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[ CAS No. 91367-05-4 ] {[proInfo.proName]}

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Chemical Structure| 91367-05-4
Chemical Structure| 91367-05-4
Structure of 91367-05-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 91367-05-4 ]

CAS No. :91367-05-4 MDL No. :MFCD00151838
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QOTGNXMPQNGYDM-UHFFFAOYSA-N
M.W :184.62 Pubchem ID :7015786
Synonyms :

Calculated chemistry of [ 91367-05-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.7
TPSA : 26.3 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) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.107 mg/ml ; 0.000577 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.0695 mg/ml ; 0.000377 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0616 mg/ml ; 0.000333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 91367-05-4 ]

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 [ 91367-05-4 ]

* 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 [ 91367-05-4 ]
  • Downstream synthetic route of [ 91367-05-4 ]

[ 91367-05-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 91367-05-4 ]
  • [ 872091-83-3 ]
Reference: [1] Patent: WO2014/144737, 2014, A1,
  • 2
  • [ 7697-29-2 ]
  • [ 74-88-4 ]
  • [ 91367-05-4 ]
YieldReaction ConditionsOperation in experiment
93% With caesium carbonate In N,N-dimethyl-formamide at 20 - 23℃; EXAMPLES Preparation 1Methyl 4-chloro-3-methylbenzoateTo a solution of 4~chloro-3-methylbenzoic acid (25 g) in DMF (550 ml) under a dry atmosphere was added portion wise 50 g of caesium carbonate and then slowly, 10,95 ml of methyl iodide. Temperature rose from 200C to 23 0C. The reaction mixture was stirred at room temperature overnight. The mixture was cooled to 10 0C and then 800 ml of an aqueous solution of NaHCO3 (2percent) and 600 ml of ethyl acetate were successively added. The aqueous layer was separated, extracted again with 400 ml of ethyl acetate. The .bul. combined organic layers were washed successively with 2x250 ml of an aqueous solution of NaHCO3 (2percent), then 2x250 ml of aqueous solution of NaCl (2percent), dried over Na2SO4 and concentrated in vacuum. The residue was purified by distillation to afford 25.31 g of a clear yellow liquid (b.p.: 78 °C/0.08 mbar). Yield: 93percentT.L.C.: Silica gel, eluents: cyclohexane-ethyl acetate 75/25
Reference: [1] Patent: WO2006/79857, 2006, A1, . Location in patent: Page/Page column 6
[2] Patent: US2010/69384, 2010, A1, . Location in patent: Page/Page column 9-10
  • 3
  • [ 67-56-1 ]
  • [ 7697-29-2 ]
  • [ 91367-05-4 ]
YieldReaction ConditionsOperation in experiment
90.1% for 8 h; Reflux 4-chloro-3-methyl benzoic acid 5.2 g (0.03 mol), CH3OH 40 mLand H2SO4 1 mL were refluxed for 8 h. After completion of the reaction as indicated by TLC. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate 100 mL. Then the liquid was washed with saturated Na2CO3, waterand saturated NaCl successively. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was dried to afford X13 5.1 g (90.1 percent), mp: 76-78 °C.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 170 - 183
  • 4
  • [ 18595-14-7 ]
  • [ 91367-05-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
  • 5
  • [ 91367-05-4 ]
  • [ 1044920-98-0 ]
YieldReaction ConditionsOperation in experiment
68.2%
Stage #1: at 0℃; for 3.5 h;
Stage #2: for 0.5 h; Reflux
17.0 mL glacial acetic acid, 16.5 mL acetic anhydride and 2.5 mL H2SO4 were cooled in ice bath. Then X13 1.84 g (0.01 mol) and Cr2O3 3 g (0.03 mol) were added in small portion. The mixture was reacted in ice bath for 3 h. The reaction solution was poured into 200.0 mL ice water and stirred vigorously for 30 min. The resulting precipitates were collected by filtration and washed with water (70.0 mL x 3) to afford gray solid which was added into 50.0 mL eggplant flask. 16.0 mL CH3OH, 16.0 mL water and 0.4 mL H2SO4 were added to and refluxed for 30 min. The residue was added into water,and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate extracts were washed with water (80 mL) and brine (80 mL) respectively, and then dried with anhydrous Na2SO4. When the solvent was evaporated, the yield of yellow solid compound X14 was 1.35 g (68.2 percent). mp: 131-133 °C. 1H NMR (300 MHz, DMSO-d6): δ 3.90 (s, 3H, OCH3), 7.79 (d, 1H, Ar-H, J = 8.4 Hz), 8.18 (d, 1H, Ar-H, J = 8.4 Hz), 8.35 (s, 1H, Ar-H), 10.34 (s, 1H, CHO). IR (KBr): 3425, 3082, 3003, 2953, 1726, 1720, 1689, 1188, 983, 759 cm-1. MS [M+H]+: 199.1.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 170 - 183
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 10188 - 10204
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