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Product Details of [ 2420-16-8 ]

CAS No. :2420-16-8 MDL No. :MFCD00016981
Formula : C7H5ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VGSOCYWCRMXQAB-UHFFFAOYSA-N
M.W : 156.57 Pubchem ID :17022
Synonyms :

Calculated chemistry of [ 2420-16-8 ]

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 : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 1.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.654 mg/ml ; 0.00417 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 0.792 mg/ml ; 0.00506 mol/l
Class : 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 : 1.02

Safety of [ 2420-16-8 ]

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 [ 2420-16-8 ]

* 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 [ 2420-16-8 ]
  • Downstream synthetic route of [ 2420-16-8 ]

[ 2420-16-8 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 123-08-0 ]
  • [ 2420-16-8 ]
YieldReaction ConditionsOperation in experiment
86% With N-chloro-succinimide In chloroform at 50℃; for 15 h; N-chlorosuccinimide (1.1 g, 8.18 mmol) was added to a solution of 4- hydroxybenzaldehyde (1.0 g, 8.18 mmol) in 10 ml of chloroform and the mixture was heated at 50 0C for 15 h. The reaction mixture was cooled and the solvent was evaporated. The residue was dissolved in ethyl acetate (25 ml), washed with water and brine, and dried over anhydrous sodium sulphate. Evaporation rendered crude material which was purified by silica column and was eluted with 12percent ethyl acetate in hexane to yield 1.1 g (86 percent) 3-chloro-4-hydroxybenzaldehyde. 1H-NMR (400 MHz, CDC13 ) δ (ppm): 9.840 (s, IH), 7.898-7.894 (d, IH, J=1.6), 7.749-7.724 (dd, IH, J=8.4Hz), 7.164- 7.143 (d, IH, J=8.4Hz), 6.288 (s, IH).
86% With N-chloro-succinimide In chloroform at 50℃; for 15 h; N-chlorosuccinimide (1.1 g, 8.18 mmol) was added to a solution of 4- hydroxybenzaldehyde (1.0 g, 8.18 mmol) in 10 ml of chloroform and the mixture was heated at 50 0C for 15 h. The reaction mixture was cooled and the solvent was evaporated. The residue was dissolved in EtOAc (25 ml), washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified by silica column and was eluted with 12percent EtOAc in hexane to yield 1.1 g (86 percent) of 3-chloro-4-hydroxybenzaldehyde as a white solid. 1H-NMR (400 MHz, CDCL3) δ 9.840 (s, IH), 7.898-7.894 (d, IH, J=1.6), 7.749-7.724 (dd, IH, J=8.4), 7.164- 7.143 (d, IH, J=8.4), 6.288 (s, IH) ppm.
77%
Stage #1: With thionyl chloride In dichloromethane at 20℃; for 14 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
To a stirred solution of 4-hydroxybenzaldehyde (5.0 g, 40.0 mmol) in DCM (50 mL) SOCl2 (3.30 mL, 40.0 mmol) was added slowly at 0 °C. After the addition was completed, the reaction mixture was brought to RT and stirred for 14 h. The reaction mixture was then quenched with water (50 mL), neutralized with a saturated NaHCO3 solution and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography to afford 3-chloro-4-hydroxybenzaldehyde (5.0 g, 77 percent) as a brown solid.
75% With chlorine In water; acetic acid Preparation 75
Synthesis of 3-chloro-4-hydroxybenzaldehyde
Acetic acid (300 ml) was bubbled with chlorine gas to make 38.38 g (0.541 mol) of chlorine. 4-Hydroxybenzaldehyde (66.1 g, 0.541 mol) was dissolved in acetic acid (300 ml) and stirred, during which the acetic acid solution containing chlorine as prepared above was slowly added thereto over 2 hours.
The resulting mixture was stirred for further 2 hours.
After completion of reaction, the reaction solution was concentrated.
To the residue was added water (1L), which was then filtered, washed with water (500 ml) and dried to give 63.16 g (0.403 mol, Yield 75percent) of the title compound.
1H NMR (CDCl3, ppm); 9.84 (1H, s), 7.89 (1H, s), 7.74 (1H, d), 7.15 (1H, d), 6.17 (1H, s)
FAB MS (m/e)=157[M++1]
64% With N-chloro-succinimide In chloroform at 60℃; for 2 h; To a well stirred solution of p-hydroxybenzaldehyde (1.0 mmol) in CHCl3 (4.5 ml) was added N-chlorosuccinimide (1.1 mmol) and the resulting mixture was allowed to react for 2 h at 60 °C. The solution was then poured into water (30 ml), and extracted with Et2O (3 x 10 ml). The combined organic phases were dried over Na2SO4 and evaporated to dryness. The desired product was obtained after crystallization from H2O. Yield = 64 percent. Analytical data were identical to those already reported for the same compound.2 Anal. Calcd for C7H5ClO2: C, 53.70; H, 3.22; O, 20.44. Found: C, 53.75; H, 3.19, O, 20.42 .
40% With sulfuryl dichloride In chloroformInert atmosphere; Reflux Compound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, protected by argon,After heating to reflux, a solution of 20 ml of sulfuryl chloride (3.2 ml, 40 mmol) in chloroform was slowly added dropwise and then refluxed overnight. The reaction solution was spin-dried and pure petroleum ether was passed through a silica gel column to obtain 2.5 g (40percent).

Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 28, p. 5043 - 5046
[2] Patent: WO2010/127212, 2010, A1, . Location in patent: Page/Page column 35
[3] Patent: WO2010/127208, 2010, A1, . Location in patent: Page/Page column 55
[4] Tetrahedron Asymmetry, 1997, vol. 8, # 24, p. 4003 - 4006
[5] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9
[6] Patent: WO2009/158393, 2009, A1, . Location in patent: Page/Page column 113
[7] Synthesis, 2002, # 17, p. 2503 - 2512
[8] Patent: US2003/125356, 2003, A1,
[9] Asian Journal of Chemistry, 2018, vol. 30, # 1, p. 167 - 170
[10] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 769 - 772
[11] Patent: CN104341347, 2018, B, . Location in patent: Paragraph 0138; 0139
[12] Chemische Berichte, 1904, vol. 37, p. 4033
[13] Journal of Organic Chemistry, 1953, vol. 18, p. 121,124
[14] Journal of the Chemical Society, 1965, p. 954 - 973
[15] Organic and Biomolecular Chemistry, 2005, vol. 3, # 7, p. 1233 - 1239
[16] Patent: US6582351, 2003, B1,
[17] Green Chemistry, 2012, vol. 14, # 6, p. 1673 - 1679
[18] Chemistry - A European Journal, 2018, vol. 24, # 43, p. 11119 - 11130
  • 2
  • [ 6640-27-3 ]
  • [ 2420-16-8 ]
Reference: [1] Green Chemistry, 2014, vol. 16, # 5, p. 2807 - 2814
  • 3
  • [ 95-57-8 ]
  • [ 100-97-0 ]
  • [ 2420-16-8 ]
  • [ 1927-94-2 ]
  • [ 3328-72-1 ]
YieldReaction ConditionsOperation in experiment
21%
Stage #1: With copper(I) oxide In trifluoroacetic acid for 5 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃; for 1 h;
General procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).
Reference: [1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8147 - 8158
  • 4
  • [ 105960-29-0 ]
  • [ 2420-16-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 19, p. 3572 - 3581
[2] Journal fuer Praktische Chemie (Leipzig), 1941, vol. <2> 158, p. 245,250
  • 5
  • [ 100-39-0 ]
  • [ 2420-16-8 ]
  • [ 66422-84-2 ]
Reference: [1] Patent: US2003/125356, 2003, A1,
  • 6
  • [ 67-66-3 ]
  • [ 95-57-8 ]
  • [ 2420-16-8 ]
Reference: [1] Journal of Chemical & Engineering Data, 1983, vol. 28, # 1, p. 139 - 141
[2] Journal of the Chemical Society, 1929, p. 469,470
  • 7
  • [ 507-40-4 ]
  • [ 123-08-0 ]
  • [ 2420-16-8 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 702
  • 8
  • [ 194017-69-1 ]
  • [ 2420-16-8 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 74, p. 46636 - 46643
  • 9
  • [ 2315-81-3 ]
  • [ 2420-16-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 5, p. 1278 - 1283
  • 10
  • [ 68243-92-5 ]
  • [ 2420-16-8 ]
Reference: [1] Magyar Kemiai Folyoirat, 1956, vol. 62, p. 76,78[2] Chem.Abstr., 1958, p. 8085
  • 11
  • [ 141805-79-0 ]
  • [ 2420-16-8 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 2141,2142,2144
  • 12
  • [ 95-57-8 ]
  • [ 2420-16-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1941, vol. <2> 158, p. 245,250
  • 13
  • [ 302-17-0 ]
  • [ 95-57-8 ]
  • [ 2420-16-8 ]
  • [ 1927-94-2 ]
Reference: [1] Nippon Kagaku Zasshi, 1955, vol. 76, p. 993[2] Chem.Abstr., 1957, p. 17859
  • 14
  • [ 95-57-8 ]
  • [ 76-03-9 ]
  • [ 2420-16-8 ]
  • [ 1927-94-2 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 496,498
  • 15
  • [ 50-00-0 ]
  • [ 95-57-8 ]
  • [ 2420-16-8 ]
Reference: [1] Patent: DE105798, , ,
  • 16
  • [ 2420-16-8 ]
  • [ 2315-81-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 11, p. 2622 - 2639
  • 17
  • [ 2420-16-8 ]
  • [ 74-88-4 ]
  • [ 4903-09-7 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1 h; Inert atmosphere To a stirred solution of 3-chloro-4-hydroxybenzaldehyde (2.9 g, 18.412 mmol) in DMF (30 mL) was added K2CO3 (7.6 g, 55.238 mmol). CH3I (7.80 g, 55.238 mmol) was then added slowly at RT under an inert atmosphere. After addition was completed, the reaction mixture was brought to 80 0C and stirred for 1 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography to afford 3-chloro-4-methoxybenzaldehyde (2.78 g, 93percent) as a yellow solid.
Reference: [1] Patent: US2003/176481, 2003, A1,
[2] Patent: WO2009/158393, 2009, A1, . Location in patent: Page/Page column 113-114
[3] Patent: US6313146, 2001, B1,
[4] Patent: US6582351, 2003, B1,
  • 18
  • [ 2420-16-8 ]
  • [ 77-78-1 ]
  • [ 4903-09-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With potassium carbonate In acetone for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; Reflux; Inert atmosphere
Finely powdered potassium carbonate (18.1 g, 0.131 mol, 2 eq) was added to a well stirred solution of 3-chloro-4-hydroxybenzaldehyde (10 g, 0.064 mol, 1 eq) in acetone (80 mL) under nitrogen. After 10 min., dimethylsulphate (8 g, 0.064 mol, 1 eq) was added slowly at room temperature and stirred for 30 min. The reaction mixture was allowed to reflux for 2h. Reaction progress was monitored by TLC, Reaction mixture cooled to room temperature and K2CO3 was filtered, acetone was distilled out in vacuo to obtain residue and was triturated with hexane (20 mL) at O0C for 30 min. to result pale green colored solid. Yield 9.2 g (85percent).
Reference: [1] Patent: WO2010/46926, 2010, A2, . Location in patent: Page/Page column 10
  • 19
  • [ 2420-16-8 ]
  • [ 584-08-7 ]
  • [ 74-88-4 ]
  • [ 4903-09-7 ]
Reference: [1] Patent: US6031003, 2000, A,
[2] Patent: US5763569, 1998, A,
[3] Patent: US5688938, 1997, A,
  • 20
  • [ 2420-16-8 ]
  • [ 1849-76-9 ]
Reference: [1] Synthesis, 2002, # 17, p. 2503 - 2512
[2] Journal of the Chemical Society, 1965, p. 954 - 973
  • 21
  • [ 2420-16-8 ]
  • [ 3964-57-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 17, p. 3931 - 3943
  • 22
  • [ 2420-16-8 ]
  • [ 86902-27-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 11, p. 1570 - 1576
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