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[ CAS No. 16357-40-7 ] {[proInfo.proName]}

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Chemical Structure| 16357-40-7
Chemical Structure| 16357-40-7
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Product Details of [ 16357-40-7 ]

CAS No. :16357-40-7 MDL No. :MFCD00532680
Formula : C9H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :FPBXWXGOFQSROI-UHFFFAOYSA-N
M.W : 180.16 Pubchem ID :9179245
Synonyms :

Calculated chemistry of [ 16357-40-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.62
TPSA : 74.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 1.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.26
Solubility : 0.984 mg/ml ; 0.00546 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.215 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.53
Solubility : 5.3 mg/ml ; 0.0294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 16357-40-7 ]

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 [ 16357-40-7 ]

* 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 [ 16357-40-7 ]
  • Downstream synthetic route of [ 16357-40-7 ]

[ 16357-40-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 2345-34-8 ]
  • [ 16357-40-7 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: at 155 - 160℃; for 5 h;
Stage #2: With hydrogenchloride In water
4-Acetoxy-benzoic acid (0.350 g, 1.95 mmol) and anhydrous AlCl3 (0.800 g, 6.02 mmol) were mixed and heated at 155-160 °C (oil bath temperature) for 5 h (after 1 h a solid, brown foamy mass formed and stirring was no longer possible). After cooling (ice bath), the reaction mixture was treated with 6.5 mL of 2 N HCl. The acidified reaction mixture was extracted with ethyl acetate (3.x.10 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford a yellow solid (0.280 g, 80percent), which was used without any further purification.
Reference: [1] Tetrahedron, 2011, vol. 67, # 34, p. 6300 - 6307
[2] Journal of the Indian Chemical Society, 1949, vol. 26, p. 235,237
[3] Journal of the Indian Chemical Society, 1993, vol. 70, # 1, p. 65 - 66
[4] Journal of the Indian Chemical Society, 1984, vol. 61, p. 651
[5] Synlett, 2005, # 20, p. 3131 - 3135
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 9, p. 4954 - 4962
[7] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062
[8] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73
  • 2
  • [ 13031-45-3 ]
  • [ 16357-40-7 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: at 150℃; for 1.5 h;
Stage #2: With hydrogenchloride In water at 0℃; for 0.0833333 h;
Stage #3: for 0.75 h; Heating / reflux
3-Acetyl-4-hvdroxy-benzoic acid: Mg(CIO4J2 (0.602 mmol, 0.134g, 2 molpercent) was added to a solution of ethyl 4-hydroxybenzoate (30.1 mmol, 5g) in Ac2O (45.15 mmol, 4.25 ml) and the mixture was stirred overnight. This was diluted with DCM then washed with water. The organics were dried (MgSO4) and the solvent evaporated to give a clear oil. This was azeotroped twice with toluene to give the product as a clear oil (5.73g, 92percent). This was mixed with AICI3 (82.5 mmol, 10.99g, 3 eq.) and KCI (28.9 mmol, 2.15g, 1.05 eq.) and heated to 15O0C for 1.5 hours during which time a dark foam was formed. This was cooled in an ice bath and ice cold 2MHCI (aq) (100 ml) was added. The solution was stirred for 5 minutes then ethanol (20 ml) was added. This was heated at reflux for 45 minutes then cooled in an ice bath. The solid formed was collected by filtration then purified by recrystallisation from THF/EtOH to give the product as a cream solid (1.3Og, 26percent).
26%
Stage #1: at 150℃; for 1.5 h;
Stage #2: at 0℃; for 0.0833333 h;
Stage #3: for 0.75 h; Heating / reflux
4.3 3-Acetyl-4-hydroxy-benzoic acid; Mg(CIO4)2 (0.602 mmol, 0.134 g, 2 molpercent) was added to a solution of ethyl 4-hydroxybenzoate (30.1 mmol, 5 g) in Ac2O (45.15 mmol, 4.25 ml) and the mixture was stirred overnight. This was diluted with DCM then washed with water. The organics were dried (MgSO4) and the solvent evaporated to give a clear oil. This was azeotroped twice with toluene to give the product as a clear oil (5.73 g, 92percent). This was mixed with AICI3 (82.5 mmol, 10.99 g, 3 eq.) and KCI (28.9 mmol, 2.15 g, 1.05 eq.) and heated to 15O0C for 1.5 hours during which time a dark foam was formed. This was cooled in an ice bath and ice cold 2MHCI (aq) (100 ml) was added. The solution was stirred for 5 minutes then ethanol (20 ml) was added. This was heated at reflux for <n="40"/>45 minutes then cooled in an ice bath. The solid formed was collected by filtration then purified by recrystallisation from THF/EtOH to give the product as a cream solid (1.30 g, 26percent).
Reference: [1] Patent: WO2006/64286, 2006, A1, . Location in patent: Page/Page column 93
[2] Patent: WO2007/144379, 2007, A1, . Location in patent: Page/Page column 38-39
[3] Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 335 - 338
  • 3
  • [ 24262-66-6 ]
  • [ 16357-40-7 ]
YieldReaction ConditionsOperation in experiment
11.5 g at 140℃; for 5 h; Methyl 4-acetylbenzoate (1002-95) (14 g, 66 mmol, 1.0 equiv)After grinding into powder, aluminum trichloride (26.3 g, 198 mmol, 3.0 equivalents) was added.Stir at 140°C for 5 hoursAfter the reaction was completed, a dark brown coagulated solid was cooled to room temperature.Crushed with a spoon and added to 300 ml of an aqueous solution. The mixture was heated to reflux for 3 hours. The reaction solution was made into a clear solution, cooled to room temperature, and concentrated hydrochloric acid was added dropwise to pH 1. A large amount of white solid was precipitated and filtered.Drying gave white solid 3-acetyl-4-hydroxybenzoic acid (11.5 g, 96.8percent overall yield over two steps).
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 3037 - 3058
[2] Archiv der Pharmazie (Weinheim, Germany), 1942, vol. 280, p. 76,82
[3] Patent: US4259340, 1981, A,
[4] Patent: WO2004/80979, 2004, A1, . Location in patent: Page 22, 35, 36
[5] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 1, p. 70 - 77
[6] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0269
  • 4
  • [ 75-36-5 ]
  • [ 99-96-7 ]
  • [ 16357-40-7 ]
Reference: [1] Canadian Journal of Chemistry, 2011, vol. 89, # 3, p. 364 - 384
[2] Tetrahedron Letters, 1998, vol. 39, # 45, p. 8207 - 8210
[3] Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14285 - 14291
  • 5
  • [ 2345-34-8 ]
  • [ 75-36-5 ]
  • [ 16357-40-7 ]
Reference: [1] Patent: US6191164, 2001, B1,
  • 6
  • [ 102297-90-5 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1985, # 12, p. 3830 - 3860
  • 7
  • [ 167897-90-7 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 692
  • 8
  • [ 57009-12-8 ]
  • [ 16357-40-7 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1942, vol. 280, p. 76,82
  • 9
  • [ 99854-67-8 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 692
  • 10
  • [ 120-47-8 ]
  • [ 75-36-5 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of the Indian Chemical Society, 1955, vol. 32, p. 117
  • 11
  • [ 167897-90-7 ]
  • [ 10034-85-2 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 690
  • 12
  • [ 99854-67-8 ]
  • [ 10034-85-2 ]
  • [ 16357-40-7 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 690
  • 13
  • [ 67-56-1 ]
  • [ 16357-40-7 ]
  • [ 57009-12-8 ]
YieldReaction ConditionsOperation in experiment
65% for 1 h; Reflux Concentrated H2SO4 (5 drops) was added to a suspension of 3-acetyl-4-hydroxybenzoic acid 2 (0.250 g, 1.38 mmol) in 12 mL of MeOH at room temperature. The resulting reaction mixture was heated at reflux for 1 h, then it was cooled to room temperature and neutralized using 2 N NaOH. The mixture was allowed to stand for 15 min, before being poured onto an iced H2O beaker and made up to 42 mL with H2O. The white precipitate was filtered and dried. The crude product was purified by flash column chromatography (ethyl acetate/hexane 13:87) to give the title compound as a white crystalline solid (0.175 g, 65percent). Mp 101-102 °C; [Found: C, 61.80; H, 5.21. C10H10O4 requires C, 61.85; H, 5.19]; Rf 0.62 (ethyl acetate/hexane 35:65); 1H NMR (300 MHz, CDCl3) δ: 12.65 (s, 1H), 8.48 (d, J 1.7 Hz, 1H), 8.21 (dd, J 1.7, 8.6 Hz, 1H), 7.01 (d, J 8.6 Hz, 1H), 3.90 (s, 3H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) δ: 204.3, 165.7 (.x.2), 136.9, 133.0, 120.8, 118.9, 118.4, 51.9, 26.5.
Reference: [1] Tetrahedron, 2011, vol. 67, # 34, p. 6300 - 6307
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 3037 - 3058
[3] Journal of the Indian Chemical Society, 1959, vol. 36, p. 659,665
[4] Patent: WO2004/80979, 2004, A1, . Location in patent: Page 36, 37
[5] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 1, p. 70 - 77
[6] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0270
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