[ CAS No. 57634-55-6 ] {[proInfo.proName]}

Name: 57634-55-6|4-(2-Amino-4-thiazolyl)phenol|97%
Brand: Ambeed
SKU: A653768
Price: 5.0 USD
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Quality Control of [ 57634-55-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 57634-55-6 ]

Product Details of [ 57634-55-6 ]

CAS No. :	57634-55-6	MDL No. :	MFCD01624171
Formula :	C₉H₈N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QGSJYYIRAFRPIT-UHFFFAOYSA-N
M.W :	192.24	Pubchem ID :	346926
Synonyms :

Calculated chemistry of [ 57634-55-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.98
TPSA :	87.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	2.11
Log Po/w (MLOGP) :	0.71
Log Po/w (SILICOS-IT) :	2.46
Consensus Log Po/w :	1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.191 mg/ml ; 0.000993 mol/l
Class :	Soluble
Log S (Ali) :	-3.71
Solubility :	0.0374 mg/ml ; 0.000195 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.253 mg/ml ; 0.00132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 57634-55-6 ]

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 [ 57634-55-6 ]

* 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.

Downstream synthetic route of [ 57634-55-6 ]

[ 57634-55-6 ] Synthesis Path-Downstream 1~88

1
[ 148-24-3 ]
[ 50-00-0 ]
[ 57634-55-6 ]
[ 103155-06-2 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 421,422

2
[ 50-00-0 ]
[ 57634-55-6 ]
[ 98-86-2 ]
[ 103096-78-2 ]

Reference： [1]Journal of the Indian Chemical Society,1958,vol. 35,p. 407,409

3
[ 17356-08-0 ]
[ 99-93-4 ]
[ 57634-55-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With iodine; In dimethyl sulfoxide; at 85℃; for 4.5h;Catalytic behavior;	General procedure: A mixture of methylcarbonyl (5 mmol), thiourea (7.5 mmol), I2(5 mmol), and nano Asp-Al2O3 (0.2 g) in DMSO was stirred at 85 C for desired time. After the completion of reaction (monitored by TLC), the heterogeneous organocatalyst was separated by simple filtration and the solvent was removed under reduced pressure. The crude product was dissolved in hot water, extracted with ether(3 x 30 mL), and adjusted to pH = 9-10 by ammonia to give the solid products. Finally, the pure product was recrystallized by ethanol in high yield. All corresponding products are known and were characterized by comparison of their physical (Mp) and spectral data (IR and 1H NMR) with those of authentic samples.
91%	With iodine; In ethanol; for 2.5h;Reflux;	General procedure: A mixture of the acetophenone (2 mmol), thiourea (3 mmol) and iodine (2 mmol), in the presence of 0.03 g nanochitosan was refluxed in EtOH. The progress of the reaction was monitored by TLC (petroleum ether-ethyl acetate 4:1). After completion of the reaction, the catalyst was separated by simple filtration. After evaporation of solvent, the crude product was dissolved in boiling water, extracted with ether (3 * 30 mL), and adjusted to pH = 8 with the amount of ammonia to give the solid products. The solid was recrystallized with ethanol-water to give pure 2-aminothiazole.
91%	With montmorillonite K10 Clay; iodine; In dimethyl sulfoxide; at 80℃; for 2h;Green chemistry;	General procedure: A mixture of methylcarbonyl (0.5 mmol), thiourea (0.5 mmol), iodine (0.5 mmol), DMSO (2 mL) and 20 mg MMT-K10 was stirred at 80 C. After completion of the reaction (monitored by TLC, petroleum:ethyl acetate, 4:1), the catalyst was separated by filtration, and then the solvent was removed under reduced pressure. The crude product was dissolved in hot water, extracted with ether (3 9 30 mL), and adjusted to pH = 9-10 by ammonia to give the solid products. Finally, the resulting precipitate was recrystallyzed by EtOH.

90%	With iodine; In dimethyl sulfoxide; at 80℃; for 1h;Green chemistry;	General procedure: A mixture of methylcarbonyl (0.5 mmol), thiourea(0.5 mmol), iodine (0.5 mmol), DMSO (2 mL) and 10 mgStarch NPs were stirred at 80 C. After completion of thereaction (monitored by TLC, petroleum:ethyl acetate, 4:1),the reaction was quenched by the addition of 10 mL distilledwater. The aqueous solution was extracted withEtOAc (3 9 10 mL) and the combined extract was driedwith anhydrous Na2SO4. The solvent was vacuumed, andfinally, the resulting precipitate was recrystallized byEtOH.
80%	With N-iodo-succinimide; In ethanol; at 20℃; for 1.5h;	General procedure: A mixture of methyl carbonyl (2 mmol), thiourea (3 mmol), NIS(2 mmol), and NH2-MMT (0.10 g) in EtOH (5 mL) at room temperature was stirred until completion of reaction. The progress of the reaction was monitored by TLC (petroleum ether-ethyl acetate 4:1). After completion of the reaction, the NH2-MMT was separated by filtration. After evaporation of EtOH under vacuum, the crude product was dissolved in boiling water and adjusted to pH 8 withthe amount of ammonia to give the solid products. The solid obtained was recrystallized from a mixture of ethanol-water.
62%	With iodine; at 130 - 150℃; for 0.166667h;Neat (no solvent); Microwave irradiation;	General procedure: Method A: A mixture of p-substituted acetophenone 1 (8.6 mmol), thiourea 2 (17.2 mmol, 1.3 g) and iodine (8.6 mmol, 2.2 g) was placed in an open vessel containing a Teflon coated stir bar. The vessel was placed in the microwave cavity (CEM, Discover) and subjected to MW irradiation (50 W) at indicated temperature for 10 min. After the completion of the reaction, the crude mixture was cooled to 70 C and then it was triturated, filtered and washed with Et2O. The crude product was dissolved in hot water and the pH was adjusted to 11-12 with NH4OH. The precipitated was filtered and crystallized from EtOH-H2O (1:4) to obtain the 2-amino-4-aryl-1,3-thiazole (3a-h).

Reference： [1]Journal of Molecular Structure,2019,vol. 1185,p. 143 - 152
[2]Catalysis Communications,2016,vol. 77,p. 108 - 112
[3]RSC Advances,2016,vol. 6,p. 64749 - 64755
[4]Research on Chemical Intermediates,2016,vol. 42,p. 8175 - 8183
[5]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84
[6]Monatshefte fur Chemie,2017,vol. 148,p. 745 - 749
[7]Journal of Molecular Structure,2017,vol. 1144,p. 58 - 65
[8]Applied Organometallic Chemistry,2018,vol. 32
[9]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 1635 - 1639
[10]Tetrahedron Letters,2012,vol. 53,p. 3934 - 3936
[11]Journal of Carbohydrate Chemistry,2010,vol. 29,p. 207 - 221
[12]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 1428 - 1433
[13]Journal of Venomous Animals and Toxins Including Tropical Diseases,2018,vol. 24
[14]Heteroatom Chemistry,2006,vol. 17,p. 254 - 260
[15]Journal of the American Chemical Society,1950,vol. 72,p. 3722
[16]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1961,vol. 252,p. 291 - 292
[17]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1391 - 1393
[18]Journal of the Serbian Chemical Society,2012,vol. 77,p. 279 - 286
[19]Chinese Chemical Letters,2012,vol. 23,p. 454 - 457
[20]Medicinal Chemistry Research,2014,vol. 23,p. 1123 - 1147
[21]Tetrahedron Letters,2014,vol. 55,p. 4987 - 4990
[22]Open Chemistry,2015,vol. 13,p. 1127 - 1136
[23]Chemical Biology and Drug Design,2017,vol. 90,p. 778 - 790
[24]Chemical Biology and Drug Design,2018,vol. 91,p. 728 - 734

4
[ 57634-55-6 ]
[ 3223-20-9 ]
2-hydroxy-<i>N</i>-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-5-nitro-benzamide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 917 - 918

5
[ 57634-55-6 ]
[ 39614-80-7 ]
[ 50728-79-5 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 917 - 918

6
[ 57634-55-6 ]
[ 39075-92-8 ]
[ 74675-81-3 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 917 - 918

7
[ 57634-55-6 ]
[ 57634-48-7 ]

Reference： [1]Journal of the Indian Chemical Society,1975,vol. 52,p. 766 - 767

8
[ 765-50-4 ]
[ 57634-55-6 ]
[ 79615-43-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 355 - 362

9
[ 148-24-3 ]
[ 57634-55-6 ]
[ 100-52-7 ]
[ 79667-26-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 606 - 607

10
[ 1199-01-5 ]
[ 57634-55-6 ]
[ 112635-04-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 478 - 479

11
[ 57634-55-6 ]
[ 15646-46-5 ]
[ 112635-06-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 478 - 479

12
[ 57634-55-6 ]
[ 72-14-0 ]
[ 103726-76-7 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

13
[ 57634-55-6 ]
[ 68-35-9 ]
[ 103726-71-2 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

14
[ 57634-55-6 ]
[ 599-84-8 ]
[ 103726-72-3 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

15
[ 57634-55-6 ]
[ 57-68-1 ]
[ 103726-75-6 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

16
[ 57634-55-6 ]
[ 127-69-5 ]
[ 103740-33-6 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

17
[ 57634-55-6 ]
[ 80-35-3 ]
[ 103726-74-5 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

18
[ 57634-55-6 ]
[ 122-11-2 ]
[ 103740-32-5 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

19
[ 57634-55-6 ]
[ 526-08-9 ]
[ 103726-73-4 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

20
[ 57634-55-6 ]
[ 6959-48-4 ]
[ 79615-42-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 355 - 362

21
[ 57634-55-6 ]
[ 4755-77-5 ]
[ 74604-53-8 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1391 - 1393

22
[ 57634-55-6 ]
[ 63-74-1 ]
[ 103726-69-8 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

23
[ 57634-55-6 ]
[ 95-92-1 ]
[ 74604-53-8 ]

Reference： [1]Synthesis,1991,p. 763 - 764

24
[ 57634-55-6 ]
[ 57-67-0 ]
[ 103726-70-1 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

25
[ 57634-55-6 ]
[ 4635-59-0 ]
[ 79340-14-0 ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

26
[ 1071-86-9 ]
[ 99-93-4 ]
[ 57634-55-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 478 - 479

28
[ 57634-55-6 ]
[ 108-24-7 ]
2-(N-acetylamino)-4-(4-acetoxyphenyl)thiazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 4261 - 4265

29
[ 57634-55-6 ]
[ 108-24-7 ]
2-amino-4-(4-acetoxyphenyl)thiazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 4261 - 4265

30
[ 57634-55-6 ]
[ 108-24-7 ]
[ 64309-02-0 ]

Reference： [1]Heteroatom Chemistry,2006,vol. 17,p. 254 - 260

31
[ 57634-55-6 ]
[ 109-86-4 ]
[ 960130-22-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃;	Example 217; (S)-benzyl 1-(4-(4-(2-methoxyethoxy)phenyl)thiazol-2-ylamino)-1-oxo-6-(sulfamoylamino)hexan-2-ylcarbamate (236) Step 1: 4-(4-(2-methoxyethoxy)phenyl)thiazol-2-amine (234) To a solution <strong>[57634-55-6]4-(2-aminothiazol-4-yl)phenol</strong> (200 mg, 1.04 mmol) and 2-methoxyethanol (0.082 mL, 1.04 mmol) in THF (7 mL) was added triphenylphosphine (409 mg, 1.56 mmol) and DEAD (0.19 mL, 1.24 mmol) sequentially. The reaction stirred at room temperature overnight. The solvent was evaporated and the residue was purified by silica gel chromatography with gradient of EtOAc (20-40%) in Hexane to afford 234 (67 mg, 26%) as a white solid. LRMS (ESI): (calc) 250.3; (found) 251.2 (MH)+.

Reference： [1]Patent: US2007/293530,2007,A1 .Location in patent: Page/Page column 96

32
[ 57634-55-6 ]
<i>N</i>-[5-bromo-4-(4-hydroxy-phenyl)-thiazol-2-yl]-acetamide [ No CAS ]

Reference： [1]Heteroatom Chemistry,2006,vol. 17,p. 254 - 260

33
[ 57634-55-6 ]
4-Dimethylamino-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

34
[ 57634-55-6 ]
4-Diethylamino-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

35
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-pyrrolidin-1-yl-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

36
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-piperidin-1-yl-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

37
[ 57634-55-6 ]
4-Diisopropylamino-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

38
[ 57634-55-6 ]
4-Dipropylamino-N-[4-(4-hydroxy-phenyl)-thiazol-2-yl]-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

39
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-piperazin-1-yl-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

40
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-morpholin-4-yl-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

41
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-(pyridin-2-ylamino)-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

42
[ 57634-55-6 ]
N-[4-(4-Hydroxy-phenyl)-thiazol-2-yl]-4-(pyrimidin-2-ylamino)-butyramide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 787 - 788

43
[ 57634-55-6 ]
[ 5292-43-3 ]
1,1-dimethylethyl 2-{4-(2-amino-4-thiazolyl)phenoxy}acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran;	Example 2 1,1-Dimethylethyl 2-{4-(2-amino-4-thiazolyl)phenoxy}acetate. Potassium carbonate (3.80 g, 27.5 mmol) and tert-butyl 2-bromoacetate (4.04 mL, 25.0 mmol) were added to a solution of the product of example 1 (4.81 g, 25.0 mmol) in THF (125 mL). The resulting mixture was heated at reflux for 72 h and then diluted with EtOAc. The mixture was washed with a saturated aqueous solution of NaHCO3 and then brine, dried (MgSO4) and concentrated under reduced pressure. The crude yellow oil obtained was purified by flash chromatography (SiO2, 1:2 to 2:3 EtOAc:hexane) to afford 3.97 g (52% yield) of the title compound as a pale yellow solid: 1 H NMR (400 MHz, DMSO-d6) delta 7.71 (d, J=8.2 Hz, 2H), 6.97 (s, 2H), 6.88 (d, J=8.2 Hz, 2H), 6.83 (s, 1H), 4.65 (s, 2H), 1.43 (s, 9H); MS (FAB) m/z 307 (MH)+.

Reference： [1]Patent: US6057451,2000,A

44
[ 99-93-4 ]
[ 57634-55-6 ]

Yield	Reaction Conditions	Operation in experiment
25%	With iodine; sodium hydrogencarbonate; thiourea; In isopropyl alcohol;	Example 1 4-(2-Amino-4-thiazolyl)phenol Thiourea (30.45 g, 400 mmol) and iodine (50.76 g, 200 mmol) were added to a solution of 4'-hydroxyacetophenone (27.23 g, 200 mmol) in isopropanol (400 mL). The resulting mixture was heated at reflux for 18 h, then diluted with H2 O and washed with Et2 O. The aqueous layer was rendered basic with a saturated aqueous solution of NaHCO3 and then extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford 15 g of an orange foam. The foam was purified by flash chromatography (SiO2, 3:1, EtOAc:hexane) to afford the title compound (9.41 g, 25% yield) as a pale yellow solid: 1 H NMR (400 MHz, DMSO-d6) delta 9.42 (s, 1H), 7.59 (d, J=8.6 Hz, 2H), 6.93 (s, 2H), 6.73 (d, J=8.6 Hz, 2H), 6.71 (s, 1H); MS (CI, NH3) m/z 193 (MH)+.

Reference： [1]Patent: US6057451,2000,A
[2]Tetrahedron,2012,vol. 68,p. 173 - 178
[3]Journal of the Chinese Chemical Society,2017,vol. 64,p. 1408 - 1416
[4]Journal of Medicinal Chemistry,2019,vol. 62,p. 3068 - 3087

45
[ 57634-55-6 ]
4-(2-sulfamoylaminothiazol-4-yl)phenyl sulfamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform;	Example 82 The procedure of Example 1 was repeated, except that 52 mg of <strong>[57634-55-6]4-(2-aminothiazol-4-yl)phenol</strong> was used in place of 2'-nitrobiphenyl-4-ol. The resulting crude product was purified by TLC (using a 10:1 mixture of chloroform and methanol as the developing solvent) to obtain 8 mg of 4-(2-sulfamoylaminothiazol-4-yl)phenyl sulfamate. 1H-NMR(CDCl3, delta): 6.96(1H, s), 7.30(2H, d, J=5.7Hz), 7.86(2H, d, J=5.7Hz), 8.21(1H, s). MS(m/z): 350(M+), 270, 192.

Reference： [1]Patent: EP1193250,2002,A1

46
[ 57634-55-6 ]
[ 17823-58-4 ]
[ 1223515-90-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1635 - 1638

47
[ 98-03-3 ]
[ 57634-55-6 ]
[ 1252678-70-8 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 1955 - 1963

48
[ 1121-60-4 ]
[ 57634-55-6 ]
[ 1253469-34-9 ]