Home Cart 0 Sign in  
X

[ CAS No. 18962-07-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 18962-07-7
Chemical Structure| 18962-07-7
Chemical Structure| 18962-07-7
Structure of 18962-07-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 18962-07-7 ]

Related Doc. of [ 18962-07-7 ]

Alternatived Products of [ 18962-07-7 ]

Product Details of [ 18962-07-7 ]

CAS No. :18962-07-7 MDL No. :MFCD01922006
Formula : C11H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PWASYRSZCSTUIW-UHFFFAOYSA-N
M.W : 178.23 Pubchem ID :249810
Synonyms :

Calculated chemistry of [ 18962-07-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.74
TPSA : 26.3 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) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 2.03
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.191 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.0873 mg/ml ; 0.00049 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.0869 mg/ml ; 0.000488 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 18962-07-7 ]

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

Application In Synthesis of [ 18962-07-7 ]

* 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 [ 18962-07-7 ]
  • Downstream synthetic route of [ 18962-07-7 ]

[ 18962-07-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 78-77-3 ]
  • [ 123-08-0 ]
  • [ 18962-07-7 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 3 h; Inert atmosphere Step 2:
Preparation of 4-isobutoxybenzaldehyde (Compound XIII)
4-Hydroxybenzaldehyde (10 g; 0.082 mol), potassium carbonate (33.95 g; 0.246 mol) and potassium iodide (1.36 g; 0.008 mol) were suspended in N,N-dimethylformamide (50 mL).
Isobutyl bromide (26.7 mL; 0.246 mol) was added and the reaction was heated at 70° C. under nitrogen for 3 hours.
The reaction was cooled down, diluted by using 150 mL of water and extracted by using 300 mL of ethyl acetate.
The organic layer was extracted five times by using 150 mL of 10percent NaCl solution, dried under Na2SO4, filtered and concentrated which resulted in 14.3 g (98percent) of yellow oily product of 4-isobutoxybenzaldehyde (Compound XIII).
96% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 85℃; for 6 h; In Three 250mL flask was added compound 7 (10.0g, 81.9mmol), anhydrous potassium carbonate (22.6g, 163.8 mmol), potassium iodide (1.4g, 8.2mmol) and 50mLDMF, heated to 85 deg C, bromine was slowly added to the reaction system on behalf of the isobutane (22.4g, 163.8mmol), the addition was completed, the reaction system for 3h at 85 deg C condition, and then continued to the system slowly added bromo-butane (11.2g, 81.9mmol), the system continues at 85 condition The reaction 3h.The reaction was stopped, cooled to room temperature, filtered and the filter cake was washed twice with 100mL of ethyl acetate.The filtrate was poured into 250mL of water, the organic phase was separated, the aqueous phase was extracted three times each with 100mL ethyl acetate and the combined organic phase was washed with 150mL saturated aqueous NaCl solution once, dried over anhydrous sodium sulfate, the drying is complete, filtered and the filtrate rotary done compound 8 14.0g, as a pale yellow liquid, yield 96percent
95% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 85℃; for 6 h; Add p-hydroxybenzaldehyde (15.0g, 122.8mmo1) to anhydrous 250mL three-necked bottle, anhydrous potassium carbonate (25.4g,184.2mmoL),Potassium iodide (1.4 g, 12.3 mmoL) and 75 mL of DMF were heated to 85 ° C, and bromoisobutane (50.5 g, 368.4 mmol) was slowly added to the reaction system. After the addition, the system was reacted at 85 ° C for 6 h.The reaction was stopped, the system was cooled to room temperature, filtered, and the filter cake was washed twice with 90 mL of ethyl acetate.The filtrate was poured into 250 mL of water, the organic phase was separated, and the aqueous phase was extracted three times with 90 mL of ethyl acetate. The organic phase was combined and washed once with 150 mL of brine.Drying over anhydrous sodium sulfate, drying was completed, filtered, and the filtrate was dried to give 20.8 g of compound, pale yellow liquid, yield 95percent.
178 g With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; 122g 4-hydroxybenzaldehyde (1mol), 600mL DMF, 256g of potassium carbonate (1.85 mol) of potassium iodide and 12g (0.07 mol) added to the reaction flask and heated to 100 deg.] C, dropwise addition of 274g bromo isobutane dropwise Bi, 100 deg.] C the reaction overnight, TLC show completion of the reaction of 4-hydroxybenzaldehyde to treatment, the reaction solution was filtered off with suction, washed with water and the filtrate washed with 600mL * 2 times 600mL dichloromethane, washed once with saturated brine 600mL, separated the organic phase was dried over anhydrous sodium sulfate, the solvent was evaporated to dryness to give 178 g product, directly into the next step.

Reference: [1] Patent: US2018/37549, 2018, A1, . Location in patent: Paragraph 0151
[2] Patent: CN105418460, 2016, A, . Location in patent: Paragraph 0053; 0056; 0057; 0058; 0059
[3] Patent: CN108358817, 2018, A, . Location in patent: Paragraph 0055; 0056; 0057
[4] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124
[5] Patent: WO2006/36874, 2006, A1, . Location in patent: Page/Page column 21
[6] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 752 - 754
[7] Patent: WO2014/85362, 2014, A1, . Location in patent: Paragraph 0066
[8] Chemical Communications, 2015, vol. 51, # 16, p. 3403 - 3406
[9] Patent: WO2017/15272, 2017, A1, . Location in patent: Paragraph 0203
[10] Patent: CN107011137, 2017, A, . Location in patent: Paragraph 0016; 0028; 0029
[11] Patent: CN107216271, 2017, A, . Location in patent: Paragraph 0054; 0055
  • 2
  • [ 513-38-2 ]
  • [ 123-08-0 ]
  • [ 18962-07-7 ]
Reference: [1] Patent: US2699448, 1952, ,
[2] Patent: WO2008/112368, 2008, A2, . Location in patent: Page/Page column 37-38
  • 3
  • [ 78-83-1 ]
  • [ 459-57-4 ]
  • [ 18962-07-7 ]
YieldReaction ConditionsOperation in experiment
0.6 g With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In water; toluene at 50 - 52℃; Example 2g: Alternatively 4-zso-butyloxybenzylamine (SM2) and 4-iso- but loxybenzylamine acetate (SM2b) are prepared according to following scheme. [0214] KOH (1.36g, 24.2 mmol, 3 eq) was dissolved in water (1.4 ml) and added to the solution of 4-fluorobenzaldehyde (1.0 g, 8.1 mmol, 1 eq). Isobutanol (0.66 g, 8.9 mmol, 1.1 eq) and tetrabutyl ammonium hydrogensulfate (TBAH, 0.27 g) in toluene (7 ml). The reaction mixture was vigorously stirred at 50-52 °C overnight and thereafter diluted with water (5 ml), dried and concentrated in vacuo to give 0.877 g of crude product. The crude product was purified by column chromatography using ethyl acetate : heptane to give 0.6 g of 4-isobutoxy benzaldehyde. 4-Isobutoxy benzaldehyde can thereafter be converted to SM2 and SM2b respectively using the procedure outline in example 2b.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 10, p. 2547 - 2550
[2] Patent: WO2017/15272, 2017, A1, . Location in patent: Paragraph 0214
  • 4
  • [ 513-38-2 ]
  • [ 497-19-8 ]
  • [ 123-08-0 ]
  • [ 18962-07-7 ]
YieldReaction ConditionsOperation in experiment
0.125 mol, 46% With potassium hydroxide In ethanol (a)
Synthesis of 4-(2-methylpropoxy)benzaldehyde
A 1000 mL, 1 neck, round-bottomed flask equipped with a magnetic stirrer and reflux condenser is charged with 4-hydroxybenzaldehyde (33.18 g, 0.272 mol), 100 ml of ethanol, and a solution of potassium hydroxide (20.42 g, 0.309 mol) in 100 mL of ethanol.
The reaction mixture is heated with stirring for one-half hour.
Next 1-iodo-2-methylpropane (100 g, 0.543 mol) is added and the mixture refluxed for 12 hours.
After cooling, the solvents are removed by rotary evaporation to yield a brown solid which is added to a separatory funnel containing 500 mL ether and 500 mL of 5percent aqueous sodium carbonate.
The layers are separated and the aqueous phase is washed with ether (2*500 mL).
The combined ether layers are washed with pH 12 sodium hydroxide solution (5*200 mL) until the washes are colorless.
The organic solution is then washed with brine (100 mL) and dried over magnesium sulfate.
After filtration and removal of the solvents by rotary evaporation, a viscous yellow liquid is obtained.
This material is purified by Kugel-Rohr distillation to give 22.3 g (0.125 mol, 46percent) of a colorless liquid.
1 H NMR (60 MHz, CDCl3): 1.00 (d, 6H); 2.0 (m, 1H); 3.65 (d, 2H); 6.75, 6.90, 7.60, 7.75 (aa'bb' quartet, 4H); 9.75 (s, 1H).
Reference: [1] Patent: US4999186, 1991, A,
  • 5
  • [ 1126-75-6 ]
  • [ 18962-07-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1956, vol. <4> 3, p. 274,275
  • 6
  • [ 100-97-0 ]
  • [ 40141-14-8 ]
  • [ 18962-07-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1956, vol. <4> 3, p. 274,275
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 18962-07-7 ]

Febuxostat Related Intermediates

Chemical Structure| 160844-75-7

[ 160844-75-7 ]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

Chemical Structure| 1761-61-1

[ 1761-61-1 ]

5-Bromo-2-hydroxybenzaldehyde

Chemical Structure| 22900-83-0

[ 22900-83-0 ]

Ethyl 2-bromo-4-methylthiazole-5-carboxylate

Chemical Structure| 7210-76-6

[ 7210-76-6 ]

Ethyl 2-amino-4-methylthiazole-5-carboxylate

Chemical Structure| 3011-34-5

[ 3011-34-5 ]

4-Hydroxy-3-nitrobenzaldehyde

Related Functional Groups of
[ 18962-07-7 ]

Aryls

Chemical Structure| 4397-53-9

[ 4397-53-9 ]

4-(Benzyloxy)benzaldehyde

Similarity: 0.95

Chemical Structure| 5736-85-6

[ 5736-85-6 ]

4-Propoxybenzaldehyde

Similarity: 0.95

Chemical Structure| 1700-37-4

[ 1700-37-4 ]

3-Benzyloxybenzaldehyde

Similarity: 0.93

Chemical Structure| 3722-80-3

[ 3722-80-3 ]

4,4'-(Propane-1,3-diylbis(oxy))dibenzaldehyde

Similarity: 0.93

Chemical Structure| 5736-88-9

[ 5736-88-9 ]

4-Butoxybenzaldehyde

Similarity: 0.93

Aldehydes

Chemical Structure| 4397-53-9

[ 4397-53-9 ]

4-(Benzyloxy)benzaldehyde

Similarity: 0.95

Chemical Structure| 5736-85-6

[ 5736-85-6 ]

4-Propoxybenzaldehyde

Similarity: 0.95

Chemical Structure| 1700-37-4

[ 1700-37-4 ]

3-Benzyloxybenzaldehyde

Similarity: 0.93

Chemical Structure| 3722-80-3

[ 3722-80-3 ]

4,4'-(Propane-1,3-diylbis(oxy))dibenzaldehyde

Similarity: 0.93

Chemical Structure| 5736-88-9

[ 5736-88-9 ]

4-Butoxybenzaldehyde

Similarity: 0.93

Ethers

Chemical Structure| 4397-53-9

[ 4397-53-9 ]

4-(Benzyloxy)benzaldehyde

Similarity: 0.95

Chemical Structure| 5736-85-6

[ 5736-85-6 ]

4-Propoxybenzaldehyde

Similarity: 0.95

Chemical Structure| 1700-37-4

[ 1700-37-4 ]

3-Benzyloxybenzaldehyde

Similarity: 0.93

Chemical Structure| 3722-80-3

[ 3722-80-3 ]

4,4'-(Propane-1,3-diylbis(oxy))dibenzaldehyde

Similarity: 0.93

Chemical Structure| 5736-88-9

[ 5736-88-9 ]

4-Butoxybenzaldehyde

Similarity: 0.93