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Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
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* Storage: {[proInfo.prStorage]}
CAS No. : | 2885-00-9 | MDL No. : | MFCD00004886 |
Formula : | C18H38S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QJAOYSPHSNGHNC-UHFFFAOYSA-N |
M.W : | 286.56 | Pubchem ID : | 17905 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 16 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 96.57 |
TPSA : | 38.8 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -1.54 cm/s |
Log Po/w (iLOGP) : | 5.1 |
Log Po/w (XLOGP3) : | 9.17 |
Log Po/w (WLOGP) : | 7.18 |
Log Po/w (MLOGP) : | 6.01 |
Log Po/w (SILICOS-IT) : | 7.29 |
Consensus Log Po/w : | 6.95 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.34 |
Solubility : | 0.000132 mg/ml ; 0.000000459 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -9.88 |
Solubility : | 0.0000000376 mg/ml ; 0.0000000001 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.25 |
Solubility : | 0.000016 mg/ml ; 0.0000000557 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.4 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 | UN#: | 3077 |
Hazard Statements: | H302-H319-H332-H372-H400 | Packing Group: | Ⅲ |
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 |
---|---|---|
With caesium carbonate; In N-methyl-acetamide; | Method G 2-(Octadecylthio)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (24) Compound 15 (743 mg; 1 mmol), octadecylthiol (315 mg; 1.1 mmol) and cesium carbonate (391 mg; 1.2 mmol) were added to dry dimethylformamide (8 ml) at room temperature under nitrogen. The reaction was followed by TLC. After 24 h, the reaction mixture was distributed between water and ether. The ether phase was dried (Na2 SO4) and evaporated. The residue was chromatographed (ethyl acetate:isooctane 1:1) to give the title compound (24) (300 mg) and the starting compound (15) (400 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | With potassium carbonate; In ISOPROPYLAMIDE; at 30 - 135℃; for 20.5h; | The reaction is carried out under an inert atmosphere in a 5-necked 750 ml sulfonating flask provided with a thermometer, a mechanical stirrer, a dropping funnel and a reflux condenser. 100.00 g (0.35 mol, 1.0 eq. ) of 1-octadecanethiol are dissolved in 200 mi of dimethylacetami- de (DMA) at 30C and added over 25 minutes to a white suspension of 48.18 g (0.35 mol, 1.0 eq. ) of p-chlorobenzonitrile and 67. 72 g (0.49 mol, 1.4 eq. ) of finely ground potassium carbonate in 200 ml of dimethylacetamide. The reaction mixture is then heated to 135C and stirred at that temperature for 4 hours. The temperature is then reduced to 80C and the re- action mixture is stirred for 16 hours to complete the reaction. The reaction mixture is then discharged into 1600.0 g of water at room temperature. The white crystalline solid that preci- pitates out over one hour is filtered off and dried at 70C and 200 mbar. There are obtained 122.6 g (90.4 % of theory) of the compound of formula The compound of formula (52) can also be prepared starting from 4-mercaptobenzonitrile in analogy to a process published by S. Karlsson, A. Hallberg and S. Gronowitz in J. Organo- met. Chem. 1992,430, 1,53-60 or in analogy to a process published by W. H. Roark, B. D. Roth, A. Holmes, B. K. Trivedi, K. A. Kieft, A. D. Essenburg, B. R. Krause and R. L. Stanfield in J. Med. Chem. 1993, 36,1662-1668 or also in analogy to a process published by D. A. Shirley and W. H. Reedy in J. Amer. Chem. Soc. 1951, 73,4885-4886. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; cyclohexane; N,N-dimethyl-formamide; | -benzenedicarbonitrile carbonitrile STR9 3-Nitro-1,2-benzenedicarbonitrile (1.731g, 0.01M), 1-octadecanethiol (2.866 g, 0.01M), anhydrbus K2 CO3 (7.0g) and DMF (20 ml) were stirred together at 75 to 80 C. for 6h, then allowed to stand cooling overnight. A solid mass formed on standing, which was dissolved in CH2 Cl2 /H2 O. An intermediate emulsion was removed by taking off as much of the organic phase as possible, then repeatedly extracting the residue with small portions of CH2 Cl2. The combined CH2 Cl2 extracts were washed with water (3 times), dried (MgSO4), and evaporated in vacuo to give a solid (3.71g). Recrystallisation of the crude product from cyclohexane (150 ml) gave 3-(n-octadecylthio)-1,2-benzenedicarbonitrile as a faintly-coloured microcrystalline powder which was collected, washed with a little cold petrol, and dried in vacuo (3.220g, 78%). 1 H NMR (CDCl3) Chemical shift 7.59 (m,3), 3.07 (t,2, J=7Hz), 1.26 (m, 35). IR(Nujol)=2234 cm-1 (C N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 5: Surfactant from n-Octadecylmercaptan and a Poly(ethylene carbonate)polyol made from Ethylene Oxide and Carbon Dioxide A poly(ethylene carbonate) polyol (Mn 2076; 27.4 wt % CO2) is prepared from ethylene oxide and carbon dioxide using diethylene glycol as initiator. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; | EXAMPLE 4 Example 4 demonstrates the preparation of pentaerythritol tetrakis(n-octadecylthiopropyl) ether. The procedure used was identical to that set forth in Example 1, except that 119.4 g of n-octadecyl mercaptan (0.417 mole) was reacted with 29.6 g of pentaerythritol tetraallyl ether (0.1 mole). The crude product was then recrystallized three times in 300 ml of hexane yielding 54 g of a white solid having a melting point of 60-63 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In toluene; | EXAMPLE 15 1-Isobutyl-2,8-di(n-octadecylthio)-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane The procedure of Example 10 is repeated using 8.72 g (28.5 mmol) of 1-isobutyl-2,8-dichloro-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane, 16.33 g (57 mmol) of n-octadecyl mercaptan and 8.74 mL (63 mmol) of triethylamine in 200 mL of toluene. A white solid (7.11 g) is isolated. The product is identified by mass spectroscopy: m/z=805. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogenchloride; methanol; | EXAMPLE 86 A solution of 3.59 g of 1-octadecanethiol in 45 ml of 1N aqueous hydrochloric acid and 170 ml of methanol is treated With 4.5 g of 5,7-dihydro-2-[[(4-methoxy-3-methyl-2 -pyridyl)methyl]sulphinyl]-5,5,7,7 -tetramethylindeno[5,6-d]imidazol-6(1H)-one. A clear solution results. The reaction mixture is stirred at room temperature, partially concentrated and the solution is cooled briefly to about 5, whereupon the crystalline solid is filtered off and washed with water. The 4-methoxy-3-methyl-2 -[(octadecyldithio)methyl]-1 -(1,5,6,7-tetrahydro-5,5,7,7-tetramethyl-6 -oxoindeno[5,6-d]imidazol-2-yl)pyridinium chloride obtained exhibits a melting point of 150 (dec.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Finally, 3-octadecylthiopropanol can also be obtained by the addition of octadecyl mercaptan to allyl alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium; In ice-water; 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide; isopropyl alcohol; | EXAMPLE 7 Bis[2-(n-octadecylthio)ethyl] 4-tert.-butyl-2,6-dimethyl-3-hydroxybenzylphosphonate 9.0 Grams of n-octadecyl mercaptan dissolved in 30 ml. of xylene was added rapidly to 0.72 grams of sodium sand dispersed by rapid stirring in 150 ml. of xylene at 60. The reaction mixture was stirred at 80 to 105 for 25 minutes and then kept at 100 to 105 for 15 minutes yielding a white dispersion of sodium n-octadecyl mercaptide. 2.0 Ml. of dry N,N-dimethylformamide was added to the reaction mixture. 5.96 Grams of bis-(2-chloroethyl) 4-tert.-butyl-2,6-dimethyl-3-hydroxybenzylphosphonate (Example 4) dissolved in 70 ml. of hot xylene was added dropwise to the reaction mixture. The reaction mixture was then heated at 120 for 10 hours. The clear yellow xylene solution was successively washed with 3N aqueous hydrochloric acid, water, and aqueous saturated sodium chloride until the wash liquors were neutral. After drying overnight over anhydrous sodium sulfate and magnesium sulfate and removing the drying agents by filtration, the clear filtrate was freed of solvent by distillation at reduced pressures. The residue was first crystallized from a solvent mixture of isopropanol-methanol, the hot solution being freed of an insoluble oil by decantation, the supernatant liquid depositing crystals on cooling in an ice-water mixture. The crystals were then recrystallized again from isopropanol-methanol by first dissolving them in isopropanol, filtering off an insoluble solid after cooling to room temperature, then adding a little methanol and cooling overnight at 15. In this manner, the desired compound was obtained as white crystals melting at 57 to 63. (compound 5) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
405 g | With sodium hydrogensulfide; tetrabutylammomium bromide; In water; chlorobenzene; at 65 - 70℃; for 16h; | The second phase (420 g) is distilled to obtain <strong>[3386-33-2]1-chlorooctadecane</strong> (V) (210 g). 210 g of the <strong>[3386-33-2]1-chlorooctadecane</strong> (V), 200 g of chlorobenzene, 180 g of a 32% by weight sodium bisulfide solution in water and 6 g of tetra-butylammonium bromide are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 65 to 70 C., the mixture is reacted for 16 h. The mixture is separated into an aqueous layer and an organic layer. The organic layer is n-octadecanethiol (III) (405 g). |
405 g | With sodium disulfide; tetrabutylammomium bromide; In water; chlorobenzene; at 65 - 70℃; for 16h; | [0158] The second phase (420g) is distilled to obtain <strong>[3386-33-2]1-chlorooctadecane</strong> (V) (210g). 210g of the <strong>[3386-33-2]1-chlorooctadecane</strong>(V), 200g of chlorobenzene, 180g of a 32% by weight sodium bisulfide solution in water and 6g of tetra-butylammoniumbromide are added into a 1000ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature inthe range of from 65 to 70C, the mixture is reacted for 16h. The mixture is separated into an aqueous layer and anorganic layer. The organic layer is n-octadecanethiol (III) (405g). |
Tags: 2885-00-9 synthesis path| 2885-00-9 SDS| 2885-00-9 COA| 2885-00-9 purity| 2885-00-9 application| 2885-00-9 NMR| 2885-00-9 COA| 2885-00-9 structure
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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 |
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H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
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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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