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[ CAS No. 18791-79-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 18791-79-2
Chemical Structure| 18791-79-2
Chemical Structure| 18791-79-2
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Product Details of [ 18791-79-2 ]

CAS No. :18791-79-2 MDL No. :MFCD09042555
Formula : C5H3BrOS Boiling Point : -
Linear Structure Formula :- InChI Key :ZKLBPUYMTHPNOQ-UHFFFAOYSA-N
M.W : 191.05 Pubchem ID :12284894
Synonyms :

Calculated chemistry of [ 18791-79-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.41
TPSA : 45.31 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) : 1.63
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 3.38
Consensus Log Po/w : 2.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.35 mg/ml ; 0.00183 mol/l
Class : Soluble
Log S (Ali) : -2.67
Solubility : 0.407 mg/ml ; 0.00213 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.47
Solubility : 0.647 mg/ml ; 0.00339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 18791-79-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18791-79-2 ]

* 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 [ 18791-79-2 ]
  • Downstream synthetic route of [ 18791-79-2 ]

[ 18791-79-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 18791-79-2 ]
  • [ 100523-84-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
  • 2
  • [ 498-62-4 ]
  • [ 18791-79-2 ]
YieldReaction ConditionsOperation in experiment
88% With aluminum (III) chloride; bromine In dichloromethane for 12.17 h; Thiophene-3-carbaldehyde (6.5 g, 0.06 mol) was dissolved in 200 mL of dichloromethane (dry), and 14 g of aluminum chloride was added. The dark solution was stirred for 10 min and solution of bromine (10 g, 0.066 mol) in 10 mL of dichloromethane was added dropwise over 10 min period. The mixture was stirred for 12 h and poured onto crush-ice. The organic layer was separated and extracted with 2 N HCl, washed by water. The organic phase was dried over anhydrous MgSO4 and reduced solvent. The white liquid product was purified by vacuum distillation, with yield of 88percent (10 g).
88%
Stage #1: With aluminum (III) chloride In dichloromethane at 0℃; for 2 h;
Stage #2: With bromine In dichloromethane at 0 - 40℃;
Anhydrous aluminum chloride (5.9 g, 44.5 mmol) was added in small portions over a period of 2 h to a solution of thiophene-3-carbaldehyde (2.0 g, 17.8 mmol) in CH2Cl2 (100 mL) maintaining the temperature at 0 °C. Bromine (2.56 g, 16.0 mmol) in CH2Cl2 (50 mL) was then added dropwise to the reaction mixture at 0 °C.
The reaction mixture was refluxed at 40 °C for 1 h, quenched with water, and extracted with CH2Cl2.
The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure.
The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10percent EtOAc in petroleum ether) to give 5-bromothiophene-3-carbaldehyde (3.0 g, yield 88percent).
64% With aluminum (III) chloride; bromine In dichloromethane at 20℃; for 6 h; Heating / reflux AlCl3 (15g, 0.112 mol) was added in portions over 2 h to a solution of thiophene- 3-carboxaldehyde (5g, 0.044 mol) in CH2Cl2 (150 mL) at rt. Br2 (2.13 mL, 0.041 mol) in CH2Cl2 (20 mL) was added drop wise. The mixture was heated at reflux for 6 h, cooled, poured into H2O (250 mL) and extracted with CH2Cl2. The combined extracts were washed with brine, dried (MgSO4), concentrated and distilled to yield the sub-title compound 5.4 g (64percent).
Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1170 - 1174
[2] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 1044-1045
[3] Patent: WO2006/77412, 2006, A1, . Location in patent: Page/Page column 85
[4] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 10, p. 1393 - 1403
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 5, p. 1190 - 1194
[6] Revue Roumaine de Chimie, 2012, vol. 57, # 4-5, p. 345 - 351
[7] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[8] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 15, p. 2011 - 2014
[9] Patent: US5597832, 1997, A,
[10] Patent: US2006/293343, 2006, A1, . Location in patent: Page/Page column 91
[11] Patent: US2009/143372, 2009, A1,
[12] Patent: US6740647, 2004, B1, . Location in patent: Page column 31-32
[13] Patent: WO2004/94430, 2004, A1, . Location in patent: Page 23
[14] Patent: WO2006/123639, 2006, A1, . Location in patent: Page/Page column 138
[15] Doklady Chemistry, 2014, vol. 454, # 2, p. 25 - 31[16] Dokl. Akad. Nauk, 2014, vol. 454, # 4, p. 417 - 423,7
[17] Patent: WO2007/131764, 2007, A2, . Location in patent: Page/Page column 135; 7/8
  • 3
  • [ 1193-69-7 ]
  • [ 18791-79-2 ]
Reference: [1] Dalton Transactions, 2017, vol. 46, # 12, p. 4111 - 4117
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