Structure of 58929-72-9
*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'.
CAS No. : | 58929-72-9 |
Formula : | C6H12Br2O |
M.W : | 259.97 |
SMILES Code : | BrCCCOCCCBr |
MDL No. : | MFCD22200244 |
InChI Key : | GOKUDEWVRNZXDZ-UHFFFAOYSA-N |
Pubchem ID : | 11230705 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
55% | With phosphorus tribromide; at 20℃;Heating / reflux;Product distribution / selectivity; | 6.2 EXAMPLES OF ILLUSTRATIVE COMPOUNDS OF THE INVENTION; Bis (3-bromopropyl) ether (104).; Under N2-atmosphere, phosphorus tribromide (7.2 mL, 20.5 g, 75.8 mmol) was added dropwise over 1 h to 103 (Buchanan, G. W. et al. Can. J Chem. 2000, 78, 316-321) (10.14 g, 75.6 mmol), causing self-heating to reflux. The reaction mixture was stirred overnight at room temperature, then distilled in vacuo to give an oil. This oil was dissolved in CH2C12 (100 mL), washed with water (100 mL), dried over Na2SO4, and concentrated in vacuo, affording 104 (10.9 g, 55 %) as a clear, colorless oil. Bp 68-70 C/0. 2 mmHg. 1H NMR (CDC13) : No. 3.56 (t, 4 H, J= 5.8), 3.51 (t, 4 H, J= 6.4), 2.10 (m, 4 H). 13C NMR (CDC13 = 77. 00 ppm) : 6 68. 17,32. 68,30. 59. |
34% | With phosphorus tribromide; at 20 - 90℃; | To a flask containing compound 2 (11 g, 82.0 mmol), PBr3 (55 mL) was added slowly drop wise and the mixture stirred for 0.5 hours at ambient temperature followed by heating to 900C. After being stirred for 3 hours at this temperature the reaction mixture was quenched with ice (500 g) slowly, stirred continuously for 10 minutes and extracted with CH2Cl2 (2 X 700 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give compound 3 as a pale yellow liquid (7.24 g). Yield: 34%. 1HNMR (400 MHz, CDCl3): δ (ppm): 3.70-3.55 (t, 4H), 3.60-3.35 (t, 4H), 2.15-1.95 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With potassium carbonate; In N-methyl-acetamide; acetone; | EXAMPLE 56 Preparation of [4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester A mixture of 2.5 g (0.0089 mole) of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester, 11.6 g (0.045 mole) of 3,3'-dibromodipropyl ether, 1.0 g (0.0072 mole) of potassium carbonate in 50 ml of anhydrous acetone and 25 ml of anhydrous dimethylformamide was stirred at reflux for 66 hours. Additional 1.0 g portions of potassium carbonate were added after 6,18,26 and 42 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield an oil which was chromatographed on 125 g of silica gel. Elution with 10% ethyl acetate-toluene gave 1.9 g (47% yield) of [4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium carbonate; In N-methyl-acetamide; acetone; | EXAMPLE 59 Preparation of 4-[4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester A mixture of 2.5 g (0.008 mole) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, 10.6 g (0.041 mole) of 3,3'-dibromodipropyl ether and 1.0 g (0.0072 mole) of potassium carbonate in 50 ml of anhydrous acetone and 25 ml of anhydrous dimethylformamide was stirred at reflux for 66 hours. Additional 1.0 g portions of potassium carbonate were added at 6, 18, 26 and 42 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield an oil which was chromatographed on 150 g of silica gel. Elution with 7% ethyl acetate-toluene gave 2.16 g (55% yield) of 4-[4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; concd HCl; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; | 5-(4-Ethoxycarbonyl-4-methylpentyloxy)-2,2-dimethylpentanoic acid ethyl ester (106). Under nitrogen atmosphere and at -78 C., to a stirred solution of ethyl isobutyrate (6.5 g, 55.9 mmol) in anhydrous THF (30 mL) was added dropwise a solution of lithium diisopropylamide (30 mL, 60.0 mmol, 2.0 M in heptane/THF/ethylbenzene). After 1 h, a solution of 104 (Kamm, O. et al. J. Am. Chem. Soc. 1921, 43, 2228-2230) (6.76 g, 26.0 mmol) and DMPU (2 mL) in THF (15 mL) was added dropwise and the reaction temperature was kept at -78 C. for additional 30 min. The reaction mixture was allowed to warn to room temperature and stirred overnight, then quenched with a mixture of ice (10 g) and concd HCl (10 mL). The product was extracted with diethyl ether (2*30 mL). The combined ether phases were washed with 5% NaHCO3 solution (30 mL), dried over MgSO4, and concentrated in vacuo to furnish the crude product (10.9 g), which was distilled in high vacuo to give pure 106 (5.96 g, 69%) as an oil. Bp 115-120 C./0.5 mmHg. 1H NMR (CDCl3): δ 4.11 (q, 4H, J=7.0), 3.37 (m, 4H), 1.62-1.43 (m, 8H), 1.25 (t, 4H, J=7.0), 1.17 (s, 12H). 13C NMR (CDCl3=77.00 ppm): δ 177.62, 70.85, 60.06, 41.75, 36.89, 25.14, 24.96, 14.09. |
69% | 5- (4-Ethoxycarbonyl-4-methylpentyloxy)-2, 2-dimethylpentanoic acid ethyl ester (106).; Under nitrogen atmosphere and at-78 C, to a stirred solution of ethyl isobutyrate (6.5 g, 55.9 mmol) in anhydrous THF (30 mL) was added dropwise a solution of lithium diisopropylamide (30 mL, 60.0 mmol, 2.0 M in heptane/THF/ethylbenzene). After 1 h, a solution of 104 (Kamm, O. et al. J. Am. Chem. Soc. 1921, 43, 2228-2230) (6.76 g, 26.0 mmol) and DMPU (2 mL) in THF (15 mL) was added dropwise and the reaction temperature was kept at-78 C for additional 30 min. The reaction mixture was allowed to warm to room temperature and stirred overnight, then quenched with a mixture of ice (10 g) and concd HCl (10 mL). The product was extracted with diethyl ether (2 x 30 mL). The combined ether phases were washed with 5 % NaHC03 solution (30 mL), dried over M 4S encEnthatYeivacuo to furnish the crude product (10. Y g), which was distilled in high vacuo to give pure 106 (5.96 g, 69 %) as an oil. Bp 115-120 C/0. 5 mmHg. lH NMR (CDCl3) : 8 4.11 (q, 4 H, J= 7. 0j, 3.37 (m, 4 H), 1. 62-1.43 (m, 8 H), 1.25 (t, 4 H, J= 7.0), 1.17 (s, 12 H). 13C NMR (CDC13 = 77.00 ppm): 5 177.62, 70.85, 60.06, 41.75, 36. 89, 25. 14, 24.96, 14.09. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | 5- (4-Ethoxycarbonyl-4-phenylpentyloxy)-2-methyl-2-phenylpentanoic acid ethyl ester (107).; Under Na-atmosphere, to a stirred solution of 2-phenylpropionic acid ethyl ester (Dasseux, J. -L. H. et al. US 20030078239,2003 ; US Pat. Appl. 09/976,938, filed October 11, 2001) (13.2 g, 74.1 mmol) in anhydrous THF (50 mL) was added dropwise a solution of lithium diisopropylamide (39 mL, 78. 0 mmol, 2.0 M in heptane/THF/ethylbenzene) at- 78 C. After 1 h, DMPU (3 mL) was added, followed by the dropwise addition of a solution of 104 (9.2 g, 35.4 mmol) in THF (20 mL). After 30 min at-78 C, the reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into a mixture of ice (30 g) and concd HCl (20 mL) and the product was extracted with diethyl ether (4 x 75 mL). The combined ether solutions were washed with 5 % NaHC03 solution (50 mL), and brine (50 mL), dried over MgS04, and concentrated in vacuo to furnish the crude product (18.9 g) as a brown oil. Purification by column chromatography (silica; hexanes/ethyl acetate = 10/1) gave 7 (4.3 g, 27 %) as a yellow oil. 'H NMR (CDC13) : 8 7.45-7. 10 (m, 10 H), 4.11 (q, 4 H, J = 7.2), 3.45-3. 25 (m, 4 H), . 2. 15-1.85 (m, 4 H), 1.54 (s, 6 H), 1.50-1. 35 (m, 4 H), 1.17 (t, 6 H, J= 7. 2). 13C NMR (CDCl3 = 77.00 ppm): 8 176.00, 143.71, 128.23, 126.50, 125.90, 70.89, 60.66, 49.86, 35.66, 25.08, 22.66, 14.02. HRMS (LSIMS, nba): Calcd for C28H390s (ME+) : 455.2797, found : 455.2796. | |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; concd HCl; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; | 5-(4-Ethoxycarbonyl-4-phenylpentyloxy)-2-methyl-2-phenylpentanoic acid ethyl ester (107). Under N2-atmosphere, to a stirred solution of 2-phenylpropionic acid ethyl ester (Dasseux, J.-L. H. et al. US 20030078239, 2003; U.S. patent application Ser. No. 09/976,938, filed Oct. 11, 2001) (13.2 g, 74.1 mmol) in anhydrous THF (50 mL) was added dropwise a solution of lithium diisopropylamide (39 mL, 78.0 mmol, 2.0 M in heptane/THF/ethylbenzene) at -78 C. After 1 h, DMPU (3 mL) was added, followed by the dropwise addition of a solution of 104 (9.2 g, 35.4 mmol) in THF (20 mL). After 30 min at -78 C., the reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into a mixture of ice (30 g) and concd HCl (20 mL) and the product was extracted with diethyl ether (4*75 mL). The combined ether solutions were washed with 5% NaHCO3 solution (50 mL), and brine (50 mL), dried over MgSO4, and concentrated in vacuo to furnish the crude product (18.9 g) as a brown oil. Purification by column chromatography (silica; hexanes/ethyl acetate=10/1) gave 7 (4.3 g, 27%) as a yellow oil. 1H NMR (CDCl3): δ 7.45-7.10 (m, 10H), 4.11 (q, 4H, J=7.2), 3.45-3.25 (m, 4H), 2.15-1.85 (m, 4H), 1.54 (s, 6H), 1.50-1.35 (m, 4H), 1.17 (t, 6H, J=7.2). 13C NMR (CDCl3=77.00 ppm): δ 176.00, 143.71, 128.23, 126.50, 125.90, 70.89, 60.66, 49.86, 35.66, 25.08, 22.66, 14.02. HRMS (LSIMS, nba): Calcd for C28H39O5 (MH+): 455.2797, found: 455.2796. |