185259-36-3|4-(tert-Butoxy)benzonitrile| Ambeed

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Quality Control of [ 185259-36-3 ] Purity: 95% SDS Specification

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Product Details of [ 185259-36-3 ]

CAS No. :	185259-36-3
Formula :	C₁₁H₁₃NO
M.W :	175.23
SMILES Code :	N#CC1=CC=C(OC(C)(C)C)C=C1
MDL No. :	MFCD03425273
InChI Key :	WLWYCCYGVDZFMS-UHFFFAOYSA-N
Pubchem ID :	7021978

Safety of [ 185259-36-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P362-P363-P501

Computational Chemistry of [ 185259-36-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	52.11
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.43
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.68
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.74
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.03
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.82
Solubility	0.263 mg/ml ; 0.0015 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.03
Solubility	0.165 mg/ml ; 0.000943 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.43
Solubility	0.065 mg/ml ; 0.000371 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.47 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.45

Application In Synthesis of [ 185259-36-3 ]

* 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.

Downstream synthetic route of [ 185259-36-3 ]

[ 185259-36-3 ] Synthesis Path-Downstream 1~35

1
[ 185259-36-3 ]
[ 99985-67-8 ]

References: [1]Journal of the Chemical Society,1956,p. 2455,246.

2
[ 623-03-0 ]
[ 865-48-5 ]
[ 185259-36-3 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5413 - 5418.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5413 - 5418.

3
[ 623-00-7 ]
[ 865-48-5 ]
[ 185259-36-3 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5413 - 5418.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5413 - 5418.

4
[ 185259-36-3 ]
[ 84697-13-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 3h;Reflux;	3.75 g of Mg(ClO4)2 (16.8 mmol, 0.1 equiv) in a 500 mL round-bottom flask was heated under vacuum at 130 C for 2 h and cooled to room temperature under argon. Then, 20 g of 4-cyanophenol (168 mmol, 1 equiv) in 200 mL of DCM was added, followed by 88.8 mL of Boc2O (387 mmol, 2.3 equiv). The resulting mixture was refluxed for at least 3 h and the reaction was monitored by TLC (20 % Et2O/hexanes). Once no more progression observed, the mixture was diluted in 300 mL of water and extracted twice with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated under vacuum. Purification with flash chromatography (20 % Et2O/hexanes) afforded 12.82g (73.2 mmol, 44 % yield) of 4-tert-butoxybenzonitrile. 1H NMR (400 MHz, CDCl3) δ 7.54 (dq, J = 9.1, 2.3 Hz, 2H, Ar), 7.02 (m, 2H, Ar), 1.40 (s, 9H, tBu-CH3). 12.82 g of 4-tert-butoxybenzonitrile (73.2 mmol) was dissolved in 110 mL of Et2O and 72.8 mL of a solution of 1M LiAlH4 in THF added dropwise. After refluxing for 3 h, the mixture was brought back to room temperature and quenched slowly with 10 mL of water, 10 mL of aqueous 1M NaOH and finally 50 mL of water. The resulting slurry was filtered, the residue washed with Et2O and the filtrate concentrated under vacuum. Afterward, 50 mL of water was added to the crude and the pH adjusted to 2.7 using aqueous 1M KHSO4. The aqueous phase was washed with Et2O, the pH readjusted to 9-10 with aqueous 1M NaOH and extracted twice with DCM. Combined organic layers were washed with brine, dried with MgSO4, filtered and evaporated to dryness under vacuum to afford 12.53 g (69.9 mmol, 95 % yield) of 4-tert-butoxybenzylamine. 1H NMR (400 MHz, CDCl3) δ 7.13 (m, 2H, Ar), 6.89 (m, 2H, Ar), 3.75 (s, 2H, CH2), 1.28 (s, 9H, tBu-CH3).
47.2%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 22h;Reflux; Inert atmosphere;	175 mL of 1M (0360) (175 mmol; 2.6 eq.) lithium aluminum hydride in THF was added to a round bottom flask with a stir bar and was cooled to 0C. A solution of 11.83 g (67.5 mmol) of 4-(tert- butoxy)benzonitrile (Alfa Aesar, Ward Hill, MA) in 50 mL of anhydrous THF was added to the stirring solution dropwise over the course of 30 minutes. The reaction was then fitted with a reflux condenser and was heated to reflux for six hours, followed by stirring overnight under argon, allowing the reaction to cool to room temperature. After 22 hours of total reaction time, the reaction mixture was cooled to 0C and was quenched with 7 mL of water, followed by 6 mL of 15% NaOH (aq) and an additional 17 mL of water. The resulting emulsion was filtered over celite, with the filter cake being washed with methanol (2 x 50 mL) and DCM (2 x 50 mL). The filtrate was evaporated, and the resulting dark yellow oil was dissolved into 75 mL of water. The solution was transferred to a separatory funnel and was extracted with ethyl acetate (4 x 150 mL). The combined extractions were washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, and evaporated in vacuo to give a dark yellow oil. The oil was separated using basic alumina chromatography and a solvent system of ethyl acetate/hexanes (20:80 to 50:50). The fractions containing the product (as evidenced by TLC) were combined and evaporated to give 5.71 g (47.2% yield) of 14 as a clear oil. lH NMR (300 MHz, CDC13) δ 7.19 (dd, J = 2.26, 6.46 Hz, 2H), 6.94 (dd, 7 = 2.32, 6.46 Hz, 2H), 4.38 (s, 2H), 1.31 (s, 9H). 13C NMR (75 MHz, CDCI3) δ 153.80, 135.32, 128.26, 124.27, 78.17, 54.93, 28.75. LRMS (EI) calculated mass (CnHisNO) (0361) [M+H]1+: 180.1388, mass found m/z: 180.1404 [M+H]1+.

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 8168 - 8172.
[2]Tetrahedron,2017,vol. 73,p. 6347 - 6355.
[3]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.
[4]European Journal of Organic Chemistry,2021,vol. 2021,p. 5135 - 5146.
[5]Patent: WO2017/100154,2017,A1 .Location in patent: Paragraph 00137.
[6]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3437 - 3440.

5
[ 98946-18-0 ]
[ 767-00-0 ]
[ 185259-36-3 ]

References: [1]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.

6
diazotized 4-<i>tert</i>-butoxy-aniline [ No CAS ]
aqueous CuCN [ No CAS ]
[ 185259-36-3 ]

References: [1]Journal of the Chemical Society,1956,p. 2455,246.

7
[ 185259-36-3 ]
[ 767-00-0 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 4162 - 4168.
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 985 - 990.

8
[ 185259-36-3 ]
[ 213820-65-6 ]

References: [1]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.

9
[ 185259-36-3 ]
[ 213820-67-8 ]

References: [1]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.

10
[ 185259-36-3 ]
2-[(2-[2-(2-{2-[Acetyl-(4-hydroxy-benzyl)-amino]-acetylamino}-acetylamino)-acetyl]-benzyl-amino}-acetyl)-isobutyl-amino]-acetamide [ No CAS ]

References: [1]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.

11
[ 185259-36-3 ]
2-[{2-[2-(2-[2-(Acetyl-isobutyl-amino)-acetyl]-benzyl-amino}-acetylamino)-acetylamino]-acetyl}-(4-hydroxy-benzyl)-amino]-acetamide [ No CAS ]

References: [1]Chemistry - A European Journal,1998,vol. 4,p. 1570 - 1580.

12
[ 185259-36-3 ]
[ 51503-08-3 ]

References: [1]Journal of the Chemical Society,1956,p. 2455,246.

13
[ 185259-36-3 ]
[ 51503-07-2 ]

References: [1]Journal of the Chemical Society,1956,p. 2455,246.

14
[ 185259-36-3 ]
[ 13205-47-5 ]

References: [1]Journal of the Chemical Society,1956,p. 2455,246.

15
(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl (Tol-BINAP) [ No CAS ]
Na(OtBu) [ No CAS ]
[ 623-00-7 ]
[ 185259-36-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	palladium diacetate; In diethyl ether; water; toluene;	EXAMPLE 12 This example demonstrates the palladium-catalyzed intermolecular synthesis of the aryl ether, 4-t-butoxybenzonitrile. A Schlenk tube was charged with Na(OtBu) (97 mg, 1.00 mmol), Pd(OAc)2 (5.6 mg, 0.025 mmol), (R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl (Tol-BINAP) (20.4 mg, 0.030 mmol), 4-bromobenzonitrile (91 mg, 0.50 mmol), and toluene (3 mL). The mixture was heated at 100 C. for 30 h under an atmosphere of argon. The mixture was cooled to room temperature and diethyl ether (20 mL) and water (20 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (19/1 hexaneethyl acetate) to afford 4-t-butoxybenzonitrile as a yellow oil (39 mg, 45% yield).

References: [1]Patent: US5847166,1998,A .

16
[ 185259-36-3 ]
[ 1264494-55-4 ]

References: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3437 - 3440.

17
(2-(diethylamino)-2-oxoethyl)zinc chloride [ No CAS ]
[ 185259-36-3 ]
C₁₃H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		General procedure: into a 25 mL round-bottomed flask was placed 4-bromobenzonitrile (0.36g, 2.0 mmol) under argon atmosphere, then 2.0 mL of THF was added into the flask. Next, 5.0 mL of 2-(N,N-diethyl amino)-2-oxoethyl)zinc chlorides (A) (0.5Min THF, 2.5 mmol) was cannulated at room temperature. Then, the whole mixture was allowed to heat to reflux over 12 h. The reaction mixture was cooled down to room temperature. To this mixture was added 5.0 mL of 3 M HCl (aq) and the resulting mixture was stirred. After 1 h, the reaction mixture was extracted with EtOAc (10 mL × 3). The combined organic solution was washed with saturated NaHCO3 (aq), brine, dried over anhydrous MgSO4, and purified by column chromatography (9/1 hexanes/EtOAc) to afford 0.29 g of yellow oily liquid (1c) in 49% isolated yield. Keto tautomer: 1H NMR (500 MHz, CDCl3, 25 C): δ = 7.89 (d, J = 8.5 Hz, 2H), 7.53 (d, J = 8.5 Hz, 2H), 4.02 (s, 2H), 3.41 (q, J = 7.2 Hz, 4H), 1.20 (t, J = 7.0 Hz, 6H) ppm. 13C NMR (125 MHz, CDCl3): δ = 193.35, 165.70, 135.07, 131.97, 128.85, 124.81, 45.70, 42.74, 14.21 ppm. Enol tautomer: 1H NMR (500 MHz, CDCl3, 25 C): δ = 15.60 (s, 1H), 7.65-7.60 (m, 4H), 5.71 (s, 1H), 3.37 (q, J = 7.0 Hz, 4H), 1.12 (t, J = 7.0 Hz, 6H) ppm. 13C NMR (125 MHz, CDCl3): δ = 171.19, 170.18, 134.10, 1132.00, 130.3, 127.43, 85.03, 40.55, 12.86 ppm. IR (KBr): = 2973, 1619, 1537, 1470, 777 cm-1. GC-MS (70 eV, EI+): m/z (%) = 297 ([M-H]+, 30), 183 (87), 102 (50, 72 (100); HRMS (EI+): m/z calcd. for C13H16BrNO2: 297.0364, found 297.0347.

References: [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2565 - 2568.

18
(2-(diethylamino)-2-oxoethyl)zinc chloride [ No CAS ]
[ 185259-36-3 ]
C₁₇H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		General procedure: The coupling reaction was conducted under the same condition used for 1c. After the reaction was completed, the reaction mixture was cooled down to room temperature. To this mixture was added 10.0 mL of saturated NaHCO3 (aq) and then extracted with EtOAc (10 mL × 3). The combined organic solution was washed with brine, dried over anhydrous MgSO4, and purified by column chromatography (90/10 hexanes/EtOAc) to afford 0.25g of yellow oily liquid (2c) in 84% isolated yield; 1HNMR (500 MHz,CDCl3): δ =7.52 (d, J =8.5 Hz, 2H), 7.42 (d, J = 8.5 Hz, 2H), 5.00 (s, 1H), 3.40 (q, J = 7.5 Hz, 2H), 3.80 (q, J = 7.5 Hz, 2H), 2.16 (s, 2H), 1.26 (t, J = 7.5 Hz, 3H), 1.18 (t, J = 7.5 Hz, 3H) ppm. 13CNMR(125 MHz, CDCl3): δ = 169.31, 157.26, 138.19, 131.80, 127.93, 123.58, 84.56, 42.24, 40.24, 14.40, 13.64 ppm. HRMS (EI+): m/z calcd. for C13H17BrN2O: 296.0524, found 296.0499. IR (KBr): = 3379, 3273, 2973, 1608, 1590, 1478 cm-1. GC-MS (70 eV, EI+): m/z (%) = 296 ([M-H]+, 16), 226 (87), 224 (86), 197 (27), 117 (34), 72 (100).

References: [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2565 - 2568.

19
[ 185259-36-3 ]
(Z)-4-(tert-butoxy)-N'-hydroxybenzimidamide [ No CAS ]