Home Cart 0 Sign in  
X

[ CAS No. 16689-02-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 16689-02-4
Chemical Structure| 16689-02-4
Chemical Structure| 16689-02-4
Structure of 16689-02-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 16689-02-4 ]

Related Doc. of [ 16689-02-4 ]

Alternatived Products of [ 16689-02-4 ]

Product Details of [ 16689-02-4 ]

CAS No. :16689-02-4 MDL No. :MFCD00052401
Formula : C5H2N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :FLYONFCGDKAMIH-UHFFFAOYSA-N
M.W : 154.15 Pubchem ID :519294
Synonyms :

Calculated chemistry of [ 16689-02-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.86
TPSA : 97.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
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) : 0.91
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : -0.82
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.25
Solubility : 0.874 mg/ml ; 0.00567 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0493 mg/ml ; 0.00032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.12
Solubility : 11.7 mg/ml ; 0.0762 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.5

Safety of [ 16689-02-4 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P310-P305+P351+P338 UN#:
Hazard Statements:H302-H312-H319-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16689-02-4 ]

* 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 [ 16689-02-4 ]
  • Downstream synthetic route of [ 16689-02-4 ]

[ 16689-02-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 6030-18-8 ]
  • [ 16689-02-4 ]
YieldReaction ConditionsOperation in experiment
83% With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Inert atmosphere General procedure: In an oven-dried two-necked 50 mLround-bottomed flask, equipped with a stirring bar, a solution of the oxime(1.0 mmol) and 2-NO2-C6H4-SO3XY(1.5 mmol) dissolved in anhydrous CH2Cl2 (5.0 mL) wasplaced under the atmosphere of nitrogen. The reaction mixture was stirred atroom temperature for 5 min, then DBU (2.5 mmol) was added drop wise over 2 min.The reaction mixture became a clear homogeneous solution after addition of DBU.The reaction was monitored by TLC. The reaction mixture was diluted with EtOAcand washed with water (2×5 mL) followed by brine (2×5 mL) upon completeconsumption of the starting material. Product was purified by columnchromatography.Furthermore, the by-product Oxymacould be readily recovered by acidifying the aqueous layer, and then extractingwith ethyl acetate. The Oxyma thus recovered can then be reused to regeneratethe sulfonate ester of Oxyma, which can be further used for a separate batch ofreaction.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 33, p. 4397 - 4400
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3173 - 3174,2
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3173 - 3174
  • 2
  • [ 104416-19-5 ]
  • [ 16689-02-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 10, p. 1775 - 1782
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2583 - 2585
[3] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 4014 - 4016
[4] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
  • 3
  • [ 4521-33-9 ]
  • [ 16689-02-4 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 46, p. 13265 - 13268
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 14, p. 3027 - 3041
[3] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
  • 4
  • [ 143-33-9 ]
  • [ 87997-11-3 ]
  • [ 16689-02-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 7, p. 1885 - 1890
  • 5
  • [ 98-03-3 ]
  • [ 16689-02-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
[2] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
  • 6
  • [ 14289-24-8 ]
  • [ 16689-02-4 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
[3] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
  • 7
  • [ 57784-57-3 ]
  • [ 16689-02-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
  • 8
  • [ 1003-31-2 ]
  • [ 16689-02-4 ]
  • [ 42137-24-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
  • 9
  • [ 1003-31-2 ]
  • [ 16689-02-4 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1982, vol. 18, # 2, p. 127 - 130[2] Khimiya Geterotsiklicheskikh Soedinenii, 1982, vol. 18, # 2, p. 167 - 170
  • 10
  • [ 1003-31-2 ]
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 16689-02-4 ]
  • [ 42137-24-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
  • 11
  • [ 16689-02-4 ]
  • [ 6317-37-9 ]
Reference: [1] Chemische Berichte, 1943, vol. 76, p. 419,428
  • 12
  • [ 16689-02-4 ]
  • [ 4377-58-6 ]
Reference: [1] Patent: US2013/137730, 2013, A1,
  • 13
  • [ 16689-02-4 ]
  • [ 52532-63-5 ]
YieldReaction ConditionsOperation in experiment
87% With ammonium chloride; zinc In methanol at 20℃; for 0.5 h; A suspension of 5-nitrothiophene-2-carbonitrile (Lancaster) (1 g, 6.5 mmol) in methanol (30 mL) was added an aqueous solution (30 mL) of NH4Cl (4.5 g, 65 mmol), followed by activated Zinc (Aldrich, 4.2 g, 65 mmol).
The reaction mixture was stirred at room temperature for 0.5 h.
The mixture was filtered through a short pad of celite.
The mixture was concentrated.
The residue was partitioned between ethyl acetate and water.
The organic layer was separated, and aqueous layer was extracted with ethyl acetate.
The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 5-amino-thiophene-2-carbonitrile as a yellow solid (0.7 g, 87percent).
Reference: [1] Patent: US2011/130398, 2011, A1, . Location in patent: Page/Page column 79; 80
[2] Patent: US6353006, 2002, B1, . Location in patent: Page column 146
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 16689-02-4 ]

Nitroes

Chemical Structure| 4521-33-9

[ 4521-33-9 ]

5-Nitrothiophene-2-carboxaldehyde

Similarity: 0.81

Chemical Structure| 166887-84-9

[ 166887-84-9 ]

2-(Bromomethyl)-5-nitrothiophene

Similarity: 0.81

Chemical Structure| 6317-37-9

[ 6317-37-9 ]

5-Nitrothiophene-2-carboxylic acid

Similarity: 0.70

Chemical Structure| 5832-01-9

[ 5832-01-9 ]

Methyl 5-nitrothiophene-2-carboxylate

Similarity: 0.66

Chemical Structure| 52003-20-0

[ 52003-20-0 ]

2-Nitrothiophen-3-amine

Similarity: 0.65

Nitriles

Chemical Structure| 52532-63-5

[ 52532-63-5 ]

5-Aminothiophene-2-carbonitrile

Similarity: 0.75

Chemical Structure| 52603-48-2

[ 52603-48-2 ]

5-Amino-3-methylthiophene-2,4-dicarbonitrile

Similarity: 0.61

Chemical Structure| 138564-58-6

[ 138564-58-6 ]

2-Amino-5-methylthiophene-3-carbonitrile

Similarity: 0.58

Chemical Structure| 1003-31-2

[ 1003-31-2 ]

2-Thiophenecarbonitrile

Similarity: 0.55

Chemical Structure| 73781-74-5

[ 73781-74-5 ]

4-Aminothiophene-2-carbonitrile

Similarity: 0.53