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[ CAS No. 121-32-4 ] {[proInfo.proName]}

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Chemical Structure| 121-32-4
Chemical Structure| 121-32-4
Structure of 121-32-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 121-32-4 ]

CAS No. :121-32-4 MDL No. :MFCD00006944
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CBOQJANXLMLOSS-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :8467
Synonyms :

Calculated chemistry of [ 121-32-4 ]

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 : 1.0
Molar Refractivity : 45.15
TPSA : 46.53 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 : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.83
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.52 mg/ml ; 0.00917 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.13 mg/ml ; 0.00679 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.842 mg/ml ; 0.00507 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 121-32-4 ]

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 [ 121-32-4 ]

* 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 [ 121-32-4 ]
  • Downstream synthetic route of [ 121-32-4 ]

[ 121-32-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 121-32-4 ]
  • [ 77-78-1 ]
  • [ 1131-52-8 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 3302,3308[2] Journal of the American Chemical Society, 1931, vol. 53, p. 1912,1914
[3] Recueil des Travaux Chimiques des Pays-Bas, 1939, vol. 58, p. 528,532, 535
[4] Bulletin de la Societe Chimique de France, 1962, p. 496 - 502
[5] Patent: CN105439837, 2016, A, . Location in patent: Paragraph 0019; 0026; 0027
  • 2
  • [ 121-32-4 ]
  • [ 74-88-4 ]
  • [ 1131-52-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1939, vol. 58, p. 528,532, 535
[2] Patent: WO2010/151258, 2010, A1, . Location in patent: Page/Page column 11
[3] Patent: CN107011209, 2017, A, . Location in patent: Paragraph 0024; 0028; 0031; 0034
  • 3
  • [ 121-32-4 ]
  • [ 75-57-0 ]
  • [ 1131-52-8 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 51, p. 11618 - 11624
[2] Acta Chimica Slovenica, 2010, vol. 57, # 1, p. 29 - 36
  • 4
  • [ 121-32-4 ]
  • [ 3111-37-3 ]
YieldReaction ConditionsOperation in experiment
80% at 20℃; for 3 h; The 3-ethoxy-4-hydroxybenzaldehyde (6.64g, 40 . 0mmol) dissolved in acetic acid (80 ml) in, is fully dissolved. Then the liquid bromine (2.46 ml) is added dropwise to the reaction solution, after the end of dropping, the reaction at room temperature 3 hours, turbid. TLC monitoring after the reaction is ended, filtering to get the solid, the solid will be 50percent ethanol aqueous solution to re-crystallization, to obtain a target compound 1.1 is 7.8g, yield 80percent.
49% With bromine In acetic acid for 2 h; Example 3
3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (intermediate VII-1) preparation.
10 g 3-ethoxy-4-hydroxybenzaldehyde dissolved in 30 ml of acetate, adding dropwisely into the system 3.08 ml of liquid bromine, reaction fluid gradually changed into yellow, after 2 hours the reaction was stopped. Filtering, the filter cake was washed with a small amount of acetic acid to give 7.247 g yellowish colored solid (Intermediate VII-1), a yield of 49percent.
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 21, p. 4744 - 4755
[2] Patent: CN103787902, 2016, B, . Location in patent: Paragraph 0033-0035
[3] Patent: CN103896965, 2016, B, . Location in patent: Paragraph 0066; 0067; 0068; 0069
[4] Journal of Organic Chemistry, 1958, vol. 23, p. 120
[5] Archiv der Pharmazie, 2015, vol. 348, # 7, p. 463 - 474
  • 5
  • [ 121-32-4 ]
  • [ 5292-43-3 ]
  • [ 51264-76-7 ]
Reference: [1] Patent: US5523302, 1996, A,
  • 6
  • [ 121-32-4 ]
  • [ 79-11-8 ]
  • [ 51264-76-7 ]
Reference: [1] Archiv der Pharmazie, 2015, vol. 348, # 6, p. 421 - 432
  • 7
  • [ 121-32-4 ]
  • [ 75-36-5 ]
  • [ 72207-94-4 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0℃; for 0.5 h; Example 8 N- [ 1 -Cyano-2-(7-ethoxy- 1 -hydroxy- 1.3 -dihydro-benzo [c] [ 1.2]oxaborol-6-yloxy )- 1 -meth yl-ethyl -4-trifluoromethoxy-benzamide To a solution of 3-ethoxy-4-hydroxy-benzaldehyde (50.0 g, 0.30 mol) and Et3N (39.2 g, 54 mL, 0.39 mol) in DCM (500 mL) at 0 °C is added CH3COCl (30.6 g, 28 mL, 0.39 mol) at 0°C. After the addition is complete, the reaction mixture is stirred at 0°C for 30 min. Then the filter cake washed with DCM, and the combined filtrate is washed with water and brine, the organic layer is dried over Na2S04 and evaporated to give the desired product (62.0 g, 100percent yield) as a yellow solid.
Reference: [1] Patent: WO2014/149793, 2014, A1, . Location in patent: Page/Page column 57
[2] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1637 - 1646
[3] Russian Journal of General Chemistry, 2005, vol. 75, # 10, p. 1562 - 1565
[4] Russian Journal of Applied Chemistry, 2005, vol. 78, # 1, p. 120 - 124
  • 8
  • [ 121-32-4 ]
  • [ 108-24-7 ]
  • [ 72207-94-4 ]
Reference: [1] Journal of the Chemical Society, 1939, p. 1159[2] Journal of the Chemical Society, 1948, p. 265
[3] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 3, p. 521 - 529
  • 9
  • [ 121-32-4 ]
  • [ 100-39-0 ]
  • [ 60186-33-6 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In N,N-dimethyl-formamide at 20 - 40℃; for 2 h; To a solution of3-ethoxy-4-hydroxy-benzaldehyde (830 mg, 5 mmol) in N'N-dimethylforrnemide (5 mL)was gradually added K2CO3 (20 mg) and then PmBr (6 mmol) was added ata temperature under 40 °C. The mixture was stirred at room temperature for 2 h.The solution was poured into ice-cold water (10 mL) and extracted with diethylether. The organic phase was washed with water and sodium hydroxide and then itwas dried and evaporated to obtain 18 (1.1g, 85percent). Compound 18 was reacted with sophoridine using same proceduredescribed in synthesis of 11−16 to obtain 14-(4-(benzyloxy)-3-ethoxyphenylmethylene)sophoridine (20) (120 mg, 30percent)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1495 - 1497
[2] Patent: EP1577290, 2005, A1, . Location in patent: Page/Page column 95
[3] Patent: EP1640360, 2006, A1, . Location in patent: Page/Page column 59
  • 10
  • [ 121-32-4 ]
  • [ 100-44-7 ]
  • [ 60186-33-6 ]
Reference: [1] Farmaco, Edizione Scientifica, 1958, vol. 14, p. 81,87
[2] Patent: WO2007/10085, 2007, A2, . Location in patent: Page/Page column 28-29
  • 11
  • [ 121-32-4 ]
  • [ 79-30-1 ]
  • [ 188417-26-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1637 - 1646
[2] Russian Journal of General Chemistry, 2005, vol. 75, # 10, p. 1562 - 1565
[3] Russian Journal of Applied Chemistry, 2005, vol. 78, # 1, p. 120 - 124
  • 12
  • [ 121-32-4 ]
  • [ 178686-24-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 1969 - 1989
[2] Patent: US2008/300270, 2008, A1, . Location in patent: Page/Page column 25
[3] Patent: WO2006/117370, 2006, A1, . Location in patent: Page/Page column 41
  • 13
  • [ 121-32-4 ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
Reference: [1] Patent: WO2017/179065, 2017, A1,
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