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CAS No. : | 932-32-1 | MDL No. : | MFCD00045170 |
Formula : | C7H8ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WGNNILPYHCKCFF-UHFFFAOYSA-N |
M.W : | 141.60 | Pubchem ID : | 136736 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.76 |
TPSA : | 12.03 Ų |
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) : | -5.37 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 2.53 |
Log Po/w (WLOGP) : | 2.19 |
Log Po/w (MLOGP) : | 2.41 |
Log Po/w (SILICOS-IT) : | 2.16 |
Consensus Log Po/w : | 2.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.74 |
Solubility : | 0.258 mg/ml ; 0.00182 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.43 |
Solubility : | 0.527 mg/ml ; 0.00372 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.43 |
Solubility : | 0.0531 mg/ml ; 0.000375 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
22% | With [18F]-tetrabutylammonium fluoride; In acetonitrile; at 180℃; for 0.5h;Microwave irradiation;Product distribution / selectivity; | Examples; General Description General description of the reaction conditions; In a microwave reaction vial (size 0.5-2 ml) fitted with a magnet stirring bar, a solution of 0.5-1.5 mg of the starting ortho-bromo anilines in 250 muL of dry acetonitrile was introduced, followed by the addition of 50 muL of an anhydrous solution of [18F]TBAF in acetonitrile. To the reaction solution, 500 muL of dry acetonitrile was added. The microwave vial was crimped with a Teflon septum, and thereafter purged with argon for 5 min. The resulting reaction vial was kept in the microwave cavity of a microwave system (Initiator EXP, Biotage, Sweden), and heated for 30 min at 180C. The reaction was quenched by cooling the vial with compressed air, after which the contents of the vial were subjected to chromatographic analysis (HPLC with RP18e Chromolith column, internal diameter 4.6 mm; length of 100 mm) eluted with a mixture of acetonitrile/water (27.5 : 72.5% v/v).; Example 1: Model Compounds and Examples of the General Method; Labeling reactions were carried out in acetonitrile in the presence of a tetrabutylammonium salt (TBA+) and [18F]fluoride. Various leaving groups were evaluated. Reaction times were 20-40 minutes, and the reaction temperature was in the range of 150C-200C to result in yields in the range of 7-68% at. The highest yields of 61 +/- 5 % resulted from the use of a ortho-bromo-leaving group and a combination of a reaction temperature of 180C and a reaction time of 30 min. No radioactive by-product except for the desired ortho-[18F]fluorinated aniline derivative has been observed as measured by analytical HPLC. The reactions were according to the general reaction scheme of Scheme 2 below and are summarized in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | To a solution of the <strong>[932-32-1]2-chloro-N-methylaniline</strong> (Intermediate 237) (8g, 0.057 mol.) in acetonitrile (340 mL) was added oxoacetic acid (42.2 g, 0.57 mol.). After stirring for 0.5 hours at room temperature, NaBH3CN (17.7 g, 0.285 mol) was added in portions by keeping the temperature below 40C. The mixture was stirred at room temperature for 2 hours then acetic acid (23 mL) was added drop-wise. After stirring for 1 hour, the solid material was removed by filtration and the filtrate was concentrated to dryness. The residue was poured in water and the pH was adjusted to 9 with aqueous NaOH. After extraction of the aqueous layer with EtOAc, the aqueous layer was acidified to pH: 4 with diluted HCI. The white solid was filtered, washed with water then dried to give the title compound as a white solid (7g, 62%). LC/MS: m/z 200.1 (M+H) Rt: 1.67 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Add oxalyl chloride (0.064 mL, 0.72 mmol) to a solution of 1- (3, 5-Bis- trifluoromethyl-benzyl)-5-phenyl-1H- [1, 2,3] TRIAZOLE-4-CARBOXYLIC acid (150 mg, 0.36 mmol) and DMF (1 drop) in CH2C12 (2 mL). Stir the solution for 2.5 h at RT, then concentrate to dryness. Dissolve the residue in 1, 2-dichloroethane (DCE) and concentrate to dryness. Dissolve the residue in pyridine (2 mL) and transfer to a sealed tube. Add 2- CHLORO-N-METHYLANILINE (200 mg, 1.44 mmol) and DMAP (5 mg, cat. ) and heat in the sealed tube at 80C for I h. Cool to RT and concentrate to dryness. Dissolve in 20% iPrOH/CHC13. Wash with saturated NAHC03 and brine, dry over NA2SO4, filter and concentrate to dryness. Purify by radial chromatography using an EtOAc/hexanes gradient to afford the title compound (75.4 mg, 39%) as a clear foam/oil. MS (ES) 539.2 (M+1) + ; HPLC (5-95% 0.1% TFA/water in 3.8 min on YMC ODS (0. 46x50mm). 05 mL; 3.0 mL; 25C) Rf= 3.34 min; 99.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Dissolve 1-(3,5-bis-trifluroomethyl-benzyl)-5-chloro-1H[1, 2,3] triazole-4- carboxylic acid (300 mg, 0.8 mmol) in CH2CI2 (5 mL) and DMF (2 drops) and add oxalyl chloride (0.14 mL, 1.6 mmol). Stir for 1 h at RT, then concentrate the mixture to dryness. Slurry the residue in 1,2-dichloroethane and concentrate to dryness twice. Dissolve the residue in pyridine (3 mL) in a sealed tube. Add DMAP (5 mg, catalytic) and N-methyl- 2-chloroaniline (120 mg, 0.8 mmol). Heat for 1 h at 80 C, then concentrate to dryness. Dissolve in 20% IPROH/CHCL3. WASH with saturated aqueous NaHC03, and brine, then dry over NA2SO4, filter, and concentrate. Purify the residue via radial chromatography using an ethyl acetate/hexanes gradient to afford 200 mg (50%) of the title compound as a colorless oil. MS (ES) 497.2 (M+1) + ; RJ= 0.625 (50% EtOAc/hexanes). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 20℃; for 16h; | To a solution of 9-cyano-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid (300 mg) in dichloromethane (10 mL) was added DMF (1 drop) and oxalyl chloride (0.165 mL) and the reaction stirred at room temperature for 30 min. The solvent was then reduced in vacuo and the residue redissolved in acetonitrile (10 mL). To this solution was added <strong>[932-32-1]2-chloro-N-methylaniline</strong> (0.165 mL) and potassium carbonate (308 mg) and the reaction stirred at room temperature for 16 h. The mixture was partitioned between water (40 mL) and ethyl acetate (30 mL). The organic layer was dried (Na2SO4), reduced in vacuo and purified on silica to give 120. NMR: (CDCl3): 3.08 (t, 2H, CH2, J=5.00 Hz), 3.41 (s, 3H, CH3), 4.29 (t, 2H, CH2, J=5.02 Hz), 6.92 (s, H, ArH), 7.03 (d, H, ArH, J=8.43 Hz), 7.38-7.47 (m, 4H, 4×ArH), 7.57 (m, H, ArH), 7.72 (d, H, ArH, J=1.65 Hz). MS: (ESI+) MH+ 395 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With sodium tris(acetoxy)borohydride; In acetonitrile; at 20℃; for 10h; | (1) methyl 3-[(2-chlorophenyl)(methyl)amino]methyl}benzoate To a solution of <strong>[932-32-1]2-chloro-N-methylaniline</strong> (0.20 g) and methyl 3-formylbenzoate (0.23 g) in acetonitrile (4 mL) was added sodium triacetoxy borohydride (0.6 g), and the mixture was stirred at room temperature for 10 hr. Saturated aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column to give the object product (0.10 g, 24%). LC-MS: [M+H]+ 290.00 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36%; 63% | With NaY-BS zeolite; at 150℃; for 1h; | General procedure: Into a pressure microreactor of stainless steel of 17 mL capacity or into a glass ampule (20 mL) (results of the parallel runs were virtually identic) was charged 5-10 wt % of catalyst (0.94HY-BS, NaY-BS, 0.72KNaX-BS), 100 mmol of aniline or its derivative, and 400 mmol of dimethyl carbonate. The reactor was hermetically closed (the ampule was sealed), and was heated for 1-4 h at 150 C. After the end of the run the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or crystallized from ethanol. |
55%; 38% | With 0.72 KNaX-BS zeolite; at 150℃; for 1h; | General procedure: Into a pressure microreactor of stainless steel of 17 mL capacity or into a glass ampule (20 mL) (results of the parallel runs were virtually identic) was charged 5-10 wt % of catalyst (0.94HY-BS, NaY-BS, 0.72KNaX-BS), 100 mmol of aniline or its derivative, and 400 mmol of dimethyl carbonate. The reactor was hermetically closed (the ampule was sealed), and was heated for 1-4 h at 150 C. After the end of the run the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or crystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With pyridine; dmap; In dichloromethane; at 0 - 20℃; | General procedure: To a solution of the appropriate aniline in dry CH2Cl2 (10 mL for 3 mmol of aniline), pyridine (1.5 eq) and catalytic DMAP (15 mg) were added, then the resulting mixture was cooled to 0 C. Subsequently, commercially available sulfonylchloride 6 (1.2 eq) in dry CH2Cl2 (10 mL for 3.6 mmol of benzenesulfonylchloride) was added dropwise and the reaction was kept under stirring at RT overnight. The reaction mixture was acidified with 1N aqueous HCl, extracted several times with CH2Cl2 and the combined organic phase was dried over anhydrous sodium sulphate. Evaporation under vacuum of the organic solvent afforded a crude product which was purified by column chromatography over silica gel, to yield the sulfonamidic derivative. |
Tags: 932-32-1 synthesis path| 932-32-1 SDS| 932-32-1 COA| 932-32-1 purity| 932-32-1 application| 932-32-1 NMR| 932-32-1 COA| 932-32-1 structure
[ 13065-93-5 ]
N1-(4-Chlorophenyl)benzene-1,4-diamine
Similarity: 0.87
[ 13065-93-5 ]
N1-(4-Chlorophenyl)benzene-1,4-diamine
Similarity: 0.87
[ 13065-93-5 ]
N1-(4-Chlorophenyl)benzene-1,4-diamine
Similarity: 0.87
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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