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Chemical Structure| 125700-67-6 Chemical Structure| 125700-67-6

Structure of TBTU
CAS No.: 125700-67-6

Chemical Structure| 125700-67-6

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Product Details of [ 125700-67-6 ]

CAS No. :125700-67-6
Formula : C11H16BF4N5O
M.W : 321.08
SMILES Code : O=N1=N[N+](C=2C=CC=CC21)=C(N(C)C)N(C)C.[F-][B+3]([F-])([F-])[F-]
MDL No. :MFCD00077413
InChI Key :JKEKMBGUVUKMQB-UHFFFAOYSA-N
Pubchem ID :2733207

Safety of [ 125700-67-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H315-H319-H335
Precautionary Statements:P302+P352-P337+P313-P304+P340-P312-P280-P332+P313-P210
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of [ 125700-67-6 ]

* 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 [ 125700-67-6 ]

[ 125700-67-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 345582-96-9 ]
  • [ 125700-67-6 ]
  • [ 475-11-6 ]
  • [ 345583-03-1 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; EXAMPLE 125 (2S)-N-{3-Chloro-4-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]phenyl}-1-methylpyrrolidine-2-carboxamide A mixture of the product from example 120 step (ii) (0.1 g), <strong>[475-11-6]N-methyl-L-proline</strong> (0.044 g), N,N-diisopropylethylamine (0.17 ml), 1-hydroxybenzotriazole (0.043 g), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.103 g) in N,N-dimethylformamide (3 ml) were stirred at room temperature overnight then partitioned between ethyl acetate and water. The organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluding with 4% methanol/dichloromethane. Yield 0.038 g. MS: APCI(+ve) 469(M+1) 1H NMR: delta(DMSO-d6) 9.73(1H, s), 7.88(1H, d), 7.59(1H, dd), 7.38(1H, t), 7.30(2H, d), 7.14-7.10(2H, m), 5.15(2H, s), 4.04-3.98(1H, m), 3.30(2H, d), 3.12-3.08(1H, m), 2.90-2.67(5H, m), 2.35-2.29(1H, m), 2.33(3H, s), 2.18-2.09(1H, m) 1.87(2H, br d), 1.82-1.75(3H, m)
  • 2
  • 4-(3-cyclopentyloxy-4-methoxybenzyl)piperidine [ No CAS ]
  • ammoniacal CH3 OH [ No CAS ]
  • [ 75-09-2 ]
  • [ 2592-95-2 ]
  • [ 125700-67-6 ]
  • [ 1072-84-0 ]
  • [ 204700-24-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In water; EXAMPLE 1 4-(3-Cyclopentyloxy-4-methoxybenzyl)-1-(imidazol-4-ylcarbonyl)piperidine A solution containing 2.1 g of 4-(3-cyclopentyloxy-4-methoxybenzyl)piperidine, 2.6 g of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU), 1.1 g of N-hydroxybenzotriazole (HOBT), 1.6 ml of diisopropylethylamine and 1.0 g of 4-imidazole-carboxylic acid is stirred, under an argon atmosphere, at room temperature for 16 hours. The reaction mixture is stirred for a few minutes with a saturated sodium carbonate solution. The organic phase is then taken up in water and subsequently dried over magnesium sulphate and concentrated. The residual oil is purified by flash chromatography using a CH2 Cl2 /ammoniacal CH3 OH mixture (95:5) as elution system. 4-(3-Cyclopentyloxy-4-methoxybenzyl)-1-(imidazol-4-ylcarbonyl)piperidine taken up in ethanolic hydrogen chloride crystallises in the form of the hydrochloride, which melts at 204-207° C.
  • 3
  • [ 109-02-4 ]
  • [ 55364-85-7 ]
  • [ 211915-62-7 ]
  • [ 125700-67-6 ]
  • [ 211915-63-8 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; g 1-Methyl-2-[(4-cyanophenyl)oxymethyl]-imidazo[4,5-b]pyridin-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)-amide 308 mg (1.0 mMol) of 1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-carboxy-imidazo[4.5-b]pyridine were suspended in 5 ml of dimethylformamide and mixed with 303 mg (3.0 mMol) of N-methyl-morpholine and 321 mg (1.0 mMol) of O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl-uronium tetrafluoroborate. After 10 minutes at room temperature a solution of 215 mg (1.2 mMol) of <strong>[55364-85-7]methyl N-(2-pyridyl)-3-amino-propionate</strong> in 2 ml of dimethylformamide was added, whereupon a clear solution was obtained. After 12 hours at room temperature the reaction solution was stirred into ice-water. After extracting 3 times with ethyl acetate the combined organic extracts were washed with a saline solution, dried over sodium sulphate and evaporated down. The residue obtained was chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1). Yield: 165 mg of white powder (35% of theory), C25 H12 N6 O4 (407.50) Melting point: 139-140 C.
  • 4
  • [ 352553-60-7 ]
  • [ 402-69-7 ]
  • [ 125700-67-6 ]
  • [ 913961-51-0 ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine; In dichloromethane; water; Example 60 N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-6-fluoro-2-pyridinecarboxamide To a solution of 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine (0.15 g, 0.68 mmol), DIPEA (0.165 mL, 0.123 g, 0.95 mmol) and 2-fluoro-6-pyridine carboxylic acid (0.115 g, 0.816 mmol) in dichloromethane (5 mL) was added O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU, 0.26 g, 0.81 mmol) and the mixture was stirred at ambient temperature for 2 h. Water was added and after 10 min, the organic phase was separated and washed with saturated NaHCO3/water, dried (Na2SO4), evaporated, and chromatographed (Silica gel, EtOAc/hexanes, 0-30percent) to provide the title compound as an off-white solid (0.13 g, 61percent yield). 1H-NMR (DMSO-d6): delta 10.92 (s, 1H), 8.8 (d, 1H), 8.2 (quartet, 1H), 8.04 (dd, 1H), 7.43 (m, 2H), 7.28 (d, 1H), 7.0 (dd, 1H), 5.37 (quartet, 1H), 2.62 (m, 2H), 2.0 (m, 3H), 1.8 (m, 1H); MS m/z 365 (M+Na).
  • 5
  • [ 345637-71-0 ]
  • [ 922516-41-4 ]
  • [ 125700-67-6 ]
  • [ 922516-42-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester To a solution of <strong>[345637-71-0](5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid</strong> (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3): delta=1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H), 3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS: m/z=209 (M+1).
  • 6
  • 6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinoline-2-carboxylic acid [ No CAS ]
  • [ 125700-67-6 ]
  • [ 131922-05-9 ]
  • [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine; In dimethyl sulfoxide; acetonitrile; Example 20 [3-(trifluoromethyl)piperazin-1-yl](6-[5-(trifluoromethyl)pyridin-2-yl]oxy}quinolin-2-yl)methanone To a mixture of the product from Example 1D (107.9 mg, 0.323 mmol) and O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU, 156.4 mg, 0.487 mmol) in dimethyl sulfoxide (1 mL) at room temperature was added triethylamine (0.1 mL, 0.72 mmol) followed by <strong>[131922-05-9]2-(trifluoromethyl)piperazine</strong> (79.5 mg, 0.518 mmol). After 3 h, the mixture was diluted with methanol (1 mL) and purified by reverse phase preparative HPLC on a Waters Nova-Pak HR C18.6 μm 60 Å Prep-Pak cartridge column (40 mm*100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 minutes at a flow rate of 70 mL/minute to yield 104.3 mg (69%) of the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1:1 mixture of rotamers 8.57-5-61 (m, 1H), 8.50 (dd, J=8.5, 4.6 Hz, 1H), 8.31 (dd, J=8.5, 2.4 Hz, 1H), 8.10 (t, J=9.0 Hz, 1H), 7.90 (t, J=2.7 Hz, 1H), 7.70-7.78 (m, 2H), 7.40 (dd, J=8.5, 3.7 Hz, 1H), 4.36 (dd, J=12.5, 3.1 Hz, 0.5H), 4.11-4.14 (m, 0.5H), 4.02 (dd, J=13.3, 2.3 Hz, 0.5H), 3.03-3.64 (m, 4H), 2.67-2.90 (m, 1.5H); MS (ESI) m/z 471.1 [M+H]+.
 

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