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| Type | HazMat fee for 500 gram (Estimated) |
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Structure of 3-Phenyl-2-propenyl bromide
CAS No.: 4392-24-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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| CAS No. : | 4392-24-9 |
| Formula : | C9H9Br |
| M.W : | 197.07 |
| SMILES Code : | BrCC=CC1=CC=CC=C1 |
| MDL No. : | MFCD00000245 |
| InChI Key : | RUROFEVDCUGKHD-QPJJXVBHSA-N |
| Pubchem ID : | 5357478 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H314 |
| Precautionary Statements: | P280-P305+P351+P338-P310 |
| Class: | 8 |
| UN#: | 3261 |
| Packing Group: | Ⅱ |
| 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 ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.46 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.39 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.99 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.62 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.33 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.16 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-3.51 |
| Solubility | 0.061 mg/ml ; 0.000309 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.07 |
| Solubility | 0.168 mg/ml ; 0.000853 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.75 |
| Solubility | 0.0352 mg/ml ; 0.000179 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.1 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.35 |
* 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.

[ 96145-98-1 ]
[ 4392-24-9 ]
| Yield | Reaction Conditions | Operation 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. |
| Yield | Reaction Conditions | Operation 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. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 23% | General procedure: General procedure: To a solution of 4-formyl-1H-1-tritylprazole (8a) (94.6 mg, 0.28 mmol) inCH2Cl2 (6 mL) was added 70% mCPBA (131.8 mg, 0.53 mmol) at 0 C, with stirring. After 5 h,saturated NaHCO3 aq (10 mL) was added to quench the reaction mixture. The mixture was extractedwith CH2Cl2 3 times. Combined organic layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude formate. To an acetone solution of the crude formate (6 mL),20% NaOH aq (4 mL) was added, then the mixture was heated under reflux for 1 h, then crotyl bromide(48 L, 0.42 mmol) was added to the cooled mixture. After stirring for 3 h, saturated NH4Cl aq wasadded to the reaction mixture to quench, the mixture was condensed under reduced pressure, extractedwith CH2Cl2 for 3 times. The combined CH2Cl2 layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude residue, which was purified with flash column chromatography(EtOAc:Hexane = 1:10) to give 4-(2-butenyl)oxy-1H-1-tritylpyrazole (1e) (54.5 mg, 51%). |