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[ CAS No. 1083-27-8 ] {[proInfo.proName]}

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Product Details of [ 1083-27-8 ]

CAS No. :1083-27-8 MDL No. :MFCD00016480
Formula : C13H18O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ULULAZKOCFNOIM-UHFFFAOYSA-N
M.W : 222.28 Pubchem ID :14127
Synonyms :

Calculated chemistry of [ 1083-27-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 7
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.78
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 4.35
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 3.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.77
Solubility : 0.0374 mg/ml ; 0.000168 mol/l
Class : Soluble
Log S (Ali) : -5.04
Solubility : 0.00202 mg/ml ; 0.00000907 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.0261 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.89

Safety of [ 1083-27-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P272-P280-P302+P352+P333+P313+P363-P305+P351+P338+P337+P313-P501 UN#:N/A
Hazard Statements:H315-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1083-27-8 ]

* 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 [ 1083-27-8 ]

[ 1083-27-8 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 1083-27-8 ]
  • phosphoric acid tris-(4-hexyloxycarbonyl-phenyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate
  • 2
  • [ 1083-27-8 ]
  • [ 100-35-6 ]
  • 4-(2-diethylamino-ethoxy)-benzoic acid hexyl ester [ No CAS ]
  • 3
  • [ 111-27-3 ]
  • [ 99-96-7 ]
  • [ 1083-27-8 ]
YieldReaction ConditionsOperation in experiment
66% With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;
53.2% With sulfuric acid In toluene for 4h; Heating;
With hydrogenchloride at 150℃;
With sulfuric acid; benzene Entfernen des entstehenden Wassers;
With sulfuric acid Heating;
With sulfuric acid In toluene for 1h; Heating;
With sulfuric acid In benzene Azeotropic water removal;
With toluene-4-sulfonic acid at 145℃; for 6h; Inert atmosphere; Dean-Stark; 1 Example 1 A stirrer, a temperature sensor and a Dean-Stark apparatusIn a 300 mL scale four-necked flask (reaction vessel), 91.2 g (0.66 mol) of 4-hydroxybenzoic acid (POB)101.1 g (0.99 mol) of 1-hexanol (HexOH) and 1.8 g of p-toluenesulfonic acid monohydrate (PTS · H 2 O) as a catalyst were added and the temperature was raised to 145 ° C. under a nitrogen flow of 38 mL / The mixture was warmed and reacted at the same temperature for 6 hours to obtain a crude composition. The obtained crude composition was quantitatively analyzed by HPLC and GC. The results are shown in Table 1.
With toluene-4-sulfonic acid at 145℃; for 6h; Dean-Stark; Inert atmosphere; 1 Reference Example 1 Preparation of hexyl paraben (hexyl 4-hydroxybenzoate) Equipped with stirrer, temperature sensor and Dean Stark deviceIn a 300 mL scale four-necked flask (reaction vessel),91.2 g (0.66 mol) of 4-hydroxybenzoic acid,101.1 g (0.99 mol) of 1-hexanol and 1.8 g of p-toluenesulfonic acid monohydrate as a catalyst are added,Under a nitrogen flow of 38 mL / min,The temperature is raised to 145 ° C., and the reaction is carried out at the same temperature for 6 hours,A crude composition containing hexyl paraben was obtained.After adding 48% sodium hydroxide to there and making it neutral,Purified by distillation,A hexyl paraben (purity 99.8 wt%) was obtained.

  • 4
  • [ 619-58-9 ]
  • [ 1083-27-8 ]
  • 4-(n-Hexyloxycarbonyl)phenyl 4'-iodobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide In diethyl ether Ambient temperature;
  • 5
  • [ 111-25-1 ]
  • [ 99-96-7 ]
  • [ 1142-39-8 ]
  • [ 1083-27-8 ]
YieldReaction ConditionsOperation in experiment
1: 7 % Spectr. 2: 83 % Spectr. With PEG 200; potassium hydroxide at 80℃; for 2h; Title compound not separated from byproducts;
1: 73 % Spectr. 2: 11 % Spectr. With PEG 200; potassium hydroxide In 1,4-dioxane at 80℃; for 2h; Title compound not separated from byproducts;
  • 6
  • [ 1083-27-8 ]
  • [ 100-44-7 ]
  • [ 56441-76-0 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate
  • 7
  • [ 678-39-7 ]
  • [ 1083-27-8 ]
  • 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;
  • 8
  • (E)-3-(4-methoxyphenyl)propenoyl chloride [ No CAS ]
  • [ 1083-27-8 ]
  • 4-[(E)-3-(4-Methoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 9
  • [ 1083-27-8 ]
  • [ 77251-75-3 ]
  • 4-[(E)-3-(4-Ethoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 10
  • [ 1083-27-8 ]
  • [ 77251-76-4 ]
  • 4-[(E)-3-(4-Propoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 11
  • [ 1083-27-8 ]
  • [ 77251-77-5 ]
  • 4-[(E)-3-(4-Butoxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 12
  • [ 1083-27-8 ]
  • [ 77251-78-6 ]
  • 4-[(E)-3-(4-Pentyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 13
  • [ 1083-27-8 ]
  • [ 77251-79-7 ]
  • 4-[(E)-3-(4-Hexyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 14
  • [ 1083-27-8 ]
  • [ 77251-80-0 ]
  • 4-[(E)-3-(4-Heptyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 15
  • [ 1083-27-8 ]
  • [ 77251-81-1 ]
  • 4-[(E)-3-(4-Octyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 16
  • [ 1083-27-8 ]
  • [ 77251-82-2 ]
  • 4-[(E)-3-(4-Decyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 17
  • [ 1083-27-8 ]
  • [ 77251-83-3 ]
  • 4-[(E)-3-(4-Dodecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 18
  • [ 1083-27-8 ]
  • [ 130286-00-9 ]
  • 4-[(E)-3-(4-Tetradecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
  • 19
  • [ 1083-27-8 ]
  • [ 77251-84-4 ]
  • 4-[(E)-3-(4-Hexadecyloxy-phenyl)-acryloyloxy]-benzoic acid hexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine for 0.166667h;
YieldReaction ConditionsOperation in experiment
4-Hydroxy-benzoesaeure, Hexan-1-ol, H2SO4;
5 A. Using the same general procedure, but using n-hexanol instead, n-hexyl 4-hydroxybenzoate was synthesised as a colorless, viscous oil. PMR (CDCl3): δ 0.92 (3H, m), 1.36 (6H, m), 1.78 (2H, m), 4.33 (2H, q, J~6.7 Hz), 6.97 (2H, d, J~8.8 Hz), 7.99 (2H, d, J~8.8 Hz).
  • 21
  • [ 1083-27-8 ]
  • hexyl 4-[(aminosulphonyl)oxy]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.4% With sulphamoyl chloride; sodium hydride In N,N-dimethyl-formamide; toluene for 10h; Heating;
Stage #1: hexyl paraben With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene
Stage #1: hexyl paraben With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene for 10h;
  • 22
  • [ 1083-27-8 ]
  • 1,3-phenylene bis(methyliminobenzoic acid) [ No CAS ]
  • C48H48N2O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
  • 23
  • [ 1083-27-8 ]
  • 4'-(n-Hexyloxycarbonyl)phenyl 4''-<(4-(S)-2'-methylbutoxy-2,3,5,6-tetrafluorophenyl)ethynyl>benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: DCC / 4-pyrrolidinopyridine / diethyl ether / Ambient temperature 2: Et3N / bis(triphenylphosphine)palladium dichloride, copper(I) iodide / Heating
  • 24
  • [ 111-25-1 ]
  • [ 1083-27-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: durch 6-taegiges Kochen 2: hydrogen chloride / 150 °C
Multi-step reaction with 2 steps 2: hydrogen chloride / 150 °C
  • 25
  • sulphur dichloride [ No CAS ]
  • zinc chloride anhydrate [ No CAS ]
  • [ 1083-27-8 ]
  • [ 107490-77-7 ]
YieldReaction ConditionsOperation in experiment
In chloroform 12 EXAMPLE 12 EXAMPLE 12 To a solution of 98 g of hexyl p-hydroxybenzoate, 150 ml of chloroform and 0.5 g of zinc chloride anhydrate is added a solution of 32.7 g of sulfur monochloride in 100 ml of chloroform at 18°-20° C. and stirred at 40° C. for 5 hours. After distilling off the chloroform, a solution of the residue thus obtained in toluene is washed with water, 3N hydrochloric acid, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution. Subsequently, the toluene is distilled off and the oil thus obtained is purified by a silica gel column chromatography with chloroform to give 3,3'-thiobis(hexyl p-hydroxybenzoate) as a viscous oil.
  • 26
  • 1,2,4-tris(4-chloroformylphenyloxycarbonyl)benzene [ No CAS ]
  • [ 1083-27-8 ]
  • [ 1194090-79-3 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In dichloromethane at 20℃; for 5h;
With triethylamine In dichloromethane at 20℃; for 5h;
  • 27
  • [ 1083-27-8 ]
  • [ 139152-08-2 ]
  • 4,5-bis[(4-hexyloxycarbonyl)phenoxy]phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.2 g With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h;
  • 28
  • (E)-1,3-diethyl-2-(hexyltriaz-2-en-1-ylidene)-2,3-dihydro-1H-imidazole [ No CAS ]
  • [ 99-96-7 ]
  • [ 111222-69-6 ]
  • [ 1083-27-8 ]
  • C7H13N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 12% In methanol; dichloromethane at 20℃; for 4h; Inert atmosphere; n-hexyl benzoate General procedure: To a solution of the carboxylic acid (0.164 mmol, 2.0 eq.) in methylene chloride (1.5 mL) was added a 0.4M solution of 1 in methylene chloride dropwise (0.02 mL, 0.082 mmol). The reaction mixture was stirred under argon at room temperature for 4 hours, concentrated, and dissolved in ether. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over sodium sulfate and concentrated under reduced pressure to yield esters below.
  • 29
  • [ 99-93-4 ]
  • [ 111-27-3 ]
  • [ 1083-27-8 ]
YieldReaction ConditionsOperation in experiment
76% With iron(III) chloride; ammonium persulfate In tetrachloromethane; 1,2-dichloro-ethane at 120℃; for 15h; General method of synthesis of 3a-f,a-d: General procedure: 1a-j (0.0299 - 0.0532 g, 0.299 mmol, 1 eq.), 2a-d (0.0166 - 0.228 g, 0.224 mmol, 0.75 eq.), FeCl3 (0.0145 g, 0.0897 mmol, 0.3 eq.), (NH4)2S2O8 (0.1363 g, 0.598 mmol, 2 eq.), and DCE / CCl4 (0.75 mL, 1 / 1) were stirred in Schott culture tubes (H × diam. 160 mm × 16 mm) at 120 °C for 3 h. Further, after adding a solution of 2a-d (0.055 - 0.0763, 0.0748 mmol, 0.25 eq.) and DCE / CCl4 (0.08 mL, 1 / 1), the reaction mixture was stirred at 120 °C for 3 h (3 times at 3-hour intervals). Next it was stirred at 120 °C for 12 h. The yields of 3a-f,a-d were determined by 1H NMR (CDCl3) after the filtration of the reaction mass through a thin pad (0.4 - 0.5 cm) of silica gel (0.015 - 0.040 mm) using 20 mL of DCM and evaporation of solvent in vacuum. Products 3c,b and 3d,a-d were isolated by gradient flash chromatography (eluent: petroleum ether / ethyl acetate).
  • 30
  • [ 123-08-0 ]
  • [ 80033-60-9 ]
  • [ 1083-27-8 ]
YieldReaction ConditionsOperation in experiment
73% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; Selectfluor In acetonitrile at 20℃; for 7h; Inert atmosphere; Irradiation; General synthetic route to hydroxy benzoates (4a’-i’). General procedure: In a 10 mL double necked roundbottom flask equipped with a magnetic stirring bar, hydroxybenzaldehydes (1 or 7) (2.0mmol), photocatalyst IrIII[df(CF3)ppy]2(dtbbpy)PF6 (45 mg, 0.04 mmol), Selectfluor (12,1.3 g, 4.0 mmol), the appropriate silyl ether 3 (6.0 mmol) and acetonitrile (5.0 mL) weretaken at room temperature. The mixture was irradiated under 445 nm blue LED array forthe required time in inert atmosphere and was monitored by TLC. After completion ofthe reaction the solvent was evaporated under reduced pressure. The residue wasdistributed in 10 mL of water and extracted by 20x3 mL ethyl acetate. The combinedorganic layers were kept over anhydrous MgSO4 and were concentrated under reducedpressure. The crude product was purified by column chromatography using 100-200mesh silica gel using 5-10% ethyl acetate in hexanes solvent mixture to afford purehydroxy benzoates (4a’-i’) as pure white crystalline solids or liquids.
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