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[ CAS No. 32202-61-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 32202-61-2
Chemical Structure| 32202-61-2
Chemical Structure| 32202-61-2
Structure of 32202-61-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 32202-61-2 ]

CAS No. :32202-61-2 MDL No. :MFCD00082598
Formula : C9H11N Boiling Point : -
Linear Structure Formula :- InChI Key :RXTJLDXSGNEJIT-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :122569
Synonyms :

Calculated chemistry of [ 32202-61-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.47
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 2.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.506 mg/ml ; 0.0038 mol/l
Class : Soluble
Log S (Ali) : -2.26
Solubility : 0.739 mg/ml ; 0.00555 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.195 mg/ml ; 0.00147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 32202-61-2 ]

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 [ 32202-61-2 ]

* 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 [ 32202-61-2 ]
  • Downstream synthetic route of [ 32202-61-2 ]

[ 32202-61-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 32202-61-2 ]
  • [ 628732-03-6 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
[2] Patent: WO2003/99795, 2003, A1, . Location in patent: Page 107
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9423 - 9428
[4] Patent: WO2016/44770, 2016, A1,
[5] Patent: CN103848811, 2016, B,
[6] Patent: CN103709163, 2016, B,
  • 2
  • [ 32202-61-2 ]
  • [ 1641-41-4 ]
Reference: [1] Chemische Berichte, 1928, vol. 61, p. 1460
[2] Patent: WO2006/135978, 2006, A1, . Location in patent: Page/Page column 24
  • 3
  • [ 496-11-7 ]
  • [ 24425-40-9 ]
  • [ 32202-61-2 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 341
  • 4
  • [ 32202-61-2 ]
  • [ 6134-53-8 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With tetrafluoroboric acid; sodium nitrite In water for 0.333333 h; Cooling with ice
Stage #2: With copper(ll) bromide In dimethyl sulfoxide for 0.5 h;
Step 1 : 4-BromoindanTo a thick mixture of 4-aminoindan (2.66 g, 20 mmol) in 48percent tetrafluoroboric acid (20 ml) cooled in an ice bath was added a solution of sodium nitrite (1.6 g, 23 mmol) in water (20 ml) over 10 minutes. The mixture was stirred in ice for 10 minutes and was filtered and the filter cake was washed with cold 5percent tetrafluoroboric acid (10 ml) and then with cold water (10 ml). The filter cake was added in portions to copper (II) bromide (5.6 g, 25 mmol) in dimethyl sulfoxide (50 ml). The mixture was stirred for 30 minutes and was added to water (150ml). The mixture was extracted with ethyl acetate (150 ml) and the organic layer was washed with water. The organic layer was dried over magnesium sulfate and was filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using heptane to give the title compound (0.6g, 15percent).
Reference: [1] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 44
  • 5
  • [ 34701-14-9 ]
  • [ 32202-61-2 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogen In ethanol for 1 h; Intermediate 8: 4-aminoindane
In a 500 mL Parr shaker vessel, 4-nitroindane (10 g, 61 mmol) was dissolved in 50 mL ethanol.
A slurry of 10percent Pd/C (1 g) in ethanol was added.
The mixture was then placed on a Parr shaker under a hydrogen atmosphere (50 psi) for 1 hour, at which point t.l.c. (20percent ethyl acetate in hexanes) showed that all the starting material had disappeared.
To work up the reaction, the mixture was filtered twice through Celite, washing with a large amount of ethanol, and once through filter paper.
The ethanol was evaporated under reduced pressure, and the crude product purified by flash chromatography over silica gel (10percent ethyl acetate in hexanes) to give 8 as a viscous, faintly colored oil (7.04 g, 86percent yield): 1H NMR (400 MHz, DMSO-D6) δ 1.95 (m, 2H) 2.61 (t, J=7.3 Hz, 2H) 2.76 (t, J=7.5 Hz, 2H) 4.77 (s, 2H) 6.36 (d, J=7.8 Hz, 1H) 6.42 (d, J=6.8 Hz, 1H) 6.80 (t, J=7.6 Hz, 1H).
86% With hydrogen In ethanol for 1 h; In a 500 mL Parr shaker vessel, 4-nitroindane (10 g, 61 mmol) was dissolved in 50 mL ethanol. A slurry of 10percent Pd/C (1 g) in ethanol was added. The mixture was then placed on a Parr shaker under a hydrogen atmosphere (50 psi) for 1 hour, at which point t.l.c. (20percent ethyl acetate in hexanes) showed that all the starting material had disappeared. To work up the reaction, the mixture was filtered twice through Celite, washing with a large amount of ethanol, and once through filter paper. The ethanol was evaporated under reduced pressure, and the crude product purified by flash chromatography over silica gel (10percent ethyl acetate in hexanes) to give 8 as a viscous, faintly colored oil (7.04 g, 86percent yield): 1H NMR (400 MHz, DMSO-D6) δ 1.95 (m, 2H) 2.61 (t, J=7.3 Hz, 2H) 2.76 (t, J=7.5 Hz, 2H) 4.77 (s, 2H) 6.36 (d, J=7.8 Hz, 1H) 6.42 (d, J=6.8 Hz, 1H) 6.80 (t, J=7.6 Hz, 1H).
Reference: [1] Patent: US2005/101569, 2005, A1, . Location in patent: Page/Page column 17
[2] Patent: US2008/125454, 2008, A1, . Location in patent: Page/Page column 17
[3] Patent: WO2006/21544, 2006, A1, . Location in patent: Page/Page column 35-36
[4] Monatshefte fuer Chemie, 1974, vol. 105, p. 1362 - 1373
[5] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 461 - 465[6] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 469 - 474
[7] Patent: US2008/194650, 2008, A1, . Location in patent: Page/Page column 28-29
  • 6
  • [ 496-11-7 ]
  • [ 32202-61-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 519 - 523
[2] Monatshefte fuer Chemie, 1974, vol. 105, p. 1362 - 1373
  • 7
  • [ 4044-54-6 ]
  • [ 32202-61-2 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 979,980
  • 8
  • [ 15115-61-4 ]
  • [ 32202-61-2 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 979,980
  • 9
  • [ 40507-80-0 ]
  • [ 32202-61-2 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 10, p. 1738 - 1746
  • 10
  • [ 496-11-7 ]
  • [ 24425-40-9 ]
  • [ 32202-61-2 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 341
  • 11
  • [ 32202-61-2 ]
  • [ 34911-25-6 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
  • 12
  • [ 32202-61-2 ]
  • [ 651735-59-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
[2] Patent: WO2016/44770, 2016, A1,
  • 13
  • [ 32202-61-2 ]
  • [ 125114-77-4 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
[2] Patent: WO2016/44770, 2016, A1,
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