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+ |
Structure of Bis(2-bromoethyl) ether
CAS No.: 5414-19-7
*Storage:
*Shipping:
4.5
*For Research Use Only !
Change View
Size | Price | US Stock | Global Stock | In Stock |
5g | łÇ˶ÊÊ | Inquiry | Inquiry | |
25g | łÇó¶ÊÊ | Inquiry | Inquiry | |
100g | łÍî¶ÊÊ | Inquiry | Inquiry | |
500g | łÇÿď¶ÊÊ | Inquiry | Inquiry |
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
łÇ˶ÊÊ
łÇó¶ÊÊ
łÍî¶ÊÊ
łÇÿď¶ÊÊ
In Stock
- +
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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'.
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'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 5414-19-7 |
Formula : | C4H8Br2O |
M.W : | 231.91 |
SMILES Code : | BrCCOCCBr |
MDL No. : | MFCD00039196 |
InChI Key : | FOZVXADQAHVUSV-UHFFFAOYSA-N |
Pubchem ID : | 21521 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H315-H318-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Class: | 9 |
UN#: | 3334 |
Packing Group: | Ⅲ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 38.17 |
TPSA ? Topological Polar Surface Area: Calculated from | 9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.32 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.6 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.92 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.02 |
Solubility | 2.21 mg/ml ; 0.00951 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.41 |
Solubility | 9.12 mg/ml ; 0.0393 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.95 |
Solubility | 0.26 mg/ml ; 0.00112 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
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) | No |
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 | -6.58 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) | 2.17 |
* 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 |
---|---|---|
9% | With triethylamine; In tetrahydrofuran; for 48h;Heating / reflux; | A solution of intermediate B (200mg, 1.01 mmol) in anhydrous THF (5ml) was added to a stirring solution of 1 -bromo-2-(2-bromoethoxy)ethane (234mg, 1.01 mmol) in anhydrous THF (15ml) and triethylamine (323ml, 2.32mmol). The mixture was heated to reflux for 48 h. The reaction mixture was cooled to r.t., diluted with water (10ml) EPO <DP n="73"/>and extracted with EtOAc (3 x 5ml). The combined organic extracts were washed with brine (2 x 5ml), then dried (MgSO4) and evaporated to dryness. The residue was purified by flash chromatography eluting with 100% DCM to 6% MeOH/DCM to give the title compound as a clear oil (24mg, 9%). m/z 269 [M+H]+, 1H NMR (300 MHz, CDCI3) δ: 1.43 (9H, s), 1.58 (2H, br s), 2.58 (4H1 m), 3.33-3.56 (5H1 m), 3.65 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt=1.75 min (Cond.-MS-WI); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H4BrN2O: 293.03; found: 293.04. | |
31% | To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04. | |
31% | To a stirred solution of 3-amino-l-bromoisoquinolirie (444 mg, 2,00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SC>;4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenity index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04. |
31% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 25 - 75℃; for 77h; | To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2,4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2- bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25C for 5 h and at 75 0C for 72 h before it was cooled to 25C} quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO45 filtered and concentrated. Purification of the residue on silica gel elutmg with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenily index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04. |
31% | To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H C13H14BrN20: 293.03; found: 293.04. | |
31% | Step a[00254] To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, Step a as a yellow solid (180 mg, 31%). Rt = 1.75 min(Cond.-MS-Wl); 90% homogenity index; LC-MS: Anal. Calc. for [M+H Ci3H14BrN2 293.03; found: 293.04. | |
31% | With sodium hydride; In N,N-dimethyl-formamide; at 25 - 75℃; for 77h; | To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 mu, 2.00 mmol) was added. This mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap- 143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04. |
31% | To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide(10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2-bromoethyl ether (90%, 250 mL, 2.00 mmol) was added. This mixture was stirred further at 25 Cfor 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution anddiluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4 filteredand concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes)afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS:Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04. | |
31% | To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04. | |
To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 L, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over a2S04, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 16h; | To a solution of [l-(4-bromo-phenyl)-l-methyl-ethyl]-carbamic acid tert-butyl ester (1 eq) inDMF in a 50 mL tube is added DIPEA (2 eq) and l-bromo-2-(2-bromo-ethoxy)-ethane (1.1 eq). the reaction mixture is heated at 1000C for 16 hrs.. After cooling to room temperature, EtOAc and water are added. The combined organic layers are dried (MgSO/i) and concentrated in vacuo to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In acetonitrile; at 60℃; | (0392) Trans-4-Aminocyclohexanol (0.5 g), 1-bromo-2-(2-bromoethoxyl)ethane (1.07 g) and triethylamine (2.42 ml) were dissolved in anhydrous acetonitrile (20 ml). The reaction mixture was heated at 60 C. overnight. The organic solvent was removed under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7%-10% methanol in dichloromethane to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In methanol; at 150℃; for 2.5h;Sealed tube; | A mixture of l-(6-amino-3,3-dimethylindolin-1-yl)ethanone (5 g, 24.5mmol), 1- bromo-2-(2-bromoethoxy)ethane (6.25 g, 26.9 mmol), and Na2CO3 (5.19 g, 49 mmol) in MeOH (25 mL) was heated to 150 C in a sealed tube. After 2.5 h, the mixture was cooled to rt. The reaction mixture was diluted with water (100 mL). The resulting solid was filtered, washed with water (300 mL), and dried in the air to give l-(3,3-dimethyl-6-morpholinoindolin-1-yl)ethanone as a grey solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1 H, s), 7.06 (1 H, d, J=8.1 Hz), 6.61 (1 H, dd, J=8.2, 2.1 Hz), 3.82 (2 H, s), 3.67 - 3.76 (4 H, m), 2.95 - 3.06 (4 H, m), 2.13 (3 H, s), 1.26 (6 H, s). Mass Spectrum (ESI) m/e = 275.2 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 95℃; | Example 160A ethyl 1-morpholinocyclohexanecarboxylate Ethy 1-aminocyclohexancarboxylate hydrogen chloride (5.800 g), triethylamine (13.62 mL) and 1-bromo-2-(2-bromoethoxy)ethane (4.21 mL) were stirred together in N,N-dimethylformamide (50 mL) at 95 C. overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (100 mL) and brine (100 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 5% to 25% ethyl acetate/hexanes provided the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile; | Step 1. Preparation of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(1-morpholinoethyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate. In a 20 mL scintillation vial were combined methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-1-(1-aminoethyl)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate TFA salt (0.020 g, 0.019 mmol) with 1-bromo-2-(2-bromoethoxy)ethane (0.00883 g, 0.038 mmol) and triethylamine (0.016 mL, 0.114 mmol) in 1,4-dioxane (0.5 mL). The mixture was heated to 85 degrees C. for 30 min which resulted in no reaction. The mixture was transferred to a 5 mL microwave vessel and was diluted with dry acetonitrile (2 mL). To the mixture was added additional 1-bromo-2-(2-bromoethoxy)ethane (another 10 equivalents; 0.0445 g, 0.190 mmol) as well as <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.023 g, 0.114 mmol). The resulting mixture was heated in the microwave to 120 degrees C. for 90 min. The contents of the vessel were concentrated under nitrogen stream, redissolved with a small quantity of a mixture of THF, acetonitrile and methanol, filtered and purified by reverse phase preparative HPLC (Prep HPLC Method 2). The desired product was thus obtained as a white solid and was carried directly into the next step. LCMS: m/z=778.6 (M+H)+, 2.13 min (method 5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; | TP5 - To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26. |
46% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere; | To 200 mg (0.984 mmol) of A dissolved in 1 mL of Dimethylformamide (DMF) was added 250 mu^ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2C03 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ oi bis (2-bromoethyl) ether and 170 mg of K2C03 were added. After 3 hours, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1H), 2.46 (d, J = 16.7, 1H), 1.24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 114.73, 66.69, 48.33, 33.93, 27.94, 16.36. TLC: Rf 0.1 (1 :50 MeOH:CH2Cl2). HPLC: Rt 1.05 min, purity > 95%. MS: 274 (M + 1). HRMS: calcd. 274.1556 (M + 1); found 274.1552. Anal. Calcd. for G5H19N3O2: C, 65.91 ; H, 7.01; N, 15.37; Found. 65.81, H, 6.66, N, |
46% | With potassium carbonate; In N,N-dimethyl-formamide; at 602℃;Inert atmosphere; | Step 1 ): (0666) To 200 mg (0.984 mmol) of <strong>[36725-28-7](R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one</strong> dissolved in 1 mL of DMF was added 250 muIota_ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 muIota_ of bis (2- bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product Compound 3 (46%). 1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1 H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1 H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1 H), 2.46 (d, J = 16.7, 1 H), 1 .24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDCI3) delta 1 66.64, 154.05, 152.18, 127.1 0, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 1 6.36. MS: 274 (M + 1 ). Anal. Calcd. for C15H19N3O2: C, 65.91 ; H, 7.01 ; N, 15.37; Found. 65.81 , H, 6.66, N, 15.26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.82 g | To a solution of <strong>[197376-47-9]ethyl (6-chloropyridin-3-yl)acetate</strong> (1.0 g) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 0.40 g) under ice-cooling, and the mixture was stirred for 40 min. To the reaction mixture was added 1-bromo-2-(2-bromoethoxy)ethane (2.3 g), and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.82 g). (1596) MS(ESI+): [M+H]+ 270.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With caesium carbonate; In N,N-dimethyl acetamide; at 120℃; | A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt |
87% | With caesium carbonate; In N,N-dimethyl acetamide; at 120℃; | A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), Cs2CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA (10mL) as stirred at 120 oC overnight. Then H2O (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | n-BuLi (2M in hexane, 22.6 mL, 45.27 mmol) was added drop wise at -40C to a solution of 6-bromo-indolin-2-one (3 g, 14.14 mmol) and diisopropylamine (6.3 mL, 45.27 mmol) in THF (60 mL). The mixture was stirred for 45 min at -40C, 1-bromo-2-(2-bromoethoxy)ethane was added drop wise at this temperature and stirring was continued at RT for 16 h. The reaction mixture was quenched with 4N hydrogen chloride solution (40 mL) and the aqueous phase was separated and extracted with EtOAc (3x 60 mL). The combined organic layers were washed with brine (50 mL), dried over Na2S04 and concentrated. The raw product was triturated with hexane (20 mL) and filtered. The filter was washed with hexane/EtOAc = 4:1 (100 mL) affording the target compound as light brown solid. Yield: 1.2 g (31 %). HPLC (method 1 ): Rt = 2.94 min, m/z [M+H]+ = 282.1 (MW calc. 282.13). |
Tags: Bis(2-bromoethyl) ether | Ethers | Bromides | PEG Linkers | Aliphatic Chain Hydrocarbons | PROTAC Linkers | Bifunctional Linkers | Organic Building Blocks | 5414-19-7
A282104 [57602-02-5]
1,14-Dibromo-3,6,9,12-tetraoxatetradecane
Similarity: 0.93
A282104 [57602-02-5]
1,14-Dibromo-3,6,9,12-tetraoxatetradecane
Similarity: 0.93
A282104 [57602-02-5]
1,14-Dibromo-3,6,9,12-tetraoxatetradecane
Similarity: 0.93
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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 |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL