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[ CAS No. 5271-67-0 ] {[proInfo.proName]}

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Chemical Structure| 5271-67-0
Chemical Structure| 5271-67-0
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Product Details of [ 5271-67-0 ]

CAS No. :5271-67-0 MDL No. :MFCD00005428
Formula : C5H3ClOS Boiling Point : -
Linear Structure Formula :- InChI Key :QIQITDHWZYEEPA-UHFFFAOYSA-N
M.W : 146.59 Pubchem ID :78928
Synonyms :

Calculated chemistry of [ 5271-67-0 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.5
TPSA : 45.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.01
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.26 mg/ml ; 0.00177 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.104 mg/ml ; 0.00071 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.21
Solubility : 0.906 mg/ml ; 0.00618 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 5271-67-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5271-67-0 ]

* 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 [ 5271-67-0 ]
  • Downstream synthetic route of [ 5271-67-0 ]

[ 5271-67-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 88-15-3 ]
  • [ 5271-67-0 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 1.75 h;
Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 14.5 h;
To a mixture of 2-acetylthiophene (0.108 ml, 1.0 mmol), pyridine (0.016 ml, 0.20 mmol), and chlorobenzene (0.35 ml) was added S2CI2 (0.16 ml, 2.0 mmol) while stirring at room temperature. After stirring for 1 h 45 min, SO2CI2 (0.162 ml, 2.0 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for 0.5 h. The mixture was then stirred at 132 °C for 14 h. The mixture was diluted with CDCI3 (2 ml), an internal standard was added (1BU3PO4, 0.0552 ml, 0.20 mmol), and the mixture was analyzed. 1H NMR indicated that 2-thiophene carbonyl chloride had been formed in 90percent yield.
72% at 70 - 140℃; for 17.75 h; A mixture of 2-acetylthiophene (0.108 ml, 1.0 mmol), 3-picoline (0.010 ml, 0.1 mmol), and thionyl chloride (0.363 ml, 5.0 mmol) was stirred at 70°C for 3 h 45 min, and then at 140°C for 14 h. The mixture was diluted with CDCI3 (1.5 ml), an internal standard was added (1BU3PO4, 0.0552 ml, 0.20 mmol), and the mixture was analyzed. 1H NMR indicated that mainly 2-thiophene carbonyl chloride (72percent yield) had been formed.
86 %Spectr. at 70 - 137℃; for 21.5 h; A mixture of 2-acetylthiophene (0.108 ml, 1.0 mmol), pyridine (0.008 ml, 0.1 mmol), anddisulfur dichloride (0.320 ml, 4.0 mmol) was stirred at 70 °C for 3.5 h. Then it was stirred at137 °C for 18 h. The mixture was diluted with CDC13 (2 ml), an internal standard was added(iBu3PO4, 0.0552 ml, 0.20 mmol), and the mixture was analyzed. 1H NMR indicated that2-thiophene carbonyl chloride (86percent yield) had been formed.
Reference: [1] Patent: WO2017/5606, 2017, A1, . Location in patent: Page/Page column 31-32
[2] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10370 - 10374
[3] Patent: WO2016/150937, 2016, A1, . Location in patent: Page/Page column 27
[4] Patent: WO2016/202757, 2016, A1, . Location in patent: Page/Page column 30; 31
[5] Patent: TW2017/36360, 2017, A,
  • 2
  • [ 527-72-0 ]
  • [ 5271-67-0 ]
YieldReaction ConditionsOperation in experiment
81% With thionyl chloride; N,N-dimethyl-formamide; sodium hydroxide In ethyl acetate at 58 - 65℃; for 2.5 h; Inert atmosphere In this experiment, the 2-thiophenecarboxylic acid was the combined solids from Experiments 13.2 and 13.3 of Example 13. [0187] The combined solids of 2-thiophenecarboxylic acid (63.1 g, 493 mmol) was dissolved in ethyl acetate (208 g) in a 3-neck round-bottom flask equipped with a thermocouple, a reflux condenser, and an additional funnel and the system was purged with nitrogen. The reflux condenser outlet was connected to a chilled receiver containing aq. NaOH (20percent, 250 g). A catalytic amount of dimethylformamide (DMF) (0.2 mL, 0.005 eq.) was added and the resulting reaction mixture was heated to 65°C with stirring, followed by a slow addition of thionyl chloride (67.2, 565 mmol, 1.15 eq.). During the addition, gases such as sulfur dioxide (S02) and hydrogen chloride (HC1) were released and the reaction temperature dropped to about 58°C. The reaction completed in 2.5 hours with no detectable unreacted 2-thiophenecarboxylic acid by GC/MS.[0188] After cooling, the flask was fitted with a distillation head and 4-Methoxyphenol (8.9 mg) was added as a stabilizer during the distillation. By vacuum distillation (short path), ethyl acetate and thionyl chloride were distilled from the mixture first under a lower vacuum (approximately 60 to 125 mmHg). The remaining mixture was cooled to room temperature and switched to a higher vacuum. Distillation (short path, approximately 4 mmHg) at a vapor temperature of approximately 63°C afforded 2-thiophenecarbonyl chloride as a clear pale yellow oil (56.5 g, 81percent). GC-FID confirmed that the obtained material was 2-thiophenecarbonyl chloride with a purity of > 98 areapercent.
76% at 20℃; for 1 h; According to Scheme 1 Step 1 : Thiophene-2-carboxylic acid (31.2 mmol, 4.00 g) was slowly added to a solution of thionyl chloride (56.2 mmol, 4.08 mL). The reaction mixture was stirred at room temperature for 1 hour. After evaporation of the thionyl chloride, the crude product was purified by bulb-to-bulb distillation (850C, 14 Torr) to yield thiophene-2-carbonyl chloride (23.7 mmol, 3.48 g, 76percent) as a colorless liquid.
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  • 3
  • [ 188290-36-0 ]
  • [ 79-37-8 ]
  • [ 5271-67-0 ]
YieldReaction ConditionsOperation in experiment
93% at 200℃; for 0.75 h; DEVICEO: piston pump 260D from ISCO TeledyneDEVICE 1: tubular reactor with a length of 6 m, with an internal volume of 96.16 mL and an outer diameter of 0.25 inchDEVICE3: pressure control valve Swagelok BPV-SS-07 A mixture MIX1 containing 90 wtpercent of a mixture MIX2 of oxalyl chloride and thiophene witha molar ratio of 2 : 1, and 10 wtpercent sulfolane, the wtpercent being based on the total weight of theMlxi, was fed by DEVICEO with a rate of 2.14 mL/min through DEVICE 1 at an averagePRESS 1 of 80 bar which was adjusted and held by the means of DEVICE3. DEVICE 1 was maintained at a temperature of 200°C by means of a heating fluid. The residence time TIME1 of the mixture in DEVICE 1 was 45 mm. A liquid sample of the reaction mixture was collected and analyzed by 1H NMR with the internal standard dioxane, yield of thiophene-2- carbonyl chloride was 93 percent based on thiophene.
Reference: [1] Patent: WO2017/76844, 2017, A1, . Location in patent: Page/Page column 18; 19; 20; 21
[2] Journal fuer Praktische Chemie (Leipzig), 1956, vol. <4> 3, p. 137,142
  • 4
  • [ 3437-95-4 ]
  • [ 201230-82-2 ]
  • [ 5271-67-0 ]
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  • 5
  • [ 3437-95-4 ]
  • [ 122-04-3 ]
  • [ 636-98-6 ]
  • [ 5271-67-0 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 6
  • [ 3437-95-4 ]
  • [ 100-20-9 ]
  • [ 5271-67-0 ]
  • [ 1711-02-0 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 7
  • [ 33311-43-2 ]
  • [ 5271-67-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 6872 - 6878
  • 8
  • [ 527-72-0 ]
  • [ 79-37-8 ]
  • [ 5271-67-0 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12149 - 12152
  • 9
  • [ 5271-67-0 ]
  • [ 39098-97-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 10
  • [ 5271-67-0 ]
  • [ 1918-77-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
[2] Journal of the American Chemical Society, 1941, vol. 63, p. 2945
  • 11
  • [ 186581-53-3 ]
  • [ 5271-67-0 ]
  • [ 1918-77-0 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 582
  • 12
  • [ 5271-67-0 ]
  • [ 60166-84-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 173 - 182
  • 13
  • [ 5271-67-0 ]
  • [ 141-78-6 ]
  • [ 13669-10-8 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667 h;
Stage #2: at -78 - 20℃; for 0.5 h;
To a stirred solution of DIPA (7.6 mL, 54 mmol) in THF (53 mL) was added n-BuLi (21.6 mL) at 0 °C. Stirring was continued at this temperature 10 minutes. The mixture was then cooled to -78 °C and EtOAc (2.4 mL, 27 mmol) was added dropwise. Stirring was continued at this temperature 30 minutes. After that, a solution of compound 13.1 (3 mL, 27 mmol) in THF (20 mL) was added dropwise. The reaction was allowed to warm to room temperature and was stirred overnight. The crude of reaction was poured in water and extracted with EtOAc (3 x 30 mL). The collected organic phase were washed with brine, dried over Na S04 and concentrated under vacuum. The title compound 13.2 was obtained as brownish oil (4.8 g, 24.3 mmol). Yield 90percent.
Reference: [1] Patent: WO2016/30534, 2016, A1, . Location in patent: Page/Page column 110
[2] Patent: WO2017/136450, 2017, A2, . Location in patent: Sheet 105/122
[3] Patent: WO2018/6074, 2018, A2, . Location in patent: Paragraph 0076; 00629
  • 14
  • [ 5271-67-0 ]
  • [ 141-97-9 ]
  • [ 13669-10-8 ]
Reference: [1] Patent: US2710867, 1954, ,
[2] Patent: US2710867, 1954, ,
  • 15
  • [ 5271-67-0 ]
  • [ 150560-58-0 ]
  • [ 1404437-62-2 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 12, p. 1034 - 1038
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