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[ CAS No. 131088-02-3 ] {[proInfo.proName]}

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Chemical Structure| 131088-02-3
Chemical Structure| 131088-02-3
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Product Details of [ 131088-02-3 ]

CAS No. :131088-02-3 MDL No. :MFCD18324145
Formula : C7H5ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IPOSHVWRFQTHGK-UHFFFAOYSA-N
M.W :172.57 Pubchem ID :14766072
Synonyms :

Calculated chemistry of [ 131088-02-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.89
TPSA : 57.53 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 : Yes
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.667 mg/ml ; 0.00386 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.361 mg/ml ; 0.00209 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.81
Solubility : 2.69 mg/ml ; 0.0156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 131088-02-3 ]

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 [ 131088-02-3 ]

* 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 [ 131088-02-3 ]
  • Downstream synthetic route of [ 131088-02-3 ]

[ 131088-02-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 95-01-2 ]
  • [ 131088-02-3 ]
YieldReaction ConditionsOperation in experiment
47% With sulfuryl dichloride In diethyl ether at 0 - 20℃; for 0.5 h; Inert atmosphere To a solution of 2,4-dihydroxybenzaldehyde (3.0 g, 22 mmol) in Et20 (100 mL, 0.22 M) was added dropwise sulfurylchloride (2.1 mL, 26 mmol) at 0 °C under argon. After being stirred at RT for 30 min, the reaction solution was poured into ice-chilled brine, washed with H2O and brine, dried over MgS04, filtered, and concentrated. Purification by flash chromatography (Et20:hexanes = 1:2) provided compound 6 as an ivory solid (47percent). NMR (DMSO-d6, 300 MHz): δ 11.38 (1H, s), 10.87 (1H, s), 9.97 (1H, s), 7.59 (1H, s), 6.58 (1H, s). LRMS (APCI+): Calc'd for C7H5C103 172.0 m/z, measured 173.1 (MH+).
47% With sulfuryl dichloride In diethyl ether at 0 - 20℃; for 0.5 h; Inert atmosphere To a solution of2,4-dihydroxybenzaldehyde (3.0 g, 22 mmol) in Et20 (100 mE, 0.22 M) was added dropwise sulfurylchloride (2.1 mE, 26 mmol) at 00 C. under argon. Afier being stirred at RT for 30 mm, the reaction solution was poured into ice-chilled brine, washed with H20 and brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (Et20:hexanes=1 :2) provided compound 6 as an ivory solid (47percent). ‘H NMR (DMSO-d6, 300 MHz): ö 11.38 (1H, s), 10.87 (1H, s), 9.97 (1H, s), 7.59 (1H, s), 6.58 (1H, s). ERMS (APCI+): Calc’d for C7H5C10C3 172.0 ink, measured 173.1 (MH+).
26% With sulfuryl dichloride In diethyl ether at 0 - 20℃; for 0.5 h; Inert atmosphere To a solution of 2,4-dihydroxybenzaldehyde (20 g, 144.92 mmol) in diethyl ether (500 mL) was added drop wise sulfuryl chloride (14 mL, 171.2 mmol) at 0° C. under argon and stirred at room temperature for 30 min. The reaction mixture was poured into ice-water, the organic layer was separated and washed with water, brine, dried over Na2SO4, filtered, and concentrated to give the crude product, which was purified on a silica gel column (pet. ether:ethyl acetate=90:10) to get 5-chloro-2,4-dihydroxybenzaldehyde as an off white solid. (6.7 g, 26percent, LC/MS; 97percent). ES−, m/z 170.9 [M−H]; [C7H5ClO3]; NMR (DMSO-d6, 400 MHz): δ 11.39 (1H, s), 10.87 (1H, s), 9.98 (1H, s), 7.0 (1H, s), 6.58 (1H, s).
Reference: [1] Chemical Biology and Drug Design, 2015, vol. 86, # 5, p. 1030 - 1035
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 19, p. 3505 - 3508
[3] Chemical Communications, 2008, # 10, p. 1217 - 1219
[4] Heterocycles, 1997, vol. 45, # 7, p. 1345 - 1361
[5] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8828 - 8830
[6] Patent: WO2011/94560, 2011, A1, . Location in patent: Page/Page column 54; 56
[7] Patent: US9075014, 2015, B2, . Location in patent: Page/Page column 40; 41
[8] Patent: US2018/65917, 2018, A1, . Location in patent: Paragraph 0379
[9] Canadian Journal of Research, Section B: Chemical Sciences, 1946, vol. 24, p. 208
[10] Patent: EP2857010, 2015, A1, . Location in patent: Paragraph 0102; 0104
  • 2
  • [ 95-01-2 ]
  • [ 131088-02-3 ]
  • [ 131088-00-1 ]
YieldReaction ConditionsOperation in experiment
65% With piperidine; sodium hypochlorite; sulfuric acid In water at 0 - 20℃; for 5 h; Sodium hypochlorite (75 mL, 0.055 mol) and piperidine (4.68 g, 0.055 mol) were cooled to 0° C., combined cautiously and added dropwise over 2 h to a solution of 2,4,-dihydroxybenzaldehyde (6.91 g, 0.05 mol) in 50percent aqueous sulfuric acid (150 mL) while cooling to 0° C.
After three additional hours, the precipitate was collected via filtration in quantitative yield.
1H NMR indicates that it is about 65percent 5-chloro-2,4-dihdroxybenzaldehyde, with the balance being 3-chloro-2,4-dihdroxybenzaldehyde.
The product can be purified via column chromatography and/or repeated recrystallizations from toluene.
However, the 3-chloro-2,4-dihdroxybenzaldehyde does not react in the next reaction, so the product was used without further purification.
32% With sulfuryl dichloride In diethyl ether at 0℃; for 0.5 h; Inert atmosphere In a scintillation vial, 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol) was dissolved in ethyl ether (18 ml). The mixture was placed under N2 atmosphere and cooled to 0° C. To the mixture was added sulfuryl chloride (0.91 ml, 11 mmol). The mixture was kept under N2 atmosphere at 0° C. for 30 minutes. The reaction mixture was poured into ice water and extracted with ethyl acetate (20 ml). Organic layer was washed with brine, concentrated and chromatographed to yield 5-chloro-2,4-dihydroxybenzaldehyde (0.55 g, 3.2 mmol, 32percent) and 3-chloro-2,4-dihydroxybenzaldehyde (0.233 g, 1.34 mmol, 13.4percent)
Reference: [1] Patent: US8343710, 2013, B1, . Location in patent: Page/Page column 17
[2] Macromolecules, 2010, vol. 43, # 6, p. 2824 - 2831
[3] Patent: US2017/182051, 2017, A1, . Location in patent: Paragraph 0137
  • 3
  • [ 557-21-1 ]
  • [ 95-88-5 ]
  • [ 131088-02-3 ]
Reference: [1] Chinese Journal of Chemistry, 2010, vol. 28, # 1, p. 55 - 60
[2] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 729 - 733
[3] Patent: EP2236508, 2010, A1, . Location in patent: Page/Page column 23-24
  • 4
  • [ 183736-75-6 ]
  • [ 183736-49-4 ]
  • [ 131088-02-3 ]
Reference: [1] Patent: US2006/8855, 2006, A1,
  • 5
  • [ 95-88-5 ]
  • [ 131088-02-3 ]
Reference: [1] Patent: US2005/42662, 2005, A1,
  • 6
  • [ 95-88-5 ]
  • [ 557-21-1 ]
  • [ 131088-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 536 - 547
  • 7
  • [ 95-88-5 ]
  • [ 131088-02-3 ]
Reference: [1] Journal of the Chinese Chemical Society, 2012, vol. 59, # 11, p. 1439 - 1445
[2] Synthesis (Germany), 2016, vol. 48, # 2, p. 245 - 255
  • 8
  • [ 7051-13-0 ]
  • [ 131088-02-3 ]
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 2, p. 245 - 255
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