Home Cart 0 Sign in  
X

[ CAS No. 21190-88-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 21190-88-5
Chemical Structure| 21190-88-5
Chemical Structure| 21190-88-5
Structure of 21190-88-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 21190-88-5 ]

Related Doc. of [ 21190-88-5 ]

Alternatived Products of [ 21190-88-5 ]

Product Details of [ 21190-88-5 ]

CAS No. :21190-88-5 MDL No. :MFCD04116913
Formula : C8H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OONBOXSIWCBAHZ-UHFFFAOYSA-N
M.W :230.06 Pubchem ID :2758810
Synonyms :

Calculated chemistry of [ 21190-88-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.02
TPSA : 39.19 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 2.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.247 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.292 mg/ml ; 0.00127 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.099 mg/ml ; 0.000431 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 21190-88-5 ]

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 [ 21190-88-5 ]

* 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 [ 21190-88-5 ]
  • Downstream synthetic route of [ 21190-88-5 ]

[ 21190-88-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 21190-88-5 ]
  • [ 39774-28-2 ]
Reference: [1] Inorganic Chemistry Communications, 2014, vol. 46, p. 137 - 139
  • 2
  • [ 626-05-1 ]
  • [ 109-94-4 ]
  • [ 21190-88-5 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 14 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 3
  • [ 626-05-1 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 21190-88-5 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 25, p. 4473 - 4476
[2] Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 7757 - 7763
  • 4
  • [ 21190-87-4 ]
  • [ 21190-88-5 ]
Reference: [1] Patent: US6251925, 2001, B1,
[2] Patent: US2004/171614, 2004, A1,
[3] Patent: US2005/85506, 2005, A1,
  • 5
  • [ 21190-87-4 ]
  • [ 64-17-5 ]
  • [ 21190-88-5 ]
Reference: [1] Chemistry - A European Journal, 1997, vol. 3, # 1, p. 99 - 104
[2] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 9, p. 2758 - 2771
  • 6
  • [ 5315-25-3 ]
  • [ 21190-88-5 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
[2] Chemistry - A European Journal, 1997, vol. 3, # 1, p. 99 - 104
  • 7
  • [ 1824-81-3 ]
  • [ 21190-88-5 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
  • 8
  • [ 21190-88-5 ]
  • [ 97483-79-9 ]
YieldReaction ConditionsOperation in experiment
60% for 16 h; Inert atmosphere; Reflux CuCN (31,1g, 348mmol) was added into ethyl 6-bromopicolinate (16 g, 69.5mmol) in 608ml pyridine. The mixture was refluxed under argon for 16h, filtered through celite, and concentrated in vacuo. Saturated NaHCO3 solution was added followed by extracted with DCM for three times. The mixture was purified with flash chromatography in hexane/EE=1:1. TLC [hexane/EE 1:1]: Rf = 0.65 Yield: 7.3 g,(60percent). 1HNMR (600 MHz, CDCl3): δ= 8.32(dd, 1H, J=1.15, 7.97Hz), 8.04(t, 1H,J=7.86, 7.86Hz), 7.88 (dd, 1H, J=1.13, 7.76Hz), 4.52(q, 2H, J=7.13, 7.13,7.12Hz), 1.40(t, 3H, J=7.13, 7.13Hz). 13C NMR (300 MHz, CDCl3): δ= 163.76,150.06, 138.70, 134,23, 131.40, 128.12, 116.62, 62.89, 14.44 HRMS: 177.0669[M +H], calculated 177.0664[M + H] +.
60% for 16 h; Inert atmosphere; Reflux CuCN (31,1g, 348mmol) was added into ethyl 6-bromopicolinate (16 g, 69.5mmol) in 608 ml pyridine. The mixture was refluxed under argon for 16h, filtered through celite, and concentrated in vacuo. Saturated NaHCO3 solution was added followed by extracted with DCM for three times. The mixture was purified with flash chromatography in hexane/EE=1:1. TLC [hexane/EE 1:1]: Rf = 0.65 Yield: 7.3 g,(60percent). 1HNMR (600 MHz, CDCl3): δ= 8.32(dd, 1H, J=1.15, 7.97Hz), 8.04(t, 1H,J=7.86, 7.86Hz), 7.88 (dd, 1H, J=1.13, 7.76Hz), 4.52(q, 2H, J=7.13, 7.13,7.12Hz), 1.40(t, 3H, J=7.13, 7.13Hz). 13C NMR (300 MHz, CDCl3): δ= 163.76,150.06, 138.70, 134,23, 131.40, 128.12, 116.62, 62.89, 14.44 HRMS: 177.0669[M +H], calculated 177.0664[M + H] +.
Reference: [1] Patent: EP2690102, 2014, A1, . Location in patent: Paragraph 0070; 0073
[2] Patent: WO2014/15993, 2014, A1, . Location in patent: Page/Page column 35
  • 9
  • [ 21190-88-5 ]
  • [ 97483-79-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3922 - 3935
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 21190-88-5 ]

Bromides

Chemical Structure| 1807149-82-1

[ 1807149-82-1 ]

Ethyl 6-bromo-5-methylpicolinate

Similarity: 0.94

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.91

Chemical Structure| 1206248-47-6

[ 1206248-47-6 ]

Methyl 4,6-dibromopicolinate

Similarity: 0.89

Chemical Structure| 21190-87-4

[ 21190-87-4 ]

6-Bromo-2-pyridinecarboxylic acid

Similarity: 0.88

Chemical Structure| 866775-09-9

[ 866775-09-9 ]

Methyl 3-amino-6-bromopicolinate

Similarity: 0.87

Esters

Chemical Structure| 1807149-82-1

[ 1807149-82-1 ]

Ethyl 6-bromo-5-methylpicolinate

Similarity: 0.94

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.91

Chemical Structure| 1206248-47-6

[ 1206248-47-6 ]

Methyl 4,6-dibromopicolinate

Similarity: 0.89

Chemical Structure| 866775-09-9

[ 866775-09-9 ]

Methyl 3-amino-6-bromopicolinate

Similarity: 0.87

Chemical Structure| 1214375-85-5

[ 1214375-85-5 ]

Ethyl 3,6-dibromopicolinate

Similarity: 0.86

Related Parent Nucleus of
[ 21190-88-5 ]

Pyridines

Chemical Structure| 1807149-82-1

[ 1807149-82-1 ]

Ethyl 6-bromo-5-methylpicolinate

Similarity: 0.94

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.91

Chemical Structure| 1206248-47-6

[ 1206248-47-6 ]

Methyl 4,6-dibromopicolinate

Similarity: 0.89

Chemical Structure| 21190-87-4

[ 21190-87-4 ]

6-Bromo-2-pyridinecarboxylic acid

Similarity: 0.88

Chemical Structure| 866775-09-9

[ 866775-09-9 ]

Methyl 3-amino-6-bromopicolinate

Similarity: 0.87