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Chemical Structure| 53137-27-2 Chemical Structure| 53137-27-2

Structure of 53137-27-2

Chemical Structure| 53137-27-2

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CAS No.: 53137-27-2

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Product Details of [ 53137-27-2 ]

CAS No. :53137-27-2
Formula : C6H7NO2S
M.W : 157.19
SMILES Code : O=C(C1=C(C)N=C(C)S1)O
MDL No. :MFCD00052943
InChI Key :MQGBARXPCXAFRZ-UHFFFAOYSA-N
Pubchem ID :736488

Safety of [ 53137-27-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 53137-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 5
Fraction Csp3 0.33
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 39.01
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

78.43 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.31
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.61
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.46
Log Po/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.

0.02
Log Po/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

2.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.34

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.13
Solubility 1.16 mg/ml ; 0.00736 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.

-2.87
Solubility 0.213 mg/ml ; 0.00135 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

-1.43
Solubility 5.85 mg/ml ; 0.0372 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

 No
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

 No
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.

-6.12 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.

0.56

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)

 2.34

Application In Synthesis of [ 53137-27-2 ]

* 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 [ 53137-27-2 ]

[ 53137-27-2 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 28599-52-2 ]
  • [ 53137-27-2 ]
  • 2
  • [ 53137-27-2 ]
  • [ 100-35-6 ]
  • 2,4-dimethyl-thiazole-5-carboxylic acid-(2-diethylamino-ethyl ester) [ No CAS ]
  • 3
  • [ 53137-27-2 ]
  • [ 258521-35-6 ]
  • 4
  • [ 7210-77-7 ]
  • [ 53137-27-2 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; In ethanol; water; for 4h;Reflux; General procedure: The appropriate ethyl ester (1c, 3c) (5.8 mmol) was refluxed for4 h in a mixture of equal volumes of aqueous 10% NaOH (20 mL) andEthanol (20 mL). After completion of the reaction, ethanol wasevaporated under reduced pressure and the remaining solutionwasthen extracted with ethyl acetate. The organic layer was discardedwhile the aqueous layer was acidified to pH 3 with aqueous 10%hydrochloric acid. The mixturewas then evaporated under reducedpressure and the solid obtained was then dissolved in methanolwhile the remaining insoluble NaCl was discarded. Evaporating themethanol afforded the desired pure acids 1d and 3d.
With potassium hydroxide; In methanol; water; After 9.7 g of potassium hydroxide were added to 50 ml of methanol and 50 ml of water, 10.2 g of ethyl 2,4-dimethyl-5-thiazolecarboxylate were added dropwise thereto at room temperature. The reaction was conducted at room temperature for 1 hour, and the reaction mixture was then acidified with 2-N hydrochloric acid. After methanol was distilled off, the crystals were collected through filtration, washed with water, and dried to obtain 6.6 g of the Compound No. 2.1 of the present invention. melting point: from 220 to 225 C.
  • 5
  • [ 7210-77-7 ]
  • [ 53137-27-2 ]
  • [ 66806-33-5 ]
  • 10
  • [ 53137-27-2 ]
  • [ 98-86-2 ]
  • [ 113366-50-0 ]
  • 12
  • [ 53137-27-2 ]
  • [ 68858-20-8 ]
  • [ 170117-43-8 ]
  • C40H52N6O6S2 [ No CAS ]
  • 13
  • [ 53137-27-2 ]
  • [ 68858-20-8 ]
  • [ 220784-31-6 ]
  • C40H52N6O5S2 [ No CAS ]
  • 14
  • [ 53137-27-2 ]
  • [ 2835-78-1 ]
  • 2,4-Dimethyl-thiazole-5-carboxylic acid (3-benzoyl-phenyl)-amide [ No CAS ]
  • 15
  • [ 53137-27-2 ]
  • [ 127000-91-3 ]
  • 2,4-Dimethyl-thiazole-5-carboxylic acid [(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-amide [ No CAS ]
  • 16
  • 2,4-dimethyl-thiazole-5-carboxylic acid methyl ester; hydrochloride [ No CAS ]
  • [ 53137-27-2 ]
  • 17
  • [ 7647-01-0 ]
  • [ 53137-27-2 ]
  • [ 173841-81-1 ]
  • 18
  • [ 53137-27-2 ]
  • [ 6638-79-5 ]
  • [ 258261-48-2 ]
YieldReaction ConditionsOperation in experiment
To a flask containing <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> (2.50 g, 15.9 mmol) was added DCM (75 mL) and DMF (3 mL) to afford a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was added and the mixture was stirred at room temperature for 2 hours. N,O-dimethylhydroxylamine hydrochloride (1.90 g, 19.9 mmol) was then added and the reaction mixture was stirred at room temperature for 18 hours, then diluted with water and 1 N NaOH and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (10-40% EtOAc-DCM) provided the title compound as a colorless oil.
To a flask containing <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> (2.5 g, 15.9 mmol) was added DCM (75 mL) to give a suspension. DMF (3 mL) was added which resulted in a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was introduced and the mixture was stirred at room temperature for 2 hours. N,O-dimethylhydroxylamine HCl (1.9 g, 19.9 mmol) was then added and the mixture was stirred at room temperature for 18 hours, at which time the reaction mixture was diluted with water and 1 N aqueous NaOH and the aqueous portion was extracted with DCM (4*50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (10% EtOAc-DCM increasing to 40% EtOAc) provided the title compound as a colorless oil.
intermediate 17: step aN-methoxy-N,2,4-trimethylthiazole-5-carboxamideTo a flask containing 2,4-dimethylthiazole~5~carboxylic acid (2.5 g, 15.9 mmol) was added DCM (75 mL) to give a suspension . DMF (3 mL) was added which resulted in a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was introduced and the mixture was stirred at, room temperature for 2 hours. N,0-dim.ethymydroxylamine HQ (1 .9 g, 19.9 mmol) was then added and the mixture was stirred at room temperature for 18 hours, at which time the reaction mixture was diluted with water and 5 N aqueous NaOH and the aqueous portion was extracted with DCM (4 x 50 mL). The combined organics were washed with brine, dried over a2S04, filtered and concentrated. Chromatography on silica gel (1 0% EtOAc-DCM increasing to 40% EtOAc) provided the title compound as a colorless oil.
  • 19
  • [ 313504-94-8 ]
  • [ 53137-27-2 ]
  • 2,4-dimethyl-thiazole-5-carboxylic acid [2-(cyclohexanecarbonyl-amino)-benzothiazol-6-yl]-amide [ No CAS ]
  • 20
  • [ 53137-27-2 ]
  • 5-(1<i>H</i>-imidazol-4-ylmethyl)-2,4-dimethyl-thiazole [ No CAS ]
  • 21
  • [ 53137-27-2 ]
  • 5-[1-(1<i>H</i>-imidazol-4-yl)-ethyl]-2,4-dimethyl-thiazole [ No CAS ]
  • 22
  • [ 53137-27-2 ]
  • 1-(2,4-dimethyl-thiazol-5-yl)-1-(1<i>H</i>-imidazol-4-yl)-ethanol [ No CAS ]
  • 23
  • [ 53137-27-2 ]
  • 5-[(1<i>H</i>-imidazol-4-yl)-phenyl-methyl]-2,4-dimethyl-thiazole [ No CAS ]
  • 24
  • [ 53137-27-2 ]
  • (2,4-dimethyl-thiazol-5-yl)-(1<i>H</i>-imidazol-4-yl)-phenyl-methanol [ No CAS ]
  • 25
  • [ 53137-27-2 ]
  • (2,4-dimethyl-thiazol-5-yl)-(1-trityl-1<i>H</i>-imidazol-4-yl)-methanol [ No CAS ]
  • 26
  • [ 53137-27-2 ]
  • [ 258261-50-6 ]
  • 27
  • (+/-)-trans-N-[4-phenyl-1-[2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]acetamide dihydrochloride.dihydrate [ No CAS ]
  • [ 53137-27-2 ]
  • (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).
  • 28
  • (+/-)-cis-1-[[1-[4-phenyl-2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]carbonyl]pyrrolidine [ No CAS ]
  • [ 53137-27-2 ]
  • C34H42N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).
  • 29
  • C26H34N2O2 [ No CAS ]
  • [ 53137-27-2 ]
  • C32H39N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).
  • 30
  • [ 53137-27-2 ]
  • [ 52273-77-5 ]
  • [ 844904-20-7 ]
YieldReaction ConditionsOperation in experiment
73% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); for 14h; N- [3- (2-HYDROXYETHYL) PHENYL]-2, 4-DIMETHYL-1, 3-THIAZOLE-5-CARBOXAMIDE; 2- (3-Aminophenyl) ethanol (1.202 g, 8.76 MMOL) was added to a solution of 2, 4-dimethyl- 1, 3-thiazole-5-carboxylic acid (1.652 g, 10.51 MMOL), 1- (3-DIMETHYLAMINOPROPYL)-3- ethylcarbodiimide hydrochloride (2.015 g, 10.51 MMOL) and 1-hydroxybenzotriazole (1.420 g, 10.51 MMOL) in dry DMF (20 mL). The mixture was stirred for 14h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1: 1 to 1: 0) affording the title compound in 73% yield (1.772 g). MS; (ES) m/z: 277 [MH+]. C14H16N202S requires 276. 1H-NMR (300 MHz, D6-DMSO) S (ppm): 9.95 (s, 1H), 7.40-7. 50 (m, 2H), 7.19 (t, 1H), 6.92 (d, 1 H), 4.60 (t, 1 H), 5.57 (dd, 2H), 2.66 (t, 2H), 2.61 (s, 3H), 2.49 (s, 3H).
  • 31
  • [ 887308-20-5 ]
  • [ 53137-27-2 ]
  • N-[5-(2-acetylamino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; In acetonitrile; for 1h;Heating / reflux; Phosphorus oxychloride (296 mg) was added to a stirred mixture of N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-l,3-thiazol-2-yl]acetamide (180 mg), 2,4-dimethylthiazole- 5-carboxylic acid (J. Med. Chem., 1999, 42, 5064; 109 mg) and acetonitrile (10 mL) that had been heated to reflux. The resultant mixture was stirred and heated to- reflux for 1 hour. The mixture was cooled to room temperature and the precipitate was collected by filtration, washed with acetonitrile and dried under vacuum. There was thus obtained the title compound(172 mg); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.39 (s, 3H), 2.62 (s, 3H), 2.68 (s, 3H), 8.21 (s, IH), 8.40 (s, IH); Mass Spectrum: M+H+ 422.
  • 32
  • [ 288-32-4 ]
  • [ 53137-27-2 ]
  • 5-imidazolylcarbonyl-2,4-dimethylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In tetrahydrofuran; EXAMPLE 1 (Compound No. 1) To a solution of imidazole (2.72 g; 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g; 10 mmol) under ice-cooling while stirring. After the resultant mixture was turned to room temperature, <strong>[53137-27-2]2,4-dimethyl-5-thiazolecarboxylic acid</strong> (1.57 g; 10 mmol) was added thereto at once, and stirring was continued for 30 minutes, whereby 5-imidazolylcarbonyl-2,4-dimethylthiazole was produced.
 

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