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[ CAS No. 4392-24-9 ] {[proInfo.proName]}

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Chemical Structure| 4392-24-9
Chemical Structure| 4392-24-9
Structure of 4392-24-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 4392-24-9 ]

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Product Details of [ 4392-24-9 ]

CAS No. :4392-24-9 MDL No. :MFCD00000245
Formula : C9H9Br Boiling Point : -
Linear Structure Formula :(C6H5)(CH)2CH2Br InChI Key :RUROFEVDCUGKHD-QPJJXVBHSA-N
M.W : 197.07 Pubchem ID :5357478
Synonyms :
Chemical Name :(3-Bromo-1-propen-1-yl)benzene

Calculated chemistry of [ 4392-24-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.21
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 3.39
Log Po/w (WLOGP) : 2.99
Log Po/w (MLOGP) : 3.62
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 3.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.061 mg/ml ; 0.000309 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.168 mg/ml ; 0.000853 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.75
Solubility : 0.0352 mg/ml ; 0.000179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 4392-24-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4392-24-9 ]

* 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.

  • Downstream synthetic route of [ 4392-24-9 ]

[ 4392-24-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 3743-22-4 ]
  • [ 4392-24-9 ]
  • [ 79833-17-3 ]
  • 2
  • [ 96145-98-1 ]
  • [ 4392-24-9 ]
  • 1-Phenyl-5-((E)-3-phenyl-allyloxy)-3-trifluoromethyl-1H-pyrazole [ No CAS ]
  • 3
  • [ 65651-80-1 ]
  • [ 4392-24-9 ]
  • [ 4105-92-4 ]
  • [ 86576-75-2 ]
  • [ 86576-76-3 ]
  • 4
  • [ 88088-95-3 ]
  • [ 4392-24-9 ]
  • [ 130759-76-1 ]
  • 5
  • [ 6940-80-3 ]
  • [ 4392-24-9 ]
  • [ 221876-43-3 ]
  • 6
  • [ 6374-91-0 ]
  • [ 4392-24-9 ]
  • C17H11Br2NO2 [ No CAS ]
  • 7
  • [ 40492-52-2 ]
  • [ 4392-24-9 ]
  • [ 108-95-2 ]
  • 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane; ethyl acetate; mineral oil; benzene; EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield). of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran. NMR (CDCl3): delta7.0-7.3 (m; 4H); 6.16-6.62 (m; 4H); 4.43 (s; 1H); 4.40 (t (8 Hz); 2H); 3.40 (d(5 Hz); 2H); 3.03 (t(8 Hz); 2H). IR: 3700, 2920, 1610, 1490, 1425, 1140, 981, 870 cm-1 (CHCl3). MS: 252 (M+) (68%); 161 (34%); 148 (100%); 91 (36%).
In hexane; ethyl acetate; mineral oil; benzene; EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield).of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran.
  • 8
  • [ 253-72-5 ]
  • [ 4392-24-9 ]
  • 5,6,7,8-tetrahydro-6-cinnamyl-1,6-naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 7 Preparation of 5,6,7,8-tetrahydro-6-cinnamyl-<strong>[253-72-5]1,6-naphthyridine</strong> (Compound No. 58) A solution of <strong>[253-72-5]1,6-naphthyridine</strong> (13.0 g, 0.1 mol) and cinnamyl bromide (23.6 g, 0.12 mol) in acetonitrile (100 ml) was stirred overnight at room temperature. The precipitated crystals were separated by filtration and washed with a small quantity of ether.
  • 9
  • [ 117976-90-6 ]
  • [ 4392-24-9 ]
  • [ 1052003-57-2 ]
  • 10
  • [ 570-02-5 ]
  • [ 4392-24-9 ]
  • [ 147729-67-7 ]
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