[ CAS No. 156-38-7 ] {[proInfo.proName]}

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

2D 3D

Structure of 156-38-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 156-38-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 156-38-7 ]

SDS Specification

Alternatived Products of [ 156-38-7 ]

Product Details of [ 156-38-7 ]

CAS No. :	156-38-7	MDL No. :	MFCD00004347
Formula :	C₈H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQXPVVBIMDBYFF-UHFFFAOYSA-N
M.W :	152.15	Pubchem ID :	127
Synonyms :	4-HPAA;NSC 27460;NSC 25066;para-Hydroxyphenylacetic Acid;p-Hydroxyphenylacetic Acid;para-HPAA;p-HPAA	Chemical Name :	4-Hydroxyphenylacetic Acid

Calculated chemistry of [ 156-38-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.01
TPSA :	57.53 ?2

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) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.88
Log Po/w (XLOGP3) :	0.75
Log Po/w (WLOGP) :	1.02
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	1.06
Consensus Log Po/w :	0.95

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.53
Solubility :	4.52 mg/ml ; 0.0297 mol/l
Class :	Very soluble
Log S (Ali) :	-1.54
Solubility :	4.41 mg/ml ; 0.029 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.58
Solubility :	3.97 mg/ml ; 0.0261 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 156-38-7 ]

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 [ 156-38-7 ]

* 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 [ 156-38-7 ]
Downstream synthetic route of [ 156-38-7 ]

[ 156-38-7 ] Synthesis Path-Upstream 1~2

1
[ 156-38-7 ]
[ 10338-51-9 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 524 - 530
[2] Patent: CN107880085, 2018, A,

2
[ 156-38-7 ]
[ 1698-53-9 ]
[ 1698-60-8 ]

Reference： [1] Patent: US4454318, 1984, A,

[ 156-38-7 ] Synthesis Path-Downstream 1~11

1
[ 156-38-7 ]
[ 60211-57-6 ]
[ 29022-11-5 ]
resin-bound phenol [ No CAS ]
{2-[4-(3,5-dichloro-benzyloxy)-phenyl]-acetylamino}-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 3763 - 3767

2
[ 78385-26-9 ]
[ 156-38-7 ]
[ 497870-35-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 7049 - 7064

3
[ 156-38-7 ]
[ 6100-60-3 ]
[ 79744-58-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With boron trifluoride diethyl etherate; for 0.25h;Heating / reflux;	A mixture of 4-methoxyresorcinol (1.3 g, 9.29 mmol) and 4-hydroxyphenylacetic acid (1.27 g, 8.36 mmol) in BF3.Et2O (6.85 ml, 55.7 mmol) was heated at reflux temperature for 15 min under N2. After cooling to room temperature, the dark solution was poured into saturated aqueous sodium acetate (100 ml) and extracted with ethyl acetate (3×50 ml). The combined ethyl acetate layer was washed with 10% aq. NaHCO3 (50 ml) and water (100 ml), respectively, and dried with MgSO4. The solvent was evaporated under reduced pressure, and the dark brown oil was subjected to chromatography (CH2Cl2: EtOAc=8:2) to give the title compound as a yellow solid (1.1 g, 48%), mp 157-159 C. 1H NMR (300 MHz, DMSO-d6) delta 12.38 (s, 1H, OH), 10.48 (br s, 1H, OH), 9.29 (br s, 1H, OH), 7.40 (s, 1H, H-6), 7.08 (d, J=8.6 Hz, 2H, H-2', 6'), 6.69 (d, J=8.6 Hz, 2H, H-3', 5'), 6.30 (s, 1H, H-3), 4.16 (s, 2H, CH2), 3.76 (s, 1H, OCH3); 13C NMR (75 MHz, DMSO-d6) delta 202.2 (C-CO), 159.3 (C-4), 156.0 (C-4'), 155.4 (C-2), 141.0 (C-5), 130.4 (C-2',6'), 125.3 (C-1'), 115.6 (C-3',5'), 113.3 (C-6), 110.3 (C-1), 103.2 (C-2), 56.3 (C-OCH3), 43.6 (C-CH2). m/z=275 (M++1, 100%), 274 (16), 257 (9), 167 (18), 212; HRMS: C15H14O5 requires 274.9841 found 274.0829.

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 8375 - 8378
[2]Journal of Natural Products,2003,vol. 66,p. 149 - 151
[3]Patent: US2007/203227,2007,A1 .Location in patent: Page/Page column 3
[4]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 346 - 360

4
[ 156-38-7 ]
[ 61439-59-6 ]

Reference： [1]Carbohydrate Research,2006,vol. 341,p. 2469 - 2477
[2]Journal of Organic Chemistry,2016,vol. 81,p. 1367 - 1377
[3]Patent: CN107880085,2018,A
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5852 - 5869

5
[ 156-38-7 ]
resin-bound phenol [ No CAS ]
[ 61439-59-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 525 - 528

6
[ 68500-37-8 ]
[ 156-38-7 ]
[ 847604-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In dimethyl sulfoxide; at 100℃;	Intermediate 87a: [4- (7-METHOXY-QUINOLIN-4-YLOXY)-PHENYL]-ACETIC acid A mixture of 4-CHLORO-7-METHOXY-QUINOLINE (200 mg, 1.036 MMOL), 4-HYDROXYPHENYLACETIC acid (158 mg, 1.036 MMOL), and Cs2CO3 (1.02 g, 3.11 MMOL) IN 2 mL of DMSO was heated at 100°C overnight. The mixture was then cooled to room temperature. EtOAc and water were added. The aqueous layer was acidified with 1 N HCI until a precipitate was formed. The solid was filtered and washed with water. The solid was dried in a vacuum-oven at 60°C overnight. The intermediate 87a (160 mg) was obtained as A brown solid NMR (300 MHz, CD30D) 8 8.63 (s, 1H), 8.39 (d, 1H, J= 9.04 Hz), 7.47-7. 28 (m, 4H), 7.16 (d, 2H, J= 7.72 Hz), 6.76 (s, 1H), 3.93 (s, 3H), 3.58 (s, 2H). LCMS (ESI+) [M+H]/Z Calc'd 310, found 310.

Reference： [1]Patent: WO2005/21554,2005,A1 .Location in patent: Page/Page column 95

7
[ 417721-36-9 ]
[ 156-38-7 ]
2-[4-(6-carbamoyl-7-methoxyquinolin-4-yloxy)phenyl]acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[417721-36-9]4-chloro-7-methoxyquinoline-6-carboxamide</strong> (1.26 g), 5 2-(4-hydroxyphenyl)acetic acid (0.85 g), caesium carbonate (5.47 g) and DMF (15 ml) was stirred and heated to 1000C for 14 hours. The mixture was cooled to ambient temperature and diethyl ether (50 ml) was added. The precipitate was isolated and dissolved in water and the solution was acidified to pH4.5 by the addition of 6N aqueous hydrochloric acid. The resultant precipitate was isolated, washed with water and with diethyl ether and dried under 0 vacuum. There was thus obtained the required starting material (0.98 g); 1HNMR: (DMSOd6) 4.04 (s, 3H), 6.48 (d, IH), 7.25 (d, 2H)5 7.42 (d, 2H), 7.52 (s, IH), 7.73 (br s, IH), 7.86 (br s, <n="135"/>IH)5 8.67 (m, 2H); Mass Spectrum: M+H+353.

Reference： [1]Patent: WO2007/99326,2007,A1 .Location in patent: Page/Page column 133-134

8
[ 156-38-7 ]
[ 55453-87-7 ]

Reference： [1]Patent: WO2011/128911,2011,A2

9
[ 156-38-7 ]
[ 34837-88-2 ]

Reference： [1]Patent: WO2013/19682,2013,A1
[2]Patent: US2019/152963,2019,A1

10
[ 30235-28-0 ]
[ 156-38-7 ]
[ 692872-55-2 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5028 - 5037

11
[ 156-38-7 ]
[ 85888-81-9 ]
[ 55453-87-7 ]

Yield	Reaction Conditions	Operation in experiment
79.3%		Reaction flask was added p-hydroxyphenyl acetic acid (150mmol) 22.67g, potassium hydroxide (200mmol) 11.22g, 90ml of methanol, stirred for 1 hour at room temperature, was added 2- (chloromethyl) benzoic acid (100mmol) 17.06g, heated at reflux The reaction, after the reaction was monitored by TLC, the solvent was distilled off under reduced pressure, 200ml of dichloromethane was added to dissolve, washed with water, dried, concentrated, Eaton reagent was added 7.5percent (mass concentration) 200ml, was heated to 80 deg.] C, stirred for 2 hours, the reaction was completed after addition of saturated sodium carbonate solution, filtration, and recrystallized from ethanol to give Isoxepac (79.3mmol) 21.27g, yield 79.3percent, HPLC purity of 99.9percent.

Reference： [1]Patent: CN105693685,2016,A .Location in patent: Paragraph 0050; 0051

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Technical Information

? Acidity of Phenols ? Appel Reaction ? Arndt-Eistert Homologation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Halogenation of Phenols ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Jones Oxidation ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Oxidation of Phenols ? Passerini Reaction ? Pechmann Coumarin Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alcohols ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Reimer-Tiemann Reaction ? Ritter Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Swern Oxidation ? Ugi Reaction

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[ CAS No. 156-38-7 ] {[proInfo.proName]}

Quality Control of [ 156-38-7 ]

Related Doc. of [ 156-38-7 ]

Product Details of [ 156-38-7 ]

Calculated chemistry of [ 156-38-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 156-38-7 ]

Application In Synthesis of [ 156-38-7 ]

[ 156-38-7 ] Synthesis Path-Upstream 1~2

[ 156-38-7 ] Synthesis Path-Downstream 1~11

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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