[ CAS No. 13205-47-5 ] {[proInfo.proName]}

Name: 13205-47-5|4-(tert-Butoxy)benzoic acid|97%
Brand: Ambeed
SKU: A218620
Price: 14.0 USD
Availability: InStock
Rating: 97 (25 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 13205-47-5

Structure of 13205-47-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 13205-47-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13205-47-5 ]

SDS Specification

Alternatived Products of [ 13205-47-5 ]

Product Details of [ 13205-47-5 ]

CAS No. :	13205-47-5	MDL No. :	MFCD00082602
Formula :	C₁₁H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHTBQELRENWGTE-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	535302
Synonyms :

Calculated chemistry of [ 13205-47-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.35
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.94
Log Po/w (WLOGP) :	2.56
Log Po/w (MLOGP) :	2.23
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	2.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.02
Solubility :	0.187 mg/ml ; 0.000965 mol/l
Class :	Soluble
Log S (Ali) :	-3.58
Solubility :	0.0512 mg/ml ; 0.000264 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.73
Solubility :	0.366 mg/ml ; 0.00188 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 13205-47-5 ]

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 [ 13205-47-5 ]

* 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 [ 13205-47-5 ]
Downstream synthetic route of [ 13205-47-5 ]

[ 13205-47-5 ] Synthesis Path-Upstream 1~6

1
[ 120-47-8 ]
[ 115-11-7 ]
[ 13205-47-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 41, p. 10745 - 10748[2] Angew. Chem., 2013, vol. 125, # 41, p. 10945 - 10948,4
[3] Patent: US5912258, 1999, A,

2
[ 1194-02-1 ]
[ 13205-47-5 ]
[ 99985-67-8 ]

Reference： [1] Patent: US5378728, 1995, A,

3
[ 1194-02-1 ]
[ 75-65-0 ]
[ 13205-47-5 ]

Reference： [1] Chemical Biology and Drug Design, 2016, vol. 87, # 3, p. 382 - 397

4
[ 507-20-0 ]
[ 99-96-7 ]
[ 13205-47-5 ]

Reference： [1] Journal of Chemical Research - Part S, 2000, # 5, p. 252 - 253

5
[ 99985-67-8 ]
[ 13205-47-5 ]

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

6
[ 185259-36-3 ]
[ 13205-47-5 ]

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

[ 13205-47-5 ] Synthesis Path-Downstream 1~48

1
[ 13205-47-5 ]
[ 51503-08-3 ]

Reference： [1]Journal of the Chemical Society,1956,p. 2455,246
[2]Journal of Organic Chemistry USSR (English Translation),1973,vol. 9,p. 2468 - 2472
Zhurnal Organicheskoi Khimii,1973,vol. 9,p. 2446 - 2451

2
[ 99985-67-8 ]
[ 13205-47-5 ]

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

3
[ 646-19-5 ]
[ 13205-47-5 ]
[ 27890-77-3 ]

Reference： [1]Patent: DE1943787,1970,
Chem.Abstr.,1970,vol. 72
[2]Patent: US4009208,1977,A

Yield	Reaction Conditions	Operation in experiment
		General procedure: 4-tert-Butoxy-3-methoxybenzaldehyde (130 mg, 0.62 mmol) was suspended in a mixture of dioxane (520 muL) and potassium hydroxide (6.5 mL of 0.20 M, 1.3 mmol). KMnO4 (150 mg, 0.93 mmol) was added and the reaction was stirred vigorously for 16 h. The reaction mixture was filtered and then concentrated to 3 mL. Hydrochloric acid (1M, 4 mL) was added and the resulting precipitate was filtered (after standing for 15 minutes) and washed with 1M HCl and a small amount of water to yield 4-tert-butoxy-3-methoxy-benzoic acid (68 mg, 49%) as a white solid. Rf=0.23 (SiO2, 40% ethyl acetate in hexanes); ESI-MS m/z calc. 224.1. found 225.2 (M+1) +. Retention time: 1.66 minutes (3 min run). 1H NMR (400 MHz, DMSO) delta 12.80 (s, 1H), 7.66-7.41 (m, 2H), 7.09 (d, J=8.8 Hz, 1H), 3.78 (s, 3H), 1.32 (s, 9H).

5
[ 507-20-0 ]
[ 99-96-7 ]
[ 13205-47-5 ]

Reference： [1]Journal of Chemical Research - Part S,2000,p. 252 - 253

6
tert-butyl 4-tert-butoxybenzoate [ No CAS ]
[ 13205-47-5 ]

Reference： [1]Synlett,2002,p. 826 - 828
[2]Journal of Organic Chemistry,2005,vol. 70,p. 3737 - 3740

7
[ 13205-47-5 ]
cholesteryl-(L-lactic acid)_n oligomer, n=25 [ No CAS ]
cholesteryl-(L-lactic acid)_n 4-(tert-butoxy)benzoate, n=25 [ No CAS ]

Reference： [1]Macromolecules,2002,vol. 35,p. 746 - 759

8
[ 99-96-7 ]
acid [ No CAS ]
[ 13205-47-5 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 3737 - 3740

9
[ 13205-47-5 ]
[ 51503-07-2 ]

10
[ 185259-36-3 ]
[ 13205-47-5 ]

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

11
[ 790689-68-8 ]
[ 13205-47-5 ]
C₂₃H₂₄N₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; for 18h;	Allyl (5-AMINO-1, 3-benzothiazol-2-yl) methyl carbonate (see above) (97.0 mg, 0.370 mmol) and <strong>[13205-47-5]4-tert-butoxybenzoic acid</strong> (71.0 mg, 0.370 mmol) were mixed in a mixture of DCM (5.00 mL) and DMF (5.00 mL) with EDC (220 mg, 1.15 mmol) and DMAP (236 mg, 1.15 mmol). ). The mixture was stirred for 18 hours, and the solvents were evaporated. The residue was dissolved in DCM and washed with a saturated solution of NAHCO3. The mixture was dried with NA2SO4, filtered and concentrated under reduced pressure. The crude product was purified by Gilson reverse phase HPLC (Luna 15 u, C18 (2) 250 mm X 21.2 mm), eluting with mixtures of H20 and MECN with 0.1% TFA the O-alloc protected derivative of the title compound: MS [M+] calc. 440.0 found 440.9.

Reference： [1]Patent: WO2004/96784,2004,A1 .Location in patent: Page 26
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6205 - 6211

12
[ 120-47-8 ]
[ 115-11-7 ]
[ 13205-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; sulfuric acid; In ethanol; dichloromethane; water;	Reference Example 3 Synthesis of 4-tert-butoxybenzoic acid Ethyl 4-hydroxybenzoate (16.6 g), isobutene (25 g), and 95% sulfuric acid (0.5 ml) were stirred in dichloromethane (300 ml) overnight at 0 C. The reaction mixture was washed with 20% sodium carbonate aqueous solution, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was dissolved in ethanol (32 ml) and the solution, with potassium hydroxide (7.5 g) and water (6 ml) added thereto, was refluxed with stirring for 2 hours. The reaction mixture was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from ethyl acetate to yield 9.3 g of the aimed compound.

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10745 - 10748
Angew. Chem.,2013,vol. 125,p. 10945 - 10948,4
[2]Patent: US5912258,1999,A

13
[ 13205-47-5 ]
[ 98-59-9 ]
tert-butyl (3R,4S)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; dmap; sodium hydroxide; In n-heptane; dichloromethane; water;	EXAMPLE 16 9.06 g of p-toluenesulphonyl chloride in 75 ml of dichloromethane were added at room temperature to 11.5 g of 4-(tert-butoxy)-benzoic acid and 13.1 g of 4-dimethylaminopyridine in 100 ml of dichloromethane. The reaction mixture was stirred for a further 2 hours. The solution was then added in the course of 1 hour to 11.5 g of the compound prepared in Example 10 dissolved in 50 ml of dichloromethane. After stirring at room temperature for 1 hour, the reaction mixture was washed with 100 ml of 1N NaOH, 100 ml of 1N HCl and 100 ml of water. All aqueous phases were extracted with 50 ml of dichloromethane. The combined organic phases were dried over sodium sulphate and the solvent was separated under reduced pressure. The foam-like residue was dissolved in 400 ml of hot heptane and left to crystallize at room temperature overnight. The crystals were washed with 25 ml of heptane and dried at 50/25 mbar to yield 17.3 g of tert-butyl (3R,4S)-3-(4-tert-butoxy-benzoylamino)-4-hydroxy-azepan-1-carboxylate of melting point 131.5-132.5 C.

Reference： [1]Patent: US5902882,1999,A

14
2-amino-5-diethylaininoethylthio-1,3,4-thiadiazole [ No CAS ]
[ 13205-47-5 ]
2-(4-tert-butoxybenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; water;	Example 8 Synthesis of 2-(4-tert-butoxybenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazole Sodium hydride (0.6 g) and 2-amino-5-diethylaininoethylthio-1,3,4-thiadiazole (2.3 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes while being cooled with ice. 4-Tert butoxybenzoic acid (1.9 g) and carbonyldiimidazole (1.8 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes at room temperature and the mixture was added to the former reaction mixture. The mixture was stirred for 4 hours at room temperature, and then concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1). The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 3.1 g of the aimed compound. 1 H-NMR(CDCl3) delta:8.16 (2H, d, J=8.8 Hz), 7.10 (2H, d, J=8.8 Hz), 3.37 (2H, t, J=6.8 Hz), 2.83 (2H, t, J=6.8 Hz), 2.56 (4H, q, J=7.3 Hz), 1.44 (9H, s), 1.01 (6H, t, J=7.3 Hz).

Reference： [1]Patent: US5912258,1999,A

15
[ 1194-02-1 ]
[ 13205-47-5 ]
[ 99985-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In sodium hydroxide; ethanol; water; dimethyl sulfoxide;	EXAMPLE 7 4-(1,1-dimethylethoxy)benzoic acid A suspension of hexane washed sodium hydride (1.3 grams of a 60% suspension in oil) in 15 ml. of dry dimethylsulfoxide is heated at 70 C. under nitrogen for 1 hour. It is then cooled to 30 C. and 1.5 grams of tertiary butanol is slowly added. The resultant mixture is stirred for 30 minutes; and then 2.4 grams of para-fluorobenzonitrile is added and stirring is continued at room temperature-overnight. The reaction mixture is heated at 60 C. for 6 hours and then cooled and diluted with diethyl ether. The ether solution is washed with water and brine and is then dried over sodium sulfate and evaporated to give an oily residue. 3.3 grams of the residue is refluxed overnight with 5.0 ml. of 2N sodium hydroxide in 40 ml. of ethanol. The mixture is then concentrated to dryness, redissolved in water and washed with diethyl ether. The aqueous phase is acidired with 2N hydrochloric acid and then extracted with methylene chloride. The organic fractions are combined, dried over sodium sulfate and then evaporated to give an oil, which is Chromatographed on silica gel with methylene chloride as the eluant to yield the title compound as a crystalline product (m.p. 132-133 C.) The sodium salt is prepared by dissolving 194 mg. of the above acid in 1.0 ml. of 1.0N sodium hydroxide. The resultant solution is evaporated to dryness, triturated with ethanol and filtered to give the sodium salt. When steps B and C of example 2 are carried out using an equivalent amount of 4-(1,1-dimethylethoxy) benzoic acid in place of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid there is obtained 4-(1,1-dimethylethoxy) benzamide (m.p. 135-136 C.).

Reference： [1]Patent: US5378728,1995,A

16
[ 13205-47-5 ]
[ 882993-83-1 ]

Yield	Reaction Conditions	Operation in experiment
20%		Intermediate 3.4-Lambda?rt-butoxy-2-methylbenzoic acidA solution of <strong>[13205-47-5]4-tert-butoxybenzoic acid</strong> (500 mg, 2.57 mmol) in THF (10.0 mL) was cooled to -78 0C. A solution of sBuLi (7.84 mmol, 5.60 mL, 1.4 M in cyclohexane) and TMEDA (930 mg, 8.00 mmol, 1.20 mL) in THF (10.0 mL) was cooled to -78 0C and added drop-wise over 20 minutes to the first solution. The mixture was stirred at -78 C for 1 hour, and then iodomethane (2.27 g, 16.0 mmol, 1.00 mL) was added. The mixture was slowly warmed to room temperature and stirred for 16 hours. The reaction was quenched with 0.5 N HCl, and the aqueous phase was extracted with EtOAc. The combined organic phases were dried with Na2SO4, filtered and concentrated. The product was purified by flash chromatography on silica gel eluting with a mixture of hexanes and EtOAc (9:1), (107 mg, 0.510 mmol, 20%). 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 1.42 (s, 9 H) 2.63 (s, 3 H) 6.85 - 6.90 (m, 2 H) 8.02 (d, J=8.40 Hz, 1 H).

Reference： [1]Patent: WO2006/38871,2006,A1 .Location in patent: Page/Page column 28

17
[ 1192829-62-1 ]
[ 13205-47-5 ]
[ 1192829-42-7 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 4-[(1 ,1-dimethylethyl)oxy]benzoic acid (Apin chemicals) (1 17 mg, 0.603 mmol), HATU (232 mg, 0.610 mmol), Hunig's base (0.263 ml_, 1.506 mmol) in N, N-Dimethylformamide (DMF) (1 ml) was stirred for 1 hr before the addition of N-hydroxy- 5-isoquinolinecarboximidamide (D1 ; 94 mg, 0.502 mmol) in N,N-dimethylformamide(DMF) (1 ml). The reaction was left to stir at room temperature for 2hrs and then heated to 120 0C for 2hr in the microwave. The reaction mixture was concentrated in vacuo and purified by preparative HPLC (Waters Sunfire C18 column, eluting with solvents A/B (A: Water + 0.1 % Formic acid, B: MeCN + 0.1% Formic acid)) to give the title compound (31 .5mg)MS (ES) C2I H19N3O2 requires 345; found 346 [M+H]+.1 H NMR (DMSO-d6) Shift: 9.57 (s, 1 H), 8.82 (d, J = 6.0 Hz, 1 H), 8.72 (d, J = 6.0 Hz, 1 H), 8.66 (d, J = 7.5 Hz, 1 H), 8.47 (d, J = 8.5 Hz, 1 H), 8.17 (d, J = 9.0 Hz, 2H), 7.96 (dd, J = 8.5, 7.5 Hz, 1 H), 7.28 (d, J = 9.0 Hz, 2H), 1.44 (s, 9H)

Reference： [1]Patent: WO2009/133136,2009,A1 .Location in patent: Page/Page column 70-71

18
[ 790689-68-8 ]
[ 13205-47-5 ]
4-tert-butoxy-N-[2-(hydroxymethyl)-1,3-benzothiazol-5-yl]benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6205 - 6211

19
[ 13205-47-5 ]
C₁₁H₁₆N₂O₂ [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4980 - 4991

20
[ 13205-47-5 ]
[ 1423160-41-1 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4980 - 4991

21
[ 13205-47-5 ]
[ 1423160-48-8 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4980 - 4991

22
[ 13205-47-5 ]
[ 1423160-58-0 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4980 - 4991

23
[ 67-56-1 ]
[ 13205-47-5 ]
[ 62370-08-5 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4980 - 4991

24
[ 13205-47-5 ]
Cu2(N,N'-(3,7,13,17-tetrathioxo-4,8,12,16-tetraazanonadecane-1,19-diyl)bis(4-tertbutoxybenzothioamide))(HSO4)2 [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10745 - 10748
Angew. Chem.,2013,vol. 125,p. 10945 - 10948,4

25
[ 13205-47-5 ]
N,N'-(3,7,13,17-tetrathioxo-4,8,12,16-tetraazanonadecane-1,19-diyl)bis(4-tert-butoxybenzothioamide) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10745 - 10748
Angew. Chem.,2013,vol. 125,p. 10945 - 10948,4

26
[ 1227185-31-0 ]
[ 13205-47-5 ]
N,N'-(3,7,13,17-tetraoxo-4,8,12,16-tetraazanonadecane-1,19-diyl)bis(4-tert-butoxybenzamide) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10745 - 10748
Angew. Chem.,2013,vol. 125,p. 10945 - 10948,4

27
[ 13205-47-5 ]
C₃₇H₆₅N₆O₉Pol [ No CAS ]
C₄₈H₇₇N₆O₁₁Pol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4473 - 4485

28
[ 13205-47-5 ]
C₃₇H₆₅N₆O₉Pol [ No CAS ]
C₄₈H₇₇N₆O₁₁Pol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4473 - 4485

29
[ 13205-47-5 ]
[ 109-76-2 ]
N,N'-(propane-1,3-diyl)bis(4-tert-butoxybenzamide) [ No CAS ]