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[ CAS No. 51-44-5 ] {[proInfo.proName]}

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Chemical Structure| 51-44-5
Chemical Structure| 51-44-5
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Product Details of [ 51-44-5 ]

CAS No. :51-44-5 MDL No. :MFCD00002492
Formula : C7H4Cl2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VPHHJAOJUJHJKD-UHFFFAOYSA-N
M.W : 191.01 Pubchem ID :5817
Synonyms :

Calculated chemistry of [ 51-44-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.42
TPSA : 37.3 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) : -5.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 3.46
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 2.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0549 mg/ml ; 0.000287 mol/l
Class : Soluble
Log S (Ali) : -3.92
Solubility : 0.0227 mg/ml ; 0.000119 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.188 mg/ml ; 0.000986 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 51-44-5 ]

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 [ 51-44-5 ]

* 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 [ 51-44-5 ]
  • Downstream synthetic route of [ 51-44-5 ]

[ 51-44-5 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 51-44-5 ]
  • [ 6148-64-7 ]
  • [ 53090-43-0 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 4 h;
Stage #2: With triethylamine; magnesium chloride In tetrahydrofuran; acetonitrile at 20℃; for 2 h;
CDI (41.5 g, 290.32 mmol, 3.70 equiv) was added to a solution of 3,4- dichlorobenzoic acid (15 g, 78.53 mmol, 1.00 equiv) in tetrahydrofuran (200 mL), The resulting solution was stirred for 4 h at 25°C. Separately, to a solution of potassium 3-ethoxy-3-oxopropanoate (37.7 g, 235 mmol, 3.00 equiv) in CH3CN (400 mL) was added MgCl2 (33.5 g, 353 mmol, 4.5 equiv) and triethylamine (23.8 g, 235 mmol, 3.00 equiv). The two solutions were combined and stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 200 mL of water. The pH of the solution was adjusted to pH 5 with HC1 (1M). The resulting solution was extracted with 4x50 mL of ethyl acetate and the organic layers were combined and dried over magnesium sulfate. The organics were concentrated in vacuo and purified by silica gel column chromatography with petroleum ether/ethyl acetate (50: 1). This resulted in 15 g (73percent) of ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate as a colorless oil
Reference: [1] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175
  • 2
  • [ 2039-83-0 ]
  • [ 51-44-5 ]
  • [ 42981-08-8 ]
  • [ 91309-68-1 ]
  • [ 91309-69-2 ]
Reference: [1] Polish Journal of Chemistry, 1986, vol. 60, # 7-12, p. 811 - 824
  • 3
  • [ 51-44-5 ]
  • [ 1805-32-9 ]
Reference: [1] Journal of the American Chemical Society, 1973, vol. 95, p. 3757 - 3763
  • 4
  • [ 6287-38-3 ]
  • [ 51-44-5 ]
  • [ 1805-32-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 1082,1087
  • 5
  • [ 67-56-1 ]
  • [ 51-44-5 ]
  • [ 2905-68-2 ]
YieldReaction ConditionsOperation in experiment
88% for 4 h; Reflux General procedure: Each substituted benzoic acid 1a-h (0.04 mol) was refluxed for 4 h in 50.0 mL (1.23 mol) of anhydrous methanol and 1.0 mL (2.0 mmol) of sulfuric acid. The solvent was evaporated and the product obtained was washed with cold water.
75% Reflux In a round bottom flask was added 50mL 3.78g3,4- dichlorobenzoic acid (20mmol) and 15mL of anhydrous methanol, was added dropwise concentrated sulfuric acid concentration of 98percent 1mL, heated to reflux, TLC tracking, petroleum ether / ethyl acetate (v / v = 5: 1), after the completion of the reaction, with saturated aqueous NaHCO3 to adjust the pH to 8-9, with a mixture of ethyl acetate (10mL × 3) and the combined oil phase, solvent removal by rotary evaporation gave a colorless and transparent liquid benzoate 3.04g, 75percent yield.
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 5031 - 5038
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2008, vol. 63, # 11, p. 1291 - 1299
[3] Patent: CN105294674, 2016, A, . Location in patent: Paragraph 0203; 0204
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 990,993
[5] Pharmazie, 1996, vol. 51, # 2, p. 83 - 88
[6] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 4229 - 4236
[7] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731
[8] Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457
[9] Chemical Biology and Drug Design, 2013, vol. 82, # 5, p. 546 - 556
  • 6
  • [ 51-44-5 ]
  • [ 107-06-2 ]
  • [ 2905-68-2 ]
YieldReaction ConditionsOperation in experiment
79% With sulfuric acid In methanol (1)
Methyl 3,4-dichlorobenzoate
The synthesis was carried out according to the method of Example 7-(1).
3,4-Dichlorobenzoic acid (25.4 g), 1,2-dichloroethane (80 ml), methanol (40 ml) and concentrated sulfuric acid (2.0 ml) were used as reagents to give 24.6 g of a white solid (yield 79percent).
IR (KBr): 3350, 1715, 1580, 1555 cm-1
1 H-NMR (CDCl3) δ: 3.88(3H, s), 7.81(1H, d, J=8.4 Hz), 7.91(1H, dd, J=8.4, 1.9 Hz), 8.09(1H, d, J=1.9 Hz)
Reference: [1] Patent: US5750545, 1998, A,
  • 7
  • [ 51-44-5 ]
  • [ 74-88-4 ]
  • [ 2905-68-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 43, p. 14079 - 14085
  • 8
  • [ 51-44-5 ]
  • [ 17287-03-5 ]
  • [ 2905-68-2 ]
Reference: [1] Chemosphere, 1997, vol. 35, # 6, p. 1233 - 1241
  • 9
  • [ 598-99-2 ]
  • [ 51-44-5 ]
  • [ 2905-68-2 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 1, p. 77 - 82
  • 10
  • [ 67-56-1 ]
  • [ 6287-38-3 ]
  • [ 51-44-5 ]
  • [ 2905-68-2 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1657 - 1659
  • 11
  • [ 67-56-1 ]
  • [ 51-44-5 ]
  • [ 18107-18-1 ]
  • [ 2905-68-2 ]
Reference: [1] Journal of the American Chemical Society, 2018,
  • 12
  • [ 64-17-5 ]
  • [ 51-44-5 ]
  • [ 28394-58-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 4, p. 1047 - 1049
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 10, p. 1627 - 1629
[3] Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1945, # 16,
[4] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 10, p. 510 - 514
[5] Archiv der Pharmazie, 2017, vol. 350, # 9,
[6] RSC Advances, 2018, vol. 8, # 12, p. 6306 - 6314
  • 13
  • [ 64-17-5 ]
  • [ 6287-38-3 ]
  • [ 51-44-5 ]
  • [ 28394-58-3 ]
YieldReaction ConditionsOperation in experiment
61% With sodium cyanide In N,N-dimethyl-formamide at 50℃; for 1 h; Molecular sieve General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification.
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 8, p. 2055 - 2061
  • 14
  • [ 51-44-5 ]
  • [ 1569262-64-1 ]
  • [ 28394-58-3 ]
YieldReaction ConditionsOperation in experiment
71% for 120 h; Reflux General procedure: Sulfonimidate 1 (0.859 g, 3.00 mmol) and 2-bromobenzoic acid (0.601 g, 3.00 mmol) were refluxed in THF (25 mL) for 5 d. TLC analysis (hexane–EtOAc, 6:1) showed that most of 1 had been converted into the sulfonamide 2. The mixture was concentrated by rotary evaporation and pentane (5 mL) was added. The pentane solution was removed by pipet and treated with NaH to precipitate any unreacted acid and residual 2. This solution was pipet filtered, concentrated in vacuo and purified by Kugelrohr distillation; yield: 0.32 g (47percent). IR and 1H NMR spectra were identical to published spectra.
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 24, p. 3361 - 3368
  • 15
  • [ 51-44-5 ]
  • [ 28394-58-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 5, p. 765 - 768
  • 16
  • [ 201230-82-2 ]
  • [ 51-44-5 ]
  • [ 100-21-0 ]
  • [ 528-44-9 ]
  • [ 1967-31-3 ]
  • [ 74-11-3 ]
Reference: [1] Chemistry Letters, 1986, p. 299 - 302
  • 17
  • [ 98-10-2 ]
  • [ 51-44-5 ]
  • [ 6574-99-8 ]
  • [ 25412-64-0 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 763,766
  • 18
  • [ 51-44-5 ]
  • [ 6574-99-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 1, p. 1 - 6
  • 19
  • [ 51-44-5 ]
  • [ 1047953-91-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3321 - 3344
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