Structure of 1-Bromooctane
CAS No.: 111-83-1
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
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'.
Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su ;
Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
Show More >
Purchased from AmBeed: 20469-65-2 ; 13675-18-8 ; 2564-83-2 ; 872-31-1 ; 192863-35-7 ; 871231-46-8 ; 192863-36-8 ; 6793-92-6 ; 3972-65-4 ; 2398-37-0 ; 850623-47-1 ; 929626-22-2 ; 705254-31-5 ; 580-13-2 ; 2635-13-4 ; 623-12-1 ; 1015082-71-9 ; 52415-29-9 ; 23145-07-5 ; 619-42-1 ; 99-90-1 ; 192863-37-9 ; 578-57-4 ; 407-14-7 ; 216434-82-1 ; 668984-08-5 ; 423118-47-2 ; 108-85-0 ; 252726-24-2 ; 101-55-3 ; 850623-36-8 ; 4923-87-9 ; 1394827-04-3 ; 850623-42-6 ; 438553-44-7 ; 460-00-4 ; 1187951-62-7 ; 705254-34-8 ; 111-83-1 ; 111-83-1 ; 906007-40-7 ; 1443282-44-7 ; 1000160-76-8 ; 1111733-01-7 ; 99-90-1
Show More >
CAS No. : | 111-83-1 |
Formula : | C8H17Br |
M.W : | 193.12 |
SMILES Code : | CCCCCCCCBr |
MDL No. : | MFCD00000276 |
InChI Key : | VMKOFRJSULQZRM-UHFFFAOYSA-N |
Pubchem ID : | 8140 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H227-H315-H318-H335-H411 |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.44 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.06 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.89 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.3 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.75 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.72 |
Solubility | 0.0366 mg/ml ; 0.00019 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.63 |
Solubility | 0.00457 mg/ml ; 0.0000237 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.96 |
Solubility | 0.0214 mg/ml ; 0.000111 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
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 |
-4.01 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.36 |
* 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 |
---|---|---|
91% | With potassium carbonate In acetonitrile for 12 h; Inert atmosphere; Reflux | 1 -bromooctane (3.0 g, 1.5 mmol), diethanolamine (2.4 g, 2.3 mmol), anhydrous potassium carbonate (4.28 g, 3.1 mmol) were taken in acetonitrile (40 mL) and the contents were refluxed for 12 h nitrogen atmosphere. After cooling reaction mixture was evaporated and extracted with dichloromethane and dried over anhy. Na2S04 removed under reduced pressure to get the crude productwhich was further purified by column chromatography using dichloromethane and methanol as eluentto obtain pure 2,2'-(octylazanediyl)bis(ethan-l-ol) as colorless oil (590 mg, 91 percent).1H NMR (CDC13): δ 4.22 (brs, 2H, OHCH2), 3.86 (t, 4H, JAB = 5 Hz, -CH2OH), 3.10 (t, 4H, JAB = 4.5 Hz, -CH2N), 2.94 (t, 2H, JAB = 8 Hz, -CH2N), 1.69-1.60 (m, 2H, -CH2), 1.30-1.25 (m, 10H, - CH2), 0.87 (t, 3H, JAB = 7 Hz, -CH3). |
76.7% | With potassium carbonate; potassium iodide In acetonitrile for 12 h; Inert atmosphere; Reflux | (1) n-octyl bromide (6.0 g, 30 mmol), diethanolamine (4.73 g, 45 mmol),Anhydrous potassium carbonate (8.29 g, 60 mmol) and potassium iodide (1.0 g) were added to a 250 mL two-necked flask, 80 mL of acetonitrile was added and the nitrogen was bubbled through for 5 minutes to replace the air in the system and then refluxed for 12 h.(2) The reaction was stopped, acetonitrile was removed by steaming, 60 mL of dichloromethane and 60 mL of water were added, and the mixture was separated. The organic phase was washed twice with water to remove excess diethanolamine. The product has a certain solubility in water, washed, the water phase and then extracted twice with methylene chloride. The organic phase was separated and dried over anhydrous sodium sulfate.(3) steamed to remove methylene chloride to obtain a light yellow liquid 5.00g, yield 76.7percent JLC detection, ethyl acetate / petroleum ether = 1: 1 as the development agent, the target product than the value of Rf = 0.33 The(4) A 250 mL single-necked flask was charged with (3) the procedure to prepare 5.00 g (23 mmol) of octyldiethanolamine, bromopropyne3.56 g (30 mmo 1) and ethanol 1 OOmL, stirred and refluxed for 12 h under stirring.(5) The excess of bromopropyne and solvent ethanol were distilled off under reduced pressure to give 7.36 g of the crude product as brownish red viscous liquid,100percent. TLC detection, dichloromethane: methanol = 6: 1, the specific value of Rf = 0.50 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium carbonate; In acetonitrile; for 12.0h;Inert atmosphere; Reflux; | 1 -bromooctane (3.0 g, 1.5 mmol), diethanolamine (2.4 g, 2.3 mmol), anhydrous potassium carbonate (4.28 g, 3.1 mmol) were taken in acetonitrile (40 mL) and the contents were refluxed for 12 h nitrogen atmosphere. After cooling reaction mixture was evaporated and extracted with dichloromethane and dried over anhy. Na2S04 removed under reduced pressure to get the crude productwhich was further purified by column chromatography using dichloromethane and methanol as eluentto obtain pure 2,2'-(octylazanediyl)bis(ethan-l-ol) as colorless oil (590 mg, 91 %).1H NMR (CDC13): delta 4.22 (brs, 2H, OHCH2), 3.86 (t, 4H, JAB = 5 Hz, -CH2OH), 3.10 (t, 4H, JAB = 4.5 Hz, -CH2N), 2.94 (t, 2H, JAB = 8 Hz, -CH2N), 1.69-1.60 (m, 2H, -CH2), 1.30-1.25 (m, 10H, - CH2), 0.87 (t, 3H, JAB = 7 Hz, -CH3). |
76.7% | With potassium carbonate; potassium iodide; In acetonitrile; for 12.0h;Inert atmosphere; Reflux; | (1) n-octyl bromide (6.0 g, 30 mmol), diethanolamine (4.73 g, 45 mmol),Anhydrous potassium carbonate (8.29 g, 60 mmol) and potassium iodide (1.0 g) were added to a 250 mL two-necked flask, 80 mL of acetonitrile was added and the nitrogen was bubbled through for 5 minutes to replace the air in the system and then refluxed for 12 h.(2) The reaction was stopped, acetonitrile was removed by steaming, 60 mL of dichloromethane and 60 mL of water were added, and the mixture was separated. The organic phase was washed twice with water to remove excess diethanolamine. The product has a certain solubility in water, washed, the water phase and then extracted twice with methylene chloride. The organic phase was separated and dried over anhydrous sodium sulfate.(3) steamed to remove methylene chloride to obtain a light yellow liquid 5.00g, yield 76.7% JLC detection, ethyl acetate / petroleum ether = 1: 1 as the development agent, the target product than the value of Rf = 0.33 The(4) A 250 mL single-necked flask was charged with (3) the procedure to prepare 5.00 g (23 mmol) of octyldiethanolamine, bromopropyne3.56 g (30 mmo 1) and ethanol 1 OOmL, stirred and refluxed for 12 h under stirring.(5) The excess of bromopropyne and solvent ethanol were distilled off under reduced pressure to give 7.36 g of the crude product as brownish red viscous liquid,100%. TLC detection, dichloromethane: methanol = 6: 1, the specific value of Rf = 0.50 |
In ethanol; for 12.0h;Reflux; | General procedure: A volume of 0.11 mol of bromoalkene, 0.1 mol diethanolamine,and 50 mL dry ethanol were added to a 250 mLround-bottom flask. The reactants were stirred by a magneticstirrer for 12 h at reflux temperature. After the reactionwas completed, the solvent was evaporated to give acrude product. The crude product bearing octyl or decyl groups was extracted three times with ether, washed oncewith dilute sodium hydroxide solution followed by water,and then dried under vacuum to obtain a viscous product.The crude product bearing dodecyl was recrystallized inacetone at low temperature, washed once by dilute sodiumhydroxide solution and distilled water respectively, andthen dried under vacuum to obtain a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium; In ethanol; | (a) Preparation of N-methyl-N-octyl amine N-methyl-N-octyl amine is prepared in the following way: STR6 405 g of a 37percent methyl amine solution in ethanol and 150 g of n-octyl bromide were introduced into a 1 liter autoclave. The autoclave is heated to 180° C. for 20 hours and then to 200° C. for 8 hours. The crude residue is evaporated to dryness after cooling. Thus, a grey crystalline residue is obtained, which is treated with 300 ml of a 20percent potassium solution. The aqueous phase is extracted with ether, the ethereal phase is dried on magnesium sulphate, followed by filtration and expulsion of the ether. The sought product is then recoered with a good yield by distillation (approximately 70percent). The boiling point is 75° to 78° C., under 13 mmHg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | A mixture of imidazole (1 .36 g, 20.0 mmol) and sodium hydroxide (0.80 g, 20.0 mmol) in DMSO was heated to 90 C for 2 h, and then cooled to room temperature. A solution of 1 -bromooctane (3.46 g, 19.0 mmol) in DMSO was added dropwise to the mixture. After stirring at room temperature for 3 h, the mixture was heated up slowly to 65 C for 16 h with constant stirring. The solution obtained was mixed with water and the product was extracted 4 times with diethyl ether. The diethyl ether phases were combined and dried with sodium sulfate. Diethyl ether was removed under vacuum and the intermediate (9) was obtained as yellow liquid (2.89 g, 89 %). 1 H NMR (DMSO-d6): delta 7.61 (s, 2H), 7.15 (s, 1 H), 6.87 (s, 1 H), 3.93 (t, 2H), 1 .68 (m, 2H), 1 .25 (m, 10H), 0.85 (t, 3H). | |
87.7% | With sodium hydroxide; In dimethyl sulfoxide; at 20 - 25℃;Inert atmosphere; | To a flask equipped with a stirrer, Add the thermometer to the three necked flask 0 · 440 g (11.0 mmol) of NaOH, 0.714 g (10.5 mmol) of imidazole and 10 mL of dimethylsulfoxide (DMSO) were stirred under nitrogen at 20 C to 25 C to give a clear solution. To this was added dropwise 1.93 g (10.0 mmol)Bromo octane, reaction 4 ~ 6 h, the reaction into 10 mL of water extracted with chloroform 3 X 10 mL, and then washed with water chloroform layer 4 ~ 5 times, and then dried with anhydrous MgS04, filtered to get the filtrate, Removal of chloroform yielded a pale yellow liquid, 1.58 g of N-octylimidazole, in 87.7% yield. |
85% | With sodium hydroxide; In tetrahydrofuran; water;Reflux; | General procedure: A solution of imidazole 3 (30 mmol) in THF (60 mL) was treated with NaOH (25 mL, 40% aq) and the alkyl bromide (30 mmol), and the reaction was refluxed overnight. The solvent was evaporated and the crude reaction mixture was extracted with CH2Cl2 against water. The organic layer was washed with water, dried over MgSO4 and concentrated. The final product was distilled under vacuum (~5 mbar) to provide 4 as yellow oily liquid in 80-85% yield. |
82.3% | General procedure: A mixture of imidazole (30 mmol, 2.04 g), potassiumhydroxide (30 mmol, 1.68 g) and dimethyl sulfoxide(10 mL) was stirred for 2 h at room temperature. Afterthat, alkyl bromide (25.0 mmol of 1-bromohexane, 1-bromooctane,1-bromodecane, 1-bromododecane, 1-bromotetradecane,1-bromohexadecane, or 1-bromooctadecane)was dropped in slowly and the mixture was stirred for anadditional 4 h. Upon completion, water (30 mL) was addedto the resulting mixture followed by extraction with chloroform(5 x 30 mL). The combined organic layer wasdried over anhydrous magnesium sulfate and the filtratewas concentrated under reduced pressure. The residue wassubjected to flash chromatography with ethyl acetate aseluent to give N-alkyl imidazole. The respective yields ofN-hexyl imidazole, N-octyl imidazole, N-decyl imidazole,N-dodecyl imidazole, N-tetradecyl imidazole, N-hexadecylimidazole and N-octadecyl imidazole are 84.6, 82.3, 81.2,80.5, 80.4, 79.8 and 79.6 %. | |
60% | Imidazole (3.41 g, 50 mmol) and NaH (1.34 g, 54 mmol) were dissolved in THF (10 mL) under N2 in an ice bath for 45 min, followed by addition of 1-bromooctane (9.65 g, 50 mmol). The solution was stirred for 24 h at room temperature and then concentrated under reduced pressure after filtration.The residue was purified by flash chromatography (SiO2; petroleum ether/ethyl acetate5 : 1 as eluent) to give 1 as alight yellow oil (5.97 g, 60 %). deltaH (CDCl3, 400 MHz) 7.42 (1H, s), 7.01 (1H, s), 6.87 (1H, s), 3.89 (2H, t, J 8.0), 1.76-1.73 (2H, m), 1.31-1.25 (10H, m), 0.87 (3H, t, J 7.2). deltaC (CDCl3, 100 MHz) 136.2, 128.4, 118.1, 46.4, 31.2, 30.6, 28.6, 28.5,26.0, 22.1, 13.6. m/z (ESI) 181 ([M + H]+). m/z 181.1708. HRMS (ESI) Anal. Calc. for C11H21N2 ([M + H]+) 181.1705. | |
General procedure: These compoundswere obtained fromthe reaction of the sodium salt of imidazole and 1-bromoalkanes, as follows: to a 3-necked round-bottom flask, provided with a reflux condenser, dropping funnel, and inlet for dry nitrogen was added a solution of imidazole (7.49 g; 0.11 mol) in dry ethanol (25 mL). Small pieces of sodium (2.53 g, 0.11 mol), were slowly introduced, the mixture was vigorously stirred until the metal has dissolved and then heated under reflux for 2 h. The mixture was cooled to room temperature; the appropriate 1-bromoalkane (0.10 mol; 16.50 g, 17.91 g, 19.31 g, 22.12 g for R ¼ C6; C7; C8 and C10, respectively)was added slowly (ca. 30 min); then the mixture was refluxed for 2 h. The mixture was cooled to room temperature, the precipitated NaBr was filtered off; the ethanol evaporated, the residual oilwas washed with water, and then dried with anhydrous MgSO4. The N-(1-alkyl)imidazoles were purified by fractional distillation (yields before distillation ca. 98%); their purity was confirmed with 1H NMR spectroscopy (results not shown). | ||
General procedure: N-Hexadecylbromide (11.35 g, 37.2 mmol) was dissolved in dimethylformamide (DMF, 50 mL) and then added to a solution of the sodium salt of imidazole, which was formed by the reaction of imidazole (5.0 g, 74 mmol) with sodium hydride (2.66 g, 111 mmol) in DMF (50 mL). The mixture was heated at 60 C for 6 h, cooled, and diluted with water. After extraction with ethyl acetate (EtOAc), the extract was washed with brine and water, and then dried with sodium sulfate. The solvent was separated by reduced pressure distillation and N-alkylimidazole was obtained as a pale yellow oily product. | ||
With potassium hydroxide; In acetonitrile; for 4h;Reflux; | General procedure: N-Butylimidazole and N-octylimidazole were synthesized fol-lowing the procedure of literature [44]: To a round-bottomedflask, imidazole (6.0 g, 88 mmol), 1-bromobutane/1-bromooctane(90 mmol), acetonitrile (50 mL) and potassium hydroxide (9.9 g,177 mmol), were added in sequence. The reaction mixture wasrefluxed for 4 h and then cooled down to room temperature. Afterevaporating the solvent, the residue was purified by a flash col-umn chromatography utilizing ethyl acetate/methanol (v/v = 25:1)as eluent. The pure product of 1-butylimidazole/1-octylimidazolewas isolated as a pale yellow oil (?83%). N-Octylimidazole:1H NMR: (CDCl3): (ppm) = 0.87 (t, J = 6.5 Hz,3H, CH3), 1.28 (br, 10H, CH2), 1.77 (br, 2H, CH2), 3.92 (t, J = 7.2 Hz,2H, CH2), 6.90 (s, 1H, ImH), 7.04 (s, 1H, ImH), 7.45 (s, 1H, ImH).13CNMR (CDCl3): (ppm) = 13.9, 22.5, 26.4, 28.9, 29.0, 31.0, 31.6, 46.9,118.7, 129.2, 136.9. | |
With sodium hydroxide; In acetone; at 20℃; for 12h; | N-alkylimidazoles were synthesized using a previously reported method with minor modification. Typically, to a solution of imidazole (1 mol equiv.) and sodium hydroxide (1 mol equiv.) in acetone (50 mE) was added 1 -bromoalkane (0.8 mol equiv.). After stirring at room temperature for 12 h, a Nal3r precipitate was filtered and acetone removed under reduced pressure. A residual oily mass was re-dissolved in dichloromethane and extracted three times with water. Finally, an organic phase was dried on anhydrous sodium sulfate and dicholoromethane was removed under reduced pressure to produce brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]3-n-octylimidazolium bromide; mp. 141.5°-143° C., from 1-[2,4dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and n-octyl bromide after an overnight reflux. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Compound 11(1 mE, 7.7 mmol, 1 eq.) was added in dry THF (20 mE), cooled to 00 C., then added NaH (203 mg, 8.5 mmol, 1.1 eq.), stirred for 5 minutes, added n-butyllithium (5.3 mE, 8.5 mmol, 1.6M, 1.1 eq.). Stirred for another 5 minutes, bromide (1.3 mE, 7.7 mmol, 1 eq.) was added and stirred at 00 C. for 12 h monitored by TEC. The reaction mixture turned into a yellow milky liquid. Afier full completion, the reaction was quenched with water (10 mE) and extracted three times with ethyl acetate (10 mE). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and purified by a flash chromatography on silica gel to give compound 12-1 (yellow oil, 647 mg, 34%). ?H NMR (300 MHz, CDC13) oe 4.19 (q, J=15 Hz, 2H), 3.42 (s, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.28 (m, 14H), 0.87 (t, J=6.3 Hz, 3H). ?H NMR (300 MHz, DMSO) oe 12.53 (s, 1H), 3.43 (s, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.23 (m, 14H), 0.85 (t, J=6.3 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23%; 22% | General procedure: To L1 (2.00 g, 13.6 mmol) dissolved in acetonitrile (60 mL) was added potassium carbonate (18.8 g, 136 mmol). The resulting solution was refluxed for 30 min and to the hot solution was added Br(CH2)nCH3 (48.0 mmol, n=3, 5 or 7). The reaction mixture was then stirred at reflux temperature for a further 24 h. After cooling, the inorganic solids were removed by filtration and the solvent was removed under reduced pressure to afford an oil, which was purified by column chromatography on silica gel (initially at a ratio of petroleum ether: ethyl acetate 80:20, followed by the ratio of 60:40). This gave the products L4A-C and L5A-C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24h;Inert atmosphere; | The reaction was performed under nitrogen. 1 (1.64 g, 6.9 mmol) and K2CO3 (anhydrous; 1.21 g, 8.8 mmol, excess) were suspended in anhydrous DMF (5 mL) at room temperature. 1-Octylbromide was added (1.25 mL, 1.39 g, 7.2 mmol, small excess). The mixture was stirred at 60 C (bath temperature) for 24 h. It was extracted with water/hexane. The organic layer was washed with water to remove DMF. It was evaporated to provide the pure product. Colorless oil: 2.47 g (7.0 mmol; 100%; C19H29NO5; MW 351.44). 1H NMR (400 MHz, CDCl3): delta = 7.77 (s, 2H), 4.47 (q, J = 7.2 Hz, 4H), 4.13 (t, J = 6.8 Hz, 2H), 1.88-1.79 (m, 2H), 1.45 (t, J = 7.2 Hz, 6H), 1.51-1.24 (m, 10H), 0.89 (t, J = 6.4 Hz, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; [2,2]bipyridinyl; sodium iodide; zinc; at 60℃;Schlenk technique; Inert atmosphere; | General procedure: An oven-dried Schlenk tube was charged with 2,2?-bipyridyl (0.05mmol), Ni(COD)2 (0.05mmol), and DMPU (2.0ml) under nitrogen and capped with a rubber septum. The mixture was stirred at 60C for 2h, and then aryl bromide (0.5mmol), activated zinc dust (1.0mmol), sodium iodide (0.125mmol), alkyl bromide (0.5mmol), pyridine (0.05mmol), and additives (if applicable) were added. The reaction mixture was stirred at 60C for 2-4 days before work-up. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.3 g | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; | Add 0.8 g of <strong>[5369-19-7]3-tert-butylaniline</strong> to a 100 mL reaction flask.2 mL bromo-n-octane,1.85 g potassium carbonate,8 mL of dimethylformamide,Stir,Heat to 90 ° C reaction,TLC tracking,The developing solvent was: petroleum ether: ethyl acetate = 90:10.After the reaction is completed, it is cooled to room temperature.Pour into 200 mL of clean water,Extracted with ethyl acetate twice,100 mL each time,The ethyl acetate layer was combined, washed with 50 mL of saturated brine, dried over anhydrous sodium sulfate for 30 min, filtered, and the filtrate was evaporated to dryness and purified by silica gel eluting with petroleum ether: ethyl acetate = 95:5. Dry to give product 1.3 g of intermediate I. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 50 mL of DMF solvent, 3 g of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.012 mol) and 4.8 g of potassium hydrogencarbonate (0.048 mol) were added, and stirred at room temperature to form a potassium salt.5.79 g of n-bromooctane (0.03 mol) was added to the mixed solution,The reaction was stirred at 90 C for 12 hours. Stop the reaction and allow the solution to cool to room temperature.It was poured into 300 mL of water and extracted with ethyl acetate.Dry over anhydrous sodium sulfate, filter and spin dry solvent.The crude product was subjected to column chromatography using petroleum ether / ethyl acetate (15/1) as eluent to afford white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 35℃; for 48h;Glovebox; Inert atmosphere; Sealed tube; | General procedure: In an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 1 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2C03 (0.60 mmol, 3.0 equiv.), the appropriate DG-containing arene (like N1-N20, 0.20 mmol, 1.0 equiv.), the appropriate alkyl (pseudo)halide (like X1-X16, 1.0 - 3.0 equiv.) and A/-methyl-2-pyrrolidone (NMP) (0.2 M - 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography. The General Procedure C was applied with Ru9 (10.9 mg, 0.02 mmol, 10 mol %), <strong>[198904-31-3]Atazanavir</strong> N4 (152.3 mg, 0.2 mmol, 1.0 equiv), n-octyl bromide X1 (104 pL, 0.60 mmol, 3.0 equiv) and NMP (1 mL, 0.2 M) for 48 hours. Column chromatography (hexane/EtOAc 1 :1 to EtOAc) afforded A3 as a yellow wax (58.2 mg, 35%). 1H NMR (500 MHz, CDCI3) d 8.60 (dd, J = 5.0, 1 .7 Hz, 1 H), 7.67 (td, J = 7.7, 1 .9 Hz, 1 H), 7.23 (dd, J = 13.4, 7.7 Hz, 2H), 7.18 - 7.10 (m, 7H), 7.08 (td, J = 6.3, 2.5 Hz, 1 H), 6.50 (s, 1 H), 6.38 (s, 1 H), 5.29 (d, J = 9.3 Hz, 1 H), 5.18 (d, J = 8.6 Hz, 1 H), 4.80 (s, 1 H), 3.97 (d, J = 11.7 Hz, 2H), 3.83 (d, J = 13.9 Hz, 1 H), 3.74 (d, J = 8.6 Hz, 1 H), 3.63 - 3.48 (m, 9H), 2.87 (d, J = 7.6 Hz, 2H), 2.80 (t, J = 11 .5 Hz, 1 H), 2.67 - 2.51 (m, 2H), 2.47 (d, J = 12.2 Hz, 1 H), 1.33 (p, J = 7.3 Hz, 2H), 1 .18 - 1.02 (m, 10H), 0.83 (s, 9H), 0.79 (t, J = 7.1 Hz, 3H), 0.74 (s, 9H); 13C NMR (126 MHz, CDCI3) d 170.9, 170.8, 160.0, 157.1 , 157.0, 149.3, 141 .4, 140.2, 138.2, 136.2, 135.3, 130.4, 130.3, 129.5, 128.4, 126.4, 124.1 , 121.8, 67.3, 63.7, 62.8, 61 .6, 61 .3, 52.6, 52.5, 52.3, 38.8, 34.4, 34.1 , 33.1 , 32.0, 31 .5, 29.7, 29.3, 29.3, 26.7, 26.4, 22.8, 14.3, One carbon was not observed; ESI-MS calcd for C46H69N607 [M+H]+: 817.5, found 817.5. |
Tags: 111-83-1 synthesis path| 111-83-1 SDS| 111-83-1 COA| 111-83-1 purity| 111-83-1 application| 111-83-1 NMR| 111-83-1 COA| 111-83-1 structure
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