Home Cart 0 Sign in  
X

[ CAS No. 14597-58-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 14597-58-1
Chemical Structure| 14597-58-1
Chemical Structure| 14597-58-1
Structure of 14597-58-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 14597-58-1 ]

Related Doc. of [ 14597-58-1 ]

Alternatived Products of [ 14597-58-1 ]

Product Details of [ 14597-58-1 ]

CAS No. :14597-58-1 MDL No. :MFCD07687259
Formula : C6H7NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :NNQTUMGJWXJMIR-UHFFFAOYSA-N
M.W :157.19 Pubchem ID :7131725
Synonyms :

Calculated chemistry of [ 14597-58-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.0
TPSA : 80.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.12
Log Po/w (MLOGP) : 0.29
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.72 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (Ali) : -2.74
Solubility : 0.288 mg/ml ; 0.00183 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.37
Solubility : 6.71 mg/ml ; 0.0427 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 14597-58-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14597-58-1 ]

* 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 [ 14597-58-1 ]
  • Downstream synthetic route of [ 14597-58-1 ]

[ 14597-58-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 5832-01-9 ]
  • [ 14597-58-1 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In ethanol To methyl 5-nitro-2-thiophenecarboxylate (11.55 mmol) in ethyl alcohol (20 mL) was added palladium on carbon (10percent, 1 g). The reaction mixture was hydrogenated with an atmosphere of H2 overnight. Methyl 5-amino-2-thiophenecarboxylate (1.67 g, 92percent) was obtained after filtration and concentration.LCMS (ESI) 157 [MH-H]+.
66%
Stage #1: With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 35℃; for 2 h;
Stage #2: basic conditions
Part A To a mixture of 2-nitrothiophene (600 mg, 3.2 mmol) and SnCl2.2H2O (4.86 g, 25.6 mmol) in 95percent EtOH(13.6 mL) was added concentrated HCl (13.6 mL) dropwise at room temperature (sufficient cooling was necessary to keep the reaction temperature under 35° C.). After the addition, the reaction mixture was stirred at 35° C. for 2 hours. EtOH was removed under vacuum and the aqueous layer was washed with hexane (50 mL.x.2). The pH of the aqueous layer was adjusted to pH 9 and was extracted three times with EtOAc (50 mL). The extracts were combined and dried over Na2SO4. After evaporation of solvent, the product was obtained as white solid (332 mg, 66percent). 1H NMR (400 MHz, DMSO-d6): 7.15(d, 1H), 6.60(s, 2H), 5.10(d, 1H), 3.65(s, 3H). LC-MS m/z 158.1 (M+H).
Reference: [1] Patent: WO2006/65788, 2006, A2, . Location in patent: Page/Page column 10
[2] Patent: US2007/43045, 2007, A1, . Location in patent: Page/Page column 59
[3] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382
[4] Patent: WO2004/108683, 2004, A1, . Location in patent: Page 564-565
[5] Patent: WO2004/18480, 2004, A1, . Location in patent: Page 156
[6] Patent: US2007/32475, 2007, A1, . Location in patent: Page/Page column 36-37
[7] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713
[8] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 302 - 310
[9] Patent: WO2008/156614, 2008, A2, . Location in patent: Page/Page column 227; 228
  • 2
  • [ 527-72-0 ]
  • [ 14597-58-1 ]
  • [ 89499-43-4 ]
Reference: [1] Patent: US2010/68178, 2010, A1, . Location in patent: Page/Page column 16-17
  • 3
  • [ 67-56-1 ]
  • [ 527-72-0 ]
  • [ 14597-58-1 ]
  • [ 89499-43-4 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: at 0 - 10℃; for 1.25 h;
Stage #2: at 20℃; Reflux
Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (compound 12); Step a:4-Nitrothiophene-2-carboxylic acid: Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 0C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2 x 50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75percent), mp 110-118 0C. The product was a mixture of two compounds by HPLC and 1H NMR and was proceeded to the next step. Step b:Methyl 4-nitrothiophene-2-carboxylate: To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85percent). 1H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:Methyl 4-aminothiophene-2-carboxylate: To a solution of methyl nitrothiophene-2- carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Cone, hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (1O g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 0C for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4 x 100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31percent), mp 76-780C. 1H NMR (400 MHz, CDCl3): δ 7.31 (IH, d, JH .6 Hz), 6.40 (IH, d, J=I.6 Hz), 3.85 (3H, s), 3.63 (2H, br s).Further elution of the column with the same solvent system provided methyl 5- aminothiophene-2-carboxylate (0.5 g, 8.5percent), mp 70-720C. 1H NMR (400 MHz, CDCl3): δ 7.45 (IH, d, J=4.0 Hz), 6.09 (IH, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).
Reference: [1] Patent: WO2010/29577, 2010, A2, . Location in patent: Page/Page column 38-39
  • 4
  • [ 5832-01-9 ]
  • [ 7439-89-6 ]
  • [ 14597-58-1 ]
Reference: [1] Patent: US5709867, 1998, A,
  • 5
  • [ 6317-37-9 ]
  • [ 14597-58-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713
[3] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 302 - 310
  • 6
  • [ 39978-57-9 ]
  • [ 14597-58-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713
  • 7
  • [ 527-72-0 ]
  • [ 14597-58-1 ]
  • [ 89499-43-4 ]
Reference: [1] Patent: US2010/68178, 2010, A1, . Location in patent: Page/Page column 16-17
  • 8
  • [ 67-56-1 ]
  • [ 527-72-0 ]
  • [ 14597-58-1 ]
  • [ 89499-43-4 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: at 0 - 10℃; for 1.25 h;
Stage #2: at 20℃; Reflux
Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (compound 12); Step a:4-Nitrothiophene-2-carboxylic acid: Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 0C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2 x 50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75percent), mp 110-118 0C. The product was a mixture of two compounds by HPLC and 1H NMR and was proceeded to the next step. Step b:Methyl 4-nitrothiophene-2-carboxylate: To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85percent). 1H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:Methyl 4-aminothiophene-2-carboxylate: To a solution of methyl nitrothiophene-2- carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Cone, hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (1O g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 0C for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4 x 100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31percent), mp 76-780C. 1H NMR (400 MHz, CDCl3): δ 7.31 (IH, d, JH .6 Hz), 6.40 (IH, d, J=I.6 Hz), 3.85 (3H, s), 3.63 (2H, br s).Further elution of the column with the same solvent system provided methyl 5- aminothiophene-2-carboxylate (0.5 g, 8.5percent), mp 70-720C. 1H NMR (400 MHz, CDCl3): δ 7.45 (IH, d, J=4.0 Hz), 6.09 (IH, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).
Reference: [1] Patent: WO2010/29577, 2010, A2, . Location in patent: Page/Page column 38-39
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 14597-58-1 ]

Esters

Chemical Structure| 5832-01-9

[ 5832-01-9 ]

Methyl 5-nitrothiophene-2-carboxylate

Similarity: 0.83

Chemical Structure| 50340-79-9

[ 50340-79-9 ]

5-(Methoxycarbonyl)thiophene-2-carboxylic acid

Similarity: 0.81

Chemical Structure| 67808-64-4

[ 67808-64-4 ]

Methyl 5-formylthiophene-2-carboxylate

Similarity: 0.81

Chemical Structure| 5751-81-5

[ 5751-81-5 ]

Ethyl 5-methylthiophene-2-carboxylate

Similarity: 0.78

Chemical Structure| 89499-43-4

[ 89499-43-4 ]

Methyl 4-aminothiophene-2-carboxylate

Similarity: 0.77

Amines

Chemical Structure| 89499-43-4

[ 89499-43-4 ]

Methyl 4-aminothiophene-2-carboxylate

Similarity: 0.77

Chemical Structure| 22288-78-4

[ 22288-78-4 ]

Methyl 3-amino-2-thiophenecarboxylate

Similarity: 0.76

Chemical Structure| 76575-71-8

[ 76575-71-8 ]

Methyl 3-amino-5-methylthiophene-2-carboxylate

Similarity: 0.75

Chemical Structure| 916214-44-3

[ 916214-44-3 ]

Methyl 4-(aminomethyl)thiophene-2-carboxylate hydrochloride

Similarity: 0.68

Chemical Structure| 85006-31-1

[ 85006-31-1 ]

Methyl 3-amino-4-methylthiophene-2-carboxylate

Similarity: 0.68