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Product Details of 1,14-Dibromotetradecane

CAS No. :37688-96-3
Formula : C14H28Br2
M.W : 356.18
SMILES Code : BrCCCCCCCCCCCCCCBr
MDL No. :MFCD00045049
InChI Key :SDENLXLNLFKRAR-UHFFFAOYSA-N
Pubchem ID :169955

Safety of 1,14-Dibromotetradecane

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of 1,14-Dibromotetradecane

* 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.

  • Downstream synthetic route of [ 37688-96-3 ]

[ 37688-96-3 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 19812-64-7 ]
  • [ 37688-96-3 ]
YieldReaction ConditionsOperation 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].
  • 2
  • [ 4549-31-9 ]
  • [ 37688-96-3 ]
  • 3
  • [ 37688-96-3 ]
  • [ 140-89-6 ]
  • tetradecane-1,14-disulfonic acid [ No CAS ]
  • 4
  • 1,13-dimethoxy-tetradecane [ No CAS ]
  • [ 37688-96-3 ]
  • 5
  • [ 37688-96-3 ]
  • [ 611-70-1 ]
  • 2,2,17,17-tetramethyl-octadecanedioic acid diamide [ No CAS ]
  • 6
  • [ 37688-96-3 ]
  • [ 37688-97-4 ]
  • [ 37689-01-3 ]
  • 7
  • [ 37688-96-3 ]
  • [ 34714-42-6 ]
  • N,N,N',N'-Tetramethyl-N,N'-bis-<1-methyl-3-(2,2,6-trimethyl-cyclohexyl)-propyl>-tetradecan-1,14-diammonium [ No CAS ]
  • 8
  • [ 17696-11-6 ]
  • [ 818-88-2 ]
  • [ 37688-96-3 ]
  • [ 106-79-6 ]
  • [ 26825-89-8 ]
  • [ 1472-93-1 ]
  • 9
  • [ 17696-11-6 ]
  • [ 37688-96-3 ]
  • 10
  • [ 37688-96-3 ]
  • [ 105-53-3 ]
  • [ 37689-05-7 ]
  • 11
  • [ 37688-96-3 ]
  • [ 105-53-3 ]
  • [ 37689-03-5 ]
  • 12
  • [ 37688-96-3 ]
  • [ 90-44-8 ]
  • [ 127354-20-5 ]
  • 13
  • [ 37688-96-3 ]
  • [ 83-56-7 ]
  • [ 94427-65-3 ]
  • 14
  • [ 37688-96-3 ]
  • [ 1066-26-8 ]
  • [ 134456-96-5 ]
  • [ 149849-72-9 ]
  • 15
  • [ 37688-96-3 ]
  • [ 1066-26-8 ]
  • [ 88736-96-3 ]
  • [ 149849-71-8 ]
  • 16
  • [ 37688-96-3 ]
  • [ 72224-15-8 ]
  • [ 86955-61-5 ]
  • 17
  • [ 37688-96-3 ]
  • [ 57526-81-5 ]
  • [ 86955-39-7 ]
  • 18
  • [ 37688-96-3 ]
  • 1-(4'-hydroxybiphenyl-4-yl)-2-(4-hydroxyphenyl)butane [ No CAS ]
  • C36H48O2 [ No CAS ]
  • 19
  • [ 534-22-5 ]
  • [ 37688-96-3 ]
  • [ 157131-03-8 ]
  • 20
  • [ 110-52-1 ]
  • [ 17036-36-1 ]
  • [ 37688-96-3 ]
  • 21
  • [ 37688-96-3 ]
  • [ 94605-71-7 ]
  • 7-Benzyl-16-(14-bromo-tetradecyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane [ No CAS ]
YieldReaction ConditionsOperation 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%).
  • 22
  • [ 37688-96-3 ]
  • [ 4346-39-8 ]
  • [ 76734-33-3 ]
  • 23
  • [ 37688-96-3 ]
  • 1,14-bis[5-(4'-hydroxyphenyl)pyrimidin-2-yloxy]-3,6,9,12-tetraoxatetradecane [ No CAS ]
  • 6,9,12,15,18,21,30,45-octaoxa-4,23,54,55-tetraazapentacyclo[44.2.2.22,5.222,25.226,29]hexapentaconta-1(48),2,4,22,24,26,28,46,49,51,53,55-dodecaene [ No CAS ]
  • 24
  • [ 37688-96-3 ]
  • [ 2725-53-3 ]
  • [ 887369-01-9 ]
  • 25
  • [ 37688-96-3 ]
  • [ 5587-42-8 ]
  • 1,14-bis-(1H-imidazol-1-yl)tetradecane [ No CAS ]
  • 26
  • [ 37688-96-3 ]
  • [ 5587-42-8 ]
  • 1,14-bis-(1H-imidazol-1-yl)tetradecane dihydrochloride [ No CAS ]
  • 27
  • [ 2961-50-4 ]
  • [ 37688-96-3 ]
  • 1,14-bis(4’-pentylpyridinium)tetradecane dichloride [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 28
  • [ 37688-96-3 ]
  • [ 1017-60-3 ]
  • [ 464896-28-4 ]
  • 29
  • [ 37688-96-3 ]
  • [ 29949-65-3 ]
  • [ 464896-39-7 ]
  • 30
  • [ 37688-96-3 ]
  • [ 887369-10-0 ]
  • 31
  • [ 37688-96-3 ]
  • [ 887369-07-5 ]
  • 32
  • [ 37688-96-3 ]
  • 5-methyl-2-tetradecylfuran [ No CAS ]
  • 33
  • [ 37688-96-3 ]
  • 5-methyl-2-(tetradec-13-en-1-yl)furan [ No CAS ]
  • 34
  • [ 37688-96-3 ]
  • 5-methyl-2-(14-hydroxytetradecyl)furan [ No CAS ]
  • 35
  • [ 37688-96-3 ]
  • 1,28-bis(2-(5-methylfuranyl))octaeicosane [ No CAS ]
  • 36
  • [ 37688-96-3 ]
  • N-[6-Acetylamino-4-(16-anthracen-9-yl-hexadec-15-ynyloxy)-pyridin-2-yl]-acetamide [ No CAS ]
  • 37
  • [ 37688-96-3 ]
  • [ 94427-68-6 ]
  • 38
  • [ 37688-96-3 ]
  • [ 102885-22-3 ]
  • 39
  • [ 37688-96-3 ]
  • 2,2,17,17-tetramethyl-octadecanedioic acid diethyl ester [ No CAS ]
  • 40
  • [ 37688-96-3 ]
  • [ 139176-07-1 ]
  • 41
  • [ 37688-96-3 ]
  • [ 107-18-6 ]
  • [ 128134-05-4 ]
YieldReaction ConditionsOperation 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 %)
  • 42
  • [ 37688-96-3 ]
  • pyridine-azo-p-dimethyl aniline [ No CAS ]
  • 1,1'-tetradecane-1,14-diylbis(2-{(E)-[4-(dimethylamino)phenyl]diazenyl}pyridinium) dibromide [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 43
  • [ 79-43-6 ]
  • [ 37688-96-3 ]
  • [ 178671-02-8 ]
YieldReaction ConditionsOperation 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.
  • 44
  • [ 6802-75-1 ]
  • [ 37688-96-3 ]
  • [ 7699-41-4 ]
  • [ 103199-02-6 ]
YieldReaction ConditionsOperation 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 <strong>[37688-96-3]1,14-dibromotetradecane</strong> 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 diethyl isopropylidenemalonate 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).
  • 45
  • [ 19812-64-7 ]
  • [ 72995-94-9 ]
  • [ 37688-96-3 ]
  • 46
  • [ 21964-49-8 ]
  • [ 37688-96-3 ]
  • 47
  • [ 571-60-8 ]
  • [ 37688-96-3 ]
  • [ 1356382-69-8 ]
YieldReaction ConditionsOperation 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.
  • 48
  • [ 37688-96-3 ]
  • [ 1356382-79-0 ]
  • 49
  • [ 37688-96-3 ]
  • 18,21-bis(trimethylsilyl)-1,16-dioxa[16]paracyclophane [ No CAS ]
  • 50
  • [ 37688-96-3 ]
  • [ 1356391-35-9 ]
  • 51
  • [ 37688-96-3 ]
  • [ 123-31-9 ]
  • [ 1356382-72-3 ]
YieldReaction ConditionsOperation 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.
  • 52
  • [ 37688-96-3 ]
  • [ 1355150-14-9 ]
  • 53
  • [ 37688-96-3 ]
  • [ 1355150-17-2 ]
  • 54
  • [ 37688-96-3 ]
  • [ 1355150-20-7 ]
 

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