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[ CAS No. 939-80-0 ] {[proInfo.proName]}

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Chemical Structure| 939-80-0
Chemical Structure| 939-80-0
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Product Details of [ 939-80-0 ]

CAS No. :939-80-0 MDL No. :MFCD00016987
Formula : C7H3ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XBLPHYSLHRGMNW-UHFFFAOYSA-N
M.W : 182.56 Pubchem ID :13655
Synonyms :

Calculated chemistry of [ 939-80-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.99
TPSA : 69.61 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 2.18
Log Po/w (WLOGP) : 2.12
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.29
Consensus Log Po/w : 1.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.409 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.0969 mg/ml ; 0.000531 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.605 mg/ml ; 0.00331 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 939-80-0 ]

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 [ 939-80-0 ]

* 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 [ 939-80-0 ]
  • Downstream synthetic route of [ 939-80-0 ]

[ 939-80-0 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 939-80-0 ]
  • [ 6393-40-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[2] Recueil des Travaux Chimiques des Pays-Bas, 1941, vol. 60, p. 811,813, 815
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 7, p. 925 - 930
  • 2
  • [ 623-03-0 ]
  • [ 939-80-0 ]
YieldReaction ConditionsOperation in experiment
75.47% With nitronium tetrafluoborate In acetonitrile at 0 - 20℃; for 20 h; In dry acetonitrile (40 ml) was dissolved 4-chlorobenzonitrile (4g, 29.2 mmol), and nitronium tetrafluoroborate (7.7g, 58.39 mmol) was added therto at 0 °C. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into cold water. The white solid precipitated out was collected by filtration, and the filterate was washed with water and dried. The compound (4.0g, 75.47percent) thus obtained was used for next step without purification.
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Patent: WO2014/24056, 2014, A1, . Location in patent: Page/Page column 40
[3] MedChemComm, 2017, vol. 8, # 10, p. 2003 - 2011
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[5] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
[6] Journal of the Chemical Society, 1927, p. 1117
[7] Journal of the Chemical Society, 1934, p. 1672,1676
[8] Journal of the American Chemical Society, 1961, vol. 83, p. 4564 - 4571
[9] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[10] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
  • 3
  • [ 16588-06-0 ]
  • [ 939-80-0 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 7,8, p. 1431 - 1436
[2] Journal of the Chemical Society, 1934, p. 1672,1676
[3] Patent: WO2011/56635, 2011, A1, . Location in patent: Page/Page column 145-146
  • 4
  • [ 59670-78-9 ]
  • [ 939-80-0 ]
  • [ 7684-30-2 ]
Reference: [1] Synthesis, 1985, # 2, p. 201 - 202
  • 5
  • [ 79-24-3 ]
  • [ 16588-34-4 ]
  • [ 939-80-0 ]
  • [ 66399-01-7 ]
  • [ 134538-49-1 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 2.2, p. 366 - 372[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, # 2, p. 426 - 433
  • 6
  • [ 96-99-1 ]
  • [ 939-80-0 ]
Reference: [1] Patent: WO2011/56635, 2011, A1,
  • 7
  • [ 16588-34-4 ]
  • [ 939-80-0 ]
Reference: [1] Chinese Journal of Chemistry, 2010, vol. 28, # 6, p. 993 - 996
  • 8
  • [ 38818-50-7 ]
  • [ 939-80-0 ]
Reference: [1] Journal of the Chemical Society, 1934, p. 1672,1676
[2] Patent: WO2011/56635, 2011, A1,
  • 9
  • [ 104-88-1 ]
  • [ 939-80-0 ]
Reference: [1] MedChemComm, 2017, vol. 8, # 10, p. 2003 - 2011
  • 10
  • [ 635-22-3 ]
  • [ 939-80-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 197
  • 11
  • [ 623-03-0 ]
  • [ 7697-37-2 ]
  • [ 939-80-0 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 1117
  • 12
  • [ 3272-08-0 ]
  • [ 98-59-9 ]
  • [ 91-66-7 ]
  • [ 939-80-0 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 1354
  • 13
  • [ 89-73-6 ]
  • [ 939-80-0 ]
  • [ 59-49-4 ]
  • [ 3272-08-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5877 - 5880
  • 14
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 3, p. 473 - 476
  • 15
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 25, p. 7725 - 7738
  • 16
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
  • [ 64248-62-0 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 25, p. 7725 - 7738
  • 17
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
  • [ 16588-06-0 ]
Reference: [1] Journal of Fluorine Chemistry, 1999, vol. 94, # 1, p. 51 - 55
  • 18
  • [ 939-80-0 ]
  • [ 1009-35-4 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 4, p. 505 - 513
[2] Synthetic Communications, 1998, vol. 28, # 23, p. 4295 - 4301
  • 19
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 25, p. 7725 - 7738
  • 20
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
  • [ 64248-62-0 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 25, p. 7725 - 7738
  • 21
  • [ 939-80-0 ]
  • [ 3272-08-0 ]
  • [ 1009-35-4 ]
  • [ 16588-06-0 ]
Reference: [1] Journal of Fluorine Chemistry, 1999, vol. 94, # 1, p. 51 - 55
  • 22
  • [ 939-80-0 ]
  • [ 53312-79-1 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydrogen sulfide In tetrahydrofuran; water at 45℃; Example 1; Preparation of N-(1-(5-cyano-2-(3,5-dichlorophenoxy)phenylsulfonyl)piperidin-4-yl)-3-fluorobenzenesulfonamide (25) Commercially available 4-chloro-3-benzonitrile was dissolved in 4 parts THF. One part water was added with sodium hydrosulfide (3 eq.) and stirred overnight at 45° C. TLC (25percent EtOAc in hexanes) confirmed completion of the reaction. THF was evaporated in vacuo and the product precipitated. The white solid was collected via vacuum filtration, washed with water and dried in a vacuum oven with gentle heating (97.0percent yield).
Reference: [1] Patent: US2011/230487, 2011, A1, . Location in patent: Page/Page column 35
[2] Synlett, 2010, # 20, p. 3019 - 3022
[3] Patent: US2012/196824, 2012, A1,
[4] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369[5] Chem.Abstr., 1948, vol. 42, p. 148
[6] Patent: US2003/139390, 2003, A1,
[7] Chemical Communications, 2015, vol. 51, # 61, p. 12197 - 12200
[8] Chemical Communications, 2015, vol. 51, # 66, p. 13086 - 13089
[9] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
[10] ACS Catalysis, 2016, vol. 6, # 11, p. 7844 - 7854
  • 23
  • [ 939-80-0 ]
  • [ 7732-18-5 ]
  • [ 53312-79-1 ]
Reference: [1] Patent: US5744643, 1998, A,
[2] Patent: US5744643, 1998, A,
  • 24
  • [ 939-80-0 ]
  • [ 53312-79-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 51, p. 9305 - 9308
  • 25
  • [ 939-80-0 ]
  • [ 53312-79-1 ]
Reference: [1] Patent: US4091011, 1978, A,
  • 26
  • [ 939-80-0 ]
  • [ 64910-46-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 12, p. 1545 - 1548
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 24, p. 5907 - 5910
[3] Journal of Organic Chemistry, 2017, vol. 82, # 17, p. 9243 - 9252
  • 27
  • [ 939-80-0 ]
  • [ 124-41-4 ]
  • [ 60979-25-1 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369[2] Chem.Abstr., 1948, vol. 42, p. 148
  • 28
  • [ 939-80-0 ]
  • [ 199327-63-4 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 11, p. 1142 - 1147
  • 29
  • [ 939-80-0 ]
  • [ 942199-56-6 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
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