Home Cart 0 Sign in  
X

[ CAS No. 13781-53-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 13781-53-8
Chemical Structure| 13781-53-8
Chemical Structure| 13781-53-8
Structure of 13781-53-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13781-53-8 ]

Related Doc. of [ 13781-53-8 ]

Alternatived Products of [ 13781-53-8 ]

Product Details of [ 13781-53-8 ]

CAS No. :13781-53-8 MDL No. :MFCD00005471
Formula : C6H5NS Boiling Point : -
Linear Structure Formula :- InChI Key :GWZCLMWEJWPFFA-UHFFFAOYSA-N
M.W : 123.18 Pubchem ID :83730
Synonyms :

Calculated chemistry of [ 13781-53-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.84
TPSA : 52.03 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.79
Solubility : 1.98 mg/ml ; 0.0161 mol/l
Class : Very soluble
Log S (Ali) : -1.95
Solubility : 1.38 mg/ml ; 0.0112 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.11
Solubility : 0.952 mg/ml ; 0.00773 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 13781-53-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13781-53-8 ]

* 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 [ 13781-53-8 ]
  • Downstream synthetic route of [ 13781-53-8 ]

[ 13781-53-8 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 13781-53-8 ]
  • [ 59311-67-0 ]
YieldReaction ConditionsOperation in experiment
67% With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 16 h; Inert atmosphere This compound was synthesized according to a procedure described in literature.5 An oven-dried round-bottom flask (25 mL) cooled under argon was fitted with a rubber septum and charged with a stir bar, anhydrous InCl3 (0.681 g, 3.079 mmol), anhydrous THF (10 mL), and NaBH4 (0.341 g, 9.014 mmol). The reaction was stirred at 25 °C for 1h, followed by the dropwise addition of 3-thiopheneacetonitrile (0.340 mL, 2.981 mmol), and the mixture was stirred at 25 °C for 16 h. The solution was quenched with 10 mL of 2.8 M hydrochloric acid, and the solution was refluxed for 2 h to dissolve remaining metal salts. The reaction mixture was cooled to 25°C, 5 mL of methanol were added, and the mixture was again refluxed for 2 h. The reaction mixture was then cooled to 25°C and filtered, and the methyl borate/methanol was removed from the filtrate by evaporation. The remaining acidic solution was extracted with DCM (3 10 mL), and the organic layers were discarded. The acidic aqueous layer was then basified with NaOH pellets to pH ≈ 11 and again extracted with DCM (3 10 mL). The combined organic layers were dried on a WA filter filtered, and evaporated under vacuum to afford 2-(3-thienyl)ethanamine 7. Yellowish oil; 0.250 g, yield: 67percent. 1H NMR (300 MHz, CDCl3): δ = 7.20-7.30 (m, 1H; ArH), 7.00 (m, 1H; ArH), 6.95 (m, 1H; ArH), 2.96 (t, 2H; J = 6.6 Hz, CH2), 2.78 (t, 2H; J = 6.6 Hz, CH2), 1.45 ppm (bs, 2H; NH2). The 1H NMR spectrum was according to literature.
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 221 - 228
[2] Tetrahedron Letters, 2013, vol. 54, # 45, p. 6087 - 6089
[3] MedChemComm, 2015, vol. 6, # 9, p. 1679 - 1686
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 4466
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 351
[6] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2624 - 2633
[7] Patent: US4904653, 1990, A,
[8] Patent: US5028602, 1991, A,
[9] Patent: US2006/3990, 2006, A1, . Location in patent: Page/Page column 12; 24
[10] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 3004 - 3008
  • 2
  • [ 34846-44-1 ]
  • [ 7677-24-9 ]
  • [ 13781-53-8 ]
YieldReaction ConditionsOperation in experiment
4.06 g With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 0 - 20℃; Inert atmosphere NBS (9.07 g, 50.9 mmol, 1 equiv) and   AIBN (836 mg, 5.1 mmol, 0.1 equiv) were added to a solution of   3-methylthiophene (5 g, 50.9 mmol, 1 equiv) in   CCl4 (20 mL). The resulting mixture was refluxed for 1 h. After cooling, the solvent was evaporated under reduced pressure and the residue obtained was dissolved in dry   acetonitrile (40 mL). To this solution,   TMSCN (20 mL, 153 mmol, 3 equiv) and   TBAF (1 M in   THF, 153 mL, 153 mmol, 3 equiv) were added dropwise at 0 °C under argon atmosphere. After stirring overnight at room temperature, the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography (5percent EtOAc/cyclohexane) affording   5 as an orange oil (4.06 g, 33 mmol, 65percent for the two steps). 1H NMR (300 MHz, CDCl3): δ 7.22 (dd, J=5.0, 3.0 Hz, 1H), 7.10 (dd, J=2.8, 1.1 Hz, 1H), 6.90 (dd, J=5.0, 1.2 Hz, 1H), 3.58 (s, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ 129.4, 127.0, 126.9, 122.9, 117.7, 18.4 ppm. IR (neat): ν 3104, 2360, 2340, 2255, 1688, 1415, 832, 771, 692 cm−1. GC–MS: m/z C6H5NS [M+⩽] 122.#10;
Reference: [1] Tetrahedron, 2013, vol. 69, # 22, p. 4473 - 4478
  • 3
  • [ 6165-69-1 ]
  • [ 107-14-2 ]
  • [ 13781-53-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
[2] Green Chemistry, 2017, vol. 19, # 19, p. 4515 - 4519
  • 4
  • [ 17249-80-8 ]
  • [ 1071-36-9 ]
  • [ 13781-53-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
  • 5
  • [ 34846-44-1 ]
  • [ 143-33-9 ]
  • [ 13781-53-8 ]
Reference: [1] Patent: WO2005/66183, 2005, A1, . Location in patent: Page/Page column 32
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 4466
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 351
  • 6
  • [ 34846-44-1 ]
  • [ 151-50-8 ]
  • [ 13781-53-8 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 4466
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 351
  • 7
  • [ 34846-44-1 ]
  • [ 13781-53-8 ]
Reference: [1] MedChemComm, 2015, vol. 6, # 9, p. 1679 - 1686
  • 8
  • [ 616-44-4 ]
  • [ 13781-53-8 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 22, p. 4473 - 4478
[2] MedChemComm, 2015, vol. 6, # 9, p. 1679 - 1686
  • 9
  • [ 498-62-4 ]
  • [ 38622-91-2 ]
  • [ 13781-53-8 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 23 - 30
  • 10
  • [ 81344-59-4 ]
  • [ 13781-53-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1231 - 1232
  • 11
  • [ 13781-53-8 ]
  • [ 34843-84-0 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With borane-dimethyl sulfide In tetrahydrofuran for 16 h; Reflux
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.333333 h;
Thiophen-3-yl-acetonitrile (2.0 g, 16.2 mmol)Soluble in tetrahydrofuran (36mL),The borane-dimethyl sulfide complex (3.0 mL, 30.4 mmol) was slowly added, and the reaction mixture was heated to reflux for 16 hours. At room temperature, the reaction was quenched by the slow addition of methanol.Then add saturated hydrogen chloride / methanol solution (10mL),Stir at room temperature for 20 minutes, concentrate to give a solid initial product.Wash with diethyl ether (20 mL).The compound 41A was obtained as a white solid (2.5 g, yield: 94percent).
94%
Stage #1: With dimethylsulfide borane complex In tetrahydrofuran for 16 h; Heating / reflux
Stage #2: With methanol In tetrahydrofuran
Preparation 1; 2-Thiophene-3-yl-ethylamine hydrochloride; Slowly add borane methyl sulfide complex (30.4 mL, 304.4 mmol) to a solution of thiophen-3-yl-acetonitrile (25.0 g, 203.0 mmol) in tetrahydrofuran (450 mL). Heat the reaction at reflux for 16 h and then cool to RT. Slowly quench the reaction with methanol (50 mL) until no foaming is observed. To this mixture slowly add methanol (100 mL) which is saturated with hydrogen chloride. Stir the mixture at RT for 20 min before concentrating in vacuo. Add methanol (100 mL) to the mixture and concentrate in vacuo. Suspend the resulting solid in diethyl ether (200 mL) and filter to afford 31.1 g (94percent) of the crude title compound. MS/ES m/z 128.3 [M+H]+.
94%
Stage #1: With dimethylsulfide borane complex In tetrahydrofuran for 16 h; Heating / reflux
Stage #2: at 20℃; for 0.333333 h;
Step 1. 2-Thiophene-3-yl-ethylamine hydrochloride; Slowly add borane methyl sulfide complex (30.4 mL, 304.4 mmol) to a solution of thiophen-3-yl-acetonitrile (25.0 g, 203.0 mmol) in tetrahydrofuran (450 mL). Heat the reaction at reflux for 16 h and then cool to RT. Slowly quench the reaction with methanol (50 mL) until no foaming is observed. To this mixture slowly add methanol (100 mL) which is saturated with hydrogen chloride. Stir the mixture at RT for 20 min before concentrating in vacuo. Add methanol (100 mL) to the mixture and concentrate in vacuo. Suspend the resulting solid in diethyl ether (200 mL) and filter to afford 31.1 g (94percent) of the crude title compound. MS/ES m/z 128.3 [M+H]+
Reference: [1] Patent: CN108250128, 2018, A, . Location in patent: Paragraph 0698; 0700; 0701; 0702
[2] Patent: WO2007/146759, 2007, A2, . Location in patent: Page/Page column 24
[3] Patent: WO2007/146758, 2007, A2, . Location in patent: Page/Page column 33
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[5] Patent: WO2012/114252, 2012, A1, . Location in patent: Page/Page column 46
  • 12
  • [ 13781-53-8 ]
  • [ 165947-52-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 3004 - 3008
  • 13
  • [ 13781-53-8 ]
  • [ 960289-03-6 ]
Reference: [1] Patent: WO2007/146759, 2007, A2,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 13781-53-8 ]

Nitriles

Chemical Structure| 1641-09-4

[ 1641-09-4 ]

3-Thiophenecarbonitrile

Similarity: 0.81

Chemical Structure| 24434-84-2

[ 24434-84-2 ]

Benzo[b]thiophene-3-carbonitrile

Similarity: 0.60

Chemical Structure| 4651-82-5

[ 4651-82-5 ]

2-Aminothiophene-3-carbonitrile

Similarity: 0.58

Chemical Structure| 1108712-56-6

[ 1108712-56-6 ]

5-Chlorothiophene-3-carbonitrile

Similarity: 0.58

Chemical Structure| 622-75-3

[ 622-75-3 ]

2,2'-(1,4-Phenylene)diacetonitrile

Similarity: 0.52