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[ CAS No. 18791-78-1 ] {[proInfo.proName]}

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Chemical Structure| 18791-78-1
Chemical Structure| 18791-78-1
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Product Details of [ 18791-78-1 ]

CAS No. :18791-78-1 MDL No. :MFCD01318960
Formula : C5H3BrOS Boiling Point : -
Linear Structure Formula :- InChI Key :ZDVHJQOCVBTMOF-UHFFFAOYSA-N
M.W : 191.05 Pubchem ID :2764207
Synonyms :

Calculated chemistry of [ 18791-78-1 ]

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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 3.38
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.564 mg/ml ; 0.00295 mol/l
Class : Soluble
Log S (Ali) : -2.33
Solubility : 0.896 mg/ml ; 0.00469 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 : 2.17

Safety of [ 18791-78-1 ]

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

Application In Synthesis of [ 18791-78-1 ]

* 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 [ 18791-78-1 ]
  • Downstream synthetic route of [ 18791-78-1 ]

[ 18791-78-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 18791-78-1 ]
  • [ 71637-34-8 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogen; sodium acetate; palladium dichloride In methanol at 35℃; for 12 h; Typical procedures: 6-bromonicotinaldehyde (930 mg, 5.0 mmol), NaOAc (820 mg, 10.0 mmol), MeOH (30 mL), and PdCl2 (45 mg) were mixed in a glass bottle capped with a balloon filled with hydrogen. After stirred at 35 °C for 4 h, the mixture was filtered and washed with MeOH. The solvent was removed and the residue was dissolved in water, neutralized with solid NaHCO3, and extracted with ethyl acetate. The organic phase was dried over anhyd Na2SO4, and then filtered. The solvent was removed and the residue was subjected to chromatography to yield pyridin-3-ylmethanol (428 mg, 78percent).
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3798 - 3801
  • 2
  • [ 7758-19-2 ]
  • [ 18791-78-1 ]
  • [ 16694-17-0 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 3
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  • [ 16694-17-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
  • 4
  • [ 3141-26-2 ]
  • [ 68-12-2 ]
  • [ 18791-78-1 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.0833333 h;
Stage #2: at -78℃; for 0.166667 h;
A stirred and cooled solution of thiophene (185 mL, 2.3 mol) at 0 °C in chloroform was treated dropwise with bromine (500 ML, 1560 g, 9.75 mol) for 5 h. During the last hour bromine was added without cooling the reaction mixture. Then the mixture was stirred and heated at reflux for 5 h, cooled to room temperature, quenched with 3 M aqueous NAOH, and stirred vigerously to consume excess bromine. The aqueous layer was separated, the organic phase was washed with water, and then with acetone (150 mL) to remove remaining water. The organic residue was dried and then dissolved at reflux in chloroform (1 L). When cooling, the target tetrabromo- thiophene was precipitated as colorless crystals (693 g, 75percent). A solution of this tetrabromo- thiophene (47 g, 0.12 mol) in dry diethyl ether (300 ML) was cooled to 0 °C and treated dropwise with butyllithium in hexane (150 ML, 0.24 mol, 1.6 M) for 80-90 min under argon. Then the mixture was stirred for an additional 20 min, and ice water (250 mL) was added carefully with stirring. The organic phase was separated, the aqueous phase extracted twice with ether, and the organic extracts all combined, dried over anhydrous calcium chloride, and concentrated in vacuo. The residue was distilled at 15 MMHG to give 22 g (77percent) of 3,4-dibromothiophene. A solution of this 3,4-dibromothiophene (72 g, 33 mL, 0.3 mol) in dry ether (120 mL) was cooled TO-78 °C, added to a solution of nBuLi (206 mL, 0.33 mol, 1.6 M) AT-78 °C, and stirred for 5 min. A cold - 78 °C solution OF DMF (35 mL, 33 g, 0.45 mol) in dry ether (120 mL) was slowly added to the reaction mixture AT-78 °C. After 10 min, the cold bath was removed and an aqueous HCI (150 mL, 6N) solution was added carefully, the mixture warmed to 23 °C and the aqueous phase separated and washed further with ether. The organic extracts were then combined, washed with saturated aqueous sodium bicarbonate, and the organic partition evaporated. The residue was distilled twice under vacuum to provide pure title compound (40 g, 69percent).
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 23, p. 8016 - 8029
[2] RSC Advances, 2015, vol. 5, # 77, p. 62336 - 62342
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3682 - 3688
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 19, p. 2735 - 2744
[5] Chemistry - A European Journal, 2016, vol. 22, # 2, p. 694 - 703
[6] Patent: WO2004/58702, 2004, A2, . Location in patent: Page 32; 24
[7] Patent: US6340759, 2002, B1, . Location in patent: Example 278
[8] Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 212, # 2-3, p. 81 - 87
[9] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8194 - 8199
[10] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[11] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 15, p. 2011 - 2014
[12] Patent: WO2016/144848, 2016, A1, . Location in patent: Page/Page column 43; 44
[13] Patent: WO2016/144846, 2016, A1, . Location in patent: Page/Page column 65
[14] Patent: WO2016/144849, 2016, A1, . Location in patent: Page/Page column 38
[15] Patent: WO2016/144847, 2016, A1, . Location in patent: Page/Page column 42
  • 5
  • [ 3141-26-2 ]
  • [ 18791-78-1 ]
YieldReaction ConditionsOperation in experiment
74% With n-butyllithium In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide Production Example 102
4-Bromothiophene-3-carboxaldehyde
After dissolving 25.2 g of 3,4-dibromothiophene in 300 ml of diethyl ether, the solution was cooled to -78° C. Next, 44.1 ml of n-butyllithium (2.6 M, n-hexane solution) was added dropwise while stirring at below -60° C.
After 1 hour, 9.66 ml of N,N-dimethylformamide was added dropwqise at below -60° C.
After an additional 45 minutes, water was added to the reaction solution, the temperature was returned to room temperature, and extraction was performed with ethyl acetate.
The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (14.78 g, 74percent yield).
1H-NMR (400 MHz, CDCl3); δ (ppm) 7.36 (1H, d, J=3.6 Hz), 8.15 (1H, d J=3.6 Hz), 9.34 (1H, s).
29% With n-butyllithium In tetrahydrofuran; N,N-dimethyl-formamide EXAMPLE 74
Preparation of N-hydroxy-N-[(4-bromo-thien-3-yl)methyl]urea
To a -78° C. stirred solution of 3,4-dibromothiophene (10 g, 41.33 mmole) in THF (25 mL) was added n-BuLi (45.5 mmole, 2.5M in hexanes).
The reaction was stirred 5 min. and cannulated into a cold (-78° C.) stirred solution of DMF (4.35 g, 62 mmole) in THF (20 mL).
The reaction was allowed to stir overnight at room temperature, poured into dilute HCl and extracted with ethyl acetate.
The combined organic layers were washed with water, dried (MgSO4) and concentrated to give a brown oil.
Distillation yielded 2.31 g (29percent) of 4-bromothien-3-yl carboxaldehyde as a liquid (bp: 65°, 0.5 mm Hg).
Reference: [1] Patent: US2004/167224, 2004, A1,
[2] Patent: US5185363, 1993, A,
[3] Patent: US4332952, 1982, A,
  • 6
  • [ 70260-05-8 ]
  • [ 18791-78-1 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 7
  • [ 18791-78-1 ]
  • [ 1024594-86-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 77, p. 62336 - 62342
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