Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C2Cl2N4
Example 1 General Phase-Transfer Protocol for Tetrazine Insertion A 50 mL glass vial, was charged with unprotected peptide 1 (20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH ?5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) to yield an orange powder after lyophilization. A 50 mL glass vial, was charged with unprotected peptide 1a (11.4 mg, 20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH 5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) (gradient 5-15% organic over 5 min) to yield 10.1 mg of 2a (78%) an orange powder after lyophilization. 1H NMR (500 MHz, D2O) delta ppm 1.36 (quin, J=7.80 Hz, 2H) 1.58-1.66 (m, 3H) 1.68 (q, J=7.90 Hz, 2H) 1.79 (ddd, J=13.90, 8.30, 5.50 Hz, 1H) 1.78 (ddd, J=13.25, 8.10, 5.30 Hz, 1H) 2.07 (q, J=7.34 Hz, 2H) 2.39 (dd, J=7.30, 5.10 Hz, 1H) 2.39 (dd, J=9.80, 7.40 Hz, 1H) 2.93 (t, J=7.48 Hz, 9H) 3.50 (dd, J=15.60, 4.06 Hz, 3H) 3.54 (dd, J=18.20, 6.20 Hz, 1H) 3.57 (dd, J=11.30, 7.70 Hz, 1H) 4.10 (t, J=6.52 Hz, 1H) 4.14 (dd, J=8.44, 5.24 Hz, 1H) 4.20 (dd, J=7.10, 6.40 Hz, 1H) 4.53 (dd, J=15.39, 2.99 Hz, 1H) 4.56 (dd, J=15.60, 4.92 Hz, 1H) 4.80 (t, J=3.42 Hz, 1H) 4.99 (dd, J=4.90, 1.90 Hz, 1H). 13C NMR (126 MHz, D2O) delta 178.6, 178.1, 171.7, 170.6, 170.5, 169.9, 169.1, 169.1, 61.8, 55.0, 53.9, 52.4, 52.3, 51.5, 39.1, 31.4, 31.1, 30.7, 30.2, 26.7, 26.2, 22.1. HRMS (ES) found m/z 647.2026 [(M+H)+. calcd for C22H35N10O9S2: 647.2024].
According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.
Reference:
Patent; The Trustees Of The University Of Pennsylvania; Smith, III, Amos B.; Brown, Stephen; (18 pag.)US2015/376579; (2015); A1;,
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