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[ CAS No. 42288-26-6 ] {[proInfo.proName]}

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Chemical Structure| 42288-26-6
Chemical Structure| 42288-26-6
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Product Details of [ 42288-26-6 ]

CAS No. :42288-26-6 MDL No. :MFCD01464022
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KJRQMXRCZULRHF-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :817965
Synonyms :

Calculated chemistry of [ 42288-26-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.04
TPSA : 73.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.09
Log Po/w (XLOGP3) : 0.34
Log Po/w (WLOGP) : 0.86
Log Po/w (MLOGP) : -1.78
Log Po/w (SILICOS-IT) : 0.76
Consensus Log Po/w : 0.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.29
Solubility : 9.04 mg/ml ; 0.0513 mol/l
Class : Very soluble
Log S (Ali) : -1.44
Solubility : 6.4 mg/ml ; 0.0363 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.861 mg/ml ; 0.00489 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 42288-26-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42288-26-6 ]

* 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 [ 42288-26-6 ]
  • Downstream synthetic route of [ 42288-26-6 ]

[ 42288-26-6 ] Synthesis Path-Upstream   1~6

  • 1
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YieldReaction ConditionsOperation in experiment
88% at 100 - 110℃; for 3 h; 3.2.3 Preparation of [(4-cyanophenyl)amino]acetic acid (V) C7H6N2 C2H3DPψ2 C9H8N2O2 MoI. Wt.: 1 18,14 MoI. Wt.: 138,95 MoI. Wt.: 176,17VIngredientsF: 90 g - 0.75 molG: 211.7 g - 1.5 molSodium bicarbonate: 35 g, 0.42 molThe starting substances F and G were mixed in 1250 ml of water and this suspension was inserted into a bath heated up to 100-110 0C. After three hours of heating the reaction container was removed from the bath, cooled in the fridge and the separated substance was sucked off. The substance was dried in a vacuum drier at the temperature of 100 °C. Yield: Crude product: 122 g (92.8percent), HPLC: 97percentThe crude product was purified by conversion to the sodium salt and re-acidification using an aqueous solution of sodium bicarbonate. The acid was released by means of diluted hydrochloric acid (1 :1). After sucking off and washing with water the product was dried in a vacuum drier (105 °C). Yield: Purified product: 115 g (88percent), HPLC: 99.1percent, water content: 0.13percent; sulphate ash: 1.8percent
Reference: [1] Patent: WO2009/111997, 2009, A1, . Location in patent: Page/Page column 11
[2] Patent: WO2013/111163, 2013, A2, . Location in patent: Page/Page column 18
[3] Patent: US2015/11589, 2015, A1, . Location in patent: Paragraph 0121-0122
[4] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 148 - 159
  • 2
  • [ 79-11-8 ]
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YieldReaction ConditionsOperation in experiment
73% Reflux In the 4-cyanato aniline (6.0g, 0 . 05mol) and 1-chloro acetic acid (10g, 0.11mol) adding water in 150 ml, heating to reflux until a large amount of yellow solid is separated out so far, the filter at room temperature, with water, anhydrous ethanol, anhydrous ethyl ether eluviation, that is, to get the yellow solid 4-cyanato anilino-acetic acid (6.4g, yield 73percent). Mass spectrometric (ESI-MS): 177.3(M+H) +, 199.2(M+Na) +; C 9 H 8 N 2 O 2 (176).
58% Heating / reflux a)
(4-Cyano-phenylamino)-acetic acid
A solution of 4-aminobenzonitrile (12 g, 101.6 mmol) and chloroacetic acid (20 g, 211.6 mmol) in water (250 mL) was refluxed until the product began to separate out.
After cooled down to the room temperature, the solids were collected by filtration, washed with ether, and dried in vacuo to afford 10.35 g (58percent) of the title compound which was pure enough for the next reaction. 1H NMR (400 MHz, DMSO-d6) δ 12.73 (s, 1H), 7.46 (dd, 2H), 6.93 (t, 1H), 6.65 (dd, 2H), 3.91 (d, 2H).
Reference: [1] Patent: CN103524559, 2016, B, . Location in patent: Paragraph 0096; 0102-0104
[2] Patent: US2005/107355, 2005, A1, . Location in patent: Page/Page column 30
[3] Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7772 - 7777
[4] Journal of Organic Chemistry, 1957, vol. 22, p. 78
  • 3
  • [ 3926-62-3 ]
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YieldReaction ConditionsOperation in experiment
73.2% for 6.5 h; Reflux e)
2-(4-Cyanophenylamino)acetic acid (compound III)
77.4 g (0.66 mol) of 4-aminobenzonitrile and 150 g (1.31 mol) of sodium chloroacetate were suspended in 1.1 L of water, and the resulting mixture was stirred at reflux temperature for 6.5 hours.
After cooling to 0°C, the resulting suspension was stirred at this temperature overnight.
The solid was filtered and washed with 200 mL of water.
The resulting solid was suspended in 200 mL of ethyl acetate and stirred at room temperature for 1 hour.
The solid was filtered, washed with 400 mL of ethyl acetate and dried at 60°C under vacuum for 5 hours to yield 84.5 g of 2-(4-cyanophenylamino)acetic acid as an off-white solid. Yield: 73.2 percent.
Purity (HPLC, method 3): 98.4 percent.
73.2% at 0℃; Reflux e) 2-(4-Cyanophenylamino)acetic acid (compound III) 77.4 g (0.66 mol) of 4-aminobenzonitrile and 150 g (1.31 mol) of sodium chloroacetate were suspended in 1.1 L of water, and the resulting mixture was stirred at reflux temperature for 6.5 hours. After cooling to 0°C, the resulting suspension was stirred at this temperature overnight. The solid was filtered and washed with 200 mL of water. The resulting solid was suspended in 200 mL of ethyl acetate and stirred at room temperature for 1 hour. The solid was filtered, washed with 400 mL of ethyl acetate and dri e d at 60 ° C under v acuum for 5 hours to yield 84.5 g of 2-(4- cyanophenylamino)acetic acid as an off-white solid. Yield: 73.2 percent. Purity (HPLC, method 3): 98.4 percent.
131 g With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 90 - 95℃; for 24 h; Sodium bicarbonate (21.35 g) was added to a mixture of 4-aminobenzonitrile compound of formula-12 (100 g) and water (1000 ml) followed by sodium 2-chloroacetate (197.42 g). Potassium iodide (5 g) followed by tertiary butyl ammonium bromide (2.5 g) were added to the reaction mixture. The reaction mixture was heated to the 90-95° C. and stirred for 24 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled to 20-25° C. and pH was adjusted to 7.5 with ammonia. The reaction mixture was stirred for 20 minutes at 20-30° C. Filtered the reaction mixture and ethylacetate was added to the filtrate. The reaction mixture was stirred for 15 minutes. Both the ethylacetate and aqueous layers were separated and the pH of aqueous layer was adjusted to 2.5 using hydrochloric acid. The reaction mixture was stirred for 3 hours at 20-30° C. to precipitate the solid. Filtered the precipitated solid, water followed by hydrochloric acid were added to the obtained solid and stirred for 4 hours at 25-30° C. Filtered the solid, the obtained solid was slurried twice in water for 30-45 minutes and then dried to get the title compound. The same process can be repeated one more time to eliminates the impurities if present. Yield: 131 g
120 g With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 85 - 90℃; for 24 h; Sodium mono chloroacetate (197.42 g), followed by potassium iodide (5 g) and tetrabutyl ammonium bromide (2.5 g) were added to a mixture of 4-aminobenzonitrile (100 g), water (1000 ml) and sodium bicarbonate (42.71 g).
The reaction mixture was heated to 85-90° C. and stirred for 24 hours.
The reaction mixture was cooled to 25-30° C. and treated with ammonia followed by hydrochloric acid.
Filtered the solid, washed with water and then dried to get title compound.
Yield: 120 g.

Reference: [1] Patent: EP2522662, 2012, A1, . Location in patent: Page/Page column 20
[2] Patent: WO2012/152855, 2012, A1, . Location in patent: Page/Page column 34; 36-37
[3] Patent: WO2012/77136, 2012, A2, . Location in patent: Page/Page column 38
[4] Patent: US2014/148601, 2014, A1, . Location in patent: Paragraph 0258
[5] Patent: US2015/87842, 2015, A1, . Location in patent: Paragraph 0227-0228
  • 4
  • [ 623-00-7 ]
  • [ 56-40-6 ]
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4153 - 4161
  • 5
  • [ 873-74-5 ]
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Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2843 - 2857
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 1, p. 81 - 86
  • 6
  • [ 42288-26-6 ]
  • [ 872728-81-9 ]
Reference: [1] Patent: WO2014/192030, 2014, A2,
[2] Patent: WO2014/192030, 2014, A2,
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