining its temperature below 15°C. After completion of addition the reaction mixture was stirred at room temperature for 2 hours. Thereafter the reaction mixture was poured in to cold saturated ammonium chloride solution (250mL) to get white precipitates. The precipitates thus formed were filtered off and dried under vacuo. The resulting solid was triturated with 100 ml of pentane:diethyl ether (4: 1) to afford 18g (yield, 82.58percent) of the desired compound as a white solid. LC-MS: m/z = 170.1 (M+H).
82.58%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 5 - 10℃; for 0.333333 h;
Stage #2: at 15 - 20℃; for 2 h;
[00435] Step 1 : Preparation of 5 -chloro-2-methoxybenzaldehyde [00436] A solution of 5-chloro-2-hydroxybenzaldehyde (20g, 128mmol) in DMF (70mL) was cooled to a temperature between 5-10 C. Sodium hydride (7.69g, 192mmol) was added to the above solution in small portions over a period of 20 minutes. Methyl iodide (23.8ml, 384mmol) was then added drop wise to the above reaction mixture whilst maintaining its temperature below 15°C. After completion of addition the reaction mixture was stirred at room temperature for 2 hours. Thereafter the reaction mixture was poured in to cold saturated ammonium chloride solution (250mL) to get white precipitates. The precipitates thus formed were filtered off and dried under vacuo. The resulting solid was triturated with 100 ml of pentane:diethyl ether (4: 1) to afford 18g (yield, 82.58percent) of the desired compound as a white solid. LC-MS: m/z = 170.1 (M+H).
82.58%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 5 - 10℃; for 0.333333 h;
Stage #2: at 15 - 20℃; for 2 h;
Step 1:
Preparation of 5-chloro-2-methoxybenzaldehyde
A solution of 5-chloro-2-hydroxybenzaldehyde (20 g, 128 mmol) in DMF (70 mL) was cooled to a temperature between 5-10° C. Sodium hydride (7.69 g, 192 mmol) was added to the above solution in small portions over a period of 20 minutes.
Methyl iodide (23.8 ml, 384 mmol) was then added drop wise to the above reaction mixture whilst maintaining its temperature below 15° C.
After completion of addition the reaction mixture was stirred at room temperature for 2 hours.
Thereafter the reaction mixture was poured in to cold saturated ammonium chloride solution (250 mL) to get white precipitates.
The precipitates thus formed were filtered off and dried under vacuo.
The resulting solid was triturated with 100 ml of pentane:diethyl ether (4:1) to afford 18 g (yield, 82.58percent) of the desired compound as a white solid. LC-MS: m/z=170.1 (M+H).
Reference: [1] Chemical Communications, 2011, vol. 47, # 9, p. 2679 - 2681
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5019 - 5032
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2768 - 2776
[4] Patent: WO2014/151472, 2014, A1, . Location in patent: Paragraph 00392-00393
[5] Patent: WO2016/40315, 2016, A1, . Location in patent: Paragraph 00435; 00436
[6] Patent: US2016/130239, 2016, A1, . Location in patent: Paragraph 0735; 0736
[7] Patent: US4595685, 1986, A,
[8] Patent: EP1820798, 2007, A1, . Location in patent: Page/Page column 30
[9] Patent: EP2025672, 2009, A1, . Location in patent: Page/Page column 39-40
  • 5
  • [ 77-78-1 ]
  • [ 635-93-8 ]
  • [ 7035-09-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 260 - 266
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1945, vol. 221, p. 202
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2251 - 2255
  • 6
  • [ 635-93-8 ]
  • [ 13589-72-5 ]
YieldReaction ConditionsOperation in experiment
93% With hydroxylamine-O-sulfonic acid In water Reference Example 1
5-chloro-2-hydroxybenzonitrile
5-chloro-2-hydroxybenzaldehyde (300 g, 1.92 mol) and hydroxylamine-O-sulfonic acid (260 g, 2.30 mol) were suspended in water (4.5 L) at room temperature, which was then stirred at 60° C. for 7 hours.
Water (3 L) was added to the reaction mixture, which was then cooled with ice, followed by filtering a crystal before further washing with water (1.5 L).
The precipitated crystal was suspended in water (1.5 L), filtered, washed with water, and subjected to tray drying at 50° C. for 22 hours to obtain 272 g of the title compound (white crystal, yield: 93percent).
1H-NMR(CDCl3)δ:6.94(1H, d, J=8.8 Hz), 7.42(1H, dd, J=8.8, 2.9 Hz), 7.47(1H, d, J=2.9 Hz)
Reference: [1] Patent: WO2006/115130, 2006, A1, . Location in patent: Page/Page column 53-54
[2] Patent: US2007/117866, 2007, A1,
[3] Gazzetta Chimica Italiana, 1959, vol. 89, p. 1009,1013
[4] Journal of Molecular Recognition, 2012, vol. 25, # 6, p. 352 - 360
[5] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1229 - 1234
[6] Patent: CN107286076, 2017, A,
  • 7
  • [ 635-93-8 ]
  • [ 39900-62-4 ]
  • [ 13589-72-5 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8657 - 8667
  • 8
  • [ 635-93-8 ]
  • [ 6386-63-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424
  • 9
  • [ 635-93-8 ]
  • [ 7048-38-6 ]
Reference: [1] Patent: WO2014/151472, 2014, A1,
[2] Patent: WO2016/40315, 2016, A1,
[3] Patent: US2016/130239, 2016, A1,
  • 10
  • [ 635-93-8 ]
  • [ 83823-06-7 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 4, p. 344 - 347
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 4, p. 344 - 347
[3] Archiv der Pharmazie, 2012, vol. 345, # 10, p. 767 - 770
[4] RSC Advances, 2014, vol. 4, # 102, p. 58397 - 58403
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