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[ CAS No. 1591-37-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1591-37-3
Chemical Structure| 1591-37-3
Chemical Structure| 1591-37-3
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Product Details of [ 1591-37-3 ]

CAS No. :1591-37-3 MDL No. :MFCD09745275
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :LBVLXRZXEOPYDW-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :12715714
Synonyms :

Calculated chemistry of [ 1591-37-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.05
TPSA : 59.04 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 : Yes
Log Kp (skin permeation) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.07
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.39 mg/ml ; 0.00936 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 0.698 mg/ml ; 0.00471 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.23
Solubility : 0.868 mg/ml ; 0.00586 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 1591-37-3 ]

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 [ 1591-37-3 ]

* 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 [ 1591-37-3 ]
  • Downstream synthetic route of [ 1591-37-3 ]

[ 1591-37-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1591-37-3 ]
  • [ 61948-59-2 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 1759,1765
  • 2
  • [ 1591-37-3 ]
  • [ 61948-86-5 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 1759,1765
  • 3
  • [ 77326-36-4 ]
  • [ 124-41-4 ]
  • [ 1591-37-3 ]
YieldReaction ConditionsOperation in experiment
83% With methanol In N,N-dimethyl-formamide at 20℃; for 18 h; Inert atmosphere NaOMe(25percentwtinMeOH,325μL,1.42mmol,1.1eq.)wasaddedtoasolutionof2-amino-6-fluorobenzonitrile (176 mg, 1.29 mmol, 1.0 eq.) in DMF (1.00 mL) at roomtemperature, and stirred for 18 hours. The solution was concentrated in vacuo and theresidue stirred with H2O (10 mL) to give a beige precipitate. This was filtered underreducedpressure,theresiduedissolvedinEtOAcandconcentratedinvacuo,tituratedwithhexanes before remaining solvent was removed in vacuo giving 2-amino-6-methoxybenzonitrile(158mg,1.07mmol,83percent)asabeigeamorphoussolid;mp143–145°C,lit.136–140°C.13
63% at 20℃; for 9 h; Heating / reflux Example 2: Methyl- (2-cyano-3-methoxy-phenyl) sulfonamide; 2.1 : 2-Amino-6-methoxy-benzonitrile A solution of 70 g (0.5 mol) of 2-amino-6-fluoro-benzonitrile (prepared, e. g. according to US 4,504, 660) in 250 ml of N, N-dimethylformamide was initially charged and a solu- tion of 30.6 g (0.55 mol) sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours under stirring. The completion of the reaction was monitored by TLC. Additional 25 g of so- dium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for additional 4 hours while stirring. The reaction mixture was concentrated under re- duced pressure, the resulting residue was triturated with water, sucked off and the ob- tained solids were dissolved in ethyl acetate. The resulting solution was concentrated in vacuo. The obtained residue was triturated with petroleum ether and sucked off to afford 48 g (63percent of theory) of a brownish solid having a melting point of 143-146°C.
63% at 20℃; for 9 h; Heating / reflux Example 2;: N,N-Dimethyl-2-cyano-3-methoxyphenylsulfonamide (Compound No. 2); 2.1 : 2-Amino-6-methoxybenzonitrile; EPO <DP n="33"/>A solution of 70 g (0.5 mol) of 2-amino-6-fluorobenzonitrile (prepared, e.g. according to US 4,504,660) in 250 ml of N,N-dimethylformamide was prepared, and a solution of 30.6 g (0.55 mol) of sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours with stirring. The completion of the reaction was monitored by TLC. An additional 25 g of sodium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for an additional 4 hours while stirring. The reaction mixture was concentrated under reduced pressure. The resulting residue was triturated with water, filtered off with suction and the solids obtained were dissolved in ethyl acetate. The resulting solution was concen- trated in vacuo. The obtained residue was triturated with petroleum ether and filtered off with suction. Yield: 48 g (63percent of theory) of a brownish solid having a melting point of 143-146°C.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
[2] Patent: WO2005/35486, 2005, A1, . Location in patent: Page/Page column 49
[3] Patent: WO2006/56433, 2006, A2, . Location in patent: Page/Page column 31-32
  • 4
  • [ 38469-85-1 ]
  • [ 1591-37-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 6, p. 742 - 748
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 434 - 444
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 449 - 469
[4] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[5] Yakugaku Zasshi, 1955, vol. 75, p. 755[6] Chem.Abstr., 1955, p. 13939
[7] Justus Liebigs Annalen der Chemie, 1912, vol. 388, p. 34
[8] Journal of the American Chemical Society, 1977, vol. 99, p. 3734 - 3744
[9] Patent: US4518597, 1985, A,
  • 5
  • [ 67-56-1 ]
  • [ 77326-36-4 ]
  • [ 1591-37-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 16, p. 4203 - 4206
  • 6
  • [ 38469-85-1 ]
  • [ 1591-37-3 ]
Reference: [1] Patent: US4404230, 1983, A,
  • 7
  • [ 35213-00-4 ]
  • [ 1591-37-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 434 - 444
  • 8
  • [ 606-21-3 ]
  • [ 1591-37-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 434 - 444
  • 9
  • [ 1591-37-3 ]
  • [ 53600-33-2 ]
Reference: [1] Chemische Berichte, 1961, vol. 94, p. 2295 - 2305
[2] Journal of the American Chemical Society, 1977, vol. 99, p. 3734 - 3744
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