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[ CAS No. 89583-07-3 ] {[proInfo.proName]}

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Chemical Structure| 89583-07-3
Chemical Structure| 89583-07-3
Structure of 89583-07-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89583-07-3 ]

CAS No. :89583-07-3 MDL No. :MFCD07776157
Formula : C6H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :CVMXEDZZSWLXPB-UHFFFAOYSA-N
M.W : 194.07 Pubchem ID :1502101
Synonyms :

Calculated chemistry of [ 89583-07-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.61
TPSA : 12.47 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 0.65
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.32
Solubility : 9.27 mg/ml ; 0.0478 mol/l
Class : Very soluble
Log S (Ali) : -0.49
Solubility : 63.2 mg/ml ; 0.325 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.73
Solubility : 3.61 mg/ml ; 0.0186 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 89583-07-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89583-07-3 ]

* 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 [ 89583-07-3 ]
  • Downstream synthetic route of [ 89583-07-3 ]

[ 89583-07-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 622-40-2 ]
  • [ 89583-07-3 ]
YieldReaction ConditionsOperation in experiment
100% With dibromotriphenylphosphorane In dichloromethane at 0 - 20℃; Example 47 80: A solution of the alcohol 79 (1 g, 7.62 mmol) in dichloromethane (76 mL) cooled in an ice bath to 0° C. was treated with dibromotriphenyl phosphorane (3.86 g, 9.15 mmol). After being stirred at room temperature overnight, the solid desired product was filtered off to afford clean bromide 80 (1.4 g, quant); 300 MHz 1H NMR (CD3OD) δ (ppm) 4.1 (m, 2H), 3.85 (m, 2H), 3.8 (t, 2H), 3.7 (t, 2H), 3.58 (m, 2H), 3.25 (m, 2H); MS: 194 (M+1).
Reference: [1] Patent: US2008/58315, 2008, A1, . Location in patent: Page/Page column 46
[2] Arhiv za Kemiju, 1946, vol. 18, p. 87,92[3] Chem.Abstr., 1948, p. 3395
[4] Patent: WO2013/33085, 2013, A1, . Location in patent: Paragraph 00179
[5] Patent: US2010/160308, 2010, A1, . Location in patent: Page/Page column 26
  • 2
  • [ 622-40-2 ]
  • [ 110-54-3 ]
  • [ 558-13-4 ]
  • [ 89583-07-3 ]
YieldReaction ConditionsOperation in experiment
57.8% With triphenylphosphine In dichloromethane 1)
Synthesis of N-(2-bromoethyl) morpholine (84)
N-(2-Hydroxyethyl)morpholine [1.312 g (10 mmol.)] and carbon tetrabromide [4.974 g (15 mmol.)] were dissolved in methylene chloride (40 m), to which was added, under ice-cooling, triphenylphosphine [3.147 g (12 mmol.), and then the mixture was then stirred for 15 hours at room temperature.
The reaction mixture was concentrated under reduced pressure.
n-Hexane was added to the residue, and the mixture was subjected to filtration.
The filtrate was concentrated under reduced pressure.
The crude product thus obtained was purified by column chromatography (silica gel: 70 g; eluent:
n-hexane/ethyl acetate = 1/3) to obtain the desired product (84) [1.122 g (57.8percent)] (colorless oily substance).
Reference: [1] Patent: EP278621, 1991, B1,
[2] Patent: US4987130, 1991, A,
  • 3
  • [ 110-91-8 ]
  • [ 106-93-4 ]
  • [ 89583-07-3 ]
YieldReaction ConditionsOperation in experiment
14.4% With potassium carbonate In acetone at 0℃; for 12 h; Reflux To a stirred solution of morpholine (15 g, 172.17 mmol, 1.0 eq) in acetone (150 ml) K2CO3 (47.5 g, 344.35 mmol, 2eq) and 1,2-dibromoethane (29.7 mL, 344.35mmol, 2eq) were added at 0°C. The reaction mixture was re fluxed for 12 hours. TLC indicated starting material was consumed and the desired product was observed. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to get the residue (4.8 g, 14.4percent) and used directly for next step without further purification. 1H NMR (300 MHz, CDCl3): δ ppm 3.74-3.71(m, 4H), 3.43 (t, J = 7.2Hz, 2H), 2.78 (t, J = 7.2Hz, 2H), 2.53-2.5 (m, 4H).
Reference: [1] Patent: WO2013/160810, 2013, A2, . Location in patent: Paragraph 0310
  • 4
  • [ 110-91-8 ]
  • [ 558-13-4 ]
  • [ 89583-07-3 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 22, p. 7399 - 7402
  • 5
  • [ 102-71-6 ]
  • [ 89583-07-3 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1934, vol. 6, p. 484
  • 6
  • [ 10035-10-6 ]
  • [ 25114-70-9 ]
  • [ 89583-07-3 ]
  • [ 3890-99-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1934, vol. 6, p. 484
  • 7
  • [ 89583-07-3 ]
  • [ 26211-90-5 ]
  • [ 92623-83-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 23, p. 7645 - 7649
  • 8
  • [ 89583-07-3 ]
  • [ 92623-83-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 3, p. 412 - 415
  • 9
  • [ 89583-07-3 ]
  • [ 269410-08-4 ]
  • [ 864754-18-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 24, p. 7934 - 7937
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