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[ CAS No. 93-02-7 ] {[proInfo.proName]}

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Chemical Structure| 93-02-7
Chemical Structure| 93-02-7
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Product Details of [ 93-02-7 ]

CAS No. :93-02-7 MDL No. :MFCD00003314
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AFUKNJHPZAVHGQ-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :66726
Synonyms :

Calculated chemistry of [ 93-02-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.81
TPSA : 35.53 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.25
Solubility : 0.944 mg/ml ; 0.00568 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 0.873 mg/ml ; 0.00526 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.424 mg/ml ; 0.00255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 93-02-7 ]

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 [ 93-02-7 ]

* 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 [ 93-02-7 ]
  • Downstream synthetic route of [ 93-02-7 ]

[ 93-02-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 93-02-7 ]
  • [ 56172-36-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 21, p. 5611 - 5618
  • 2
  • [ 93-02-7 ]
  • [ 33524-31-1 ]
YieldReaction ConditionsOperation in experiment
91% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h; Inert atmosphere A solution of 2,5-dimethoxybenzaldehyde 8 (3.32 g, 20mmol) in THF (20 mL) was slowly added to a suspension of LiAlH4 (748 mg, 22 mmol) in THF (20 mL) at 0 °C over aperiod of 30 min. After 30 min, the reaction was carefully quenched with saturated Na2SO4 solution (10 mL) at 0 °C and the resulting suspension was stirred for 3 h before it was filtered through a pad of silica gel. The filtrate was dried over Na2SO4, the solvent was evaporated under reduced pressure and the residue purified by column chromatography(petroleum ether--- EtOAc, 1:1) to give corresponding alcohol as colorless thick liquid (3.06 g, 91 percent). Rf = 0.4(petroleum ether--- EtOAc, 1:1).
90.5% With sodium tetrahydroborate In ethanol at 20℃; for 3 h; General procedure: To a solution of substituted phenylaldehyde 13, 15a-15d (8 mmol) in anhydrous ethyl alcohol (12 ml) was added 96percent NaBH4 (0.32 g, 8 mmol) and then stirred at room temperature for 3.0 h. After the solvent was evaporated, the residue was extracted with ethyl acetate, washed with brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure to afford 14a, 17a-17d as pale yellow oils. The 14a, 17a-17d were used directly for the next step without further purification. 4-chloro-2-(hydroxymethyl)phenol 14a, yield 91.0percent, ESI-MS(m/z): 159.1[M+H]+.
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9190 - 9194
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 17, p. 3965 - 3974
[3] Tetrahedron Letters, 2011, vol. 52, # 9, p. 983 - 986
[4] European Journal of Organic Chemistry, 2011, # 27, p. 5331 - 5335
[5] Green Chemistry, 2017, vol. 19, # 14, p. 3296 - 3301
[6] Patent: WO2018/194537, 2018, A1, . Location in patent: Page/Page column 13-14
[7] Tetrahedron Letters, 1992, vol. 33, # 37, p. 5417 - 5418
[8] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 182 - 183
[9] Synthetic Communications, 2001, vol. 31, # 8, p. 1177 - 1185
[10] Journal of the American Chemical Society, 2014, vol. 136, # 38, p. 13233 - 13239
[11] Angewandte Chemie - International Edition, 2006, vol. 45, # 40, p. 6718 - 6722
[12] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 8, p. 2873 - 2880
[13] Synlett, 2017, vol. 28, # 9, p. 1046 - 1050
[14] European Journal of Medicinal Chemistry, 2019, p. 864 - 882
[15] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 165, p. 165 - 170
[16] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1895, vol. 20, p. 221
[17] Journal of the Chemical Society, 1954, p. 1165,1168
[18] Bulletin de la Societe chimique de France, 1971, vol. 5, p. 1676 - 1686
[19] Journal of Organic Chemistry, 1980, vol. 45, # 13, p. 2614 - 2620
[20] Synthetic Communications, 1985, vol. 15, # 14, p. 1315 - 1324
[21] Journal of the American Chemical Society, 1993, vol. 115, # 3, p. 850 - 854
[22] Journal of Medicinal Chemistry, 1999, vol. 42, # 6, p. 1007 - 1017
[23] Patent: EP1460062, 2004, A1, . Location in patent: Page 67
[24] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 18, p. 5383 - 5386
[25] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 4, p. 1190 - 1198
[26] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 125 - 136
[27] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5971 - 5975
[28] Molecules, 2013, vol. 18, # 4, p. 3872 - 3893
[29] Applied Organometallic Chemistry, 2013, vol. 27, # 8, p. 459 - 464
[30] Organic Letters, 2016, vol. 18, # 8, p. 1752 - 1755
[31] Organic Letters, 2017, vol. 19, # 20, p. 5701 - 5704
  • 3
  • [ 93-02-7 ]
  • [ 31558-41-5 ]
YieldReaction ConditionsOperation in experiment
56% at 0 - 20℃; for 1 h; To a solution of 2,5-dimethoxybenzaldehyde (1.0 g, 6.02 mmol) in glacial acetic acid (7 mL) was added a solution of Br2 (0.34 mL, 6.62 mmol) in glacial acetic acid (3 mL) at 0 °C and the reaction mixture was warmed up and stirred at room temperature for 1 h. Water (30 mL) was added and the precipitate was collected by filtration. Water (30 mL) and CH2Cl2 (30 mL) were added to the white solid and the two phases were separated. The aqueous layer was extracted with CH2Cl2 (3 x 25 mL) and the combined organic layers were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product which was further purified by column chromatography on silica (20percent EtOAc/hexanes) to furnish 4-bromo-2,5-dimethoxybenzaldehyde as a pale yellow solid (0.83 g, 3.37 mmol, 56 percent).
44% With bromine; tin(IV) chloride In dichloromethane at 20℃; Inert atmosphere; Reflux SnCl4 (11.5 g, 44 mmol) was added to a solution of the 2,5-dimethoxybenzaldehyde (6.65 g, 40 mmol) in anhydrous CH2Cl2, followed by bromine (2.1 ml, 44 mmol) dropwise over 20 min. The reaction mixture was heated to reflux for 2 h and then left stirring overnight at room temperature. The orange black suspension was poured onto ice and the layers separated. The organic layer was washed with a saturated sodium hydrogen carbonate solution, then dried with sodium sulfate and the solvent removed in vacuo to give a brown solid. The product was re-precipitated from methanol/water to give a yellow/cream powder: 4.31 g (44percent yield); mp 132–134 °C; 1H NMR (400 MHz, CDCl3) δ ppm 10.40 (s, 1H, ArH), 7.34 (s, 1H, ArH), 7.25 (s, 1H, ArH), 3.90 (s, 3H, OCH3), 3.89 (s, 3H, OCH3).
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 35, p. 5782 - 5786
[2] Tetrahedron, 2011, vol. 67, # 21, p. 3904 - 3914
[3] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15870 - 15873
[4] Synthetic Communications, 1998, vol. 28, # 24, p. 4629 - 4637
[5] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3281 - 3284
[6] Tetrahedron, 2013, vol. 69, # 22, p. 4389 - 4394
[7] Journal of medicinal chemistry, 1971, vol. 14, # 4, p. 370 - 372
  • 4
  • [ 93-02-7 ]
  • [ 31558-41-5 ]
  • [ 85432-87-7 ]
Reference: [1] Organic Preparations and Procedures International, 1991, vol. 23, # 4, p. 419 - 424
  • 5
  • [ 93-02-7 ]
  • [ 52428-09-8 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1316 - 1327
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915[3] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062
[4] Patent: WO2014/82379, 2014, A1,
[5] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057
[6] Patent: EP2730572, 2014, A1,
[7] Patent: EP2730572, 2015, B1,
[8] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282
  • 6
  • [ 75-16-1 ]
  • [ 93-02-7 ]
  • [ 1201-38-3 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 29, p. 15011 - 15013
  • 7
  • [ 93-02-7 ]
  • [ 5312-97-0 ]
Reference: [1] Synthesis, 1989, # 6, p. 451 - 452
[2] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1182 - 1186
[3] Synthetic Communications, 1998, vol. 28, # 24, p. 4629 - 4637
[4] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2177 - 2179
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 14, p. 4241 - 4245
  • 8
  • [ 93-02-7 ]
  • [ 1758-25-4 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1895, vol. 20, p. 221
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