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CAS No. : | 135-68-2 | MDL No. : | MFCD00477989 |
Formula : | C12H10ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OREQWMWYRYXCDF-UHFFFAOYSA-N |
M.W : | 203.67 | Pubchem ID : | 8675 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 61.29 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 2.65 |
Log Po/w (WLOGP) : | 3.6 |
Log Po/w (MLOGP) : | 3.61 |
Log Po/w (SILICOS-IT) : | 3.44 |
Consensus Log Po/w : | 3.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.34 |
Solubility : | 0.093 mg/ml ; 0.000457 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.85 |
Solubility : | 0.289 mg/ml ; 0.00142 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.18 |
Solubility : | 0.00135 mg/ml ; 0.00000665 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.34 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P273-P280-P301+P312+P330-P305+P351+P338+P310 | UN#: | 3077 |
Hazard Statements: | H302-H318-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 platinum on activated charcoal; ethanol; hydrazine hydrate | ||
With hydrogenchloride; tin | ||
With hydrogenchloride; iron In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | With potassium carbonate In ethanol at 80℃; for 6h; Green chemistry; | |
88% | With potassium carbonate In ethanol; water at 65℃; for 4h; | |
88% | With sodium carbonate; triphenylphosphine In water at 80℃; for 18h; Schlenk technique; | Suzuki-Miyaura cross-coupling reaction General procedure: A mixture of aryl halide (0.25 mmol), phenylboronicacid (0.3 mmol), Na2CO3 (0.25 mmol), PPh3 (0.025 mmol)and Pd(at)PAAs-CD (0.5 mg, 0.2 mol% Pd per mol of arylhalide) were placed into a 10 mL Schlenck tube with1 mL H2O. The reaction mixture was reacted at 80 °C for18 h, and the reaction progress was monitored via gaschromatography mass spectrometry (GC-MS). The reactionmixture was allowed to cool to room temperature, andthen 3 mL water was added, and the product was extractedwith ethyl acetate (3 mL × 3). The organic layers werecombined and dried over anhydrous Na2SO4 and solventswere evaporated via rotary evaporator. The crude productwas purified by column chromatography (200-300 meshsilica) using a mixture of petroleum ether/ethyl acetate(10:1, v:v) as eluent. The structures of the products wereconfirmed by 1H NMR and 13C NMR spectroscopies. |
61% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; | General procedure for the synthesis of biphenyls 19a-c General procedure: To a stirred solution of 4-bromoaniline (2.0 mmol) in toluene (20 mL) was added Pd(Ph3P)4(0.14 mmol), a solution of sodium carbonate (12 mmol) in water (10 mL) and a solution ofphenylboronic acid (18a-c) (1.6 mmol) in ethanol (10 mL). All the solutions werepreviously degassed for 1 h under nitrogen atmosphere. The reaction was stirred andrefluxed overnight, under nitrogen atmosphere. The reaction mixture was poured into waterand extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 andconcentrated in vacuo, and then purified by column chromatography (SiO2,ciclohexane/ethyl acetate).4-Amino-4’-chlorobiphenyl (19a). Yield: 0.48 g, 61%. 1H NMR (500 MHz, CDCl3): δ 7.48- 7.42 (m, 2H), 7.40 - 7.32 (m, 4H), 6.77 - 6.73 (m, 2H), 3.74 (br s, 2H). |
43% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 75℃; for 22h; Inert atmosphere; | (Synthesis of Exemplified Compound 101) A 2 M aqueous solution of sodium carbonate (1.5 ml) was added to a solution of 4-bromoaniline (170 mg, 1.0 mmol) and Pd (PPh3) 4 (58 mg, 0.05 mmol) in toluene (2 ml). A solution of 4-chlorophenylboronic acid (258 mg, 1.5 mmol) in ethanol (2 ml) was slowly added to the reaction solution under argon flow, and stirred at 75 ° C. for 22 hours. After stirring, it was filtered through celite and the celite was washed with ether. The organic layer was washed sequentially with water and brine and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1: 2) to give compound II-1 (88 mg, 43%). |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; benzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 41% 2: 13% | With manganese(IV) oxide In acetonitrile at 20℃; Overall yield = 54 %; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 16h; | Solid NaBH(OAc)3 (1.4 g, 6.8 mmol) was added to a DCE solution (10 mL) of <strong>[85118-24-7]2-bromo-4-(trifluoromethyl)benzaldehyde</strong> (860 mg, 3.4 mmol), 4'-chloro-[1,1'-biphenyl]-4-amine (761 mg, 3.7 mmol), and AcOH (0.78 mL, 13.6 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; | Neat i-Pr2NEt (0.21 mL, 1.19 mmol) was added to a DCM mixture (5 mL) of <strong>[42860-02-6]3-bromo-5-chlorobenzoic acid</strong> (140 mg, 0.60 mmol), 4'-chloro-[1,1'-biphenyl]-4-amine (145 mg, 0.71 mmol), HOBt (92 mg, 0.60 mmol) and EDCI (114 mg, 0.60 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting precipitate was filtered off, washed with water and MeOH, and dried in vacuo to yield the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44% 2: 12% | With sodium hydroxide In water at 75℃; | II.13 II.13 4′-Chlorobiphenyl-2-amine and 4′-chlorobiphenyl-4-amine 0344] 4′-Chlorobiphenyl-2-amine and 4′-chlorobiphenyl-4-amine were synthesized from aniline (20.0 mmol, 2.33 g) and 4-chlorophenyldiazonium chloride (2.00 mmol, 5.00 ml of the 0.4 M aryldiazonium chloride solution prepared by general method GM 1) analogously to general method GM 3 at 75° C. Diethyl ether was used for extraction. Excess aniline was removed by means of vacuum distillation. The two regioisomers were separated by means of column chromatography (silica gel, hexane/EtOAc=4:1). 4′-Chlorobiphenyl-2-amine (0.88 mmol, 179 mg, 44%) and 4′-chlorobiphenyl-4-amine (0.24 mmol, 49 mg, 12%) were obtained. RRN 65 4′-Chlorobiphenyl-2-amine [0345] Rf 0.6 (hexane/EtOAc=4:1) [UV] [0346] 1H NMR (360 MHz, CDCl3): δ=6.76 (dd, J=0.9 Hz, J=8.0 Hz, 1H), 6.82 (dt, J=1.1 Hz, J=7.47 Hz, 1H), 7.09 (dd, J=1.4 Hz, J=7.6 Hz, 1H), 7.16 (ddd, J=1.6 Hz, J=7.4 Hz, J=8.0 Hz, 1H), 7.37-7.45 (m, 4H). [0347] 13C NMR (90.6 MHz, CDCl3): δ=115.7 (CH), 118.8 (CH), 126.3 (Cq), 128.8 (CH), 129.0 (2×CH), 130.3 (CH), 130.4 (2×CH), 133.1 (Cq), 137.9 (Cq), 143.4 (Cq). [0348] MS (EI) m/z (%): 205 (29) [37Cl-M+], 204 (10), 203 (100) [35Cl-M+], 202 (12), 169 (17), 168 (56), 167 (37), 166 (14), 83 (29). [0349] HRMS (EI) calculated for C12H10ClN [M+]: 203.0502. found: 203.0502. RRN 66 4′-Chlorobiphenyl-4-amine [0350] Rf 0.3 (hexane/EtOAc=4:1) [UV] [0351] 1H NMR (600 MHz, CDCl3): δ=6.75 (d, J=8.6 Hz, 2H), 7.35 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.6 Hz, 2H), 7.45 (d, J=8.5 Hz, 2H). [0352] 13C NMR (151 MHz, CDCl3): δ=115.4 (2×CH), 127.5 (2×CH), 127.8 (2×CH), 128.7 (2×CH), 130.2 (Cq), 132.1 (Cq), 139.6 (Cq), 146.1 (Cq). [0353] MS (EI) m/z (%): 205 (32) [37Cl-M+], 204 (18), 203 (100) [35Cl-M+], 169 (12), 168 (9), 167 (24), 139 (10), 101 (11), 83 (21). [0354] HRMS (EI) calculated for C12H10ClN [M+]: 203.0502. found: 203.0502. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 51% 2: 9% | With oxygen; sodium hydroxide In water at 60℃; for 33h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 1h; | 3. General procedure for Suzuki-Miyaura coupling: General procedure: To a mixture of aryl halide (1 mmol), arylboronic acid (1.2 mmol), Pd-AcAc-Am-Fe3O4/SiO2 (30 mg ), and K2CO3 (3 mmol), DMF: water (8:2, 5 mL) was added and stirred at 80 °C under aerobic conditions. After completion of reaction, monitored by TLC, the reaction mixture was cooled. The catalyst was separated by using external magnet. The product was extracted with ethylacetate (2×10 mL) The organic layer was dried with Na2SO4 and then concentrated on a rotary evaporator afforded corresponding biaryls in excellent yield. The crude products were then purified by column chromatography (2 % ethyl acetate). All synthesized products were confirmed from physical constant IR, 1H and 13C NMR. |