Structure of 1-Bromododecane
CAS No.: 143-15-7
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CAS No. : | 143-15-7 |
Formula : | C12H25Br |
M.W : | 249.23 |
SMILES Code : | CCCCCCCCCCCCBr |
MDL No. : | MFCD00000225 |
InChI Key : | PBLNBZIONSLZBU-UHFFFAOYSA-N |
Pubchem ID : | 8919 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 10 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 67.67 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.97 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
7.06 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.05 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
5.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.17 |
Solubility | 0.00167 mg/ml ; 0.00000671 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-6.88 |
Solubility | 0.0000331 mg/ml ; 0.000000133 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.58 |
Solubility | 0.00066 mg/ml ; 0.00000265 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
No |
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) |
Yes |
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 |
-2.81 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.76 |
* 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 |
---|---|---|
40% | at 20 - 25℃; for 20 h; | A mixture of a 38percent aqueous solution of dimethylamine (12.5 mL, 93.8 mmol) and dodecyl bromide (11.7 g, 46.9 mmol) in benzene (15 mL) was stirred at 20—25 °C for 20 h. Then, a 50percent aqueous solution of NaOH (1.9 g, 46.9 mmol) was added to the reaction mixture, and the resulting mixture was evaporated in vacuo. The residue was dissolved in CHCl3 (20 mL), the formed precipitate was filtered off, and the filtrate was evaporated in vacuo. According to the 1H NMR spectral data, the isolated mixture contained amine 6a (4.1 g, 40percent), N,N-didodecyl-N,N-dimethylammonium bromide (4.9 g, 46percent), and unreacted dodecyl bromide (1.7 g, 14percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium hydroxide; In water; at 65℃; for 16h; | The resulting product of step 5A-1, triphenylen-2,3,6,7,10,11-hexanol (10 mmol)Bromododecyl (60 mmol) andPotassium hydroxide (306 mmol) was added to distilled water (50 mL)And the mixture was refluxed at 65 ° C for 16 hours to obtain 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (3, Compound 51) (yield: 74percent). |
74% | With potassium hydroxide; In water; at 65℃; for 16h; | Triphenylene-2,3,6,7, 10,11 -hexanol (10 mmol) obtained from Step 5A- 1 was added to a solution in which bromododecyl (60 mmol) and potassium hydroxide (306 mmol) were dissolved in distilled water (50 ml), and the mixture was refluxed at 65° C. for 16 hours to obtain 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene (3, compound 51) (yield: 74percent). 10400] 2,3,6,7,10,11 -hexakis (dodecyloxy) triphenylene:H NMR (600 MHz, CDC13) oe 7.92 (s, 6H), 4.16 (t, 8H),1.76 (m, 8H), 1.43-1.26 (m, 72H), 0.88 (t, 12H)10401] FIG. 22 is a ?H-NMR spectrum of 2,3,6,7,10,11-hexakis (dodecyloxy) triphenylene according to PreparationExample 5A measured in a CDC13 solvent. |
35% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; | In a 100 ml double-necked flask, <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong> (50 mg, 0.15 mmol) was dissolved in dry DMF (5 ml) in a nitrogen stream. To the solution were added finely ground potassium carbonate (0.13 g, 6.0 eq.) and dodecyl bromide (246.7 mg, 6.6 eq.) and the resultant mixture was stirred overnight at 60° C. There was added 200 ml of distilled water and the precipitate was collected by filtration and washed with methanol. The crude product was dissolved in chloroform and purified by column chromatography (silica gel; hexane: chloroform=2:1) to give compound 3 as white solid (70 mg/35percent). The product was identified by MALDI-TOF-MS, elemental analysis and 1H-NMR (see Table 2). MALDI-TOF-MS (CHCA): m/z 1334.82 (Calcd for [M+H]+1334.50); Anal. Calcd for C90H156O6.0.75CHCl3: C, 76.56; H, 11.10percent. Found: C, 76.45; H, 11.52percent. TABLE 2 1H-NMR(RT, CDCl3, 600MHz, TMS standard) split integral theoretical delta (J/Hz) ratio ratio assignment 0.86 t 20.0 18Ha(CH3) 1.20-1.55 m 196.3 108H b(CH2) 1.97 m 18.2 12Hc(OCH2CH2) 4.23 q 13.9 12Hd(OCH2) 7.83 s 6.0 12H e |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sodium chloride; In ethanol; | REFERENTIAL EXAMPLE 11 Synthesis of 4-n-dodecyloxy-3-chlorophenyl(4-hydroxy-benzyl) ether STR48 In ethanol was dissolved 5.0 g of 4-hydroxy-3-chlorophenol, and an aqueous solution of 1.38 g of sodium hydroxide and 8.6 g of n-dodecyl bromide were added to the solution under reflux in a nitrogen atmosphere. The mixture was refluxed for 6 hours and cooled, and the thus-obtained solution was put into a 1N aqueous solution of hydrochloric acid and extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dehydrated on anhydrous magnesium sulfate and concentrated. The concentrate was purified by using a silica gel column to obtain 1.73 g of 4-dodecyloxy-3-chlorophenol. | |
With potassium hydroxide; In ethanol; | REFERENTIAL EXAMPLE 13 Synthesis of 3-chloro-4-dodecyloxyphenyl 4-hydroxybenzoate STR50 In ethanol, <strong>[615-67-8]chlorohydroquinone</strong> was reacted with dodecylbromide in ethanol by using 1 equivalent of potassium hydroxide to obtain 3-chloro-4-dodecyloxyphenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With n-butyllithium; In tetrahydrofuran; hexane; water; ethyl acetate; toluene; | EXAMPLE 1 Preparation of 2-n-dodecyltetrahydrothiophene (a cyclic sulfide having a five member ring). A solution of tetrahydrothiophene-1, 1-dioxide (36.0 g, Aldrich #T2,220-9) in dry tetrahydrofuran (800 ml, Aldrich #18,656-2) was cooled to -78 C. (dry-ice acetone bath) and treated dropwise with 2.6 molar n-butyllithium in hexane (115 ml, Aldrich #23,070-7). The mixture was stirred for 20 minutes after which 1-bromododecane (72 ml, Aldrich #14,578-5) was added in one portion and the solution stirred for an additional 6 hours at -78 C. The mixture was then allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0 C. and treated carefully with water (500 ml) to destroy any remaining butyllithium. The resulting mixture was diluted with ether (500 ml) and placed in a separatory funnel (2000 ml). The aqueous phase was further extracted with ether (twice with 500 ml). The ether phases were washed with water (500 ml) and brine (500 ml). The combined ether extracts were dried over anhydrous magnesium sulphate, filtered and evaporated on a rotary evaporator to form a solid (84.5 g) The solid reaction mixture was dissolved in toluene (25 ml) and purified by column chromatography using approximately 900 g of silica gel (100-200 mesh) as adsorbant and the following solvents: 1000 ml hexane 1000 ml 2% ether in hexane 1000 ml 4% ether in hexane 1000 ml 8% ether in hexane 4000 ml 16% ether in hexane 3000 ml ethyl acetate The following fractions were obtained as a result of the above procedure: Fractions 1-100 were 80 ml Fractions 101-103 were 1000 ml Fractions 100-103 were combined and the solvent evaporated to yield the 2-n-dodecyltetrahydrothiophene-1, 1-dioxide (63.3 g, 73% yield). A solution of the 2-n-dodecyltetrahydrothiophene-1, 1-dioxide thus prepared (2.78 g) in toluene (6 ml) was added dropwise over 10 minutes to a solution of 1 molar diisobutylaluminum hydride (30 ml, Aldrich #21,500-7) in toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With potassium carbonate; In acetonitrile; at 20℃; for 12h; | Step 1 : fert-Butyl 4-(2-(didodecylamino)ethyl)piperazine-l -carboxylate Chemical Formula: C35H71N3O2 Molecular Weight: 565.97 [00570] A mixture of 1 -bromododecane (1.1 mL, 4.6 mmol), 4-(2-aminoethyl)-l -boc- piperazine (1.0 g, 4.4 mmol), K2CO3 (0.61 g, 4.4 mmol), in 10 mL MeCN was allowed to stir at rt for 12 h. After this time the reaction was filtered and concentrated. The crude material was purified by silica gel chromatography (0-20percent MeOH in DCM with 1percent NH4OH to afford tert- butyl 4-(2-(didodecylamino)ethyl)piperazine-l-carboxylate (450 mg, 0.80 mmol, 18percent). UPLC/ELSD: RT = 2.87 min. MS (ES): m/z (MH+) 566.655 for C35H71N3O2 (1296) XH NMR (400 MHz, CDCI3) delta: ppm 3.40 (m, 4H); 2.56 (m, 2H); 2.40 (m, 10H); 1.44 (s, 9H); 1.40-1.24 (m, 40H); 0.86 (t, 6H). |
18% | With potassium carbonate; In acetonitrile; at 20℃; for 12h; | A mixture of 1 -bromododecane (1.1 mL, 4.6 mmol), 4-(2-aminoethyl)-1-boc-piperazine (1.0 g, 4.4 mmol), K2CO3 (0.61 g, 4.4 mmol), in 10 mL MeCN was allowed to stir at rt for 12 h. After this time the reaction was filtered and concentrated. The crude material was purified by silica gel chromatography (0-20percent MeOH in DCM with 1percent NH4OH to afford tert- butyl 4-(2-(didodecylamino)ethyl)piperazine-l-carboxylate (450 mg, 0.80 mmol, 18percent).UPLC/ELSD: RT = 2.87 min. MS (ES): m/z (MH+) 566.655 for C35H71N3O21H NMR (400 MHz, CDCl3) delta: ppm 3.40 (m, 4H); 2.56 (m, 2H); 2.40 (m, 10H); 1.44 (s, 9H); 1.40-1.24 (m, 40H); 0.86 (t, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium sulfite; In ethanol; water; at 80℃; | To a 250 mL row1d bottom f1ask vas added a solution of 1-bromododecane 222a (5 g,20 06 mmol, 1.00 equiv.) in ethanol (40 mL) and a solution ofNa2S03 (5.2 g, 2.00 equiv.) inwater (40 mL) The resulting mixture was heated at 80C overnight. After cooling to roomtemperature, the mixture was extracted with ethyl acetate (100 mL x 2). The combinedorganic extracts were washed with brine (30 mL x 2), dried over anhydrous sodium sulfate15 and concentrated to a residue which was triturated ·with hex:mes (20 mL x 3) to give sodiumdodecane-1-sulfonate 222b (5 2 g, 92%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In acetonitrile; at 20℃; for 18h;Reflux; Inert atmosphere; | General procedure: In 100 ml round-bottom flask, a suspension of 0.01 mol amino acid ethyl ester hydrochloride (II) and 0.05Mole of NaHCO3 in 40 ml freshly distilled acetonitrile was stirred at room temperature during dropwise addition of 0.015 mol 1-bromododecane (III). After complete addition,the mixture was refluxed for 18 h under nitrogen atmosphere. After cooling to room temperature, acetonitrile was removed under vacuum and thewhite residue of ethyl dodecyl amino acid surfactant (IV) is dissolved in 30ml dichloromethane. It was washed with 0.1M HCl (25ml× 3) and distilled water (25 ml × 2). Dichloromethane was evaporated to give the pure product (V) in 66-92% yield. The product obtained is dissolved in 30 ml of absolute ethanol and 3 ml of 3.0 M NaOH is added dropwise to the solution. The reaction mixture stirred at room temperature for 6 h. The precipitate sodium dodecyl amino acid surfactant (VI) was filtered-off and washed twice with absolute ethanol in poor yield (22-46% yield). The reactions are represented in Scheme1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Add 3g to 50mL DMF solvent<strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.012 mol) and 4.8 g potassium hydrogencarbonate (0.048 mol),Stir at room temperature to form a potassium salt.7.48g of n-bromodedodecane (0.03mol) 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 then dry the solvent.Column chromatography with petroleum ether/ethyl acetate (15/1) as eluentIsolation gave a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Add 3 g of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.012 mol) and 4.8 g of potassium bicarbonate to 50 mL of DMF solvent.(0.048 mol), stirred at room temperature to form a potassium salt. 6.64g of n-bromodecane (0.03mol) was added to the mixed solution and stirred at 90 CReaction for 12 hours. The reaction was stopped, the solution was cooled to room temperature, poured into 300 mL of water and extracted with ethyl acetate. noDrying with sodium sulfate, filtering and drying the solvent. The crude product was subjected to column chromatography using petroleum ether/ethyl acetate (15/1) as eluent.Leave to give a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; for 5h;Inert atmosphere; Reflux; | General procedure: 1.65 g (0.012 mol) of butyl bromide was added dropwise at stirring at 80 to a solution of 2.14 g (0.010 mol) of diphenylethylphosphine in 20 mL of anhydrous acetonitrile. The mixture was refluxed during 5 h and then evaporated in vacuum.20 mL of diethyl ether was added to the residue, the mixture was kept at 8 during 2 h, and the ethereal layer was decanted. |
Tags: 143-15-7 synthesis path| 143-15-7 SDS| 143-15-7 COA| 143-15-7 purity| 143-15-7 application| 143-15-7 NMR| 143-15-7 COA| 143-15-7 structure
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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 |
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