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[ CAS No. 3581-89-3 ] {[proInfo.proName]}

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Chemical Structure| 3581-89-3
Chemical Structure| 3581-89-3
Structure of 3581-89-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3581-89-3 ]

CAS No. :3581-89-3 MDL No. :MFCD00005335
Formula : C4H5NS Boiling Point : -
Linear Structure Formula :- InChI Key :RLYUNPNLXMSXAX-UHFFFAOYSA-N
M.W : 99.15 Pubchem ID :137980
Synonyms :

Calculated chemistry of [ 3581-89-3 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 27.08
TPSA : 41.13 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.45
Log Po/w (MLOGP) : 0.05
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.92
Solubility : 1.19 mg/ml ; 0.012 mol/l
Class : Very soluble
Log S (Ali) : -1.82
Solubility : 1.52 mg/ml ; 0.0153 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.6
Solubility : 2.49 mg/ml ; 0.0251 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 3581-89-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3581-89-3 ]

* 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 [ 3581-89-3 ]
  • Downstream synthetic route of [ 3581-89-3 ]

[ 3581-89-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3581-89-3 ]
  • [ 68-12-2 ]
  • [ 13838-78-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1203 - 1208
[2] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 85
  • 2
  • [ 3581-89-3 ]
  • [ 4394-85-8 ]
  • [ 13838-78-3 ]
YieldReaction ConditionsOperation in experiment
70.8%% With n-butyllithium In hexane (a)
To a solution of n-butyllithium (24 ml, 0.06 mol, 2.5M in hexane) in 50 ml of ether under argon at -78° C. was added dropwise a solution of 5-methylthiazole (5 g, 0.05 mol) in 25 ml of ether.
The mixture was stirred at -78° C. for 1 h, and then a solution of N-formyl-morpholine (5.5 ml 0.055 mol) in 30 ml of ether was added within 15 min.
The mixture was stirred for 1 h at -78° C., then at 0°--5° C. overnight.
The reaction mixture was then extracted with 4N HCl (4*10 ml), the aqueous layers were combined, cooled in an ice-bath, and neutralized with sodium bicarbonate solution (pH 9).
The aqueous layer was extracted with ether (4*20 ml), the organic layer was dried over magnesium sulfate and concentrated in vacuo.
The residue was dried in vacuo to afford 4.5 g (70.8percentpercent) of 5-methyl-2-thiazolylcarboxaldehyde.
Reference: [1] Patent: US5569655, 1996, A,
  • 3
  • [ 3581-89-3 ]
  • [ 34241-39-9 ]
  • [ 25742-12-5 ]
YieldReaction ConditionsOperation in experiment
44% With N-Bromosuccinimide; NaCN In tetrachloromethane; water; N,N-dimethyl-formamide EXAMPLE 10
COMPOUND 10: The (2'R,6'S)-3,3"-dimethyl-1'-(2-thiazol-5-yl-ethyl)-1',2',3',4',5',6'-hexahydro-[2,2';6',2"]terpyridine (HBr Salt)
A mixture of 5-methyl-thiazole (1.00 g, 10.1 mmol), NBS (2.06 g, 11.6 mmol) and 2,2'-azobisisobutyronitrile (0.164, 1.00 mmol) in CCl4 (60 mL) was stirred and heated at reflux for 3 h.
After the solution was cooled to room temperature NaS2O3 (5 g) in water (50 mL) was added, and the organic layer was collected.
The aqueous layer was extracted with CH2Cl2 (3*60 mL).
The organic layers were combined, washed with water (50 mL), and concentrated to ~150 mL by evaporation under vacuum. DMF (40 mL) and NaCN (1.00 g, 20.4 mmol) in water (20 mL) were then added, and the low boiling solvents (CH2Cl2 and CCl4) were removed by evaporation under vacuum.
The residue was then stirred overnight.
Water (40 mL) was added, and the mixture was extracted with Et2O (5*100 mL).
The extracts were combined, washed with water (50 mL) and dried over Na2SO4.
After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (3:4 Et2O/CH2Cl2) to afford thiazole-5-carbonitrile as a pale yellow liquid (0.550 g, 44percent).
1H NMR (CDCl3) δ 3.97 (s, 2H), 7.85 (s, 1H), 8.81 (s, 1H).
Reference: [1] Patent: US2005/154201, 2005, A1,
  • 4
  • [ 3581-89-3 ]
  • [ 41731-23-1 ]
Reference: [1] Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 758,763
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