1,14-Dibromotetradecane | Aliphatic Linkers

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Quality Control of 1,14-Dibromotetradecane Purity: 98% SDS Specification

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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 1~35

1
[ 19812-64-7 ]
[ 37688-96-3 ]

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].

References: [1]Synthesis,2014,vol. 46,p. 2771 - 2779.
[2]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2354 - 2365.
[3]Journal of the American Chemical Society,1940,vol. 62,p. 571.
[4]Helvetica Chimica Acta,1926,vol. 9,p. 265.
[5]Journal of Medicinal Chemistry,2012,vol. 55,p. 10674 - 10684.
[6]Journal of the American Chemical Society,2019,vol. 141,p. 6740 - 6747.

2
[ 4549-31-9 ]
[ 37688-96-3 ]

References: [1]Chemische Berichte,1938,vol. 71,p. 691.

3
[ 37688-96-3 ]
[ 140-89-6 ]
tetradecane-1,14-disulfonic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 571.

4
1,13-dimethoxy-tetradecane [ No CAS ]
[ 37688-96-3 ]

References: [1]Helvetica Chimica Acta,1926,vol. 9,p. 265.

5
[ 37688-96-3 ]
[ 611-70-1 ]
2,2,17,17-tetramethyl-octadecanedioic acid diamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 5388,5395.

6
[ 37688-96-3 ]
[ 37688-97-4 ]
[ 37689-01-3 ]

References: [1]Synthesis,1972,p. 426 - 428.

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 ]

References: [1]Journal of Medicinal Chemistry,1963,vol. 6,p. 780 - 787.

8
[ 17696-11-6 ]
[ 818-88-2 ]
[ 37688-96-3 ]
[ 106-79-6 ]
[ 26825-89-8 ]
[ 1472-93-1 ]

References: [1]Canadian Journal of Chemistry,1964,vol. 42,p. 1788 - 1791.

9
[ 17696-11-6 ]
[ 37688-96-3 ]

References: [1]Canadian Journal of Chemistry,1962,vol. 40,p. 1846 - 1850.

10
[ 37688-96-3 ]
[ 105-53-3 ]
[ 37689-05-7 ]

References: [1]Synthesis,1972,p. 426 - 428.

11
[ 37688-96-3 ]
[ 105-53-3 ]
[ 37689-03-5 ]

References: [1]Synthesis,1972,p. 426 - 428.

12
[ 37688-96-3 ]
[ 90-44-8 ]
[ 127354-20-5 ]

References: [1]Journal of the American Chemical Society,1990,vol. 112,p. 4650 - 4656.

13
[ 37688-96-3 ]
[ 83-56-7 ]
[ 94427-65-3 ]

References: [1]Journal of the American Chemical Society,1985,vol. 107,p. 1124.

14
[ 37688-96-3 ]
[ 1066-26-8 ]
[ 134456-96-5 ]
[ 149849-72-9 ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 8091 - 8095.

15
[ 37688-96-3 ]
[ 1066-26-8 ]
[ 88736-96-3 ]
[ 149849-71-8 ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 8091 - 8095.

16
[ 37688-96-3 ]
[ 72224-15-8 ]
[ 86955-61-5 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1561 - 1569.

17
[ 37688-96-3 ]
[ 57526-81-5 ]
[ 86955-39-7 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1561 - 1569.

18
[ 37688-96-3 ]
1-(4'-hydroxybiphenyl-4-yl)-2-(4-hydroxyphenyl)butane [ No CAS ]
C₃₆H₄₈O₂ [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1319 - 1334.

19
[ 534-22-5 ]
[ 37688-96-3 ]
[ 157131-03-8 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2481 - 2485.

20
[ 110-52-1 ]
[ 17036-36-1 ]
[ 37688-96-3 ]

References: [1]Acta Chemica Scandinavica,1994,vol. 48,p. 570 - 577.

21
[ 37688-96-3 ]
[ 94605-71-7 ]
7-Benzyl-16-(14-bromo-tetradecyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane [ No CAS ]

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%).

References: [1]Synthesis,2014,vol. 46,p. 2771 - 2779.
[2]Chemical Communications,1998,p. 2477 - 2478.

22
[ 37688-96-3 ]
[ 4346-39-8 ]
[ 76734-33-3 ]

References: [1]Synthesis,2003,p. 1279 - 1285.

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[44.2.2.2^2,5.2^22,25.2^26,29]hexapentaconta-1⁽⁴⁸⁾,2,4,22,24,26,28,46,49,51,53,55-dodecaene [ No CAS ]

References: [1]Journal of Materials Chemistry,2003,vol. 13,p. 778 - 784.

24
[ 37688-96-3 ]
[ 2725-53-3 ]
[ 887369-01-9 ]

References: [1]European Journal of Organic Chemistry,2006,p. 1508 - 1524.

25
[ 37688-96-3 ]
[ 5587-42-8 ]
1,14-bis-(1H-imidazol-1-yl)tetradecane [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3583 - 3591.

26
[ 37688-96-3 ]
[ 5587-42-8 ]
1,14-bis-(1H-imidazol-1-yl)tetradecane dihydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3583 - 3591.

27
[ 2961-50-4 ]
[ 37688-96-3 ]
1,14-bis(4’-pentylpyridinium)tetradecane dichloride [ No CAS ]

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.

References: [1]Patent: WO2007/128059,2007,A1 .Location in patent: Page/Page column 38-39.
[2]ChemMedChem,2018,vol. 13,p. 1421 - 1436.

28
[ 37688-96-3 ]
[ 1017-60-3 ]
[ 464896-28-4 ]

References: [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 1859 - 1870.

29
[ 37688-96-3 ]
[ 29949-65-3 ]
[ 464896-39-7 ]

References: [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 1859 - 1870.

30
[ 37688-96-3 ]
[ 887369-10-0 ]

References: [1]European Journal of Organic Chemistry,2006,p. 1508 - 1524.

31
[ 37688-96-3 ]
[ 887369-07-5 ]

References: [1]European Journal of Organic Chemistry,2006,p. 1508 - 1524.

32
[ 37688-96-3 ]
5-methyl-2-tetradecylfuran [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2481 - 2485.

33
[ 37688-96-3 ]
5-methyl-2-(tetradec-13-en-1-yl)furan [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2481 - 2485.

34
[ 37688-96-3 ]
5-methyl-2-(14-hydroxytetradecyl)furan [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2481 - 2485.

35
[ 37688-96-3 ]
1,28-bis(2-(5-methylfuranyl))octaeicosane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2481 - 2485.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Heat of Combustion • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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CAS No.: 37688-96-3

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CAS No.: 37688-96-3

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Product Details of 1,14-Dibromotetradecane

Safety of 1,14-Dibromotetradecane

Application In Synthesis of 1,14-Dibromotetradecane

[ 37688-96-3 ] Synthesis Path-Downstream 1~35

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