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[ CAS No. 20925-27-3 ] {[proInfo.proName]}

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Chemical Structure| 20925-27-3
Chemical Structure| 20925-27-3
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Product Details of [ 20925-27-3 ]

CAS No. :20925-27-3 MDL No. :MFCD00035926
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZFBKYGFPUCUYIF-UHFFFAOYSA-N
M.W : 152.58 Pubchem ID :88728
Synonyms :

Calculated chemistry of [ 20925-27-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.57
TPSA : 49.81 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) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.679 mg/ml ; 0.00445 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.549 mg/ml ; 0.00359 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.289 mg/ml ; 0.00189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 20925-27-3 ]

Signal Word:Warning Class:
Precautionary Statements:P280 UN#:
Hazard Statements:H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20925-27-3 ]

* 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 [ 20925-27-3 ]
  • Downstream synthetic route of [ 20925-27-3 ]

[ 20925-27-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 873-74-5 ]
  • [ 21803-75-8 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
95% With N-chloro-succinimide In dichloromethane; acetonitrile 3-chloro-4-cyanoaniline.
PREPARATION 2
(2-chloro-4-cyanoaniline)
To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux.
After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours.
The solvent was then removed under reduced pressure.
The residue was then dissolved in dichloromethane, washed with a 5percent sodium hydroxide solution, dried (Na2 SO4) and evaporated under reduced pressure to afford 24.5 g (95percent) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.
Reference: [1] Patent: US5034410, 1991, A,
  • 2
  • [ 28163-00-0 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
78% With hydrazine hydrate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate Step 4
A portion of 2-chloro-4-nitrobenzonitrile (5 g, 0.027 m) was heated with hydrazine monohydrate (110 ml) until the reaction began.
Another portion of 2-chloro-4-nitrobenzonitrile (35 g, 0.192 m) was added in predetermined amounts.
Once the evolution of nitrogen gas ceased, the reaction mixture was refluxed approximately thirty minutes, and then poured into stirred ice water.
The precipitate was filtered and the solid was crystallized from water to yield 2-chloro-4-aminobenzonitrile (25 g, 78percent, mp 117° C.).
Reference: [1] Patent: US4424371, 1984, A,
  • 3
  • [ 21402-26-6 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
60% at 145℃; Inert atmosphere General procedure: A mixture of compound 3a or 3b (19 mmol) and CuCN (29 mmol, 1.5 eq) in DMF (20 ml) was heated at 145 °C under nitrogen overnight. The reaction mixture was cooled to room temperature and then poured into ice water (50 ml). Ethyl acetate (100 ml) was added and the insoluble solid was filtered off (washed with ethyl acetate [2 x 30 ml]). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 ml). The combined extracts were washed with saturated aqueous NaHCO3 solution (1 x 150 ml), brine (3 x 100 ml) and dried over Na2SO4. The resulting material was concentrated and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate, 10:1) to afford the title compound (4a or 4b) as a gray solid (60–65 percent yield).
Reference: [1] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
  • 4
  • [ 154607-01-9 ]
  • [ 20925-27-3 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 26, p. 4689 - 4692
  • 5
  • [ 873-74-5 ]
  • [ 21803-75-8 ]
  • [ 20925-27-3 ]
YieldReaction ConditionsOperation in experiment
95% With N-chloro-succinimide In dichloromethane; acetonitrile 3-chloro-4-cyanoaniline.
PREPARATION 2
(2-chloro-4-cyanoaniline)
To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux.
After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours.
The solvent was then removed under reduced pressure.
The residue was then dissolved in dichloromethane, washed with a 5percent sodium hydroxide solution, dried (Na2 SO4) and evaporated under reduced pressure to afford 24.5 g (95percent) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.
Reference: [1] Patent: US5034410, 1991, A,
  • 6
  • [ 108-42-9 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
[2] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
  • 7
  • [ 588-07-8 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 8
  • [ 22459-81-0 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 9
  • [ 22304-33-2 ]
  • [ 20925-27-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 10
  • [ 20925-27-3 ]
  • [ 3336-16-1 ]
YieldReaction ConditionsOperation in experiment
62.5% With urea; sodium nitrite In sulfuric acid; water Step 5
A mixture of 2-chloro-4-aminobenzonitrile (25 g, 0.187 m) in stirred concentrated sulfuric acid (58 g) and water (570 ml) was heated at between 49° and 61° C. for approximately thirty minutes.
The suspension was cooled to approximately 0° C. and a cold solution of sodium nitrite (13.2 g, 0.187 m) in water (125 ml) was added dropwise at a solution temperature of between 0° and 6° C.
Stirring continued thereafter for approximately three hours and then urea (1.5 g) was added to the mixture.
The resulting insoluble impurity was filtered off.
An aqueous solution of 50percent sulfuric acid (600 ml) was added while the reaction mixture was heated at a temperature between 74° and 81° C. and stirred until the evolution of nitrogen gas ceased.
The reaction product was separated by filtration and then recrystallized from water to yield 2-chloro-4-hydroxybenzonitrile (17.9 g, 62.5percent, mp 160°
Reference: [1] Patent: US4424371, 1984, A,
  • 11
  • [ 20925-27-3 ]
  • [ 154607-01-9 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: at 0 - 20℃; for 2 h;
General procedure: 4-Cyano-3-(substituted) aniline 4a or 4b (38 mmol) was dissolved in conc. HCl (27 ml). After cooling to 0 C, sodium nitrite (39 mmol, 1.5 eq) was added very slowly to the stirred solution with the temperature being kept within (0 and 5 °C). This diazonium salt solution was then poured into a flask containing CuBr (53 mmol, 1.4 eq) and 22 ml of conc. HCl. The solution was stirred for 2 h, and then, the reaction mixture was poured into ice water (50 ml) extracted with Ethyl acetate (100 ml). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 50 ml). The combined extracts were washed with saturated aqueous NaHCO3 solution (1 x 150 ml), brine (3 x 100 ml) and dried over Na2SO4. The resulting material was concentrated, and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate, 10:1) to afford the title compound (5a or 5b) as white solid (72–75 percent yield).
Reference: [1] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
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