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Chemical Structure| 63012-03-3
Chemical Structure| 63012-03-3
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Product Details of [ 63012-03-3 ]

CAS No. :63012-03-3 MDL No. :MFCD06201252
Formula : C13H11ClO Boiling Point : -
Linear Structure Formula :- InChI Key :DDCJHFYXAPQYLA-UHFFFAOYSA-N
M.W : 218.68 Pubchem ID :569907
Synonyms :

Calculated chemistry of [ 63012-03-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.07
TPSA : 20.23 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) : -4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 3.1
Log Po/w (MLOGP) : 3.61
Log Po/w (SILICOS-IT) : 3.71
Consensus Log Po/w : 3.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.02
Solubility : 0.0207 mg/ml ; 0.0000945 mol/l
Class : Moderately soluble
Log S (Ali) : -3.88
Solubility : 0.029 mg/ml ; 0.000133 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00213 mg/ml ; 0.00000975 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.16

Safety of [ 63012-03-3 ]

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 [ 63012-03-3 ]

* 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 [ 63012-03-3 ]
  • Downstream synthetic route of [ 63012-03-3 ]

[ 63012-03-3 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1016-78-0 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
94.4% With sodium tetrahydroborate In tetrahydrofuran; ethanol at 20℃; for 3 h; (1)
(3-Chlorophenyl)(phenyl)methanol
To a solution of 3-chlorobenzophenone (10.0 g, 46.2 mmol) in ethanol (100 ML) and THF (100 ML) was added sodium borohydride (876 mg, 23.1 mmol), the mixture was stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure..
The residue was poured into water, and was extracted with ethyl acetate..
The extracted solution was washed with water, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain the titled compound as oil. 9.53 g (94.4percent) 1H-NMR (CDCl3) δ; 2.55 (1H, d, J = 3.6 Hz), 5.80 (1H, d, J = 3.6 Hz), 7.25 to 7.40 (9H, m)
Reference: [1] Organic Letters, 2000, vol. 2, # 5, p. 659 - 661
[2] Patent: EP1437344, 2004, A1, . Location in patent: Page 48
[3] Recueil des Travaux Chimiques des Pays-Bas, 1912, vol. 31, p. 311
[4] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 162
[5] Recueil des Travaux Chimiques des Pays-Bas, 1919, vol. 38, p. 121
[6] Journal of the Chemical Society, 1940, p. 1011,1014
[7] Journal of the American Chemical Society, 1955, vol. 77, p. 4007,4008
[8] Journal of Organic Chemistry, 1967, vol. 32, p. 2692 - 2695
[9] Tetrahedron: Asymmetry, 1991, vol. 2, # 5, p. 339 - 342
[10] Bulletin de la Societe Chimique de France, 1994, vol. 131, # 6, p. 632 - 635
[11] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 3, p. 311 - 314
[12] Journal of Medicinal Chemistry, 1997, vol. 40, # 6, p. 851 - 857
[13] Journal of Physical Organic Chemistry, 1998, vol. 11, # 3, p. 223 - 229
[14] Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656
[15] Archiv der Pharmazie, 2011, vol. 344, # 6, p. 402 - 410
[16] Tetrahedron, 2019, vol. 75, # 2, p. 308 - 314
  • 2
  • [ 587-04-2 ]
  • [ 98-80-6 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
75% With bis(acetylacetonate)nickel(II); potassium carbonate In toluene at 180℃; for 0.166667 h; Microwave irradiation Aldehyde (1.0 mmol), arylboronic acid (1.5 mmol, 1.5 equiv), K2CO3 (138 mg, 1.0 mmol, 1 equiv), and Ni(acac)2 (2.6 mg, 0.01 mmol, 1 mol percent) were added to a 10 mL microwave processing vial containing a Teflon coated stir bar. After the vial was sealed dry toluene (2 mL) was transferred to the vial and mixture was pre-stirred for 5 min. The vial was placed in the microwave cavity and heated for 10 min at 180 °C (fixed hold time). After cooling, diethyl ether or ethyl acetate (10 mL) was added and the crude reaction mixture was subsequently washed with 25percent aqueous NH3 (2 .x. 10 mL). The aqueous ammonium layer was reextracted again with diethyl ether or ethyl acetate (2 .x. 10 mL). The combined organic phase was dried over MgSO4 and the residue after evaporation purified by flash chromatography using a petroleum ether/ethylacetate (10:1-2.5:1) as eluent phase.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 14, p. 1677 - 1679
  • 3
  • [ 108-86-1 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With iodine; magnesium In diethyl ether at 0℃; for 0.166667 h;
Stage #2: for 12 h;
General procedure: A 50 mL round-bottom flask was charged with bromobenzene (157 mg, 1 mmol), anhydrous Et2O (10 mL), magnesium powder (24 mg, 1 mmol) and a little iodine added. The mixture was cooled to 0 °C and stirred for 10 min, then a solution of 3-methoxybenzaldehyde (136 mg, 1 mmol) and anhydrous Et2O was added slowly. The solution was stirred for 12 h after the temperature rose to room temperature; 5 mL NH4Cl aqueous solution was dropped slowly, and the mixture extracted with Et2O (3×30 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was isolated by flash column chromatography on silica gel to give the products.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1747 - 1750
[2] Patent: US5719168, 1998, A,
  • 4
  • [ 3262-89-3 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 6, p. 924 - 927
  • 5
  • [ 4405-42-9 ]
  • [ 100-52-7 ]
  • [ 63012-03-3 ]
Reference: [1] Angewandte Chemie, 1981, vol. 93, # 3, p. 287 - 288
[2] Chemische Berichte, 1985, vol. 118, # 9, p. 3872 - 3899
  • 6
  • [ 1623-99-0 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
0.160 mol, 91.0% With hydrogenchloride; sodium In chlorobenzene; toluene Example 2
(Preparation of 3-chlorobenzhydrol)
To phenylsodium, prepared from 9.2 g (0.400 mol) of a sodium dispersion and 22.0 g (0.196 mol) of chlorobenzene in 200 g of toluene, was added, dropwise, a solution of 24.8 g (0.176 mol) of 3-chlorobenzaldehyde in toluene (24 g), with the temperature kept at 0 °C to 3 °C.
After stirring at that temperature for 1 hour, hydrolysis with 100 ml of 20percent-diluted hydrochloric acid was carried out, and the obtained organic layer was separated and washed with water three times.
After the solvent was concentrated, the remained pale orange oil was distilled under reduced pressure, to give 34.9 g (0.160 mol, 91.0percent) of the intended product (b.p.: 147.0 to 148.0 °C/2 mmHg).
Reference: [1] Patent: EP801048, 1997, A1,
  • 7
  • [ 618-46-2 ]
  • [ 63012-03-3 ]
Reference: [1] Journal of Organic Chemistry, 1967, vol. 32, p. 2692 - 2695
  • 8
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656
  • 9
  • [ 587-04-2 ]
  • [ 100-58-3 ]
  • [ 63012-03-3 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 12, p. 1973 - 1978
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383
[3] Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545
  • 10
  • [ 156543-39-4 ]
  • [ 63012-03-3 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 38, p. 6919 - 6922
  • 11
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1925, vol. 56, p. 150[2] Chem. Zentralbl., 1926, vol. 97, # I, p. 919
  • 12
  • [ 13391-39-4 ]
  • [ 63012-03-3 ]
  • [ 27798-38-5 ]
Reference: [1] Journal of the Chinese Chemical Society, 1997, vol. 44, # 3, p. 249 - 252
  • 13
  • [ 861532-09-4 ]
  • [ 103-73-1 ]
  • [ 1016-78-0 ]
  • [ 63012-03-3 ]
Reference: [1] Diss. <Univ. Berlin 1933> S. 31, 35,
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