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[ CAS No. 56542-67-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 56542-67-7
Chemical Structure| 56542-67-7
Chemical Structure| 56542-67-7
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Product Details of [ 56542-67-7 ]

CAS No. :56542-67-7 MDL No. :MFCD00203480
Formula : C7H4ClNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BHNRGBRMCNHNQD-UHFFFAOYSA-N
M.W :201.63 Pubchem ID :2801360
Synonyms :

Calculated chemistry of [ 56542-67-7 ]

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 : 44.24
TPSA : 66.31 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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 2.57
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 1.29
Consensus Log Po/w : 1.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.47
Solubility : 0.691 mg/ml ; 0.00343 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.395 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.188 mg/ml ; 0.000933 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 56542-67-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 56542-67-7 ]

* 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 [ 56542-67-7 ]
  • Downstream synthetic route of [ 56542-67-7 ]

[ 56542-67-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 2237-30-1 ]
  • [ 56542-67-7 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃;
Stage #2: With sulfur dioxide; copper(l) chloride In water; acetic acid at 0℃; for 1.17 h;
3-Aminobenzonitrile (2.5g, 21 mmol) was dissolved in conc. HCl (20 mL) and water (20 mL), cooled to 0 °C and a solution of sodium nitrite (1.5 g, 22 mmol) in water (5 mL) was added dropwise.
The reaction mixture was stirred for 10 min to complete the diazonium salt formation.
In a separate flask was added copper(I) chloride (0.2g) over a saturated solution of sulfur dioxide in AcOH (25 mL) and stirred at 0 °C for 10 min.
The resulting solution was added dropwise to the diazonium salt and stirred at 0 °C for 1 h.
The reaction mixture poured into ice water and the product was extracted with tert-butylmethylether.
The combined organic layer was washed with water and brine.
The crude product was purified by column chromatography (silica gel 60-120 mesh using 5percent EtOAc in petroleum ether) to get the pure 3-cyanobenzene-1-sulfonyl chloride (1.9 g, yield 45percent) as an off-white solid. 1H NMR (300MHz, CDCl3) δ 8.35 (t, J = 1.5 Hz, 1 H), 8.31-8.27 (m, 1 H), 8.06-8.02 (m, 1 H), 7.82 (t, J = 7.9 Hz, 1 H).
Reference: [1] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 11, p. 1833 - 1848
[2] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 0335-0336
[3] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[4] Patent: US2002/128480, 2002, A1,
[5] Patent: EP1258252, 2002, A1,
[6] Patent: US2004/18192, 2004, A1,
[7] Organic and Biomolecular Chemistry, 2010, vol. 8, # 23, p. 5324 - 5332
  • 2
  • [ 636-76-0 ]
  • [ 56542-67-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1945, vol. <5>12, p. 954,960
  • 3
  • [ 4025-64-3 ]
  • [ 56542-67-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1945, vol. <5>12, p. 954,960
  • 4
  • [ 10026-13-8 ]
  • [ 636-76-0 ]
  • [ 56542-67-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1945, vol. <5>12, p. 954,960
  • 5
  • [ 56542-67-7 ]
  • [ 3118-68-1 ]
YieldReaction ConditionsOperation in experiment
99% With ammonia In water; acetonitrile at 20℃; NH4OH (22ml_, excess) can be added to a solution of 3-cyanobenzene-l-sulfonyl chloride (1.Og, 4.97mmol) in acetonitrile (22ml_) and the reaction stirred overnight at r.t. The reaction can be concentrated and the solid obtained washed with water to give 500mg of product. The water phase can be extracted with AcOEt, dried with MgSO4 anh, filtered and evaporated to give 400mg of product that can be combined with the solid obtained before (0.90g,99percent).
82% With ammonia In 1,4-dioxane at 20℃; for 0.5 h; Step 1: 3-cyanobenzenesulfonamideTo a solution of ammonia in dioxane (0.5 M in dioxane; 50 ml
25 mmol) was added a solution of 3-cyanobenzene-1-sulfonyl chloride (ABCR; 605 mg; 3 mmol) in dioxane (10 ml_) and the mixture was allowed to stir at RT for 30 min. The solvent was removed in vacuo to give the title compound as a white solid (450 mg; 82percent). 1H NMR: (DMSOd6, 400MHz) δ 8.25 (1 H, t, J = 1.7 Hz), 8.18-8.12 (2H, m), 7.85 (1 H, t, J = 7.9 Hz), 7.63 (2H, br s). LC/MS (Method C): 181 (M+H)+. HPLC (Method E) Rt 2.42 min (Purity: 99.3percent).
75% for 1 h; A solution of 3-cyano-benzenesulfonyl chloride (1.07 g) in ammonia (33percent aqueous solution, 40 mL) was stirred for 1 h and then evaporated under reduced pressure to approx. 20 mL and cooled. The precipitate was filtered and washed with water and dried in vaccuo to afford the intermediate (722 mg; 75percent) as a colourless solid. [MH]+=183.
75% With ammonia In water at 20℃; for 1 h; A solution of commercially available 3-cyano-benzenesulfonyl chloride (1.07 g) in a 33percent solution of NH3 in H2O (40 mL) was stirred at room temperature for 1 h, then concentrated to ~ 20 mL and placed in an ice bath. The formed precipitate was separated by filtration, washed with H2O and dried in vacuo to afford the title compound as a colorless solid (722 mg, 75percent). [MH]+ = 183.
56.6% With ammonia In methanol at 20℃; for 0.5 h; Inert atmosphere; Cooling with ice r under the protection, 3-cyanobenzenesulfonyl chloride (400 mg, 2. Ommo 1) Excess ammonia methanol solution (3.5 mL, 17.5 mmol) Ice bath to room temperature reaction, 0.5h after stopping the reaction, steaming solution, adding 10mL of ice water, DCM extracted four times, combined organic phase, recrystallized pale yellow solid (206mg 56.6percent)

Reference: [1] Patent: WO2009/24585, 2009, A2, . Location in patent: Page/Page column 77
[2] Patent: WO2009/80663, 2009, A1, . Location in patent: Page/Page column 119
[3] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 86
[4] Patent: WO2006/128184, 2006, A2, . Location in patent: Page/Page column 160
[5] Patent: CN107098846, 2017, A, . Location in patent: Paragraph 2475; 2477; 2478
[6] Bulletin de la Societe Chimique de France, 1945, vol. <5>12, p. 954,960
[7] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[8] Patent: US2007/3539, 2007, A1, . Location in patent: Page/Page column 37
  • 6
  • [ 56542-67-7 ]
  • [ 62-53-3 ]
  • [ 56542-65-5 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine In dichloromethane at 20℃; General procedure: A mixture of 3- or 4-cyanobenzenesulfonyl chloride (605 mg, 3 mmol), the amine (3.3 mmol) and pyridine (736 mg, 9.3 mmol) was stirred overnight at room temperature in abs dichloromethane (40 mL). After removal of the solvent at reduced pressure, nitriles B were obtained by flash column chromatography (dichloromethane) and recrystallisation from ethyl acetate/hexane or toluene.#10;
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6489 - 6505,17
[2] Bulletin de la Societe Chimique de France, 1945, vol. 12, p. 954,963,964
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