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[ CAS No. 6232-12-8 ] {[proInfo.proName]}

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Chemical Structure| 6232-12-8
Chemical Structure| 6232-12-8
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Product Details of [ 6232-12-8 ]

CAS No. :6232-12-8 MDL No. :MFCD00859552
Formula : C10H14ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KMZNTLYGVGINKN-UHFFFAOYSA-N
M.W : 215.68 Pubchem ID :16236386
Synonyms :

Calculated chemistry of [ 6232-12-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.17
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 1.97
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.451 mg/ml ; 0.00209 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.198 mg/ml ; 0.000919 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.258 mg/ml ; 0.00119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 6232-12-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6232-12-8 ]

* 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 [ 6232-12-8 ]

[ 6232-12-8 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 75-15-0 ]
  • [ 50-00-0 ]
  • [ 6232-12-8 ]
  • [ 100-46-9 ]
  • [ 41931-39-9 ]
  • 3
  • [ 6232-12-8 ]
  • [ 758670-25-6 ]
  • [ 219922-49-3 ]
  • 4
  • [ 6287-86-1 ]
  • [ 6232-12-8 ]
  • C20H21NO4 [ No CAS ]
  • 5
  • [ 6232-12-8 ]
  • [ 131065-88-8 ]
  • 6
  • [ 6232-12-8 ]
  • C23H29NO6 [ No CAS ]
  • 7
  • [ 6232-12-8 ]
  • 4-N-(N,N-bis(p-ethoxycarbonylbenzyl)formamidinyl)-2',3'-dideoxy-3'-thiacytidine [ No CAS ]
  • 9
  • [ 56-91-7 ]
  • [ 64-17-5 ]
  • [ 6232-12-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; In water;Reflux; Aminomethyl benzoic acid 79(560 mg, 2.98 mmol) was refluxed in 30mL of ethanol with 1 mL of HCl 12 N overnight. The solvent was evaporated toobtain aminomethyl benzoic ester 80as hydrochloride salt (640 mg, quantitative yield). The ester derivative (640mg, 2.97 mmol, 1 equiv) was dissolved in a dioxane/water solution, then TEA(911 muL, 6.53 mmol, 2.2 equiv) and Boc2O (779 mg, 3.57 mmol,1.2 equiv) were added and the solution was stirred at 0 C for 1 h, then overnight at rt. The solvent wasevaporated, the slurry was taken up in EtOAc, washed with a solution of citricacid 10% (3 X 10 mL), water (2 X 10 mL), dried over Na2SO4,filtered and evaporated in vacuum to give 78as oil (810 mg, quantitative yield). 1H NMR (200MHz, DMSO-d6) delta 7.88 (s, 2H), 7.40 (m, 1H), 7.32- 7.24 (m, 1H), 5.17(br, NH), 4.31-4.28 (m, 4 H), 1.39 (s, 9H), 1.34-1.30 (m, 3H) ppm.
With thionyl chloride; at 0℃; for 3.0h;Heating / reflux; 4-Aminomethylbencoic acid-ethylester hydrochloride (1):; 20.0 g (132 mM) of 4- aminomethylbencoic acid were suspended in 200 ml EtOH abs. and cooled with ice. 28.0 g (17 ml) (236 mM) thionylchloride were added drop by drop. The clear mixture was then refluxed for 3 hours. After cooling to room temperature, EtOH was evaporated. 50 ml of toluene/EtOH 1/1 were added and evaporated three times. The residue was dried to get 27 g of 1.
  • 10
  • [ 4053-08-1 ]
  • [ 6232-12-8 ]
  • [ 889651-03-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 90℃; 4-Chloro-naphthalimidyl-methylbencoic acid- ethylester (2):; 20.0 g (93.2 mM) 4- aminomethylbencoic acid-ethylester hydrochloride , 21.68 g (93.2 mM) 4-Chloro-l,8-naphthalic anhydride and 19.78 g triethylamine (195.5 mM) in 400 ml DMF were heated to 900C and stirred overnight.[0044] After cooling to room temperature, 100 ml H2O were added to precipitate the desired product.[0045] The 4-Chloro-naphthalimidyl-methylbencoic acid-ethylester was recrystallized from EtOH. Yield: 15.8 g.[0046] The HPLC (Vydac 10-90- 15) shows a single peak at t = 14.04 and the mass peak MH+ = 394.8 ( M = 393.82) was found in the Matrix Assisted Laser Desorption/Ionization Time-of- Flight (MALDI-TOF) mass spectrum.
  • 11
  • [ 1141446-21-0 ]
  • [ 6232-12-8 ]
  • [ 1141446-22-1 ]
YieldReaction ConditionsOperation in experiment
50% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; Step 2; Preparation of ethyl 4-((2-(4-fluorophenyl)-3-(3,4,5 trimethoxyphenyl) acrylamido) methyl)benzoate.; To a solution of 3-(3,4,5-trimethoxyphenyl)-2-(4-fluorophenyl) acrylic acid (0.6 g, 18 mmol) in DMF (5 mL) was added ethyl-4-aminomethylbenzoate.HCI (0.375 g, 21.6 mmol), EDCI (0.69 g, 36 mmol) and HOBt (0.24 g, 18 mmol). TEA (0.75 mL, 36 mmol) was added dropwise with constant stirring to the above reaction mixture and stirred overnight at room temperature. Subsequently the reaction mixture was evaporated to dryness, the residue was dissolved in ethyl acetate and washed successively with IN HCl (3x50 mL), saturated NaHCOs (3x50 mL) and brine solution (3x50 mL). The organic layer was dried over Na2Stheta4 and concentrated to give the pure compound (0.4 g, 50 % yield).
50% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; To a solution of 3-(3,4,5-trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acid (0.6 g, 18 mmol) in DMF (5 mL) was added ethyl-4-aminomethylbenzoate.HCl (0.375 g, 21.6 mmol), EDCI (0.69 g, 36 mmol) and HOBt (0.24 g, 18 mmol). TEA (0.75 mL, 36 mmol) was added dropwise with constant stirring to the above reaction mixture and stirred overnight at room temperature. Subsequently the reaction mixture was evaporated to dryness, the residue was dissolved in ethyl acetate and washed successively with 1N HCl (3*50 mL), saturated NaHCO3 (3*50 mL) and brine solution (3*50 mL). The organic layer was dried over Na2SO4 and concentrated to give the pure compound (0.4 g, 50% yield).
  • 12
  • C10H7ClN2O4S [ No CAS ]
  • [ 6232-12-8 ]
  • ethyl 5-[({4-[(ethyloxy)carbonyl]phenyl}methyl)amino]carbonyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In tetrahydrofuran; at 10 - 35℃; for 12.0h; Reference Example 178 ethyl 5-[({4-[(ethyloxy)carbonyl]phenyl}methyl)amino]carbonyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (2089) (2090) To a mixture of 2-[(ethyloxy)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid (600 mg, 2.24 mmol) obtained in Reference Example 176 and THP (6 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) and DMF (0.0500 mL, 0.650 mmol) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. To a suspension of the concentrated residue in THF (6 mL) were added <strong>[6232-12-8]ethyl 4-(aminomethyl)benzoate hydrochloride</strong> (966 mg, 4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol), and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure and ethyl acetate was added to the obtained residue. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was crystallized from ethyl acetate to give the title compound as a white powder (771 mg, 80%). (2091) melting point: 227-228 C. (2092) 1H NMR (300 MHz, DMSO-d6) delta 1.31 (3H, t, J=6.2 Hz), 1.36 (3H, t, J=6.2 Hz), 4.31 (2H, q, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz), 4.65 (2H, d, J=5.5 Hz), 7.50 (2H, d, J=8.5 Hz), 7.93 (2H, d, J=8.5 Hz), 8.57 (1H, s), 11.27 (1H, s), 13.53 (1H, s).
771 mg With triethylamine; In tetrahydrofuran; at 20℃; for 12.0h; To a mixture of compound 33c (600 mg, 2.24 mmol) in THF(6.0 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) andN,N-dimethylformamide (1 drop). After being stirred for 1 h atroom temperature, the mixture was concentrated in vacuo. Theresidue was resuspended in THF (6.0 mL), and to the mixture wereadded <strong>[6232-12-8]ethyl 4-(aminomethyl)benzoate hydrochloride</strong> (965 mg,4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol). After beingstirred for 12 h at room temperature, the mixture was concentratedin vacuo. The residue was taken up in ethyl acetate, washedwith 1 M hydrochloric acid (2), saturated sodium hydrogen carbonatesolution, 1 M hydrochloric acid, brine, dried over Na2SO4and concentrated in vacuo. The residue was crystallized from ethylacetate to give 34b (771 mg, 80%) as a white powder. mp 227-228 C. 1H NMR (300 MHz, DMSO-d6) d 1.31 (3H, t, J = 6.2 Hz),1.36 (3H, t, J = 6.2 Hz), 4.31 (2H, q, J = 7.1 Hz), 4.40 (2H, q,J = 7.1 Hz), 4.65 (2H, d, J = 5.5 Hz), 7.50 (2H, d, J = 8.5 Hz), 7.93(2H, d, J = 8.5 Hz), 8.57 (1H, s), 11.3 (1H, s), 13.5 (1H, s). Anal. Calcdfor C20H19N3O6S0.20H2O: C, 55.47; H, 4.52; N, 9.70. Found: C,55.50; H, 4.39; N, 9.73.
  • 13
  • [ 6232-12-8 ]
  • 2-((5-(3-(aminomethyl)phenyl)-4-phenethyl-4H-1,2,4-triazol-3-yl)thio)-N-cyclopentylacetamide hydrochloride [ No CAS ]
  • 14
  • [ 6232-12-8 ]
  • [ 161948-58-9 ]
  • 15
  • [ 6232-12-8 ]
  • tert-butyl (4-(5-mercapto-4-phenethyl-4H-1,2,4-triazol-3-yl)benzyl)carbamate [ No CAS ]
  • 16
  • [ 6232-12-8 ]
  • C29H37N5O3S [ No CAS ]
  • 17
  • [ 24424-99-5 ]
  • [ 6232-12-8 ]
  • [ 157311-42-7 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In 1,4-dioxane; water; at 0 - 20℃; Aminomethyl benzoic acid 79(560 mg, 2.98 mmol) was refluxed in 30mL of ethanol with 1 mL of HCl 12 N overnight. The solvent was evaporated toobtain aminomethyl benzoic ester 80as hydrochloride salt (640 mg, quantitative yield). The ester derivative (640mg, 2.97 mmol, 1 equiv) was dissolved in a dioxane/water solution, then TEA(911 muL, 6.53 mmol, 2.2 equiv) and Boc2O (779 mg, 3.57 mmol,1.2 equiv) were added and the solution was stirred at 0 C for 1 h, then overnight at rt. The solvent wasevaporated, the slurry was taken up in EtOAc, washed with a solution of citricacid 10% (3 X 10 mL), water (2 X 10 mL), dried over Na2SO4,filtered and evaporated in vacuum to give 78as oil (810 mg, quantitative yield). 1H NMR (200MHz, DMSO-d6) delta 7.88 (s, 2H), 7.40 (m, 1H), 7.32- 7.24 (m, 1H), 5.17(br, NH), 4.31-4.28 (m, 4 H), 1.39 (s, 9H), 1.34-1.30 (m, 3H) ppm.
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