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[ CAS No. 880652-93-7 ] {[proInfo.proName]}

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Chemical Structure| 880652-93-7
Chemical Structure| 880652-93-7
Structure of 880652-93-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 880652-93-7 ]

CAS No. :880652-93-7 MDL No. :MFCD20524977
Formula : C10H9Br Boiling Point : -
Linear Structure Formula :- InChI Key :OJSMHHJBFNVCAV-UHFFFAOYSA-N
M.W :209.08 Pubchem ID :12162479
Synonyms :

Calculated chemistry of [ 880652-93-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.89
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 3.32
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 3.78
Log Po/w (SILICOS-IT) : 3.81
Consensus Log Po/w : 3.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.63
Solubility : 0.0488 mg/ml ; 0.000234 mol/l
Class : Soluble
Log S (Ali) : -3.0
Solubility : 0.211 mg/ml ; 0.00101 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.22
Solubility : 0.0125 mg/ml ; 0.0000597 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.66

Safety of [ 880652-93-7 ]

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 [ 880652-93-7 ]

* 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 [ 880652-93-7 ]
  • Downstream synthetic route of [ 880652-93-7 ]

[ 880652-93-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 869063-68-3 ]
  • [ 880652-93-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium tetrahydroborate In THF-methanol; toluene 7-Bromo-2-methyl-1H-indene
To a solution of 116 g (0.52 mol) of 4-bromo-6-chloro-2-methyl-1-indanone in 950 ml of THF-methanol (2:1, vol.), 38.3 g (1.02 mol) of NaBH4 were added in small portions for 2 h at -5° C. (Caution: temperature must be lower 0° C.).
The mixture was stirred overnight at ambient temperature.
The resulting mixture was poured on 1000 cm3 of ice and acidified with 10percent HCl to pH=4.
The organic layer was separated and the aqueous layer was extracted with 3*300 ml of methyl-tert-butyl ether.
This combined extract was dried over K2CO3 and evaporated to dryness.
To the residue 1500 ml of toluene were added and the resulting toluene solution was treated with catalytic amount of pTolSO3H (ca. 2 g) for 2 h at reflux.
Then this mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 60 mm, 1 40 mm).
This column was additionally eluted with 250 ml of toluene.
The combined extract was evaporated to dryness.
Fractional distillation gave a mixture of the title indenes, b.p. 104-108° C./5 mm Hg. Yield 100 g (93percent) of colorless solid.
Anal. calc. for C10H9Br: C, 57.44; H, 4.34. Found: C, 57.59; H, 4.40. 1H NMR (CDCl3): δ 7.23 (dd, J=7.9 Hz, J=1.0 Hz, 1H, 6-H), 7.18 (dd, J=7.4 Hz, J=1.0 Hz, 1H, 4-H), 7.10 (m, 1H, 5-H), 6.51 (m, 1H, 3-H), 3.28 (m, 2H, 1,1'-H), 2.17 (s, 3H, 2-Me).
13C NMR (CDCl3): δ 147.3, 146.8, 143.3, 128.2, 127.1, 126.6, 118.7, 118.3,44.2,16.7.
93% With sodium tetrahydroborate In THF-methanol; toluene 7-Bromo-2-methyl-1H-indene
To a solution of 116 g (0.52 mol) of 4-bromo-6-chloro-2-methyl-1-indanone in 950 ml of THF-methanol (2:1, vol.) 38.3 g (1.02 mol) of NaBH4 were added in small portions for 2 hours at -5° C. (Caution: temperature must be lower than 0° C.).
The mixture was stirred overnight at ambient temperature.
The resulting mixture was poured over 1000 cm3 of ice and acidified with 10percent HCl to pH=4.
The organic layer was separated; the aqueous layer was extracted with 3*300 ml of methyl-tert-butyl ether.
The combined organic fractions were dried over K2CO3 and evaporated to dryness.
To the residue 1500 ml of toluene were added.
This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 2 g) for 2 hours at reflux.
Then this mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 μm, d 60 mm, 140 mm).
This column was additionally eluted with 250 ml of toluene.
The chromatographed product was evaporated to dryness.
Fractional distillation gave the title indene, b.p. 104-108° C./5 mm Hg. Yield 100 g (93percent) of colorless solid.
Anal. calc. for C10H9Br: C, 57.44; H, 4.34. Found: C, 57.59; H, 4.40.
1H NMR (CDCl3): δ 7.23 (dd, J=7.9 Hz, J=1.0 Hz, 1H, 6-H), 7.18 (dd, J=7.4 Hz, J=1.0 Hz, 1H, 4-H), 7.10 (m, 1H, 5-H), 6.51 (m, 1H, 3-H), 3.28 (m, 2H, 1,1'-H), 2.17 (s, 3H, 2-Me).
13C{1H} NMR (CDCl3): δ 147.3, 146.8, 143.3, 128.2, 127.1, 126.6, 118.7, 118.3, 44.2, 16.7.
Reference: [1] Patent: US2007/135595, 2007, A1,
[2] Patent: US2007/135596, 2007, A1,
  • 2
  • [ 880653-70-3 ]
  • [ 880652-93-7 ]
Reference: [1] Patent: WO2007/70040, 2007, A1, . Location in patent: Page/Page column 105-106
[2] Patent: WO2007/70041, 2007, A1, . Location in patent: Page/Page column 96-97
  • 3
  • [ 174702-59-1 ]
  • [ 880652-93-7 ]
Reference: [1] Patent: EP2532687, 2012, A2,
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