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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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.28 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
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