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Product Details of [ 19438-10-9 ]

CAS No. :19438-10-9 MDL No. :MFCD00002295
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :YKUCHDXIBAQWSF-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :88068
Synonyms :
Chemical Name :Methyl 3-Hydroxybenzoate

Calculated chemistry of [ 19438-10-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.74
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) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.18
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.21
Consensus Log Po/w : 1.45

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 : 0.864 mg/ml ; 0.00568 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.493 mg/ml ; 0.00324 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.88
Solubility : 2.0 mg/ml ; 0.0132 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 19438-10-9 ]

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 [ 19438-10-9 ]

* 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 [ 19438-10-9 ]
  • Downstream synthetic route of [ 19438-10-9 ]

[ 19438-10-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 19438-10-9 ]
  • [ 618-49-5 ]
YieldReaction ConditionsOperation in experiment
10% With ammonia In methanol at 50℃; for 16 h; Sealed tube . Example 25 Synthesis of 3-hydroxybenzamideTo a reactor was charged methyl 3-hydroxybenzoate (160 mg) and 7N ammonia in methanol (4 ml). The reactor was then sealed, heated to 50 °C, and stirred for 16 hours. The reaction mixture was cooled to ambient temperature then reduced by rotary evaporation to yield an oil. This was purified by flashchromatography, eluting with n-hexane and ethyl acetate. Appropriate fractions were collected for the product peak and were reduced by rotary evaporation to obtain the desired product as yellow oil (15 mg, 10percent). The structure was confirmed as 3-hydroxybenzamide by 1H NMR.
Reference: [1] Patent: WO2016/114668, 2016, A1, . Location in patent: Page/Page column 37
[2] Biochemical Journal, 1948, vol. 43, p. 561,562
  • 2
  • [ 19438-10-9 ]
  • [ 1700-37-4 ]
Reference: [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250
  • 3
  • [ 19438-10-9 ]
  • [ 873-62-1 ]
Reference: [1] Synthesis, 1998, # 3, p. 329 - 332
  • 4
  • [ 19438-10-9 ]
  • [ 106291-80-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1596 - 1609
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277
  • 5
  • [ 19438-10-9 ]
  • [ 106291-80-9 ]
  • [ 154607-00-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6451 - 6457
  • 6
  • [ 19438-10-9 ]
  • [ 17100-63-9 ]
Reference: [1] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277
  • 7
  • [ 19438-10-9 ]
  • [ 676-58-4 ]
  • [ 7765-97-1 ]
YieldReaction ConditionsOperation in experiment
72.5% at 20℃; for 2 h; Inert atmosphere Step 1: Synthesis of INT-04 INT-04 To a 1 M solution of methyl magnesium chloride in THF (30 mL, 30.6 mmol) at RT was added a solution of methyl 3-hydroxybenzoate (2.0 g, 13.3 mmol) in THF (10 mL) drop-wise at RT under argon atmosphere. After 2 h the reaction mixture was quenched with a saturated solution of ammonium chloride and extracted with EtOAc (2 x 15 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography to yield 3- (2-hydroxypropan-2-yl)phenol (INT-04) as a liquid (1 .45 g, 72.5percent yield); TLC =20percent EtOAc/hexanes (0.5 Rf).
72.5% With ammonium chloride In tetrahydrofuran at 20℃; for 2 h; Inert atmosphere Step 1:
Synthesis of INT-04
To a 1M solution of methyl magnesium chloride in THF (30 mL, 30.6 mmol) at RT was added a solution of methyl 3-hydroxybenzoate (2.0 g, 13.3 mmol) in THF (10 mL) drop-wise at RT under argon atmosphere.
After 2 h the reaction mixture was quenched with a saturated solution of ammonium chloride and extracted with EtOAc (2*15 mL).
The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated.
The residue was purified by column chromatography to yield 3-(2-hydroxypropan-2-yl)phenol (INT-04) as a liquid (1.45 g, 72.5percent yield); TLC=20percent EtOAc/hexanes (0.5 Rf).
Reference: [1] Patent: WO2015/106164, 2015, A1, . Location in patent: Page/Page column 65
[2] Patent: US2017/66791, 2017, A1, . Location in patent: Paragraph 0348; 0349
  • 8
  • [ 100-97-0 ]
  • [ 19438-10-9 ]
  • [ 24589-98-8 ]
  • [ 131524-43-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 10, p. 2170 - 2173
[2] Patent: EP1489078, 2004, A1, . Location in patent: Page 195
[3] Patent: EP1666478, 2006, A1, . Location in patent: Page/Page column 90
[4] Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17408 - 17416
  • 9
  • [ 19438-10-9 ]
  • [ 89942-77-8 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 26, p. 10208 - 10212
  • 10
  • [ 19438-10-9 ]
  • [ 17672-21-8 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 26, p. 10208 - 10212
  • 11
  • [ 19438-10-9 ]
  • [ 247092-10-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
  • 12
  • [ 19438-10-9 ]
  • [ 247092-10-0 ]
  • [ 166272-81-7 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
  • 13
  • [ 19438-10-9 ]
  • [ 123656-35-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 310 - 319
  • 14
  • [ 19438-10-9 ]
  • [ 74597-04-9 ]
Reference: [1] Patent: WO2016/114668, 2016, A1,
  • 15
  • [ 19438-10-9 ]
  • [ 148438-00-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 2, p. 471 - 484
[2] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 2, p. 471 - 484
  • 16
  • [ 19438-10-9 ]
  • [ 247092-10-0 ]
  • [ 166272-81-7 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
  • 17
  • [ 19438-10-9 ]
  • [ 157942-12-6 ]
YieldReaction ConditionsOperation in experiment
76% With iodine; iodic acid In ethanol; water at 80℃; for 1 h; Inert atmosphere To a stirred solution of benzoate 4a (1.52 g, 10 ramol) in EtOH (4 mL) was added I2 ( 1.02 g, 4 mmol) in one portion. The reaction was heated to reflux before an aqueous solution (2 mL) of HIO3 (352 mg, 2 mmol) was added. The mixture was refluxed for 1 hour before it was cooled to RT. The product was recovered by filtration and washed with water to give compound 4b as a w hite solid. (2.11 g, 76percent yield). 1H NMR (400 MHz, CDCI3) δ 7.75 (d, 7=8.2 Hz, 1H), 7.47 (d, 7=1.9 Hz, 1H), 7.24 (dd, 7=8.2, 1.9 Hz, 1H), 3.88 (s, 3H). 13C NMR (101 MHz, CDC13) δ 167.34, 156.30, 139.41, 131.76, 122.61, 115.64, 91.51, 52.74. MS (ES-): m/z calc. for C8H7C1IC>3:277.9; found: 276.9 [M- H]-.
Reference: [1] Patent: WO2017/130191, 2017, A1, . Location in patent: Paragraph 00133; 00135
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