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[ CAS No. 59337-89-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 59337-89-2
Chemical Structure| 59337-89-2
Chemical Structure| 59337-89-2
Structure of 59337-89-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 59337-89-2 ]

CAS No. :59337-89-2 MDL No. :MFCD00043888
Formula : C5H3ClO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BXEAAHIHFFIMIE-UHFFFAOYSA-N
M.W : 162.59 Pubchem ID :701269
Synonyms :

Calculated chemistry of [ 59337-89-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.29
TPSA : 65.54 Ų

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) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.1
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 2.58
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.503 mg/ml ; 0.00309 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.13 mg/ml ; 0.000801 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.65
Solubility : 3.67 mg/ml ; 0.0226 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 59337-89-2 ]

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 [ 59337-89-2 ]

* 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.

  • Upstream synthesis route of [ 59337-89-2 ]
  • Downstream synthetic route of [ 59337-89-2 ]

[ 59337-89-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 88105-17-3 ]
  • [ 59337-89-2 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With water; sodium hydroxide In methanol at 0 - 25℃; for 2 h;
Stage #2: With hydrogenchloride In water
To a solution of methyl 3-chlorothiophene-2-carboxylate (50 g, 0.28 mol) in MeOH(100 mL) was added a solution of aq. NaOH (2M) (400 mL) dropwise at 0 °C. The resulting mixture was stirred at RT for 2h. After removing MeOH, the aqueous was washed with ether and acidified with 2 N HCl. The solid formed was collected by filtration and dried to give 45 g of 3-chlorothiophene-2-carboxylic acid in 98percent yield. MS (M+H+): 163.
45 g With water; sodium hydroxide In methanol at 0℃; for 2 h; l-(5-Bromo-3-chlorothiophen-2-yl)ethanone (ketone in Table 1 1, entry 2) was prepared as follows: To a solution of methyl 3-chlorothiophene-2-carboxylate (50 g, 0.28 mol) in MeOH (100 mL) was added a solution of aq. NaOH (2M) (400 mL) dropwise at 0 °C. The resulting mixture was stirred at RT for 2h. After removing MeOH, the aqueous was washed with ether and acidified with 2 N HCl. The solid formed was collected by filtration and dried to give 45 g of 3-chlorothiophene-2-carboxylic acid. MS (M+H): 163.
45 g With water; sodium hydroxide In methanol at 0 - 20℃; for 2 h; 1-(5-Bromo-3-chlorothiophen-2-yl)ethanone (ketone in Table 11, entry 2) was prepared as follows: To a solution of methyl 3-chlorothiophene-2-carboxylate (50 g, 0.28 mol) in MeOH (100 mL) was added a solution of aq. NaOH (2M) (400 mL) dropwise at 0° C. The resulting mixture was stirred at RT for 2 h. After removing MeOH, the aqueous was washed with ether and acidified with 2 N HCl. The solid formed was collected by filtration and dried to give 45 g of 3-chlorothiophene-2-carboxylic acid. MS (M+H): 163.
Reference: [1] Heterocycles, 1985, vol. 23, # 6, p. 1431 - 1435
[2] Patent: WO2012/139425, 2012, A1, . Location in patent: Page/Page column 119
[3] Heterocycles, 2007, vol. 71, # 1, p. 87 - 104
[4] Patent: WO2013/28670, 2013, A1, . Location in patent: Page/Page column 96
[5] Patent: US9181236, 2015, B2, . Location in patent: Page/Page column 107
  • 2
  • [ 86427-02-3 ]
  • [ 59337-89-2 ]
YieldReaction ConditionsOperation in experiment
20 mg at 100℃; Sealed tube Preparation of 1-(3-chlorothiophen-2-yl)-1,4-dihydro-5H-tetrazol-5-one 6w
A stirred mixture of azidotrimethylsilane (2.4 mL, 18 mmol) and 3-chlorothiophene-2-carbonyl chloride (543 mg, 3.0 mmol) was heated from room temperature to 100° C. (block temperature) in a sealed vial with pressure-release cap.
The mixture was then stirred at 100° C. overnight (Note: pressure developed during heating).
After cooling, the mixture was concentrated under vacuum and the residue partitioned between EtOAc (10 mL) and a saturated aqueous solution of NaHCO3 (10 mL).
The organic layer was extracted with a further quantity of saturated aqueous NaHCO3 (1*10 mL) [note:
organic layer was assessed by TLC to ascertain if tetrazolone product was completely removed.
If tetrazolone was still present in organic layer, then further extractions with saturated NaHCO3 were used]. EtOAc (20 mL) was added to the combined NaHCO3 layers, and the pH was adjusted to <3 using 6N HCl with efficient stirring.
The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (2*10 mL).
The combined organic layers were dried (Na2SO4), filtered and the solvent removed under vacuum to afford a mixture of the desired product and 3-chlorothiophene-2-carboxylic acid.
Reference: [1] Patent: US2016/213648, 2016, A1, . Location in patent: Paragraph 0400; 0401; 0402; 0403; 0404; 0405
  • 3
  • [ 5118-06-9 ]
  • [ 7440-44-0 ]
  • [ 59337-89-2 ]
Reference: [1] Patent: US4076709, 1978, A,
  • 4
  • [ 17249-80-8 ]
  • [ 124-38-9 ]
  • [ 59337-89-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 3, p. 369 - 371
  • 5
  • [ 17249-80-8 ]
  • [ 124-38-9 ]
  • [ 59337-89-2 ]
  • [ 59614-95-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3471 - 3488
  • 6
  • [ 22288-78-4 ]
  • [ 59337-89-2 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 87 - 104
[2] Heterocycles, 1985, vol. 23, # 6, p. 1431 - 1435
  • 7
  • [ 4648-54-8 ]
  • [ 86427-02-3 ]
  • [ 59337-89-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9338 - 9342
  • 8
  • [ 67482-48-8 ]
  • [ 59337-89-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1964, vol. &lt;4&gt; 24, p. 38,50, 64
  • 9
  • [ 89581-82-8 ]
  • [ 59337-89-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1964, vol. &lt;4&gt; 24, p. 38,50, 64
  • 10
  • [ 17249-79-5 ]
  • [ 59337-89-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 250,279
  • 11
  • [ 59337-89-2 ]
  • [ 59804-37-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 678 - 682
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 678 - 682
  • 12
  • [ 59337-89-2 ]
  • [ 59337-92-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 678 - 682
  • 13
  • [ 17249-80-8 ]
  • [ 124-38-9 ]
  • [ 59337-89-2 ]
  • [ 59614-95-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3471 - 3488
  • 14
  • [ 59337-89-2 ]
  • [ 98827-44-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 678 - 682
  • 15
  • [ 67-56-1 ]
  • [ 59337-89-2 ]
  • [ 88105-17-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 8, p. 2463 - 2468
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