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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of α,α'-Dibromo-p-xylene
CAS No.: 623-24-5
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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.
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CAS No. : | 623-24-5 |
Formula : | C8H8Br2 |
M.W : | 263.96 |
SMILES Code : | BrCC1=CC=C(CBr)C=C1 |
MDL No. : | MFCD00000182 |
InChI Key : | RBZMSGOBSOCYHR-UHFFFAOYSA-N |
Pubchem ID : | 69335 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H330-H314-H290 |
Precautionary Statements: | P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P403+P233 |
Class: | 6.1(8) |
UN#: | 2928 |
Packing Group: | Ⅱ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.49 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.04 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.17 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.84 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.28 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.7 |
Solubility | 0.0522 mg/ml ; 0.000198 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.71 |
Solubility | 0.52 mg/ml ; 0.00197 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.91 |
Solubility | 0.00323 mg/ml ; 0.0000122 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.75 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 |
1.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.49 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; N,N-dimethyl-formamide; | EXAMPLE 1 N,N'-Dihydroxy-N,N'-di-tert-butyl-p-xylylenediamine A suspension of 3.0 g tert-butylhydroxylamine hydrochloride, 5.0 g of anhydrous sodium carbonate and 3.15 g of p-xylylene dibromide in 20 ml of N,N-dimethylformamide is heated at 80° C. under nitrogen for 3 hours. Dilution of the reaction mixture with water followed by crystallization from heptane affords 2.1 g of product as a white solid; m.p. 137°-138° C. Analysis: Calculated for C16 H28 N2 O2: C, 68.53; H, 10.06; N, 9.99. Found: C, 68.7; H, 9.8; N, 10.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals. | |
General procedure: Initially, mono (5 or 7) or di-substituted (5,7) or unsubstitutedisatins 1(ael) (10 mmol) were dissolved in anhydrous DMF (30 mL)and cooled on ice with stirring. Solid dry K2CO3 (11 mmol) wasadded in one portion, and the dark-colored suspensionwas broughtto room temperature and stirred for a further 1 h. 1,4-bis(bromomethyl)benzene (40 mmol) was added slowly withconstant stirring until the mono or di-substituted isatin startingmaterial had been consumed (TLC). The reaction mixture waspoured into cold water and extracted with ethyl acetate. The ethylacetate layer was washed with water, brine, and dried over MgSO4.The solvent was removed, and the crude product was purified bysilica gel column chromatography using (hexanes/EtOAc, 80:20) aseluent to yield the key intermediates (-N-(p-bromomethyl benzyl)isatins 2(ael) (yield 75-80%) as orange-red crystals. | ||
5,7-dibromoisatin (10 mmol) was dissolved in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (11 mmol) was added and the dark-colored suspension was brought to room temperature and stirred for 1 hour. 1,4-bis(bromomethyl)benzene (40 mmol) was added slowly with constant stirring until the starting material had been consumed (monitored by TLC). The reaction mixture was poured into cold water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography using (hexanes/ethyl acetate, 80:20) as the eluent to yield the intermediate 5,7-dibromo-1-(4- bromomethylbenzyl)-1H-indole-2,3-dione as orange-red crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In butanone; at 20℃; for 3h; | General procedure: A butanone solution (40 mL) of the linker (2 equiv.) and the corresponding 4-substituted pyridine (1 equiv.) was stirred at room temperature for 3 h 21, 22, 23, 25 and 26 were isolated after filtration and thorough washing with butanone, ethyl acetate and diethyl ether. In the case of 24, 27 and 28, the reaction mixture was evaporated, and the crude products purified by flash column chromatography on silica gel using CH2Cl2/MeOH (10/0.5) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; | General procedure: A solution of compound 1 (0.838 g, 2.5 mmol), 2 (0.567g, 2.5mmol), or 3 (0.540 g, 2.5 mmol), Cs2CO3 (0.888 g, 2.725 mmol), and 1,4-bis(bromomethyl)benzene (1.96 g, 7.5 mmol) in anhyd DMF (14 mL) was stirred for 2 h at r.t. under argon. The solvent was evaporated; the residue was dissolved in CH2Cl2 and washed with H2O (2 × 50 mL). The organic layer was dried (Na2SO4), filtered,and concentrated under vacuum. The residue was purified by column chromatography [silica gel, EtOAc (for 4) and CH2Cl2-EtOAc, 4:1 (for 7 and 8)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In acetonitrile; for 3h;Reflux; | General procedure: To a solution of 1,4-bis(bromomethyl)benzene (1 mmol) in anhydrous acetonitrile (10 mL) was added potassium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 3 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (150:1, v/v) to give the title compound as a colorless liquid or a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.3% | With potassium hydroxide; In toluene; at 20℃; for 3h;Sonication; Microwave irradiation; Heating; | (Fixed power 150 W) was charged with 50 mL of toluene, 10.0 g of 3-cyano-4-trifluoromethylsulfinyl-5-amino-1- (2,6-dichloro-4-trifluoromethylbenzene And the mixture was stirred at room temperature for 60min. After the shock, the spray switch was turned on. The mist was sent to the top of the microwave reactor through the trachea, and the microwave reactor was turned on. The power The reaction was started at 300W. When the solvent in the ultrasonic atomizer was about to be atomized, the atomization was stopped and the inlet of the microwave reactor was turned off and the reaction was continued for 120 min.After the completion of the reaction, the product was washed with water and dried by filtration to obtain 14.24 g of compound 8.Yield: 89.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In dichloromethane; at 120℃; for 12 - 16h;Schlenk technique; Glovebox; Inert atmosphere; | General procedure: In a typical run, a 10-mL thick wall pressure tube was charged with 1,4-bis(bromomethyl)benzene (0.20 g,0.76 mmol), the corresponding 1-alkyl-1H-1,2,4-triazoles(1.60 mmol) and DCM (3 mL). The reaction mixture was heated at 120 C for 12?16 h. The reaction mixture was cooled to room temperature and extracted with water(3 9 5 mL). The collected aqueous phase was dried by rotovap, and the crude product was recrystallized from methanol/acetone (1:4) to give the product as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In tetrahydrofuran; at 70℃; | A mixture of (9) (1 .80 g 10.0 mmol,) and alpha,alpha'-dibromo-p- xylene (13.20 g, 50.0 mmol) was stirred in THF (150 mL) at 70 °C. After overnight stirring, the precipitate was washed with diethyl ether 3 times and then dried under vacuum (2.5 g, 56 percent). 1 H NMR (DMSO-d6): 59.43 (s, 1 H), 7.87 (m, 2H), 7.42 (d, 2H), 7. 30 (d, 2H),7.19 (s, 1 H), 6.87 (s, 1 H), 5.45 (s, 2H), 5.22 (s, 2H), 4.18 (m, 2H), 1 .77 (m, 2H), 1 .23 (m, 6H), 0.83 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium azide; copper(I) oxide; In water; at 100℃; for 1h; | General procedure: In round-bottomed flask α,α'-dibromo-p-xylene (0.5 mmol,1 equiv.), NaN3, (1.2 mmol, 1.2 equiv.), terminal alkyne(1.2 mmol, 1.2 equiv.) and 5 mg Cu2ONPs were taken inwater (10 mL). The mixture was magnetically stirred underreflux (100 C) for 60 min. The progress of the reaction wasmonitored by the formation of solid on the wall of thereaction container. After completion of the reaction, themixture was cooled to room temperature and the solutionwas decanted. The leftover residue was washed with dil.NH4Cl : NH3 solution (2 x 9 10 mL) whereupon copper gotremoved as blue colour copperamine species followed bywashing with ethyl acetate (2 x 9 10 mL) and the remainingsolid product was dried under vacuum. |
Tags: 623-24-5 synthesis path| 623-24-5 SDS| 623-24-5 COA| 623-24-5 purity| 623-24-5 application| 623-24-5 NMR| 623-24-5 COA| 623-24-5 structure
A306114 [27129-86-8]
1-(Bromomethyl)-3,5-dimethylbenzene
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A172038 [81093-21-2]
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Similarity: 0.96
A321511 [4761-00-6]
2-(Bromomethyl)-1,3,5-trimethylbenzene
Similarity: 0.92
A306114 [27129-86-8]
1-(Bromomethyl)-3,5-dimethylbenzene
Similarity: 1.00
A172038 [81093-21-2]
1-(Bromomethyl)-2,3-dimethylbenzene
Similarity: 0.96
A321511 [4761-00-6]
2-(Bromomethyl)-1,3,5-trimethylbenzene
Similarity: 0.92
A306114 [27129-86-8]
1-(Bromomethyl)-3,5-dimethylbenzene
Similarity: 1.00
A172038 [81093-21-2]
1-(Bromomethyl)-2,3-dimethylbenzene
Similarity: 0.96
A321511 [4761-00-6]
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P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
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Code | Phrase |
P301 | IF SWALLOWED: |
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P307 | IF exposed: |
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P390 | Absorb spillage to prevent material damage. |
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P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
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Physical hazards | |
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H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
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Health hazards | |
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H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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