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CAS No. : | 37688-96-3 | MDL No. : | MFCD00045049 |
Formula : | C14H28Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SDENLXLNLFKRAR-UHFFFAOYSA-N |
M.W : | 356.18 | Pubchem ID : | 169955 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogen bromide; acetic anhydride; at 0℃; for 24h;Reflux; | Aq HBr (48%, 7 mL, 42 mmol) was added dropwise to Ac2O (12mL, 126 mmol) at 0 C. To this solution, HO(CH2)14OH (0.44 g, 1.9mmol) was added and the mixture was brought to reflux for 24 h. After the mixture had cooled to r.t., the dihalide was extracted with hexanes and was then washed with excess H2O to remove the remaining AcOH, leaving an off-white solid; yield: 0.65 g (95%). The spectroscopic properties were identical to those previously published. |
85% | With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; for 16h;Schlenk technique; Inert atmosphere; | A Schlenk flask was charged with 7 (5.00 g, 21.70 mmol),CBr4 (21.59 g, 65.10 mmol), and THF (250 mL). Then PPh3 (17.80 g, 65.10 mmol) was addedin portions with stirring. After 16 h, water (200 mL) was added and the aqueous phase extractedwith CH2Cl2 (3 × 200 mL). The combined organic layers were dried (MgSO4) and filtered. Thesolvents were removed by rotary evaporation. Hexanes (500 mL) were added to the brown residue,and the precipitate (O=PPh3) removed by filtration. The solvent was removed from the filtrateby rotary evaporation and the residue chromatographed (SiO2 column, 4 cm × 30 cm, hexanes).The solvent was removed from the product containing fractions to give 8 (6.57 g, 18.45mmol, 85%) as a white powder, mp 51 C; lit: 47.5-48.0 C [S5]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 24h;Inert atmosphere; Reflux; | General procedure: A mixture of 1,8-dibromooctane (0.63 mL, 3.4 mmol), N-benzyl-4,13-diaza-18-crown-6 (3; 1.09 g, 1.3 mmol), and DIPEA (0.86 mL,4.6 mmol) was heated to reflux for 24 h in MeCN (30 mL) under argon.The solvent was evaporated. The remaining oil was redissolved in CH2Cl2 (60 mL), the solution was washed with H2O (3 ×10 mL) and dried (MgSO4), and then chromatography followed (silicagel, MeOH-CHCl3, 0:100 to 25:75) to afford a yellow oil; yield:0.64 g (38%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | 1,14-Dibromotetradecane (0.50 g, 1.40 mmol) was dissolved in 4-methyl-2- pentanone (2.0 ml) and 4-pentylpyridine (0.52 g, 3.50 mmol) was added. The mixture was stirred at reflux for 18 h under a nitrogen atmosphere, and the solvent was removed under reduced pressure. The residue was then diluted with H2O (~ 15 ml) and washed with dry Et2O (3 x 20 ml). The aqueous layer was extracted with CH2Cl2 (3 x 20 ml), then the CH2Cl2 layer was concentrated under reduced pressure. The residue was purified by Al2O3 chromatography (neutral, activity II-III), using gradient elution (starting with CHCl3/MeOH = 2% to 10 %). The combined fractions were then passed down a column of Lewatit MP-64 anion resin (Cl"), eluting with EtOH. The resulting fractions were combined and the solvent removed under reduced pressure to give the above compound as a light brown waxy oil (0.67 g, 85 %). 1H NMR (300 MHz, J4-MeOD): δ 8.94 (4H, d, J = 6.5 Hz, CH(2',6')), 8.02 (4H, d, J = 6.5 Hz, CH(3',5')), 4.65 (4H, t, J = 7.5 Hz, CH2(I)), 3.02 (4H, t, J= 7.5 Hz, CH2(I")), 2.07 (4H, m, CH2(2)), 1.82 (4H, m, CH2(2")), 1.42 (28H, m, CH2(3,4,5,6,7,3",4")), 0.98 (6H, m, CH3(5")). 13C NMR (300 MHz, J4- MeOD): 164.2, 144.1, 128.5, 61.2, 35.6, 31.6, 31.5, 29.8, 29.7, 29.6, 29.2, 26.2, 22.5, <n="40"/>13.6, 1 signal obscured or overlapping. MS: m/z ESI (positive ion) 233 [M-2C1"]2+ (100 %), 465 [M-2Cr-H+]+ (100) Found [M-2Cr]2+ 233.2136, [C16H27N]2+ requires 233.2138. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 11.(1) Synthesis of 14-bromotetradecyl allyl ether The procedure in 4.(1) in Example 4 was repeated with the exception that 2.0 g of allyl alcohol, 1.7 g of 60 % sodium hydride, and 30 g of <strong>[37688-96-3]1,14-dibromotetradecane</strong> were used, to obtain 7.9 g of the objective ω -haloalkyl allyl ether. (Yield: 69 %) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 110℃; for 6h; | In a three-necked flask with a top-mounted condenser compound 1 (4.5 g) was stirred in the presence of 3.56 g of <strong>[37688-96-3]1,14-dibromotetradecane</strong> in 50 ml of DMF at 110 C. for 6 hours. Following the reaction, the reaction mixture was cooled to ambient temperature and then poured into diisopropyl ether (500 ml). The precipitate obtained was filtered off and then washed a number of times with diisopropyl ether and then with ethyl acetate, and finally was dried under vacuum. The residue obtained was purified by chromatography. 3.16 g of a dark violet powder were obtained, corresponding to compound 11. The analyses were in accordance with the expected product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.58 g (23%) | Example 4 16-Bromo-2,2-dichlorohexadecanoic acid (4) Analogously to example 1 from 2.0 g (5.6 mmol) <strong>[37688-96-3]1,14-dibromotetradecane</strong> and 2.3 g (22.5 mmol) dichloroacetic acid. Yield 0.58 g (23%), melting point 61-63 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | copper(l) chloride; In tetrahydrofuran; petrol ether; benzene; | EXAMPLE 20 1,1,18,18-tetra(carboethoxy)-2,2,17,17-tetramethyloctadecane The procedure of Example 1 was followed except that the bis-Grignard reagent was prepared from 3.0 g of 1,14-dibromotetradecane and 0.75 g of Mg turnings in 40 ml of dry THF. The bis-Grignard reagent was then added dropwise to a stirred suspension of 0.031 g CuCl and 3.72 g of <strong>[6802-75-1]diethyl isopropylidenemalonate</strong> in 15 ml of dry THF. The addition product was protonated and extracted into ether as in Example 1 followed by silicic acid (400 mesh) chromatography in benzene:petrol ether 1:2.5 to yield the title compound. 86% yield. NMR (CDCl3): 4.3 (q, 8H); 3.5 (s, 2H); 1.5 (m, 40H); 1.1 (m, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;Inert atmosphere; | General procedure: Hydroquinone or 1,4-dihydroxynaphthalene (5.0 mmol) and the corresponding dibromide (5.0 mmol) in dehydrated DMF (30 mL) were added dropwise over 12 h to a suspension of K2CO3 (12.5 mmol) in dehydrated DMF (50 mL) at 140 C. The reaction mixture was cooled to rt and filtered with Celite. The filtrate was treated with saturated NH4Cl aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and brine. The extract was dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a short plug of silica gel with dichloromethane and the filtrate was evaporated under reduced pressure. The crude products were purified by flash column chromatography (hexane/AcOEt=30/1∼20/1) and GPC (1,2-dichloroethane) to give dioxaparacyclophanes 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 12h;Inert atmosphere; | General procedure: Hydroquinone or 1,4-dihydroxynaphthalene (5.0 mmol) and the corresponding dibromide (5.0 mmol) in dehydrated DMF (30 mL) were added dropwise over 12 h to a suspension of K2CO3 (12.5 mmol) in dehydrated DMF (50 mL) at 140 C. The reaction mixture was cooled to rt and filtered with Celite. The filtrate was treated with saturated NH4Cl aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and brine. The extract was dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a short plug of silica gel with dichloromethane and the filtrate was evaporated under reduced pressure. The crude products were purified by flash column chromatography (hexane/AcOEt=30/1∼20/1) and GPC (1,2-dichloroethane) to give dioxaparacyclophanes 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Example 13: Process for the preparation of 2,2,17,17-Tetramethyl(D12)- octadecanedioic acid (compound 8) A 250-mL round bottom flask was equipped with a large magnetic stir bar, an internal temperature probe, and a nitrogen line. The apparatus was flushed thoroughly with nitrogen. Into the flask, lithium diisopropylamide solution (2.0M in heptanes/THF/ethylbenzene from Aldrich; 57 mL, 114 mmol) and anhydrous THF (46 mL) were charged. The solution was cooled to 0-5 C with stirring. 85% Isobutyric acid (ISOPROPYL-D7; contains 15wt% ethyl ether; 6.3 g; 56.3 mmol) was added dropwise. The reaction was stirred for 5 min, the cold bath was removed, and the reaction was stirred an additional 1.5h. The reaction was cooled to 0-5C. A solution of <strong>[37688-96-3]1,14-dibromotetradecane</strong> (7.4 g, 20.8 mmol) in anhydrous THF (15 mL) was added rapidly, and the reaction was stirred for 5 min. The cooling bath was removed, and the reaction was stirred at room temperature (15-20C) for 15-18 h. The disappearance of <strong>[37688-96-3]1,14-dibromotetradecane</strong> was confirmed by silica gel TLC (100% hexanes eluent; KMn04(aq) visualization). The reaction was cooled to 0C. 12% HCl(aq) (65 mL) was added slowly with swirling. Toluene (65 mL) was added, and the mixture was swirled until all solids had dissolved. The phases were separated using a separatory funnel. The aqueous layer was extracted twice with toluene (30 mL each). The organic layers were combined and were diluted to -300 mL with toluene. The organic solution was washed with deionized water (100 mL), washed with saturated NaCl(aq) (100 mL), dried with MgS04(s), filtered and concentrated in vacuo to a solid (7.9 g). The solid was taken up in hexanes (55 mL) and heated to 60C to dissolve. The solution was stirred and allowed to cool slowly to room temperature. The resulting slurry was stirred for 2 h and then allowed to stand overnight. The slurry was filtered, and the solids were washed with hexanes (20 niL). The solid was air-dried to obtain an off white solid (6.4 g, 80% yield; impure compound 8 (D12) by HPLC analysis). The solid was dissolved in EtOH (33 mL) with warming to 40-45 C. With stirring, deionized water (33 mL) was added portionwise. The heating bath was removed, and the resulting slurry was stirred for 6h. The slurry was filtered, and the solids were washed with 50% EtOH(aq) (25 mL). The solids were dried in vacuo at 40C for 16h to obtain compound 8 (D12) (6.2 g, 78% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; at 120℃; for 0.333333h;Alkaline conditions; Microwave irradiation; | General procedure: All compounds were prepared according to previously described procedures [16,17]. Briefly, a phenol derivative (0.015 mol) and a dibromoalkane (0.0075 mol) were dissolved in a mixture of ethanol and water (9/1) containing an alkaline hydroxide (0.015 mol). The mixture was heated under microwave irradiation in an Initiator Biotage oven for 20 min at 120 C. After cooling, the precipitate was filtered and thoroughly washed with water, ethanol and ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With sodium hydrogencarbonate; In acetonitrile; at 90℃; for 528h;Inert atmosphere; | General procedure: A Kimax tube was charged with an equimolar quantity of benzoic acid 33-37 (1.3mmol, 1 equiv.), sodium bicarbonate (1.3mmol, 1 equiv), and the dibromoalkane (1.3mmol, 1 equiv.) in anhydrous acetonitrile or DMF (10mL). The tube was flushed with argon, stopped, and the reaction mixture was stirred at 65C or 90C for the time indicated in each case. The solvent was evaporated under vacuum to give a crude solid residue. The different products were isolated by silica chromatography (5g SI prepacked column) using hexane/EtOAc (100/0?50/50) as eluent. The structure of the obtained isomer (i.e. the benzoate product and not the 4-alkyloxy-substituted benzoic acid isomer) was checked by 1H-13C HMBC and NOESY experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26%; 5% | With sodium hydrogencarbonate; In acetonitrile; at 90℃; for 48h;Inert atmosphere; | General procedure: A Kimax tube was charged with an equimolar quantity of benzoic acid 33-37 (1.3mmol, 1 equiv.), sodium bicarbonate (1.3mmol, 1 equiv), and the dibromoalkane (1.3mmol, 1 equiv.) in anhydrous acetonitrile or DMF (10mL). The tube was flushed with argon, stopped, and the reaction mixture was stirred at 65C or 90C for the time indicated in each case. The solvent was evaporated under vacuum to give a crude solid residue. The different products were isolated by silica chromatography (5g SI prepacked column) using hexane/EtOAc (100/0→50/50) as eluent. The structure of the obtained isomer (i.e. the benzoate product and not the 4-alkyloxy-substituted benzoic acid isomer) was checked by 1H-13C HMBC and NOESY experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.6%; 6%; 7% | With sodium hydrogencarbonate; at 65℃; for 68h;Inert atmosphere; | General procedure: A Kimax tube was charged with an equimolar quantity of benzoic acid 33?37 (1.3mmol, 1 equiv.), sodium bicarbonate (1.3mmol, 1 equiv), and the dibromoalkane (1.3mmol, 1 equiv.) in anhydrous acetonitrile or DMF (10mL). The tube was flushed with argon, stopped, and the reaction mixture was stirred at 65°C or 90°C for the time indicated in each case. The solvent was evaporated under vacuum to give a crude solid residue. The different products were isolated by silica chromatography (5g SI prepacked column) using hexane/EtOAc (100/0?50/50) as eluent. The structure of the obtained isomer (i.e. the benzoate product and not the 4-alkyloxy-substituted benzoic acid isomer) was checked by 1H?13C HMBC and NOESY experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9%; 4%; 3% | With sodium hydrogencarbonate; at 65℃; for 24h;Inert atmosphere; | General procedure: A Kimax tube was charged with an equimolar quantity of benzoic acid 33-37 (1.3mmol, 1 equiv.), sodium bicarbonate (1.3mmol, 1 equiv), and the dibromoalkane (1.3mmol, 1 equiv.) in anhydrous acetonitrile or DMF (10mL). The tube was flushed with argon, stopped, and the reaction mixture was stirred at 65C or 90C for the time indicated in each case. The solvent was evaporated under vacuum to give a crude solid residue. The different products were isolated by silica chromatography (5g SI prepacked column) using hexane/EtOAc (100/0→50/50) as eluent. The structure of the obtained isomer (i.e. the benzoate product and not the 4-alkyloxy-substituted benzoic acid isomer) was checked by 1H-13C HMBC and NOESY experiments. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 150℃;Schlenk technique; Inert atmosphere; | A Schlenk flask was charged withP(OEt)3 (5.83 g, 35.10 mmol) and 8 (5.00 g, (14.04 mmol), and fitted with a distillation head. The mixture was stirred at 150 C overnight, and monitored by TLC (hexanes). In cases where 8was not completely consumed, an additional portion of P(OEt)3 was added and stirring continueduntil full conversion. Excess P(OEt)3 was removed by distillation under oil pump vacuum. Aftercooling, 9 (6.33 g, 13.45 mmol, 96%) was obtained as a colorless liquid. Anal. calcd (%) forC22H48O6P2 (470.56): C 56.15, H 10.28; found C 56.28, H 9.98. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 20 - 80℃; for 40h; | (1) C. 1mol C. The 2202g mol of hydroquinone was dissolved in, ml of solvent ethanol to 80 C, C. 40min, and then cooled to room temperature, and cooled to room temperature 0.5mol and then cooled to room temperature and cooled to room temperature for 1,14- hours to remove solvent ethanol, and then extracted 80 C, with, ethyl ether to give organic layer 500rpm, i.e. intermediate 40h, was 660.6g added, dropwise 880.8g to distillation flask at, a temperature of, C. during, hours of reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium azide; In N,N-dimethyl-formamide; at 90℃; for 24h; | To a solution of compound 78 (500 mg, 1.40 mmol, 1.0 eq) in DMF (20 mL) was added NaN (274 mg, 4.21 mmol, 3.0 eq). The resulting mixture was stirred at 90 C for 24 h and was quenched with cold H2O (40 mL). The water layer was then extracted with EtOAc (2 x 50 mL). The organic layers were finally combined, washed with water, brine, and dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane /Ethyl acetate 20: 1 to 1 :4) to afford product 79 (339 mg, 86%). NMR (400 MHz, CDCb) d 3.26 (t, J = 7.2 Hz, 4H), 1.62-1.56 (m, 4H), 1.38-1.27 (m, 20H). |
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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.
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