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[ CAS No. 83-40-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 83-40-9
Chemical Structure| 83-40-9
Chemical Structure| 83-40-9
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Product Details of [ 83-40-9 ]

CAS No. :83-40-9 MDL No. :MFCD00002448
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WHSXTWFYRGOBGO-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :6738
Synonyms :
Hydroxytoluic acid;o-Cresotic acid;3-methyl SA;NSC 50796;NSC 17561;NSC 1772;3-methyl-2-Hydroxybenzoic Acid
Chemical Name :2-Hydroxy-3-methylbenzoic acid

Calculated chemistry of [ 83-40-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.39
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 : No
Log Kp (skin permeation) : -5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.182 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -3.73
Solubility : 0.0285 mg/ml ; 0.000187 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 4.13 mg/ml ; 0.0272 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.05

Safety of [ 83-40-9 ]

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 [ 83-40-9 ]

* 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 [ 83-40-9 ]
  • Downstream synthetic route of [ 83-40-9 ]

[ 83-40-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 83-40-9 ]
  • [ 917-54-4 ]
  • [ 699-91-2 ]
YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; Inert atmosphere Step 46.1: 1-(2-hydroxy-3-methylphenyl)ethanone To a colorless solution of 3-methyl-salicylic acid (1 g, 6.57 mmol) in Et2O (50 mL) under argon and cooled down to 0° C. was added dropwise methyllithium 1.6M in Et2O (12.32 mL, 19.72 mmol) over 20 min. The resulting mixture was stirred at this temperature for 30 min then allowed to warm up and stir overnight at RT. The reaction mixture was slowly poured into a stirred mixture of 100 g of ice and HCl 4N (50 mL) and extracted twice with EtOAc. The combined organic layers were washed with 10percent NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (920 mg, 5.94 mmol, 90percent yield) as a pale yellow oil. tR: 0.91 min (LC-MS 2); ESI-MS: 481/483 [M+H]+, ESI-MS: 479/501 [M−H] (LC-MS 2); Rf=0.55 (hexane/EtOAc 3:1).
90% at 0 - 20℃; Inert atmosphere To a colorless solution of 3-methyl-salicylic acid (1 g, 6.57 mmol) in Et20 (50 mL) under argon and cooled down to 000 was added dropwise methyllithium 1.6M in Et20 (12.32 mL, 19.72mmol) over 20 mm. The resulting mixture was stirred at this temperature for 30 mm then allowed to warm up and stir overnight at RT. The reaction mixture was slowly poured into a stirred mixture of 100 g of ice and HCI 4N (50 mL) and extracted twice with EtOAc. The combined organic layers were washed with 10percent NaHCO3 solution and brine, dried over Mg504, filtered and concentrated under reduced pressure to afford the title product (920 mg, 5.94 mmol, 90percentyield) as a pale yellow oil. tR: 0.91 mm (LC-MS 2); ESl-MS: 481/483 [M+H], ESl-MS: 479/501 [M-H] (LC-MS 2); R = 0.55 (hexane/EtOAc 3:1).
49% at 0 - 20℃; Inert atmosphere To a colorless solution of 3-methyl-salicylic acid (10 g, 65.7 mmol) in Et20 (350 mL) under Ar and cooled down to 0 0 was added dropwise methyllithium 1.6M in Et20 (123 mL, 197 mmol) over 30 mm. The resulting mixture was stirred at this temperature for 30 mm then allowed to warm up and stir overnight at RT. The reaction mixture was poured onto a cold 2N HCI and the product was extracted with EtOAc. Combined extracts were washed with 10 percent NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (5.14 g, 32.5 mmol, 49 percent yield) as a pale yellow oil. tR: 0.99 mm (LC-MS 2); ESI-MS: no ionisation [M+H] (LC-MS 2); TLC (hexane/EtOAc 3:1) Rf = 0.55.
Reference: [1] Patent: US2014/349990, 2014, A1, . Location in patent: Paragraph 0739; 0740
[2] Patent: WO2014/191896, 2014, A1, . Location in patent: Page/Page column 147
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 36, p. 9418 - 9426
[4] Patent: WO2014/191894, 2014, A1, . Location in patent: Page/Page column 104; 105
  • 2
  • [ 83-40-9 ]
  • [ 186312-96-9 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 9, p. 2408 - 2421
  • 3
  • [ 83-40-9 ]
  • [ 1427363-87-8 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 9, p. 2408 - 2421
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