Category: 106131-61-7

Electric Literature of 106131-61-7,Some common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, molecular formula is C2Cl2N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1,2,4-Triazole (3:5 g 50 mmol) was dissolved in 200 mL acetone, and 20 mL (12 mmol) of a 0:6M solution of 3,6-dichloro-tetrazine in acetonitrile was added. The solution was refluxed for 20 h. After cooling the resulting precipitate was washed with water and acetone. 2:1 g (9:9 mmol,83%) of (7) was isolated as an orange powder. – Elemental analysis (C6H4N10, 212.21) exp. (calcd.) in %: C33.43 (33.34), N 64.33 (64.80), H 1.87 (1.87). – DSC(5 C min1): Tdec:: 245 C (onset). – 1H NMR ([D6]DMSO,25 C, ppm): d =8.34 (s, 1H, C-H), 9.46 (s, 1H, C-H). -13C NMR ([D6]DMSO, 25 C, ppm): d =144.9 (1C), 147.2(1C), 154.2 (1C). – MS ((+)-DEI): m=z=216 [M]+ (50), 94(100), 67 (92). – Raman: n (cm-1)= 3139 (8), 3124 (12),1912 (2), 1557 (2), 1511 (63), 1483 (100), 1426 (4), 1379(21), 1336 (2), 1293 (2), 1264 (12), 1135 (19), 980 (43), 947(5), 813 (20), 662 (2). – IR (25 C, ATR): n (cm-1) = 3135(w), 3120 (w), 1813 (vw), 1755 (vw), 1551 (vw), 1514 (s),1480 (vs), 1384 (m), 1365 (m), 1337 (w), 1293 (vs), 1266 (m), 1196 (s), 1170 (vw), 1155 (s), 1116 (s), 1112 (s), 1054(s), 976 (vs), 953 (m), 939 (m), 910 (m), 880 (m), 672 (vs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dichloro-1,2,4,5-tetrazine, its application will become more common.

Reference:
Article; Klapoetke, Thomas M.; Preimesser, Andreas; Stierstorfer, Joerg; Zeitschrift fur Naturforschung, B: Chemical Sciences; vol. 68; 12; (2013); p. 1310 – 1320;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 106131-61-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Dichloro-s-tetrazine (1 mmol) and fluorinated alcohol (1 mmol) were dissolved in anhydrous dichloromethane (10 mL). 2,4,6-collidine (1 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 12 h under N2 atmosphere.The solvent was evaporated and the residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give compound 2 as a pink solid, with a ?yellow? fluorescence on TLC (using a standard laboratory UV lamp with a broad band centred at 365 nm).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3,6-Dichloro-1,2,4,5-tetrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ben Chaabane, Radhia; Guermazi, Refka; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Dyes and Pigments; vol. 108; (2014); p. 64 – 69;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 106131-61-7,Some common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, molecular formula is C2Cl2N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.33 mmol), s-collidine (0.39 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After2 h the reaction is complete (TLC) and the solvent removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent petroleumether/ethyl acetate 1/1). Compound 4a was isolated as pink solid in 42 % yield(0.19 g). M. p.: 100 C.1H NMR (400 MHz, Acetone-d6): delta (ppm) 5.46 (t, 4H,3JH-F = 13.19 Hz, (CF2)8CH2 – O). 13CNMR (100MHz, Acetone-d6): delta (ppm) 167.1 (CTz-O);166 (CTz-Cl); 100-120 ((CF2)8); 65.4 (t, 2JC-F = 25.83 Hz,(CF2)8CH2 – O).19F NMR (376 MHz, Acetone-d6): delta (ppm) -119.99(m, 4F); -122.29 (m, 8F); -123.92 (m, 4F).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dichloro-1,2,4,5-tetrazine, its application will become more common.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 106131-61-7,Some common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, molecular formula is C2Cl2N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 3,6-dichloro-1,2,4,5-tetrazine (500 mg, 3.31 mmol) in Tol. (5 mL) was added 2-methylbut-3-yn-2-ol at 20 C. The mixture was stirred at 115 C. for 16 hours under sealed tube. LCMS showed desired MS. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 4:1, TLC) to give 33a. MS mass calculated for [M+1]+ (C7HCl2N2O) required m/z 207.0, LCMS found m/z 207.0; 1H NMR (400 MHz, CDCl3) delta 7.98 (s, 1H) 2.17 (s, 1H) 1.77 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dichloro-1,2,4,5-tetrazine, its application will become more common.

Reference:
Patent; Terns, Inc.; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; ROMERO, F. Anthony; US2020/62742; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 106131-61-7, Application In Synthesis of 3,6-Dichloro-1,2,4,5-tetrazine

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.33 mmol), s-collidine (0.39 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After2 h the reaction is complete (TLC) and the solvent removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent petroleumether/ethyl acetate 1/1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dichloro-1,2,4,5-tetrazine, and friends who are interested can also refer to it.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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., Recommanded Product: 106131-61-7

To a solution of 3,6-dichloro-1,2,4,5-tetrazine (1.51 g, 10 mmol) in acetonitrile (70 ml) was added the sodium salt of 5-amino-1H-tetrazole (2.14 g, 10 mmol). The mixture was refluxed for 24 hours then allowed to cool to room temperature. The suspension was centrifuged until the supernatant liquid was clear. The liquid was decanted and the brown solid washed successively with acetonitrile and water. With each wash the solid was separated from the solvent by centrifugation followed by decantation. The isolated crude yield was 1.5 g (60%), this material was recrystallized from DMSO/methanol yielding an orange brown powder mp 264 C. dec; 1H NMR(deuteriomethylsulfoxide) 12.5(b,r s,4H); 13 C NMR (deuteriomethylsulfoxide) 151.74, 158.25; IR (KBr) 3421, 3000, 1615, 1436, 1127 cm-1. A gas pycnometer density of 1.76 g/cm3 was also determined and a drop height of 195 cm was measured (Type 12, HMX=24-27 cm).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 106131-61-7.

Reference:
Patent; The Regents of the University of California; US6657059; (2003); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

106131-61-7, The chemical industry reduces the impact on the environment during synthesis 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, I believe this compound will play a more active role in future production and life.

General procedure: Dichloro-s-tetrazine (1 mmol) and fluorinated alcohol (1 mmol) were dissolved in anhydrous dichloromethane (10 mL). 2,4,6-collidine (1 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 12 h under N2 atmosphere.The solvent was evaporated and the residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give compound 2 as a pink solid, with a ?yellow? fluorescence on TLC (using a standard laboratory UV lamp with a broad band centred at 365 nm).

The chemical industry reduces the impact on the environment during synthesis 3,6-Dichloro-1,2,4,5-tetrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ben Chaabane, Radhia; Guermazi, Refka; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Dyes and Pigments; vol. 108; (2014); p. 64 – 69;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics