[ CAS No. 193290-27-6 ] {[proInfo.proName]}

Name: 193290-27-6|3-(2-Hydroxyethyl)benzonitrile|97%
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SKU: A153415
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Quality Control of [ 193290-27-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 193290-27-6 ]

SDS Specification

Alternatived Products of [ 193290-27-6 ]

Product Details of [ 193290-27-6 ]

CAS No. :	193290-27-6	MDL No. :	MFCD10001394
Formula :	C₉H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SDFBOAJVHGKEAO-UHFFFAOYSA-N
M.W :	147.17	Pubchem ID :	14926727
Synonyms :

Calculated chemistry of [ 193290-27-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.09
TPSA :	44.02 Å²

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) :	-10.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.67
Log Po/w (XLOGP3) :	-4.3
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	1.98
Consensus Log Po/w :	0.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.68
Solubility :	7120.0 mg/ml ; 48.4 mol/l
Class :	Highly soluble
Log S (Ali) :	3.99
Solubility :	1430000.0 mg/ml ; 9690.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.7
Solubility :	0.296 mg/ml ; 0.00201 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.39

Safety of [ 193290-27-6 ]

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 [ 193290-27-6 ]

* 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 [ 193290-27-6 ]
Downstream synthetic route of [ 193290-27-6 ]

[ 193290-27-6 ] Synthesis Path-Upstream 1~6

1
[ 1878-71-3 ]
[ 193290-27-6 ]

Reference： [1] Patent: WO2009/66084, 2009, A1, . Location in patent: Page/Page column 100
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134

2
[ 28229-69-8 ]
[ 557-21-1 ]
[ 193290-27-6 ]

Reference： [1] Patent: WO2007/69986, 2007, A1, . Location in patent: Page/Page column 89

3
[ 109346-98-7 ]
[ 193290-27-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 8, p. 2597 - 2610

4
[ 52798-00-2 ]
[ 193290-27-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134

5
[ 5338-96-5 ]
[ 193290-27-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S404 - S406

6
[ 6952-59-6 ]
[ 193290-27-6 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S404 - S406

[ 193290-27-6 ] Synthesis Path-Downstream 1~31

1
[ 5338-96-5 ]
[ 193290-27-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S404 - S406

2
[ 193290-27-6 ]
2-(3-aminomethyl-phenyl)-ethanol [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S404 - S406

3
[ 193290-27-6 ]
[ 484065-64-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

4
[ 109346-98-7 ]
[ 193290-27-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

6
[ 193290-27-6 ]
2-(3-cyanophenyl)ethanesulfonyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

7
[ 193290-27-6 ]
2-(3-cyano-phenyl)-ethanesulfonic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

8
[ 193290-27-6 ]
[ 484065-65-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

9
[ 193290-27-6 ]
N-{4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]phenyl}-2-(3-cyanophenyl)ethanesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

10
[ 193290-27-6 ]
3-{2-[4-(piperidin-4-yloxy)-phenylsulfamoyl]-ethyl}-benzamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

11
[ 193290-27-6 ]
3-(2-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenylsulfamoyl}-ethyl)-benzamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610

12
[ 6952-59-6 ]
[ 193290-27-6 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S404 - S406

13
[ 193290-27-6 ]
[ 655251-02-8 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S404 - S406

14
[ 193290-27-6 ]
[ 655251-05-1 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S404 - S406

15
[ 28229-69-8 ]
[ 557-21-1 ]
[ 193290-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃;	Zn(CN)2 (5.03 g, 0.028 mol) and Pd(PPh3)4 (2.3 g, 0.002 mol) were added to a solution of 2-(3-bromophenyl)ethanol (8.3 g, 0.412 mol; see step (i) above) in dry DMF (75 mL). The reaction mixture was stirred overnight at 100C before being cooled to room temperature and quenched with water. The resulting mixture was extracted with ethyl acetate and the organic layer was separated, dried over anhydrous Na2SO4 and then concentrated. The resulting crude product was purified by column chromatography, using 15% ethyl acetate / petroleum ether as eluent, to give 4.2 g of the sub-title compound as yellow liquid.

Reference： [1]Patent: WO2007/69986,2007,A1 .Location in patent: Page/Page column 89

16
[ 193290-27-6 ]
3-(2-bromoethyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃;	Triphenylphosphine (14.97 g, 0.0571 mol) was added to a solution of 3-(2- hydroxyethyl)benzonitrile (4.2 g. 0.0285 mol; see sterho(ii) above) in DCM (50 mL). The reaction mixture was cooled to 00C and solution of CBr4 (18.93 g, 0.0571 mol) in DCM was added, dropwise. After stirring at room temperature overnight, the reaction mixture was filtered and the solids washed with petroleum ether. The filtrate was concentrated and the resulting crude product was purified <n="91"/>by column chromatography (using 3% ethyl acetate / petroleum ether as eluent) to give 4.2 g of the title compound as yellow liquid.

Reference： [1]Patent: WO2007/69986,2007,A1 .Location in patent: Page/Page column 89-90

17
[ 337519-64-9 ]
[ 193290-27-6 ]
[ 1049708-21-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 758 - 770

18
[ 1878-71-3 ]
[ 193290-27-6 ]

Yield	Reaction Conditions	Operation in experiment
		2-(3-cyanol-phenyl)-ethanol was prepared as follows: To a solution of 3- cyanophenylacetic acid (250mg, 1.55mmol) in dry THF (3ml) at O0C was added borane- tetrahydrofuran complex (LOM solution in THF, 1.4 equiv, 2.17ml) dropwise. The reaction was allowed to warm up to room temperature overnight and then quenched with water. DCM/brine extraction gave 2-(3-cyanol-phenyl)-ethanol as a yellow oil (170mg).

Reference： [1]Patent: WO2009/66084,2009,A1 .Location in patent: Page/Page column 100
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 131 - 134

19
[ 5292-43-3 ]
[ 193290-27-6 ]
[ 1141474-49-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In toluene; at 20℃; for 9h;	To a solution of 3-(2-hydroxy-ethyl)-benzonitrile (1 g; 6.79 mmol) in toluene (20 ml_), was added tetrabutylammonium hydrogen sulfate (230.70 mg; 0.68 mmol; 0.10 eq.) and NaOH (20 ml 5 M; 10 mmol) followed by the addition of tert-butyl bromoacetate (2 ml 13.59 mmol). Reaction mixture was stirred at RT under vigorous stirring for 9h. After this time, the aqueous phase was removed and the organic phase was diluted with EtOAc (50 ml_), washed with water (50 ml_) and brine (50 ml_). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow powder (1.42 g; 80%). 1H NMR (DMSO-d6, 300 MHz) delta 7.74-7.73 (m, 1 H), 7.68-7.65 (m, 1 H), 7.63- 7.59 (m, 1 H), 7.51-7.46 (m, 1 H), 3.97 (s, 2H), 3.69 (t, J = 6.5 Hz, 2H), 2.88 (t, J = 6.5 Hz, 2H), 1.40 (s, 9H). LC/MS (Method B): 262.1 (M+H)+.

Reference： [1]Patent: WO2009/43889,2009,A2 .Location in patent: Page/Page column 168

20
[ 193290-27-6 ]
C₅₉H₅₆N₄O₇S₃ [ No CAS ]