[ CAS No. 1671-87-0 ] {[proInfo.proName]}

Name: 1671-87-0|3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine|97%
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SKU: A130224
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Quality Control of [ 1671-87-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1671-87-0 ]

Product Details of [ 1671-87-0 ]

CAS No. :	1671-87-0	MDL No. :	MFCD00121717
Formula :	C₁₂H₈N₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JFBIRMIEJBPDTQ-UHFFFAOYSA-N
M.W :	236.23	Pubchem ID :	315109
Synonyms :

Calculated chemistry of [ 1671-87-0 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.08
TPSA :	77.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	-0.14
Log Po/w (WLOGP) :	1.39
Log Po/w (MLOGP) :	0.85
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	1.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.82
Solubility :	3.54 mg/ml ; 0.015 mol/l
Class :	Very soluble
Log S (Ali) :	-1.03
Solubility :	22.0 mg/ml ; 0.0933 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-5.2
Solubility :	0.00148 mg/ml ; 0.00000625 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.27

Safety of [ 1671-87-0 ]

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

Application In Synthesis of [ 1671-87-0 ]

* 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.

Upstream synthesis route of [ 1671-87-0 ]
Downstream synthetic route of [ 1671-87-0 ]

[ 1671-87-0 ] Synthesis Path-Upstream 1~7

1
[ 19081-87-9 ]
[ 1671-87-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With nitric acid; acetic acid In water at 0℃;	8.0 g (0.077 mole) of 2-cyanopyridine was dissolved in 200 ml of anhydrous ethanol, the solution was added into a three-neck flask, and 9.54 ml (0.308 mole) of 95percent hydrazine hydrate was then added thereto. The mixture was refluxed for 6 hours to obtain 7.54 g (81.7percent yield) of orange-colored dianhydride base. The base was filtered, washed several times with ethanol, dissolved in glacial acetic acid and cooled on an ice bath, and 5-6 ml of concentrated nitric acid was slowly added dropwise thereto. The mixture was poured over crushed ice, made basic with sodium bicarbonate and then extracted two times with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, thus obtaining 6.3 g (85percent yield) of 3,6-bis(2'-pyridyl)-l,2,4,5-tetrazine as a purple solid. 6.3 g (0.027 mole) of the obtained 3,6-bis(2'-pyridyl)-l,2,4,5-tetrazine was dissolved in dimethyl- formamide (hereinafter, referred to as DMF), and the solution was added into a three- neck flask and refluxed with bubbling of acetylene. As the reaction progressed, the mixture was changed from a purple color to a clear color. DMF was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The resulting solid material was purified by silica gel column chromatography using ethylacetate: n- hexane (1:4, v/v)

Reference： [1] Patent: WO2007/7943, 2007, A1, . Location in patent: Page/Page column 8

2
[ 100-70-9 ]
[ 1671-87-0 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 12, p. 2156 - 2166
[2] Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8468 - 8471
[3] Chemical Communications, 2012, vol. 48, # 12, p. 1736 - 1738
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14112 - 14116[5] Angew. Chem., 2013, vol. 125, # 52, p. 14362 - 14366,5
[6] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3950 - 3955
[7] Patent: US2016/106859, 2016, A1,

3
[ 1671-86-9 ]
[ 1671-87-0 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 12, p. 1736 - 1738
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14112 - 14116[3] Angew. Chem., 2013, vol. 125, # 52, p. 14362 - 14366,5
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3950 - 3955

4
[ 1671-86-9 ]
[ 1671-87-0 ]

Reference： [1] Patent: US2016/106859, 2016, A1, . Location in patent: Paragraph 0192; 0193
[2] Dalton Transactions, 2017, vol. 46, # 24, p. 7878 - 7887

5
[ 100-70-9 ]
[ 75-05-8 ]
[ 57537-63-0 ]
[ 1671-87-0 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 39, p. 13985 - 13998

6
[ 74222-83-6 ]
[ 65520-11-8 ]
[ 6830-78-0 ]
[ 1671-87-0 ]
[ 73720-51-1 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 15, p. 1393 - 1396

7
[ 1671-87-0 ]
[ 1676-81-9 ]
[ 36901-11-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 243 - 247[2] Angew. Chem., 2017, vol. 129, # 1, p. 249 - 253,5

[ 1671-87-0 ] Synthesis Path-Downstream 1~27

1
[ 1671-87-0 ]
[ 27584-70-9 ]
[ 65647-72-5 ]

Reference： [1]Tetrahedron Letters,1977,p. 3115 - 3118

2
[ 1671-87-0 ]
[ 91645-64-6 ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
49%	In toluene at 110℃; for 1h;

Reference： [1]Balogh, Maria; Laszlo, Pierre; Simon, Kalman [Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 2026 - 2029]

3
[ 1671-87-0 ]
[ 91645-64-6 ]
[ 107599-31-5 ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	In toluene at 110℃; for 1h;

Reference： [1]Balogh, Maria; Laszlo, Pierre; Simon, Kalman [Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 2026 - 2029]

4
[ 19081-87-9 ]
[ 1671-87-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With nitric acid; acetic acid In water at 0℃;	1 8.0 g (0.077 mole) of 2-cyanopyridine was dissolved in 200 ml of anhydrous ethanol, the solution was added into a three-neck flask, and 9.54 ml (0.308 mole) of 95% hydrazine hydrate was then added thereto. The mixture was refluxed for 6 hours to obtain 7.54 g (81.7% yield) of orange-colored dianhydride base. The base was filtered, washed several times with ethanol, dissolved in glacial acetic acid and cooled on an ice bath, and 5-6 ml of concentrated nitric acid was slowly added dropwise thereto. The mixture was poured over crushed ice, made basic with sodium bicarbonate and then extracted two times with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, thus obtaining 6.3 g (85% yield) of 3,6-bis(2'-pyridyl)-l,2,4,5-tetrazine as a purple solid. 6.3 g (0.027 mole) of the obtained 3,6-bis(2'-pyridyl)-l,2,4,5-tetrazine was dissolved in dimethyl- formamide (hereinafter, referred to as DMF), and the solution was added into a three- neck flask and refluxed with bubbling of acetylene. As the reaction progressed, the mixture was changed from a purple color to a clear color. DMF was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The resulting solid material was purified by silica gel column chromatography using ethylacetate: n- hexane (1:4, v/v)

Reference： [1]Current Patent Assignee: CHUNGNAM NATIONAL UNIVERSITY - WO2007/7943, 2007, A1 Location in patent: Page/Page column 8

5
copper(II) bis(tetrafluoroborate) [ No CAS ]
[ 19845-69-3 ]
[ 1671-87-0 ]
[ 12775-96-1 ]
(C₃₀H₃₂P₂)Cu(C₁₂H₈N₆)Cu(C₃₀H₃₂P₂)⁽¹⁺⁾*BF₄^(1-) = [(C₃₀H₃₂P₂)Cu(C₁₂H₈N₆)Cu(C₃₀H₃₂P₂)]BF₄ [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1999,p. 3855 - 3857

6
copper(II) bis(tetrafluoroborate) [ No CAS ]
[ 41625-30-3 ]
[ 1671-87-0 ]
copper [ No CAS ]
(C₃₂H₃₆P₂)Cu(C₁₂H₈N₆)Cu(C₃₂H₃₆P₂)⁽¹⁺⁾*BF₄^(1-) = [(C₃₂H₃₆P₂)Cu(C₁₂H₈N₆)Cu(C₃₂H₃₆P₂)]BF₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane

Reference： [1]Barra, Anne-Laure; Brunei, Louis-Claude; Baumann, Frank; Schwach, Manuela; Moscherosch, Michael; Kami, Wolfgang [Journal of the Chemical Society, Dalton Transactions, 1999, # 21, p. 3855 - 3857]

7
[ 766-99-4 ]
[ 1671-87-0 ]
[ 1031820-31-1 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 1597 - 1607

8
[ 931-89-5 ]
[ 1671-87-0 ]
[ 4277-34-3 ]
C₂₀H₂₂N₄ [ No CAS ]
(4aSR,7RS,10aSR)-1,4-di(pyridin-2-yl)-4a,5,6,7,8,9,10,10a-octahydrocycloocta[d]pyridazin-7-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 9646 - 9649

9
[ 1671-87-0 ]
[ 4277-34-3 ]
C₂₀H₂₂N₄O [ No CAS ]
(4aSR,7RS,10aSR)-1,4-di(pyridin-2-yl)-4a,5,6,7,8,9,10,10a-octahydrocycloocta[d]pyridazin-7-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 9646 - 9649

10
[ 1671-87-0 ]
[ 153286-94-3 ]
3,6-di(2-pyridyl)4-pyrimidylpyridazine [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 8206 - 8212

11
[ 1671-86-9 ]
[ 1671-87-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With acetic acid; sodium nitrite In water at 20℃;
	With sodium nitrite In acetic acid
	With acetic acid; sodium nitrite at 0℃;

Reference： [1]Chen, Weixuan; Wang, Danzhu; Dai, Chaofeng; Hamelberg, Donald; Wang, Binghe [Chemical Communications, 2012, vol. 48, # 12, p. 1736 - 1738]
[2]Versteegen, Ron M.; Rossin, Raffaella; Ten Hoeve, Wolter; Janssen, Henk M.; Robillard, Marc S. [Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14112 - 14116][Angew. Chem., 2013, vol. 125, # 52, p. 14362 - 14366,5]
[3]Wang, Danzhu; Chen, Weixuan; Zheng, Yueqin; Dai, Chaofeng; Wang, Ke; Ke, Bowen; Wang, Binghe [Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3950 - 3955]

12
[ 1671-87-0 ]
[ 104942-18-9 ]
[ 135-48-8 ]
[ 1370025-49-2 ]
[ 36901-11-8 ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	In dipentyl ether for 2h; Reflux;

Reference： [1]Location in patent: experimental part Bula, Rafael P.; Oppel, Iris M.; Bettinger, Holger F. [Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3538 - 3542]

13
[ 1671-87-0 ]
[ 104942-18-9 ]
[ 1370025-49-2 ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 13.1 mg	In 1,4-dioxane Reflux;

Reference： [1]Location in patent: experimental part Bula, Rafael P.; Oppel, Iris M.; Bettinger, Holger F. [Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3538 - 3542]

14
[ 1671-87-0 ]
[ 4277-34-3 ]
C₂₀H₂₂N₄O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 3365 - 3375

15
[ CAS Unavailable ]
[ 1671-87-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 5-vinyl-2'-deoxyuridine-5'-O-triphosphate sodium salt; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In 1,4-dioxane; water at 20℃; Stage #2: With triethylamine carbonate Stage #3: With sodium perchlorate In acetone	18 5-[3,6-di(pyridin-2-yl)pyridazine-4-yl]-2′-deoxyuridine-5′-O-triphosphate 7: The sodium salt of 5-vinyl-2′-deoxyuridine-5′-O-triphosphate 4 (500mg, 0.89mmol) and 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (254mg, 1.07mmol) were dissolved in dioxane/water mixture (2:1, 20mL) and stirred at room temperature overnight by keeping the reaction flask open to air. Upon reaction completion, the reaction mixture was evaporated to dryness under reduced pressure. The residue thus obtained was dissolved in water (50mL) and the aqueous solution was adjusted to pH 6.5 for loading on a DEAE Sepharose column. The desired product was eluted using a linear gradient of 0-1M triethylammonium bicarbonate (TEAB) and the fractions containing the product were pooled, evaporated, and co-evaporated with water (3×10mL). The triethylammonium salt of 7 thus obtained was subjected to ion-exchange with sodium perchlorate (1g) in acetone (20mL) for two times to afford the sodium salt of 5-[3,6-di(pyridin-2-yl)pyridazine-4-yl]-2′-deoxyuridine-5′-O-triphosphate 7 as solid (547mg, 80%). 1H NMR (D2O, 400MHz) δ (ppm) 8.81-8.82 (m, 1H), 8.62-8.63 (m, 1H), 8.53 (s, 1H), 8.37-8.39 (m, 1H), 8.08-8.13 (m, 2H), 7.91-7.93 (m, 1H), 7.77 (s, 1H), 7.57-7.61 (m, 2H), 6.24-6.28 (m, 1H), 6.25 (dd, J=9.6Hz, J=7.8Hz, 1H), 4.42-4.44 (m, 2H), 4.12-4.14 (m, 1H), 4.03-4.07 (m, 2H); 31P NMR (D2O, 162MHz) δ -7.03 (d, J=22.68Hz, 1P), -11.42 (d, J=19.44Hz, 1P), -22.47 (t, J=21.06Hz, 1P); MS (ESI, m/z): calcd for C23H23N6O14P3 [M-H]-: 699.2, found 699.2.

Reference： [1]Kore, Anilkumar R.; Yang, Bo; Srinivasan, Balasubramanian [Tetrahedron Letters, 2015, vol. 56, # 6, p. 808 - 811]

16
[ 1671-87-0 ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,2-diphenylacetic acid; triethylphosphine In acetonitrile; hexan-1-ol for 25h;

Reference： [1]Polezhaev, Alexander V.; Maciulis, Nicholas A.; Chen, Chun-Hsing; Pink, Maren; Lord, Richard L.; Caulton, Kenneth G. [Chemistry - A European Journal, 2016, vol. 22, # 39, p. 13985 - 13998]

17
[ CAS Unavailable ]
[ 7732-18-5 ]
[ 1671-87-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In tetrahydrofuran for 8h; Inert atmosphere; Schlenk technique; Stage #2: water With silver trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique; Darkness;	4.1 Synthesis of complex 1 General procedure: A mixture of [Cp IrCl2]2 (80.0mg, 0.1mmol), and L1 (23.6mg, 0.1mmol) in MeOH (10mL) was stirred for 8h, then AgOTf (51.2mg, 0.2mmol) was added to the solution and the reaction was stirred in the dark for 12h. The solution was concentrated to give a dark red solid, which was washed with diethyl ether and dried under vacuum. X-ray quality crystals for complex 1 were obtained by slow diffusion of diethyl ether into methanol. Yield: 99.3mg (91%).

Reference： [1]Lin, Lin; Fan, Qi-Jia; Jin, Guo-Xin [Journal of Organometallic Chemistry, 2017, vol. 829, p. 85 - 91]

18
[ 1671-87-0 ]
[ 2222-33-5 ]
1,4-di(pyridin-2-yl)-2,4a-dihydro-9H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazin-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In toluene at 120℃; for 10h; Sealed tube;	General procedure A: invers-Diels-Alder cycloaddition reactions betweendibenzosuberenone (1) and tetrazine derivatives General procedure: Dibenzosuberenone (1) or p-quinone metide 11 and tetrazine 2 were dissolved intoluene in an ACE pressure tube. The reaction mixture was head and stirred. At theend of the reaction, the red color of tetrazine disappeared. The mixture was cooled tort and some of the solvent was evaporated under reduced pressure. The precipitatedproduct was purified by crystallization or silica gel column chromatography to givedihydropyridazines.
94%	In toluene at 120℃; for 20h;	1,4-di(Pyridin-2-yl)-2,4a-dihydro-9H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazin-9-one (5) Dibenzosuberenone (1) (1.0 g, 4.85 mmol), and 3,6-di-2-pyridyl-1,2,4,5-tetrazine (DPT) (1.15 g, 4.85 mmol) were dissolved in toluene (6 mL) in an ACE pressure tube. The reaction mixture was stirred at 120 °C for 20 h. At the end of the reaction, the red color of DPT disappeared and the pale green color of 5 appeared. The mixture was cooled to RT and precipitated product was filtrated, washed with Et2O and recrystallized from n-hexane/CH2Cl2 (1:9) to give 5 (1.88 g, 94%). m.p. 276-278 °C (Uncorrected); 1H-NMR (400 MHz, CDCl3): δ= 9.36 (bs, 1H, -NH), 8.61 (s, 1H), 8.59 (d, J = 2.9 Hz, 1H), 8.43 (d, J = 4.7 Hz, 1H), 8.26 (d, J = 8.1 Hz, 1H), 8.01 (dd, J = 7.6 Hz, J = 1.1 Hz, 1H), 7.71 (dt, J = 7.8 Hz, J = 1.6 Hz, 1H), 7.44-7.12 (m, 8H), 7.02 (d, J = 8.0 Hz, 1H), 6.89 (d, J = 7.5 Hz, 1H), 5.82 (s, 1H).13C-NMR (100 MHz, CDCl3): δ= 192.9, 154.2, 151.1, 149.1, 148.9, 139.7, 139.5, 138.7, 138.1, 137.4, 136.1, 135.8, 132.8, 132.2, 132.1, 132.00, 131.98, 131.2, 127.5, 126.6, 126.1, 124.1, 123.4, 123.1, 120.7, 107.1, 39.8. HRMS (ESI-TOF): m/z: (M+Na)+ Calculated for [C27H18N4OH]+: m/z = 415.1553, found: 415.1550.

Reference： [1]Koçak, Ramazan; Dastan, Arif [Beilstein Journal of Organic Chemistry, 2021, vol. 17, p. 719 - 729]
[2]Koçak, Ramazan; Yıldız, Dilan; Bozkaya, Uğur; Daştan, Arif; Bozdemir, Özgür Altan [Tetrahedron Letters, 2017, vol. 58, # 30, p. 2981 - 2985]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃;

20
[ 87-44-5 ]
[ 1671-87-0 ]
(6aR,8aS)-4a,7,7-trimethyl-9-methylene-1,4-di(pyridin-2-yl)-4a,5,6, 6a,7,8,8a,9,10,11-decahydro-2H-cyclobuta[5,6]cyclonona[1,2-d]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In methanol; at 20℃; for 4h;	The compound 1beta-caryophyllene (33.7 mg, 0.165 mmol) was dissolved in a dry methanol solution (3 ml) and passed to it at room temperature.Tetrazine compound 2 (35.3 mg, 0.150 mmol) was added and the mixture was stirred at room temperature for four hours and the yellow color faded, indicating that the tetrazine starting material was consumed.After depletion, stirring was continued for 3 days in methanol solution. The solvent was suspended under reduced pressure and the residue was separated by column chromatography (dichloromethane:Methanol = 20:1, v/v) to give a pale yellow solid 63.9 mg, 96% yield.

Reference： [1]Patent: CN107746367,2018,A .Location in patent: Paragraph 0049; 0065; 0074; 0075; 0076

21
[ 1671-87-0 ]
[ 210574-45-1 ]
benzyl (1,4-di(pyridin-2-yl)-5,6,7,8-tetrahydrophthalazin-6-yl)carbamate [ No CAS ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 92% 2: 92%	In acetonitrile for 72h; Reflux; Inert atmosphere;

Reference： [1]Kocak, Ramazan; Dastan, Arif; Saracoglu, Nurullah [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 6, p. 1489 - 1493]

22
[ CAS Unavailable ]
[ 1671-87-0 ]
[ 1345667-94-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	In water; dimethyl sulfoxide at 20℃;
81%	With water In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere;	R34 Reaction 34 was performed by adding n-butyl isocyanide (77 mg, 0.93 mmol) to a solution of 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (110 mg, 0.47 mmol) in DMSO: H2O (10: 1, 2 mL) with stirring at room temperature for 2 h. The solution was left to stand at ambient temperature and subjected to a low stream of nitrogen gas until a precipitate formed. The precipitate was collected and dried to give 3,5-di(pyridine-2-yl)-1H-pyrazol-4-amine (DPPA; Structure 32) (90 mg, 81% yield) as golden crystals. 1H NMR (400 MHz, DMSO-d6) 5 13.16 (s, 1H), 8.60 (dd, Ji = 4.6 Hz, Ji = 9.2 Hz, 2H), 7.98 (d, J= 8.0 Hz, 1H), 7.89 - 7.76 (m, 3H), 7.27-7.17 (m, 2H), 6.01 (s, 2H). The 1H NMR data agreed with the reported spectrum of this compound.

Reference： [1]Tu, Julian; Xu, Minghao; Parvez, Saba; Peterson, Randall T.; Franzini, Raphael M. [Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8410 - 8414]
[2]Current Patent Assignee: UNIVERSITY OF UTAH - WO2019/232269, 2019, A1 Location in patent: Page/Page column 52

23
[ 1671-87-0 ]
[ 95-12-5 ]
C₂₀H₂₀N₄O [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2018,vol. 29,p. 3054 - 3059

24
[ 19209-60-0 ]
[ 1671-87-0 ]
1-(1,4-di(pyridin-2-yl)-9H-dibenzo[b,f]pyridazino[4,5-d]azepin-9-yl)ethan-1-one [ No CAS ]
[ 1671-86-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	In toluene at 140℃; for 15h; Sealed tube; Inert atmosphere;	General procedure B: Reaction of N-substituted dibenzoazepine derivatives 16-17 with tetrazines 18-19 and to yield diazin-dibenzoazepine derivates 36-39 General procedure: N-substituted dibenzoazepine derivatives 16-17 (1.000 mmol) and tetrazines 18-19 (1.100 mmol) were dissolved in solvent toluene in a sealed tube and the resulting reaction mixture was heated at the required temperature. The reaction was monitored by TLC. The resulting reaction mixture was then cooled to r.t and the solvent was removed under reduced pressure. The crude products were purified via column chromatography on silica gel without workup. Dimethyl 9-acetyl-9H-dibenzo[b,f]pyridazino[4,5-d]azepine-1,4-dicarboxylate (36) The reaction was carried out by the general procedure B using 1-(5H-dibenzo[b,f]azepin-5-yl)ethan-1-one 16 (0.100 g, 0.425 mmol), DET 18 (0.092 g, 0.467 mmol) and toluene (5 mL). The resulting reaction mixture was heated at 130 °C for 12 h. The residue was purified via column chromatography on silica gel (100 g) by eluting with 75% EtOAc/n-hekzane to give diazine-dibenzoazepine derivate 36, (0.085 g, 50%).

Reference： [1]Erdoğan, Musa; Daştan, Arif [Synthetic Communications, 2020, vol. 50, # 24, p. 3845 - 3853]

25
[ 298-46-4 ]
[ 1671-87-0 ]
[ 2513813-11-9 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 150℃; for 72h; Sealed tube; Inert atmosphere;	General procedure A: Reaction of N-substituted dibenzoazepine derivatives 1-2, 4-15 with tetrazines 18-19 (Step I): Oxidation of obtained the products with PIFA (Step II) General procedure: Step I: N-substituted dibenzoazepine derivatives 1-2 or 14-15 (1.000 mmol) and tetrazines 18-19 (1.100 mmol) were dissolved in toluene in a sealed tube and the resulting reaction mixture was heated at the required temperature. The reaction was monitored by TLC. The resulting reaction mixture was then cooled to r.t and the solid precipitated to the bottom of the thermolysis tube was washed with a 10 mL ether/n-hexane (4:1) mixture and dried under reduced pressure. The crude products were directly used for the next step (Step II) without workup or purification.

Reference： [1]Erdoğan, Musa; Daştan, Arif [Synthetic Communications, 2020, vol. 50, # 24, p. 3845 - 3853]

26
[ 498-66-8 ]
[ 1671-87-0 ]
[ 145846-80-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: norborn-2-ene; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In dichloromethane at 20℃; Inert atmosphere; Stage #2: With air In dichloromethane at 20℃; for 6h; UV-irradiation;	4.2 Optimization of the reaction conditions General procedure: A solution of tetrazine 5a (0.20 mmol, 47 mg) and norbornene (0.40 mmol, 38 mg) in the indicated solution (2 mL) was stirred at ambient temperature until the disappearance of 5a. Then, the mixture was irradiated with light for the indicated time period. After consumption of the dihydropyridazine intermediates, the solvent was removed under reduced pressure (DMSO was removed by partitioning the mixture between diethyl ether and water layers). The residue was purified by column chromatography (silica gel, chloroform/methanol, 100:0 to 100:1) to furnish pyridazine 2a as yellow powder. The spectral data for 2a coincided with the previous report [23]. Spectral data for unreacted 1,4-dihydropyridazine 4a and the by-product diketone 6a are as follows.

Reference： [1]Karaki, Fumika; Kiguchi, Takuto; Itoh, Kennosuke; Sato, Noriko; Konishi, Kazuhide; Fujii, Hideaki [Tetrahedron, 2021, vol. 97]

27
[ CAS Unavailable ]
[ 1671-87-0 ]
[ 1610626-87-3 ]

Yield	Reaction Conditions	Operation in experiment
77.6%	Stage #1: (E)-cyclooctene; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With air In dichloromethane at 20℃; for 5h; UV-irradiation;	4.3.1 Method a (photoirradiation was initiated after completion of the iEDDA reaction) General procedure: A solution of tetrazine (0.20 mmol) and norbornene or trans-cyclooctene (0.40 mmol) in dichloromethane (2 mL) was stirred at ambient temperature under an argon atmosphere until the disappearance of the tetrazine. Then, the mixture was irradiated with 365 nm LED under air at ambient temperature. After consumption of the dihydropyridazine intermediates, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography as indicated below.

Reference： [1]Karaki, Fumika; Kiguchi, Takuto; Itoh, Kennosuke; Sato, Noriko; Konishi, Kazuhide; Fujii, Hideaki [Tetrahedron, 2021, vol. 97]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 1671-87-0 ] Synthesis Path-Upstream 1~7

[ 1671-87-0 ] Synthesis Path-Downstream 1~27

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