There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
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+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 92642-09-6 | MDL No. : | MFCD12031102 |
Formula : | C12H10Br2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OESAKGGTMNBXLT-UHFFFAOYSA-N |
M.W : | 342.03 | Pubchem ID : | 11056981 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 73.14 |
TPSA : | 25.78 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 2.81 |
Log Po/w (XLOGP3) : | 2.6 |
Log Po/w (WLOGP) : | 3.63 |
Log Po/w (MLOGP) : | 2.28 |
Log Po/w (SILICOS-IT) : | 4.47 |
Consensus Log Po/w : | 3.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.96 |
Solubility : | 0.0379 mg/ml ; 0.000111 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.79 |
Solubility : | 0.554 mg/ml ; 0.00162 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -6.65 |
Solubility : | 0.0000767 mg/ml ; 0.000000224 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.41 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 | UN#: | 3261 |
Hazard Statements: | H302+H312-H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
88% | With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 18h;Reflux; | To a solution of 5 , 5 '-dimethyl-2,2'-bipyridine (10 mmol) in 50 . mL of 1 dry. I ''- 1 ' . . . . carbontetrachloride was added N-bromosuccinimide (20.5 mmol) and AIBN. The reactionI . i i . j . mixture was refluxed for 18h, cooled, filtered and the solvents were removed underI j 1 I . . reduced pressure to give the crude product which was further purified by recrystalliza'tion from CC14. 88%; mp. 188 C ; ; H NMR (CDC13 300 Hz) δ 4;53 (s, 4H , CH2Br), 7.79 (m, 2H, aromatic), 8.34 (m, 2H , aromatic), 8.61 (m, i 2H, aromatic). 13C NMR (CDCI3[ 75. I 1 : MHz) δ 29.43, 121.25, 133.28, 137.70, 149.27 , 155.19. |
80 - 90% | With bromine;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 18 - 20h;Heating / reflux; | To a solution of 5,5'-dimethyl-2,2'-bipyridine (10 mmol) in 50 mL of dry carbontetrachloride was added N-bromosuccinimide (20.5 mmol) and AIBN (Azobisisobutyronitrile). The reaction mixture was refluxed for 18-20 h., cooled, filtered and the solvents were removed under reduced pressure to give the crude product which was further purified by recrystallization from CCI4. Yield 80-90%; mp.188 0C; 1H NMR (CDCI3, 300 M Hz) δ 4.53 (s, 4H1 CH2Br), 7.79 (m, 2H, aromatic),8.34 (m, 2H, aromatic), 8.61 (m, 2H, aromatic). 13C NMR (CDCI3, 75 MHz) δ 29.43, 121.25, 133.28, 137.70, 149.27, 155.19. |
73.1% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; | (1) 5,5'-dimethyl-2,2'-bipyridine (0.146 g, 0.8 mmol) with N-bromosuccinimide (0.313 g, 1.76 mmol) and azobisisobutyronitrile (0.328g, 2mmol) was heated to 80 C in carbon tetrachloride (20mL), the bromination reaction occurred, yielded 0.200 g of 5,5'-dibromomethyl-2,2'-bipyridine (0.585 mmol), Yield 73.1%; |
54% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h;Inert atmosphere; Reflux; | A solution of 1 (1 g, 5.42 mmol), NBS (1.93 g, 10.85 mmol), andAIBN (17 mg, 0.10 mmol) in CCl4 (50 mL) was refluxed under N2for 2 h and the precipitated succinimide was removed immediately from the hotmixture by filtration. The precipitate was washed with CCl4 and thecombined CCl4 phases were evaporated. The remaining solid wasdissolved in CH2Cl2 (100 mL) and extracted with 0.5 M Na2S2O3solution (2×150mL). The combined Na2S2O3 fractions wereextracted with CH2Cl2 (50 mL) and the combined CH2Cl2layers were dried (Na2SO4) and concentrated it.. Thecrude product was purified by column chromatography (silica gel, EtOAc/hexane,1:4) white powder. Yield is 54%,m.p 193-194C; 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J= 3 Hz, 2H), 8.39 (d, J = 9 Hz, 2H), 7.87-7.84 (m, 2H), 4.53 (s, 4H).13CNMR (75 MHz, CDCl3) δC 149.78, 143.67, 131.82, 128.19,115.44, 23.74. ESI-MS( M+); 342.88 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90 - 95% | at 80 - 85℃; for 10 - 12h; | Bisphosphonate were prepared by the reaction- of the corresponding bisbromomethyl derivatives (2 mmol) with 3 mL of triethyl phosphite at 80-85 0C for 10-12 h followed by the removal of the -unreacted triethyl phosphite by vacuum. Yield 90- 95%; 1H NMR (CDCI3, 300 MHz) δ 1.12 (m, 12H1 CH3), 3.21 (s, 4H, CH2P), 4.14 (m, 8H, OCH2), 7.34 (m, 2H, aromatic), 8.01 (m, 2H, aromatic), 8.30 (m, 2H, aromatic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 85℃; for 12h; | Bisphosphonate were prepared by the reaction of the corresponding bisbromomethyi derivatives (2 mmol) with 3 mL of triethyl phosphite at 85 C for 12 h followed by the removal of the unreacted triethyl phosphite by vacuum. Yield 90- 95%; NMR (C QC13,300 MHz) δ 1. 12 (m, 12H, CH (s , 4H , CH2P), 4.14 (m| 8H, OCH2), 7.34 (m, 2H, aromatic), 8.01 (m, 2H , aromatic), 8.30 (m, 2H , aromatic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Compound (12).[0087]Sodium hydride, (108 mg, 60% dispersion in mineral oil; 2.71 mmol) was suspended in dry THF (8.0 mL) in a flame-dried flask and it was cooled to 0 C. Di(ethylene glycol)methyl ether (360 mg, 3.0 mmol) was added slowly and stirred under an argon atmosphere for 30 min. The solution was slowly added to 5,5′-bis(bromomethyl)-2,2′-dipyridyl (1.0 g, 5.4 mmol) in THF (50 mL) and stirred for 2 h. See Zhang, L.; Clark, R. J.; Zhu, L. Chem. Eur. J. 2008, 14, 2894-2903. Then most of the THF was removed under vacuum. The residue was partitioned between CH2Cl2 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified using silica chromatography, using THF in CH2Cl2 (gradient 0-10%). The yield of (12) was 1.1 g (53%). 1H NMR (300 MHz, CDCl3, 25 C.) 8.68 (s, 1H), 8.63 (s, 1H), 8.38 (d, J=8.1 Hz, 2H), 7.82-7.86 (m, 2H), 4.65 (s, 2H), 4.53 (s, 2H), 3.65-3.54 (m, 8H), 3.39 (s, 3H). 13C NMR (125 MHz, CDCl3, 25 C.) 155.8, 154.9, 149.3, 148.6, 137.6, 136.6, 134.1, 133.6, 121.1, 121.0, 72.0, 70.7, 70.6, 69.9, 59.1, 29.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: The 30% CH3ONa/CH3OH (1.1 g) and RfCH2OH (6.0 mmol) were charged into a round-bottomed flask, then continuously stirred at ca 80 C under N2 atmosphere for 4 h before CH3OH was vacuum removed. The resulting fluorinated alkoxide (6.0 mmol) was then dissolved in 20 mL of dry THF, and bis(BrCH2)-2,2'-bpy (5.8 mmol; at 4,4'- or 5,5'-positions) added. The mixture was brought to reflux for overnight, and the completeness of the reaction was checked by the GC/MS. After the reaction, the solvent was removed by vacuum pump. The crude product was extracted using the separatory funnel from the CH2Cl2/H2O system several times. Then the crude product was further purified by either vacuum sublimation or column chromatography to obtain white solids. Analytical data of 2a: Yield 75%; 1H NMR (500 MHz, d-Me2SO): δ = 8.66 (2H, s, H-6), 8.39 (2H, d, 3JHH = 8.24 Hz, H-4), 7.92 (2H, d, 3JHH = 8.24 Hz, H-3), 4.77 (4H, s, bpyCH2), 4.17 (4H, q, 3JHF = 9.34 Hz, CF3CH2). 19F NMR (470.5 MHz, d-Me2SO): δ = -73.1 (6F, t, 3JHF = 10.8 Hz, CH2CF3). 13C NMR (126 MHz, d-Me2SO): δ = 71 (bpyCH2), 67 (bpyCH2OCH2), 121-128 (CF3), 120, 133, 137, 149, 155 (bpy); FT-IR [νmax(KBr)/cm-1]: 1598m, 1554m, 1469m, 1359m (νbpy), 1156vs, 1123vs (νCF2); m.p. = 120 C.GC/MS (m/z; EI mode): 380.1 [M]+, 297.1 [M-CH2CF3]+, 281.1 [M-OCH2CF3]+, 198.1 [M-O(CH2CF3)2]+, 182.1 [M-(OCH2CF3)2]+, 91.1 [M-(OCH2CF3)2-C6H5N]+.(m/z; CI mode): 420.9 [M+C3H5]+, 408.9 [M+C2H5]+, 381 [M+H]+, 360.9 [M-HF]+, 340.9 [M-(HF)2]+, 281 [M-OCH2CF3]+, 198.9 [M-O(CH2CF3)2+H]+, 100.9 [OCH3CF3+H]+, 80.9 [OCH3CF3-HF+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: The 30% CH3ONa/CH3OH (1.1 g) and RfCH2OH (6.0 mmol) were charged into a round-bottomed flask, then continuously stirred at ca 80 C under N2 atmosphere for 4 h before CH3OH was vacuum removed. The resulting fluorinated alkoxide (6.0 mmol) was then dissolved in 20 mL of dry THF, and bis(BrCH2)-2,2'-bpy (5.8 mmol; at 4,4'- or 5,5'-positions) added. The mixture was brought to reflux for overnight, and the completeness of the reaction was checked by the GC/MS. After the reaction, the solvent was removed by vacuum pump. The crude product was extracted using the separatory funnel from the CH2Cl2/H2O system several times. Then the crude product was further purified by either vacuum sublimation or column chromatography to obtain white solids. Analytical data of 2b: Yield 76%; 1H NMR (500 MHz, d-Me2SO): δ = 8.64 (2H, s, H-6), 8.39 (2H, d, 3JHH = 8.51 Hz, H-4), 7.89 (2H, d, 3JHH = 8.24 Hz, H-3), 4.77 (4H, s, bpyCH2), 4.23 (4H, t, 3JHF = 14.01 Hz, CF3CH2). 19F NMR (470.5 MHz, d-Me2SO): δ = -122.9 (4F, t, 3JHF = 15.0 Hz, CH2CF2), -83.2 (6F, CH2CF2CF3). 13C NMR (126 MHz, d-Me2SO): δ = 71 (bpyCH2), 66 (bpyCH2OCH2), 111-122 (C2F5), 120, 133, 137, 149, 155 (bpy); FT-IR [νmax(KBr)/cm-1]: 1602m, 1554m, 1469m, 1366m (νbpy), 1189vs, 1152vs, 1115vs (νCF2); m.p. = 106 C.GC/MS (m/z; EI mode): 480.1 [M]+, 347.1 [M-CH2C2F5]+, 331.1 [M-OCH2C2F5]+, 198.1 [M-O(CH2C2F5)2]+, 182.1 [M-(OCH2C2F5)2]+, 91.1 [M-(OCH2C2F5)2-C6H5N]+.(m/z; CI mode): 520.9 [M+C3H5]+, 508.9 [M+C2H5]+, 480.9 [M+H]+, 330.9 [M-OCH2C2F5]+, 198.9 [M-O(CH2C2 F5)2+H]+, 150.9 [OCH3C2F5+H]+, 130.9 [OCH3C2F5-HF+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: The 30% CH3ONa/CH3OH (1.1 g) and RfCH2OH (6.0 mmol) were charged into a round-bottomed flask, then continuously stirred at ca 80 C under N2 atmosphere for 4 h before CH3OH was vacuum removed. The resulting fluorinated alkoxide (6.0 mmol) was then dissolved in 20 mL of dry THF, and bis(BrCH2)-2,2'-bpy (5.8 mmol; at 4,4'- or 5,5'-positions) added. The mixture was brought to reflux for overnight, and the completeness of the reaction was checked by the GC/MS. After the reaction, the solvent was removed by vacuum pump. The crude product was extracted using the separatory funnel from the CH2Cl2/H2O system several times. Then the crude product was further purified by either vacuum sublimation or column chromatography to obtain white solids. Analytical data of 2c: Yield 80%; 1H NMR (500 MHz, d-Me2SO): δ = 8.64 (2H, s, H-6), 8.39 (2H, d, 3JHH = 7.97 Hz, H-4), 7.90 (2H, d, 3JHH = 8.24 Hz, H-3), 4.78 (4H, s, bpyCH2), 4.28 (4H, t, 3JHF = 14.28 Hz, CF3CH2). 19F NMR (470.5 MHz, d-Me2SO): δ = -127.5 (4F, s, CH2CF2), -120 (4F, m, CH2CF2CF2), -80.8 (6F, t, 3JFF = 8.63 Hz, CF2CF3). 13C NMR (126 MHz, d-Me2SO): δ = 71 (bpyCH2), 66 (bpyCH2OCH2), 105-118 (C3F7), 120, 133, 137, 149, 155 (bpy); FT-IR [νmax(KBr)/cm-1]: 1606m, 1554m, 1473m, 1359 (νbpy), 1174vs, 1119 vs (νCF2).GC/MS (m/z; EI): 580 [M]+, 397 [M-CH2C3F7]+, 381 [M-OCH2C3F7]+, 182 [M-(OCH2C3F7)2]+; m.p. = 95 C.GC/MS (m/z; EI mode): 580.1 [M]+, 397.1 [M-CH2C3F7]+, 381.1 [M-OCH2C3F7]+, 198.1 [M-O(CH2C3F7)2]+, 182.1 [M-(OCH2C3F7)2]+, 91.1 [M-(OCH2C3F7)2-C6H5N]+.(m/z; CI mode): 620.9 [M+C3H5]+, 608.9 [M+C2H5]+, 580.9 [M+H]+, 380.9 [M-OCH2C3F7]+, 198.9 [M-O(CH2C3F7)2+H]+, 200.9 [OCH3C3F7+H]+, 180.9 [OCH3C3F7-HF+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: The 30% CH3ONa/CH3OH (1.1 g) and RfCH2OH (6.0 mmol) were charged into a round-bottomed flask, then continuously stirred at ca 80 C under N2 atmosphere for 4 h before CH3OH was vacuum removed. The resulting fluorinated alkoxide (6.0 mmol) was then dissolved in 20 mL of dry THF, and bis(BrCH2)-2,2'-bpy (5.8 mmol; at 4,4'- or 5,5'-positions) added. The mixture was brought to reflux for overnight, and the completeness of the reaction was checked by the GC/MS. After the reaction, the solvent was removed by vacuum pump. The crude product was extracted using the separatory funnel from the CH2Cl2/H2O system several times. Then the crude product was further purified by either vacuum sublimation or column chromatography to obtain white solids. Analytical data of 2d: Yield 92%; 1H NMR (500 MHz, d-Me2SO): δ = 8.65 (2H, s, H-6), 8.38 (2H, d, 3JHH = 8.2 Hz, H-4), 7.90 (2H, d, 3JHH = 8.2 Hz, H-3), 7.15 (2H, tt, 2JHF = 50.0 Hz, 2JHF = 5.2 Hz, CF2H), 4.78 (4H, s, bpyCH2), 4.27 (4H, t, 3JHH = 14.6 Hz, CF2CH2). 19F NMR (470.5 MHz, d-Me2SO): δ = -119.2, -122.6, -123.4, -123.5, -129.5 (20F; CH2(CF2)5), -138.8 (4F, d, 2JHF = 51.6 Hz, HCF2). 13C NMR (126 MHz, d-Me2SO): δ = 71 (bpyCH2), 66 (bpyCH2OCH2), 105-117 (C6F12H), 120, 133, 137, 149, 155 (bpy); FT-IR [νmax(KBr)/cm-1]: 1602m, 1560m, 1474m (νbpy), 1194vs, 1122vs (νCF2); m.p. = 96.6 C.GC/MS (m/z; EI mode): 844.1 [M]+, 529.1 [M-CH2C6F12H]+, 513.1 [M-OCH2C6F12H]+, 198.1 [M-O(CH2C6F12H)2]+, 182.1 [M-(OCH2C6F12H)2]+, 91.1 [M-(OCH2C6F12H)2-C6H5N]+.(m/z; CI mode): 884.9 [M+C3H5]+, 872.9 [M+C2H5]+, 844.9 [M+H]+, 512.9 [M-OCH2C6F12H]+, 182.9 [M-(OCH2C6F12H)2+H]+, 332.8 [OCH3C6F12H+H]+, 312.8 [OCH3C6F12H-HF+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran;Reflux; | General procedure: A mixture of <strong>[92642-09-6]5,5'-bis(bromomethyl)-2,2'-bipyridine</strong>2 (0.1g, 10 mmol), cinchona derivatives 3 (3a/ 3b, 20 mmol)was dissolved in 5 ml of THF and heated to reflux for overnight, the brown solid was filtered, washed withdiethylether and dried it to get pure di site chiral PTC. (96% yield of 4a and 98% yield of 4b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran;Reflux; | General procedure: A mixture of <strong>[92642-09-6]5,5'-bis(bromomethyl)-2,2'-bipyridine</strong>2 (0.1g, 10 mmol), cinchona derivatives 3 (3a/ 3b, 20 mmol)was dissolved in 5 ml of THF and heated to reflux for overnight, the brown solid was filtered, washed withdiethylether and dried it to get pure di site chiral PTC. (96% yield of 4a and 98% yield of 4b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium sulfite; In methanol; water; for 5h;Inert atmosphere; Reflux; | 4,4’-bis(bromomethyl)-2,2’-bipyridine (230 mg, 0.673 mmol) and potassium sulfite(218 mg, 1.38 mmol) was added to water-methanol mixed solvent (3:1 in v/v). Themixture was refluxed under N2 atmosphere for 5 hours. After cooling to roomtemperature naturally, the reaction solution was concentrated by rotary evaporator andthen extracted by four potions of ethyl acetate (5 mL each). Obtained aqueous solutionwas concentrated and the added to hot isopropanol to afford white precipitates. Theprecipitate was collected by filtration, washed by isopropanol and diethylether, anddried under vacuum. Yield: 244 mg, 86%. 1 H NMR(D2O) : δ 8.65(d, 2H), 8.12(s, 2H),7.58(d, 2H), 4.34(s, 4H) |
[ 81998-05-2 ]
4-(Bromomethyl)-4'-methyl-2,2'-bipyridine
Similarity: 0.87
[ 1119454-23-7 ]
2-(4-(Bromomethyl)phenyl)-5-methylpyridine
Similarity: 0.85
[ 718608-10-7 ]
5-(Bromomethyl)-2-methylpyridine hydrobromide
Similarity: 0.81
[ 792187-67-8 ]
5-(Bromomethyl)-2-methylpyridine
Similarity: 0.81
[ 53006-07-8 ]
2-(4-(Bromomethyl)phenyl)pyridine hydrobromide
Similarity: 0.78
[ 81998-05-2 ]
4-(Bromomethyl)-4'-methyl-2,2'-bipyridine
Similarity: 0.87
[ 1119454-23-7 ]
2-(4-(Bromomethyl)phenyl)-5-methylpyridine
Similarity: 0.85
[ 718608-10-7 ]
5-(Bromomethyl)-2-methylpyridine hydrobromide
Similarity: 0.81
[ 792187-67-8 ]
5-(Bromomethyl)-2-methylpyridine
Similarity: 0.81