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Structure of 2-Methoxybenzylamine
CAS No.: 6850-57-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Synthesis of N-Sulfenylimines from Disulfides and Primary Methanamines
Robert Kawȩcki ;
Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.
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CAS No. : | 6850-57-3 |
Formula : | C8H11NO |
M.W : | 137.18 |
SMILES Code : | COC1=C(CN)C=CC=C1 |
MDL No. : | MFCD00008110 |
InChI Key : | PXJACNDVRNAFHD-UHFFFAOYSA-N |
Pubchem ID : | 81292 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 2735 |
Packing Group: | Ⅱ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.87 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.0 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.55 |
Solubility | 3.86 mg/ml ; 0.0281 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.19 |
Solubility | 8.77 mg/ml ; 0.0639 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.54 |
Solubility | 0.396 mg/ml ; 0.00288 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
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 |
-6.52 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
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 |
1.0 |
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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
82% | With ammonia borane; In methanol; at 50℃; for 12h;Inert atmosphere; | Add PdNPore (2.7mg, 5mol%) catalyst into the mesoporous reactorAnd ammonia borane complex (30.86mg, 1mmol),Add methanol (3mL) under nitrogen,Add the substrate <strong>[6609-56-9]o-methoxybenzonitrile</strong> (58.5mg, 0.5mmol),Put it in an oil bath and react at 50 for 12h,After separation and purification by column chromatography (silica gel, 200-300 mesh; the developing solvent is ethyl acetate: methanol = 2:1),Obtained 55.9 mg of o-methoxybenzylamine with a yield of 82%. |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; In isopropyl alcohol; at 200℃; under 75007.5 Torr; | General procedure: A solution (50 mL) containing the nitrile (5 mmol), and dichloro(p-cymene)ruthenium(II) dimer (0.05mmol) in 2-propanol (solution was sonicated until the catalyst was solubilized 10-50 min) was pumpedat 4 mL/min through the reactor coil heated at 200 C. The Phoenix backpressure regulator was set tomanual at 30%, which correlated to approximately 100 bar. A 10 mL fraction of the solution obtainedfrom the system in steady state was used to prepare the hydrochloric salt by method A or B dependingon substrate. Yields are reported as isolated hydrochloride salts, unless otherwise stated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethylethylenediamine; copper(l) chloride; In toluene; at 80℃; for 24h;Sealed tube; Schlenk technique; | General procedure: A mixture of benzylamine 1a (107.0 mg, 1.0 mmol), CuCl (5.0 mg, 0.05 mmol, 5 mol%), 2,2,6,6-tetramethyl-1-piperidyloxy (TEMPO, 7.8 mg, 0.05 mmol, 5 mol%), and N,N-dimethylethane-1,2-diamine (DMEDA, 4.4 mg, 0.05 mmol, 5 mol%) in toluene (0.5 mL) sealed in a Schlenk tube (100 mL) with an air balloon was stirred at 80 C for 24 h. The reaction was then monitored by TLC and/or GC-MS. After completion of the reaction, solvent was evaporated under vacuum. The residue was purified by scosh column chromatography on silica gel using petroleum ether and ethyl acetate (0-100/1) as the eluent, giving product 2a in 80% isolated yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With nickel(IV) oxide; In toluene; at 75℃; | EXAMPLESThe following examples exemplify oxidation reactions on a laboratory scale that were carried out with the inventive process in a flow-through reactor. The present invention is of course not limited to these.Glass tubes with a length of 12 cm and an internal diameter of 8.5 mm were used as the tubular reactor. The tubes were provided with screw connections on both ends so as to be able to attach the HPLC and suitable tubing. After having filled the reactor, the free internal volume for the fluid was 4 ml. For experiments under pressure (example group B and example 4 of the example group C), a PEEK (polyether ether ketone) reactor having the same dimensions was used and was equipped with a reaction pressure regulator. In the following reaction schemes the reactor in the inductor is indicated with the designated graphic symbol “1”.The inductor had the following performance characteristics: inductivity: 134 μHenry, winding count for the spool:=16, cross sectional area=2.8 mm2 (the cross sectional area results from the number of the conductor wires in the inductor and their diameter.) The diameter of the gap for receiving the tubular reactor was 12 mm. For all experiments the inductor was operated with a frequency of 25 kHz.In the experiments the specified frequency of 25 kHz was left constant and the heating control was undertaken solely through the PWM (PWM=on/off switch for a square wave signal at a fixed fundamental frequency). In addition, the PWM is given in ‰ and/or the achieved reaction temperatures in C. The induced temperature was measured with a thermocouple and an infrared thermometer. The thermocouple was mounted directly behind the reactor in the fluid so as to permit an accurate as possible measurement. However, due to the metallic components of the thermocouple, a minimum distance of 4 cm had to be observed. A laser infrared thermometer with close focus optics was used for the second temperature measurement. The measurement point had a diameter of 1 mm. With this method the surface temperature of the reactor should be measured in order to obtain a second measurement point for the temperature determination. The emission factor of the material is an important constant for an infrared measurement. It is a measure of the heat emission. An emission factor of 0.85 was used and corresponds to that of an average glass.For the example groups A and B, particles of CrO2 were employed as the oxygen carrier; they can be obtained by heating Cr(III) oxide at 300 C. in an oxygen atmosphere for 2 hours. The length and diameter of the particles were approx. 0.3 μm and approx. 0.03 μm respectively. The surface area determined by BET (nitrogen) was approx. 30 m2/g. A commercial product is available under the name MagTrieve These particles are themselves not heatable by electromagnetic induction. They were therefore employed as the heating medium in a mixture with manganese ferrite powder (reaction example A1) and in a mixture with MagSilica (each in the volume ratio 1:1) for the other reaction examples.For the example group C, particles of NiO2 (nickel peroxide) mixed with MagSilica (each in the volume ratio 1:1) as the heating medium.For each reaction the reactor, charged with the oxidizing agent and the heating medium was inserted into the inductor and connected on the inlet side with a pump, on the outlet side with a collection vessel. Initially, toluene was pumped through the reactor until constant flow conditions were obtained. The reaction temperature was then adjusted by regulating the power of the inductor. Once a constant temperature was reached the reaction solution was fed through the reactor. The reaction temperatures and the flow rates as well as the isolated yields are given for the individual examples (yields after distilling off the solvent under vacuum and downstream processing of the residue by flash chromatography (SiO2, ethyl acetate/petroleum ether). The products were identified from their 1H nuclear magnetic resonance spectra and further analytical literature data. The listed yields were each obtained with a single pass of the reactants.Reaction Examples Group C:Reactions involving nickel peroxide as the oxidizing agent. Reactions 1-3: glass reactor under normal pressure, starting product 0.15 molar in toluene, reaction 4 under 6.9 bar reaction pressure in the PEEK reactor, starting product 0.125 molar in toluene. |
With oxygen; In toluene; at 90℃; under 760.051 Torr; for 27h; | General procedure: Oxidation reactions were performed on amine compounds having various structures under a molecular oxygen atmosphere using a small amount of Ru / E-MoS2 catalyst (0.01 g, Ru: 5 mol%). At this time no additional oxidizing agent was used and all reactions were carried out in toluene at 90 C without a cocatalyst. The results are shown in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | at 120℃; | 5-Nitro-2-chloroquinoline (CAS 13067-94-2,3 g, 14 mmol) and 2-methoxy-benzylamine (4.2 g, 31 mmol) were stirred in a sealed tube at 120 C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0?30:70 gradient). (2-Methoxy-benzyl)-(5-nitro-quinolin-2-yl)-amine was obtained as a yellow solid (2.2 g, 50%), MS: m/e=310.1 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | The solution of 2-methoxybenzylamine (211 muIota_, 0.226 g, 1.65 mmol) in ethanol (4 mL) was added 37percent formaldehyde (62 mu, 0.049 g, 1.65 mmol). The mixture was stirred for 1 hour. Then the solution of <strong>[1198-14-7]5-bromoquinolin-8-ol</strong> (0.336 g, 1.5 mmol) in ethanol (5 mL) was added to the reaction mixture. After that the mixture was refluxed at 50°C for 56 hours. The reaction mixture was allowed to cool down and the obtained precipitate was filtered off, washed with ethanol and crystallized from ethanol to give the titled compound (0.130 g, 23percent) as yellow crystals. Mp. 135-137 °C. 1 H NMR (300 MHz, CDCI3): delta 3.83 (s, 3H), 3.93 (s, 2H), 4.1 1 (s, 2H), 6.84-6.94 (m, 2H), 7.21-7.29 (m, 2H), 7.46-7.51 (m, 1 H), 7.60 (s, 1 H), 8.40 (d, 1 H), 8.84 (d, 1 H). 13C NMR (75 MHz, CDCI3): delta 48.2, 49.3, 55.2, 109.2, 1 10.0, 110.2, 120.5, 122.2, 125.9, 127.1 , 129.0, 130.5, 131.0, 135.3, 139.8, 149.0, 152.8, 157.7. LCMS RT= 4.08 min. ESI+ m/z: 375.4 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; N,N-dimethyl-formamide; at 120℃; for 6h; | Three-necked flask was charged with 100 g of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate,Then, a mixed solvent of 600 mL of DMF: DMSO = 1: 1 was added thereto and stirred. 44.8 mL of 2-methoxybenzylamine was added and the temperature was raised to 120 C. for 6 h. The temperature was lowered and the reaction mixture was poured into 1 mol / L of dilute hydrochloric acid. Stirring, adding 500mLEA extraction, the organic layer was separated, the aqueous phase was extracted with EA300mL × 2, the organic layer was combined, dried, filtered and evaporated to give a yellow product 92.3g, which was used in the next step without purification. |
Tags: 6850-57-3 synthesis path| 6850-57-3 SDS| 6850-57-3 COA| 6850-57-3 purity| 6850-57-3 application| 6850-57-3 NMR| 6850-57-3 COA| 6850-57-3 structure
A104360 [31963-35-6]
1-(2-Phenoxyphenyl)methanamine hydrochloride
Similarity: 0.91
A160454 [102503-23-1]
1-(2,4-Dimethoxyphenyl)-N-methylmethanamine
Similarity: 0.91
A104360 [31963-35-6]
1-(2-Phenoxyphenyl)methanamine hydrochloride
Similarity: 0.91
A160454 [102503-23-1]
1-(2,4-Dimethoxyphenyl)-N-methylmethanamine
Similarity: 0.91
A104360 [31963-35-6]
1-(2-Phenoxyphenyl)methanamine hydrochloride
Similarity: 0.91
A160454 [102503-23-1]
1-(2,4-Dimethoxyphenyl)-N-methylmethanamine
Similarity: 0.91
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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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