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[ CAS No. 3438-16-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3438-16-2
Chemical Structure| 3438-16-2
Chemical Structure| 3438-16-2
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Product Details of [ 3438-16-2 ]

CAS No. :3438-16-2 MDL No. :MFCD00017546
Formula : C8H7ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HULDRQRKKXRXBI-UHFFFAOYSA-N
M.W : 186.59 Pubchem ID :76970
Synonyms :

Calculated chemistry of [ 3438-16-2 ]

Physicochemical Properties

Num. heavy atoms : 12
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 : 44.9
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) : 1.57
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.846 mg/ml ; 0.00453 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.825 mg/ml ; 0.00442 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.569 mg/ml ; 0.00305 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 3438-16-2 ]

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 [ 3438-16-2 ]

* 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 [ 3438-16-2 ]
  • Downstream synthetic route of [ 3438-16-2 ]

[ 3438-16-2 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 33924-48-0 ]
  • [ 3438-16-2 ]
YieldReaction ConditionsOperation in experiment
74.9% With water; sodium hydroxide In ethanol at 15 - 30℃; for 4 h; To a solution of Methyl 5-chloro-2- methoxybenzoate (2.0g, 0.01 mol) [Alfa Aesar] in ethanol (60 mL) was added in one portion 1M aqueous sodium hydroxide (60 mL, 0,06 mol) and the mixture was stirred at ambient temperature for 4 hr. Thin layer chromatography indicated that the reaction was complete. Concentrated the mixture in vacuo to remove the ethanol and extracted the aqueous residue with ethyl acetate. Chilled the aqueous phase in an ice bath and adjusted the pH to 2 with concentrated aqueous hydrogen chloride. After stirring in an ice bath for 1 hr., the resulting solid was filtered, washed with water and air dried to give 1.4g (74.9percent) of 3-chloro- 2-methoxy benzoic acid as a white solid MS: m/z 185.1 (MH~). 1H NMR (500 MHz, DMSO-d6): δ 3.818 (s, 3H), 7.162 (d, 1H), 7.551 (dd,lH)5 7.607 (d, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 21, p. 6819 - 6829
[2] Patent: WO2014/165816, 2014, A1, . Location in patent: Page/Page column 98-99
[3] Journal of the American Chemical Society, 1988, vol. 110, p. 7178
[4] Patent: US4895860, 1990, A,
  • 2
  • [ 321-14-2 ]
  • [ 77-78-1 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 1759,1762
[2] Patent: CN105461549, 2016, A, . Location in patent: Paragraph 0012; 0013
[3] Patent: CN106699717, 2017, A, . Location in patent: Paragraph 0032-0034
[4] RSC Advances, 2017, vol. 7, # 61, p. 38171 - 38178
  • 3
  • [ 55877-79-7 ]
  • [ 3438-16-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1929, vol. <2> 120, p. 211,212
[2] Tetrahedron, 2016, vol. 72, # 17, p. 2072 - 2083
  • 4
  • [ 201230-82-2 ]
  • [ 553-82-2 ]
  • [ 3438-16-2 ]
YieldReaction ConditionsOperation in experiment
270 mg
Stage #1: With potassium carbonate In methanol at 20℃; for 0.333333 h;
Stage #2: With dicobalt octacarbonyl In methanol for 0.0833333 h;
General procedure: K2CO3 (2.5 g, 18 mmol), methanol (10 mL), and appropriate amount of substrate (see below) were placed in a jacketed glass reactor. The intensively stirred mixture was subjected to flow of carbon monoxide, preliminary passed through methanol, at room temperature for 20 min followed by thei nsertion of 2()8 (0.050 g, 0.15 mmol) under CO atmosphere. The orange colour of the mixture disappeared after 5 min. The reaction mixture was heated to 62 °C, and methyl oxirane (0.35 g, 6 mmol) was added by a syringe. The conversion was controlled by measurement of the absorbed carbon monoxide volume. After reaching of the desired conversion (see below) the reaction mixture was cooled to room temperature and an excess of thionyl chloride (about 0.6 g, 5 mmol) was carefully added into the reaction mixture to pH < 2. The mixture was kept at room temperature for 24 h. A small sample was taken, dissolved with DCM and H2O, and the organic layer was analysed by GC to check the conversion. Then the solvent and excess of thionyl chloride were removed from the reaction mixture under reduced pressure. The rest was dissolved with DCM and H2O, the organic layer was divided, washed with brine, and dried with Na2SO4. The solvent was removed under reduced pressure, the resulting mixture was analysed by TLC and 1H-NMR methods, and then the methoxycarbonylation products were isolated by column chromatography (eluent—ethyl acetate-hexane, 1:5). The regioselectivity of methoxycarbonylation for compounds 2, 3, 5, 8, 9 and 11 has been reported by us previously [36,38].
Reference: [1] Molecules, 2014, vol. 19, # 5, p. 5876 - 5897
  • 5
  • [ 623-12-1 ]
  • [ 124-38-9 ]
  • [ 3438-16-2 ]
Reference: [1] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 1010 - 1016
  • 6
  • [ 321-14-2 ]
  • [ 74-88-4 ]
  • [ 3438-16-2 ]
Reference: [1] Patent: US4474792, 1984, A,
  • 7
  • [ 623-12-1 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of the American Chemical Society, 1941, vol. 63, p. 545,548
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 2327,2333
[3] Journal of the American Chemical Society, 1941, vol. 63, p. 545,548
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 2327,2333
[5] Journal of Organic Chemistry, 1959, vol. 24, p. 1759,1762
  • 8
  • [ 60633-25-2 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 830
  • 9
  • [ 63213-94-5 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 1759,1762
  • 10
  • [ 6342-64-9 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020
  • 11
  • [ 1450-74-4 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020
  • 12
  • [ 3260-85-3 ]
  • [ 3438-16-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1898, vol. 28 I, p. 211
  • 13
  • [ 579-75-9 ]
  • [ 3438-16-2 ]
Reference: [1] Proceedings - Indian Academy of Sciences, Section A, 1938, vol. &lt;A&gt; 8, p. 208,212, 213
  • 14
  • [ 1570-64-5 ]
  • [ 3438-16-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1898, vol. 28 I, p. 211
  • 15
  • [ 95-48-7 ]
  • [ 3438-16-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1898, vol. 28 I, p. 211
  • 16
  • [ 110175-20-7 ]
  • [ 3438-16-2 ]
Reference: [1] Acta Chemica Scandinavica, 1996, vol. 50, # 10, p. 885 - 898
  • 17
  • [ 623-12-1 ]
  • [ 917-54-4 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of the American Chemical Society, 1941, vol. 63, p. 545,548
  • 18
  • [ 109-72-8 ]
  • [ 60-29-7 ]
  • [ 623-12-1 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2327,2333
  • 19
  • [ 60-29-7 ]
  • [ 623-12-1 ]
  • [ 917-54-4 ]
  • [ 3438-16-2 ]
Reference: [1] Journal of the American Chemical Society, 1941, vol. 63, p. 545,548
  • 20
  • [ 3438-16-2 ]
  • [ 10238-21-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[2] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5545 - 5549[4] Angew. Chem., 2016, vol. 128, # 18, p. 5635 - 5639,5
[5] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11788 - 11801
  • 21
  • [ 3438-16-2 ]
  • [ 60633-25-2 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 15, p. 3860 - 3865
  • 22
  • [ 3438-16-2 ]
  • [ 52807-27-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536
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