Structure of 1035373-85-3
*Storage:
*Shipping:
Synonyms: 2-(2-(6-chlorohexyloxy)ethoxy)ethanamine hydrochloride
4.5
*For Research Use Only !
Change View
Size | Price | US Stock | Global Stock | In Stock |
100mg | łÍͶÊÊ | Inquiry | Inquiry | |
250mg | łďď¶ÊÊ | Inquiry | Inquiry | |
1g | łËďÿ¶ÊÊ | Inquiry | Inquiry | |
5g | łÇÇÿʶÊÊ | Inquiry | Inquiry |
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
łÍͶÊÊ
łďď¶ÊÊ
łËďÿ¶ÊÊ
łÇÇÿʶÊÊ
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. : | 1035373-85-3 |
Formula : | C10H23Cl2NO2 |
M.W : | 260.20 |
SMILES Code : | NCCOCCOCCCCCCCl.[H]Cl |
Synonyms : |
2-(2-(6-chlorohexyloxy)ethoxy)ethanamine hydrochloride
|
MDL No. : | MFCD32706550 |
InChI Key : | KRGPBUVQAULFOQ-UHFFFAOYSA-N |
Pubchem ID : | 89239696 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
In N,N-dimethyl-formamide; for 4h; | [00196] Sodium 2-((l£,3Z)-3-(l-(6-(2-(2-(6-chlorohexyloxy)ethoxy)ethylamino)-6- oxohexyl)-l-methyl-9-sulfonato-5,6-dihydro-lH-pyrrolo[3,2,l-//]quinolin-2(4H)- ylidene)prop-l-enyl)-l-methyl-l-(4-sulfonatobutyl)-l,4,5,6-tetrahydropyrrolo[3,2,l- //]quinolinium-9-sulfonate (PBI 3838). To the above dye in the free acid form (60 mg, 0.078 mmol) dissolved in 5 mL DMF was added Λ/,Λ/,N',Λ/r'-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate (32.4 mg, 0.11 mmol) and 37.5 μL diisopropylethylamine. The reaction was stirred 0.5 hr in the dark before the addition of 2-(2-(6-chlorohexyloxy)ethoxy)ethanaminium chloride (28.0 mg, 0.11 mmol). The reaction was stirred for 4 hrs, diluted with water and purified by RP-ΗPLC giving desired product (85.0 mg, 46.7 %) as a blue solid. MS m/z calculated for C47H66 Cl3N3Na2Oi2S3 (M+HC1): 1076.3 Found 1076.5 (M +HCl, ESI+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6 mg | Example 27. Bis(piperidineazepino)-5-((2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)sulfonyl) sulforhodamine (PBI [00188] A solution of bis(piperidineazepino)-3,5-bissulforhodamine (PBI 3904, 70 mg) in POCI3 (2 mL) and THF (2 mL) was stirred for 1 hour and then concentrated under reduced pressure. This crude sulfonyl chloride was dissolved in CH2C12 (5 mL), and triethylamine (0.23 mL) and 2-(2-((6-chlorohexyl)oxy)ethoxy)ethylamine HC1 (43 mg) were added. After stirring for 3 days, the reaction mixture was concentrated. The crude product was dissolved in DMF and purified by preparative HPLC (gradient of ACN in 0.1% TFA in H20) to provide the title compound (6 mg) as a blue solid: MS expected 840 (C43H54CI 3O8S2 , M+), found 840. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 mg | Example 21. Bis(piperidineazepino)-6-((2-(2-((6-chlor ohexyl)oxy)ethoxy)ethyl)- carbamoyl)rhodamine [00182] To a solution of bis(piperidineazepino)-6-carboxyrhodamine (10 mg) and diisopropylethylamine (0.02 mL) in DMF (1 mL), TSTU (8 mg) was added. After stirring for 1 minutes, 2-(2-((6-chlorohexyl)oxy)ethoxy)ethylamine HC1 (7 mg) was added, which was synthesized according to the procedure described in H. Benink, M. McDougall, D. Klaubert, G. Los, BioTechniques 2009, 47, 769-774 (which is incorporated by reference herein). After stirring another 30 minutes, the reaction mixture was purified by preparative HPLC (gradient of ACN in 0.1% TFA in H20) to provide the title compound (1 mg) as a blue solid: MS expected 769 (C45H55C1N306+, M+), found 769. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 3h; | 50 mg of methotrexate hydrate was stirred in 3 mL of DMF and treated with ED AC (63 mg, 330 umol) and triethylamine (77 uL, 550 umol). After 10 min, 12-chloro-3, 6-dioxo- dodecylamine hydrocholide (21.5 mg, 83 umol) was added. After 3 h, the product was isolated by preparative HPLC (2->50% MeCN in 0.1% aqueous formic acid). The appropriate fractions were concentrated and lyophilized to yield an orange solid. Calculated for M+H: 660.3; found 660.7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25 mg | With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 36h; | Resorcinol (3.31 g, 30 mmol) was dissolved in 10 mL of DMF, and K2C03 (3.32 g, 24 mmol) added. The mixture was stirred until all solid had dissolved, and the reaction turned a dark brown. 6-Bromohexanoate ethyl ester (4.69 g, 21 mmol) was added all at once, the reaction stirred overnight, and then poured into 1 M HCl and extracted with 3 x 50 mL EtOAc. The combined organic layers were washed with brine, then adsorbed onto Celite and subjected to column chromatography eluting with 0->50% EtOAc in heptanes. Calculated for M+H: 254.1; found 253.8. Ethyl 6-(3-hydroxyphenoxy)hexanoate (0.96 g, 3.8 mmol) was dissolved in a mixture of MeOH and H20, and LiOH hydrate (639 mg, 15.2 mmol) added. After 2 h, the reaction was concentrated under reduced pressure and then acidified with 1 M HCl to give a white precipitate, which yielded 550 mg of a white solid after filtration and drying under vacuum. Calculated for M+H: 225.1; found 225.2 Ethyl 4-aminobenzoate (405 mg, 2.45 mmol) was stirred in 7.7 mL of a mixture of acetone/2 N HC1 in an ice bath. A solution of sodium nitrite (215 mg, 3.12 mmol) dissolved in 8 mL of H20 was added dropwise over 10 min, and the reaction was stirred for an additional 20 min. The reaction was then added dropwise over 20 min to a stirred solution of 6-(3-hydroxyphenoxy)hexanoate in 18 mL of 1 N NaOH in an ice bath, generating a dark red color. Stirring and cooling was continued for 40 min, and the reaction was then neutralized with 1 N HC1 and diluted with water. The resulting brown precipitate was collected by filtration and directly carried on to the next step. To a solution of the carboxylic acid from the previous step (50mg, 0.12 mmol) in DMF (4mL), 1 -( 1 -(4-(aminomethyl)phenyl)-3 -tertbutyl- 1 H-pyrazol-5 -yl)-3 -(naphthalen- 1 -yl) urea (50mg, 0.14mmol), ethyl dimethylaminopropylcarbodiimide (EDAC, 30mg, 0.16mmol) and 1-hydroxybenzotriazole (HOBt, 22mg, 0.16mmol) was added. After stirring for 40h, the reaction was partitioned between EtOAc and NaHC03 (sat. aq.), the layers separated and the organic layer washed with water and NaCl (sat. aq.), dried and concentrated. The resulting red solid was purified by preparative HPLC (10%->100% ACN in 0.1% aqueous TFA) and subsequent concentration yielded 44 mg of an orange solid. Calculated for M+H: 745, found 745. To a solution of the ester from the previous reaction (44mg, 0.06mmol) in THF (3mL), NaOH (IN, ImL) was added. After stirring for 8 days, the reaction was acidified and purified by preparative HPLC (10%>->100%> ACN in 0.1%> aqueous TFA) and subsequently concentrated to yield 25 mg of an orange solid. Calculated for M+H: 717, found 717. To a solution of the carboxylic acid (14mg, 0.02mmol) from the previous reaction in DMF (2mL), N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate (TSTU, 12mg, 0.04mmol) and diisopropylethylamine O. lmmol) was added. After stirring for 30min, 2-[2-(6-chloro-hexyloxy)-ethoxy]-ethylammonium hydrochloride (Promega, lOmg, 0.04mmol) was added. After stirring for 36h, the reaction was acidified and purified by preparative HPLC (10%>->100%> ACN in 0.1 % aqueous TFA) and subsequently concentrated to yield 25 mg of PBI 5131 as an orange solid. Calculated for M+H: 923, found 923. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With triethylamine; In acetonitrile; for 18h; | To a solution of S72 (820 mg, 2.05 mmol) in MeCN (20 mL), 2-(2-((6-chlorohexyl)oxy)ethoxy)ethan-1-amine hydrochloride (S07) (588 mg, 2.26 mmol) was added, followed by trimethylamine (1.43 mL, 10.3 mmol). The resulting yellow solution was stirred for 18 hours, at which point TLC analysis indicated complete consumption of starting material. The reaction mixture was concentrated approximately under vacuum and purified by silica gel chromatography (0→100% EtOAc/Heptane) to provide 674 mg (68% yield) of S73 as a clear oil. 1H NMR (300 MHz, DMSO-d6) δ 7.16 (t, J=5.5 Hz, 1H), 4.16-3.89 (m, 2H), 3.72-3.53 (m, 6H), 3.53-3.43 (m, 8H), 3.38 (m, 4H), 3.11 (q, J=6.0 Hz, 2H), 2.41 (t, J=6.2 Hz, 2H), 1.70 (dq, J=8.0, 6.5 Hz, 2H), 1.58-1.44 (m, 2H), 1.39 (s, 13H); 13C NMR (75 MHz, DMSO-d6) δ 170.4, 156.2, 79.7, 70.2, 69.6, 69.5, 69.4, 69.1, 68.8, 66.2, 63.1, 45.3, 35.8, 32.0, 29.0, 27.7, 26.1, 24.9; MS (ESI+) calc'd for C22H42ClNNaO8+ [M+Na]+ 506.3, found 506.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine; In acetonitrile; for 20h; | To a solution of SL_0723 (27 mg, 45 μmol) in MeCN (7 mL), J1454T (13 mg, 50 μmol) was added, followed by NEt3 (31 μL, 0.22 mmol). The resulting yellow solution was allowed to react for 20 hours, at which point TLC analysis indicated complete consumption of starting material. Solvent was removed under vacuum, and crude residue was purified by silica gel chromatography (0→10% MeOH/DCM) to provide 26 mg (85% yield) of SL_0725 as a yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.18 (t, J=5.1 Hz, 1H), 5.74-5.67 (m, 2H), 4.55 (t, J=5.4 Hz, 1H), 4.07-4.01 (m, 2H), 3.99-3.84 (m, 4H), 3.62 (t, J=6.6 Hz, 2H), 3.58-3.44 (m, 32H), 3.44-3.33 (m, 6H), 3.11 (q, J=5.9 Hz, 2H), 1.70 (p, J=6.7 Hz, 2H), 1.49 (p, J=6.8 Hz, 2H), 1.43-1.22 (s, 4H); MS (ESI+) calc'd for C3J-161ClNO13+ [M+H]+ 690.38, found 690.62. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine; In tetrahydrofuran; at 22℃; for 20h; | To a solution of SL_0209 (307 mg, 805 μmol) in THF (20 mL) was added J1454T (230 mg, 886 μmol) followed by triethylamine (340 μL, 2.41 mmol), white precipitate forms (NEt3HCl). The resulting suspension was left stirred at 22 C. for 20 hours at which point TLC analysis indicated complete consumption of starting material. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (0→60% EtOAc/hexanes) to provide 280 mg (75% yield) of SL_0210 as a clear oil. 1H NMR (300 MHz, CDCl3) δ 5.82-5.66 (m, 2H), 5.29 (br. s, 1H), 4.63 (m, 1H), 4.31-4.19 (m, 3H), 4.14-4.04 (m, 3H), 3.89-3.79 (m, 1H), 3.65-3.50 (m, 11H), 3.49-3.44 (m, 2H), 3.40-3.33 (m, 2H), 1.84-1.72 (m, 3H), 1.54-1.57 (m, 6H, overlap with H2O), 1.94-1.31 (m, 5H, overlap with H2O). MS (ESI+) calc'd for C22H41ClNO7+ [M+H]+ 466.25, found 466.43. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With triethylamine; In tetrahydrofuran; at 22℃; for 5h; | To a solution of SL_0469 (104 mg, 273 μmol) in THF (10 mL) was added J1454T (78 mg, 300 μmol) followed by triethylamine (190 μL, 1.36 mmol), white precipitate forms (NEt3HCl). The resulting suspension was left stirred at 22 C. for 5 hours at which point TLC analysis indicated complete consumption of starting material. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (0→100% EtOAc/hexanes) to provide 94 mg (74% yield) of SL_0476 as a clear oil. 1H NMR (300 MHz, DMSO-d6) δ 7.17 (t, J=5.6 Hz, 1H), 5.82-5.67 (m, 2H), 4.58 (s, 1H), 4.12 (m, 1H), 4.05 (m, 2H), 3.97-3.87 (m, 3H), 3.73 (m, 1H), 3.62 (t, J=6.6 Hz, 2H), 3.53 (m, 2H), 3.49-3.45 (m, 5H), 3.42-3.34 (m, 4H), 3.11 (q, J=6.0 Hz, 2H), 1.75-1.57 (m, 3H), 1.54-1.23 (m, 11H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; In tetrahydrofuran; at 22℃; for 2h; | To a solution of SL_0493 (220 mg, 429 μmol) in THF (15 mL) was added J1454T (117 mg, 451 μmol) followed by triethylamine (120 μL, 859 μmol), murky solution forms ( NEt3.HCl precipitates). The resulting suspension was left stirred at 22 C. for 2 hours at which point TLC analysis indicated complete consumption of starting material. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (0→100% EtOAc/Heptane) to provide 164 mg (64% yield) of SL_0495 as a clear oil. 1H NMR (300 MHz, DMSO-d6) δ 7.17 (t, J=5.6 Hz, 2H), 5.78 (m, 2H), 4.58 (m, 1H), 4.45 (m, 2H), 4.13 (dd, J=13.1, 3.8 Hz, 1H), 4.04 (m, 2H), 3.91 (dd, J=13.0, 4.3 Hz, 1H), 3.72 (ddd, J=11.4, 7.9, 3.4 Hz, 1H), 3.62 (t, J=6.6 Hz, 2H), 3.55 (dd, J=5.6, 3.9 Hz, 2H), 3.52-3.44 (m, 8H), 3.43-3.34 (m, 7H), 3.12 (m, 4H), 1.78-1.58 (m, 4H), 1.55-1.42 (m, 6H), 1.42-1.25 (m, 4H). MS (ESI+) calc'd for C22H42ClN2O9+ [M-THP+H]+ 513.26, found 513.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine; In tetrahydrofuran; for 18h; | To a solution of SL_0160 (400 mg, 1.09 mmol) was added 2-(2-((6-chlorohexyl)oxy) ethoxy) ethylamine hydrochloride (312 mg, 1.20 mmol) followed by Et3N (290 μL, 20.7 mmol). The resulting yellow solution was left stirred for 18 hours at which point TLC indicated consumption of the starting material. The reaction mixture was absorbed on silica and purified by silica gel chromatography (0→30% EtOAc/hexanes) to provide 395 mg (80% yield) of SL_0161 as a clear oil. 1H NMR (300 MHz, CDCl3) δ 5.71 (dt, J=11.4, 5.7 Hz, 1H), 5.56 (dt, J=11.3, 6.2 Hz, 1H), 5.19 (br. s, 1H), 4.63 (d, J=6.2 Hz, 2H), 4.27 (d, J=5.7 Hz, 2H), 3.67-3.50 (m, 8H), 3.47 (t, J=6.6 Hz, 2H), 3.37 (q, 5.2 Hz, 2H), 1.78 (p, J=6.8 Hz, 2H), 1.60 (p, J=6.8 Hz, 2H), 1.44-1.32 (m, 4H), 0.90 (s, 9H), 0.07 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40%Spectr. | 0.255 mmol of (E) 4-(1-methyl-2,3,6,7-tetrahydro-1H-silepin-1-yl)butyl (4- nitrophenyl) carbonate silver complex was treated with 2 mL dichloromethane and 2mL brine. Organic layer was separated. The aqueous layer was extract with 1.3 mL dichloromethane. The organic layer was combined and dried with Na2SO4. The dichloromethane solution of (E) 4-(1-methyl-2,3,6,7-tetrahydro-1H-silepin-1-yl)butyl (4-nitrophenyl) carbonate was transferred to a 10 mL flame-dried flask. Then 2-(2-((6- chlorohexyl)oxy)ethoxy)ethanamine hydrochloride (33.2 mg, 0.12 mmol, 1.0 equiv)and TEA (88. 9 pL, 0.64 mmol, 5.3 equiv) was added to the solution. The reaction was stirred at room temperature over 2.5 h. After reaction, the mixture was loaded onto silica gel column directly. Purification by flash column chromatography (10% acetone/hexane, Rf=) afforded 4-(1-methyl-2,3,6,7-tetrahydro-1H-silepin-1-yl)butyl (2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)carbamate as a solution in acetone/hexane.The solution was loaded onto a plug of 265 mg silica gel (impregnated with 10% w/w AgNO3), which was packed in an hg Biotage SNAP cartridge (contained a bed of unmodified silica gel). The SNAP cartridge was eluted with 100 mL 30% acetone/hexane over 2.5 h. Then the silica gel column was washed with 100 mL 30% acetone/hexane, followed by 150 mL EtCH to give the desired EtCH solution of 4-(1-methyl-2,3,6,7-tetrahydro-1H-silepin-1-yl)butyl (2-(2-((6- chlorohexyl)oxy)ethoxy)ethyl)carbamate. The ethanol solution was concentrated via rotary evaporation, affording the 4-(1-methyl-2,3,6,7-tetrahydro-1H-silepin-1-yl)butyl (2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)carbamate silver complex (40% NMR yield) as white sticky oiL 1H NMR (600 MHz, MeOD) O: 5.61-5.53 (m, 2H), 4.04 (t, J=6.3 Hz,2H), 3.61-3.55 (m, 6H), 3.53 (t, J=5.6 Hz, 2H), 3.49 (t, J=6.6 Hz, 2H), 3.28 (t, J=5.5Hz, 2H), 2.55-2.52 (m, 2H), 2.33-2.27 (m, 2H), 1.80-1.75 (m, 2H), 1.66-1.58 (m, 4H),1.47 (dt, J=l4.4, 7.1 Hz, 2H), 1.42-1.36 (m, 4H), 1.09-1.05 (m, 1H), 1.03-0.98 (m,1H), 0.88 (dt, J=14.8, 7.5 Hz, 1H), 0.82 (dt, J=14.S, 7.6 Hz, 1H), 0.63-0.54 (m, 2H),0.02 (s, 3H); 13C NMR (150MHz, MeOD) ö: 120.1 (CH), 119.9 (CH), 72.2 (CH2), 71.2(CH2), 71.1 (CH2), 71.0 (CH2), 65.4 (CH2), 45.7 (CH2), 33.9 (CH2), 33.7 (CH2), 30.5(CH2), 28.73 (CH2), 28.69 (CH2), 27.7 (CH2), 26.4 (CH2), 21.1 (CH2), 18.81 (CH2),18.78 (CH2), 16.2 (CH2), -2.8 (CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Dasatinib (15 mg, 31 umol)P-Nitrophenyl chloroformate(8. 4 mg, 42 umol, 1.36 equiv)And 10 μL of TEA in 1.8 mL of DMF: THF (2: 1).The reaction was stirred overnight and then added as a solution in DMF2- (2 - ((6-chlorohexyl) oxy) ethoxy) ethan-1-amine hydrochloride(32 mg, 4 equiv)Was added.Additional TEA was also added and the reaction was stirred overnight again.Preparative HPLC (20 - & gt; 60% MeCN in 0.1% aqueous TFA) gave colorlessThe desired product was obtained as a residue (6.7 mg, 30% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50 mg of methotrexate hydrate,Stir in 3 mL of DMF,EDAC (63 mg, 330 umol) and triethylamine (77 uL, 550 umol).After 10 minutes, 2- (2 - ((6-chlorohexyl) oxy) ethoxy) ethylamine hydrochloride (Promega 21.5 mg, 83 umol) was added.After 3 h, the product was isolated by preparative HPLC (2-> 50% MeCN in 0.1% aqueous formic acid).Appropriate fractions were concentrated and lyophilized to give an orange solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.4% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;Sealed tube; | To a solution of 2,5-dioxopyrrolidin-1-yl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate (50.0 mg, 1.14 mmol) in 10 mL DMF, 2-(2-((6-chlorohexyl)oxy)ethoxy)ethanamine-HCl (53.0 mg, 0.22 mmol) and N,N-diisopropylethylamine (0.14 mL, 0.79 mmol) was added. The reaction was capped and stirred overnight. Volatiles were removed under reduced pressure giving a yellow solid that was dissolved in DCM, absorbed on celite, dried and subjected to flash chromatography (EtOAc/Hep) purification giving the product (37.0 mg, 56.4%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ 7.61 (m, 1H), 7.63 (m, 1H), 7.40 (m, 1H), 4.34 (d, 5.7 Hz, 1H), 3.54 (m, H), 1.72 (m, 2H), 1.53 (s, 9H), 1.44 (s, 9H). MS (ESI) m/z calcd for C23H38ClN2O5 (M+H+) 457.2. found 457.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.8% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;Sealed tube; | To a solution of 2,5-dioxopyrrolidin-1-yl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate (50.0 mg, 0.14 mmol) in 10 mL DMF, 2-(2-((6-chlorohexyl)oxy)ethoxy)ethanamine-HCl (42.4 mg, 0.17 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.72 mmol) was added. The reaction was capped and stirred overnight. Volatiles were removed under reduced pressure giving a yellow solid that was dissolved in EtOAc, washed with water, dried over Na2SO4 and concentrated. The residue was dissolved in DCM, absorbed on celite, dried and subjected to flash chromatography (EtOAc/Hep) purification giving the product (32.0 mg, 48.8%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ 7.73 (d, 8.4 Hz, 2H), 7.32 (d, 8.4 Hz, 2H), 4.34 (d, 6.6, 2H), 3.65-3.42 (m, 8H), 2.75 (m, 4H), 1.5 (s, 9H) 1.2 (m, 10H). MS (ESI) m/z calcd for C23H38ClN2O5 (M+H+) 457.2. found 457.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.3% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;Sealed tube; | To a solution of 2,5-dioxopyrrolidin-1-yl 4-(((tert-butoxycarbonyl)amino)methyl)cyclohexanecarboxylate (81.7 mg, 0.14 mmol) in 5 mL DMF, 2-(2-((6-chlorohexyl)oxy)ethoxy)ethanamine-HCl (50.0 mg, 0.19 mmol) and N,N-diisopropylethylamine (0.10 mL, 0.57 mmol) was added. The reaction was capped and stirred overnight. Volatiles were removed under reduced pressure giving a yellow residue that was dissolved in DCM, absorbed on celite, dried and subjected to flash chromatography (MeOH/DCM) purification giving the product (35.0 mg, 39.3%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogenchloride; In 1,4-dioxane; at 20℃; for 2h; | 700 mg (2.16 mmol, 1.0 eq) product of step 14.3 was dissolved in 2.5 mL 4 M HC1 in dioxane (9.73 mmol, 4.55 eq) and was stirred at room temperature for 2 hours. The solvent was removed in vacuum and the product was obtained as white solid, which was used without further purification. |
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1h; | Commercially available chloro- alcohol was converted into tosylate. Condition (a) 6-Chloro-l-hexanol (1.0 eq.), p- Toluenesulfonyl chloride (1.1 eq), 4-dimethylaminopyridine (0.1 eq) in pyridine for 1.5 hours at 0C. The reaction mixture was extracted with diethyl ether against diluted HC1. The organic phase was collected and evaporated under reduced pressure, yielding crude colorless crystal 6. The product was carried on to the next step without further purification. Commercially available amino-alcohol was protected with t-butyl carbonate group. Condition (b) 2-(2- (0303) Aminoethoxy)ethanol (1.0 eq.), Di-tert-butyl dicarbonate (1.0 eq.) in methanol stirred for 3 h at room temperature. The reaction mixture was extracted with PBS Buffer against dichloromethane. The organic fraction was dried in vacuo. Compounds were further purified by flash chromatography (1 :1 ethyl acetate/hexane) to yield 7, a colorless oil. 6 and 7 were combined to become protected PEG linker. Condition (c) 6 (1 eq), 7 (1.1 eq), and Potassium tert-butoxide (1 M in THF, 1.5 eq) in DMF stirred overnight at room temperature. The reaction was quenched with water and extracted with diethyl ether. The product was further purified by flash chromatography (1 :2 ethyl acetate: hexane). Colorless oil 8 was obtained. Deprotection of 8 yielded the PEG amine hydrochloride. Condition (d) 8 (1 eq), HC1 (4 M in Dioxane, 6 eq) stirred for 1 h at room temperature. Concentrated and then dried under high-vac to yield 9 a white solid. | |
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1h; | Add 1 equivalent of compound 8, 6 equivalents of HCl (4M in Dioxane) at room temperature, and mix and stir for 1 h. After the reaction is complete, filter with suction and dry in vacuo to obtain a white solid, namely compound 9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; at 20℃; | Commercially available cyclohexane linker was coupled with homemade PEG linker. Condition (e) 9 (1 eq.), trans-4-[[(l,l-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acid (1 eq.), dimethylaminopyridine (0.1 eq.), N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (2 eq.) in triethylamine (4 eq.) stirred overnight at room temperature. The reaction mixture was quenched by water and extracted with DCM. Product was purified by flash chromatography (100% ethyl acetate). Sticky white solid 10 was obtained. Deprotection was of 10 yields final rigid linker amine hydrochloride. Condition (f) 10 (1 eq.), in HC1 (4 M in Dioxane, 6 eq.) for lh at room temperature. Reaction was concentrated and put under high-vac to yield fluffy white solid 11 |
Tags: 2-(2-(6-chlorohexyloxy)ethoxy)ethanamine HCl | 2-(2-(6-chlorohexyloxy)ethoxy)ethanamine hydrochloride | Chlorides | Amines | Aliphatic Chain Hydrocarbons | Ethers | Inorganic Salts | Organic Building Blocks | Synthetic Reagents | 1035373-85-3
A1004866 [744203-60-9]
2-(2-((6-Chlorohexyl)oxy)ethoxy)ethanamine
Reason: Free-salt
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