[ CAS No. 121207-31-6 ] {[proInfo.proName]}

Name: 121207-31-6|5,5-Difluoro-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide|99%
Brand: Ambeed
SKU: A411914
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Quality Control of [ 121207-31-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 121207-31-6 ]

Product Details of [ 121207-31-6 ]

CAS No. :	121207-31-6	MDL No. :	MFCD00467372
Formula :	C₁₄H₁₇BF₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DRJHPEGNOPSARR-UHFFFAOYSA-N
M.W :	262.11	Pubchem ID :	14766991
Synonyms :	Pyrromethene 546;BDP 493/503 lipid stain;Bodipy495	Chemical Name :	5,5-Difluoro-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide

Safety of [ 121207-31-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 121207-31-6 ]

* 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 [ 121207-31-6 ]

[ 121207-31-6 ] Synthesis Path-Downstream 1~88

1
[ 1122-58-3 ]
[ 27607-77-8 ]
[ 121207-31-6 ]
(CH₃C(C₄HN(CH₃)2)2)BF(NC₅H₄N(CH₃)2)⁽¹⁺⁾*CF₃SO₃^(1-)*H₂O=[((CH₃)5C₉H₂N₂)BF(NC₅H₄N(CH₃)2)]CF₃SO₃*H₂O [ No CAS ]

Reference： [1]Chemical Communications,2008,p. 4596 - 4597

2
[ 27607-77-8 ]
[ 121207-31-6 ]
[ 1082830-07-6 ]

Reference： [1]Chemical Communications,2008,p. 4596 - 4597
[2]Chemical Communications,2008,p. 4596 - 4597
[3]Chemical Communications,2008,p. 4596 - 4597
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 4603 - 4606
[5]Angewandte Chemie - International Edition,2012,vol. 51,p. 4603 - 4606

3
[ 121207-31-6 ]
[ 1031443-53-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-iodo-succinimide; In dichloromethane; at 20℃;Inert atmosphere;	In a 50 ml two-necked flask, 393.2 mg (1.5 mmol) of compound 1,338 mg of iodosuccinimide (1.5 mmol) was added, and 20 ml of dichloromethane was stirred to react at room temperature.The reaction was detected by TLC. The ethyl acetate of petroleum ether was passed through the column.419 mg of red solid was obtained,The yield was 72%.

Reference： [1]Organic Letters,2008,vol. 10,p. 2183 - 2186
[2]Patent: CN110776525,2020,A .Location in patent: Paragraph 0038; 0043-0045
[3]Journal of Materials Chemistry C,2013,vol. 1,p. 2249 - 2256
[4]ChemPhysChem,2016,vol. 17,p. 433 - 442

4
[ 121207-31-6 ]
[ 1031443-53-4 ]
[ 1031443-55-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3756 - 3760
[2]Organic Letters,2008,vol. 10,p. 2183 - 2186
[3]Journal of Physical Chemistry B,2019,vol. 123,p. 5601 - 5607

5
[ 1122-58-3 ]
[ 27607-77-8 ]
[ 121207-31-6 ]
4-fluoro-4-dimethylaminopyridine-1,3,5,7,9-pentamethyl-3a,4a-diaza-4-bora-s-indacene triflate [ No CAS ]

Reference： [1]Chemical Communications,2008,p. 4596 - 4597
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 4603 - 4606
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 4603 - 4606

6
[ 1259292-34-6 ]
[ 121207-31-6 ]
[ 1259292-43-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 438 - 441

7
[ 121207-31-6 ]
[ 1268614-83-0 ]
[ 1268614-84-1 ]
[ 1312700-10-9 ]
[ 1312700-16-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1916 - 1919

8
[ 7790-99-0 ]
[ 121207-31-6 ]
[ 1031443-53-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4996 - 4999

9
[ 33513-42-7 ]
[ 121207-31-6 ]
[ 198149-19-8 ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 696 - 700
[2]Angewandte Chemie - International Edition,2021,vol. 60,p. 5168 - 5172
Angew. Chem.,2021,vol. 133,p. 5228 - 5232,5
[3]Supramolecular Chemistry,2019,vol. 31,p. 695 - 702

10
[ 625-82-1 ]
[ 75-36-5 ]
[ 121207-31-6 ]

Yield	Reaction Conditions	Operation in experiment
40%		Add 1ml acetyl chloride, 3mL 2,4-dimethylpyrrole, 100ml dichloromethane to a 250ml three-necked flask, and stir the reaction at room temperature under the protection of light and nitrogen. The reaction is detected by TLC, and 6ml triethylamine is added. Add 9 ml of boron trifluoride ether complex, and the reaction was detected by TLC. The mixture was cooled to room temperature.Petroleum ether ethyl acetate was passed through a column to obtain 1.5 g of a red solid.Yield 40%.

Reference： [1]Patent: CN110776525,2020,A .Location in patent: Paragraph 0038-0042
[2]New Journal of Chemistry,2012,vol. 36,p. 1457 - 1462
[3]Chemical Communications,2012,vol. 48,p. 8913 - 8915

11
[ 121207-31-6 ]
[ 1031443-55-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-iodo-succinimide; choline chloride; at 25℃; for 0.25h;Green chemistry;	General procedure: A mixture of the BODIPY 1 (0.2 mmol) and either NBS or NIS (0.48 mmol) in ChCl/HFIP (2 mL) was stirred at room temperature for a certain time (usually <30 min) according to the TLC (EtOAc/petroleum, 1:5). After reaction, the mixture was extracted with CH2Cl2, washed with H2O, dried over Na2SO4, and concentrated under reduced pressure. The crude product was further purified using column chromatography (EtOAc/petroleum ether or CH2Cl2/hexane) to afford either the bromo-products 2 or the iodo-products 3. The ChCl/HFIP, which was insoluble in CH2Cl2, was readily recovered by evaporation of the water and reused for the next run. All the products were known compounds and were characterized by comparison with authentic samples.
72%	With iodine; iodic acid; In ethanol; water; at 25℃; for 2.33h;	Compound 3: 14 2,6-diiodo-<strong>[121207-31-6]1,3,5,7,8-pentamethyl-pyrromethene fluoroborate</strong> (I2C-CH3) (0167) (0168) 15 Iodic acid (2.0 equiv) dissolved in a minimum amount of 16 water was added dropwise over 20 min to a solution of 17 1 (1.0 equiv) and 18 iodine (2.5 eq.) in 6 ml of 19 EtOH. This mixture was then warmed for 2 hours at 25 C. After cooling, the mixture was evaporated under reduced pressure. The crude product was purified by silica gel chromatography using 10% ethyl acetate/hexane as the eluent and recrystallized from chloroform and n-hexane to afford I2B-OAc as bright red needles (yield 72%). 1H NMR (CDCl3, 400 MHz) δ ppm 2.67 (s, 3H), 2.64 (s, 6H), 2.50 (s, 6H); 13C NMR (CDCl3, 126 MHz): δ ppm 155.04, 142.91, 141.10, 132.13, 122.39, 19.82, 17.86, 16.01; HRMS (ESI) for C16H17BI2F2N2O2Na (M++Na) calcd 536.9287. found 536.9453.

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3756 - 3760
[2]RSC Advances,2013,vol. 3,p. 9219 - 9222
[3]Dyes and Pigments,2015,vol. 112,p. 274 - 279
[4]Chemistry - A European Journal,2014,vol. 20,p. 10669 - 10678
[5]Journal of the American Chemical Society,2016,vol. 138,p. 1215 - 1225
[6]Patent: US2017/197993,2017,A1 .Location in patent: Paragraph 0167; 0168
[7]Chemical Communications,2012,vol. 48,p. 8913 - 8915
[8]Chemistry - A European Journal,2016,vol. 22,p. 15772 - 15777
[9]Inorganic Chemistry Communications,2013,vol. 35,p. 355 - 359
[10]ChemPhysChem,2016,vol. 17,p. 433 - 442
[11]Chemistry - A European Journal,2017,vol. 23,p. 1379 - 1385

12
[ 121207-31-6 ]
[ 1426145-08-5 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6335 - 6350

13
[ 121207-31-6 ]
[ 1426145-09-6 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 6335 - 6350

14
[ 625-82-1 ]
[ 109-63-7 ]
[ 75-36-5 ]
[ 121207-31-6 ]

Yield	Reaction Conditions	Operation in experiment
45%		A 1L round bottom flask under a nitrogen atmosphere charged with 2,4-dimethyl-pyrrole 15.0 g (158 mmol), acetyl chloride 6.2 g (79mmol) and dichloromethane (DCM) 450 ml were added and stirred at room temperature for 24 hours. Then, triethylamine (TEA) 55 ml, boron trifluoride diethyl ether (BF3OEt2) 55 ml was added and stirred for 4 hours at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give red solid of intermediate (1) 9.4 g of a (yield: 45%).

Reference： [1]Dalton Transactions,2019,vol. 48,p. 8488 - 8501
[2]Chemical Communications,2021,vol. 57,p. 1818 - 1821
[3]Journal of Materials Chemistry C,2013,vol. 1,p. 2249 - 2256
[4]Patent: KR2015/131807,2015,A .Location in patent: Paragraph 0074-0077
[5]Chemistry - A European Journal,2016,vol. 22,p. 15772 - 15777
[6]New Journal of Chemistry,2020,vol. 44,p. 14650 - 14661
[7]Chemistry - A European Journal,2020,vol. 26,p. 863 - 872
[8]Chemistry - A European Journal,2012,vol. 18,p. 14957 - 14961
[9]Chemistry - A European Journal,2014,vol. 20,p. 10669 - 10678
[10]European Journal of Organic Chemistry,2017,vol. 2017,p. 2170 - 2178
[11]ChemPlusChem,2021,vol. 86,p. 87 - 94
[12]Journal of Materials Chemistry C,2019,vol. 7,p. 3471 - 3478
[13]New Journal of Chemistry,2017,vol. 41,p. 2296 - 2308
[14]Journal of Physical Chemistry B,2019,vol. 123,p. 5601 - 5607

15
[ 7782-68-5 ]
[ 121207-31-6 ]
[ 1031443-55-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14957 - 14961

16
[ 121207-31-6 ]
[ 134382-52-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide; choline chloride; at 25℃;Green chemistry;	General procedure: A mixture of the BODIPY 1 (0.2 mmol) and either NBS or NIS (0.48 mmol) in ChCl/HFIP (2 mL) was stirred at room temperature for a certain time (usually <30 min) according to the TLC (EtOAc/petroleum, 1:5). After reaction, the mixture was extracted with CH2Cl2, washed with H2O, dried over Na2SO4, and concentrated under reduced pressure. The crude product was further purified using column chromatography (EtOAc/petroleum ether or CH2Cl2/hexane) to afford either the bromo-products 2 or the iodo-products 3. The ChCl/HFIP, which was insoluble in CH2Cl2, was readily recovered by evaporation of the water and reused for the next run. All the products were known compounds and were characterized by comparison with authentic samples.
88%	With bromine; In dichloromethane; at 20℃; for 3h;Inert atmosphere;	Compound 4: 2, 22 6-dibromo-<strong>[121207-31-6]1,3,5,7,8-pentamethyl-pyrromethene fluoroborate</strong> (Br2C-CH3) (0169) (0170) To 17 1 (1 equiv) in 40 mL of dry 23 CH2Cl2 was added dropwise liquid 24 bromine (3 equiv) in CH2Cl2 (5 mL) over a period of 1 h. The mixture was left stirring for an additional 2 h under Ar at room temperature, washed with an aqueous solution of 25 sodium thiosulfate, and extracted with CH2Cl2. Organic layers were combined, dried over Na2SO4, and evaporated to dryness. Purification was performed by column chromatography on silica gel using 10% 26 ethyl acetate/27 hexane as eluent, from which the desired product Br2B-OAc was obtained as red solid in 88% yield. 1H NMR (CDCl3, 400 MHz) δ ppm 2.67 (s, 3H), 2.60 (s, 6H), 2.47 (s, 6H); 13C NMR (CDCl3, 126 MHz): δ ppm 152.23, 141.28, 138.27, 131.05, 124.22, 17.34, 16.40, 13.61; HRMS (ESI) for C14H15BBr2F2N2Na (M++Na) calcd 442.8921. found 442.9235.

Reference： [1]RSC Advances,2013,vol. 3,p. 9219 - 9222
[2]Dyes and Pigments,2015,vol. 112,p. 274 - 279
[3]Journal of the American Chemical Society,2016,vol. 138,p. 1215 - 1225
[4]Patent: US2017/197993,2017,A1 .Location in patent: Paragraph 0169; 0170

17
[ 122-85-0 ]
[ 121207-31-6 ]
[ 1449105-35-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4454 - 4457

18
[ 105-07-7 ]
[ 121207-31-6 ]
[ 1449105-36-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4454 - 4457

19
[ 555-16-8 ]
[ 121207-31-6 ]
[ 1449105-37-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4454 - 4457

20
[ 123-11-5 ]
[ 121207-31-6 ]
[ 1449105-38-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4454 - 4457

21
[ 123-11-5 ]
[ 121207-31-6 ]
[ 1449105-47-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4454 - 4457

22
[ 121207-31-6 ]
4-ethynylpyridine hydrochloride [ No CAS ]
C₂₈H₂₅BN₄ [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1362 - 1365

23
[ 1066-54-2 ]
[ 121207-31-6 ]
4,4-bis(trimethylsilylethynyl)-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2646 - 2653

24
[ 1414345-95-1 ]
[ 594-27-4 ]
[ 121207-31-6 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 5064 - 5074

25
[ 96-10-6 ]
[ 121207-31-6 ]
4,4-diethyl-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 10981 - 10987

26
[ 79-22-1 ]
[ 121207-31-6 ]
C₁₆H₁₉BF₂N₂O₂ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4364 - 4367

27
[ 33513-42-7 ]
[ 121207-31-6 ]
C₁₆H₂₂BF₂N₃ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4364 - 4367

28
[ 1147550-11-5 ]
[ 121207-31-6 ]
5,5-difluoro-1,3,7,9,10-pentamethyl-2-thiocyanato-5H-5λ⁴,6λ⁴-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6031 - 6038

29
[ 1147550-11-5 ]
[ 121207-31-6 ]
5,5-difluoro-1,3,7,9,10-pentamethyl-2-thiocyanato-5H-5λ⁴,6λ⁴-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinine [ No CAS ]
5,5-difluoro-1,3,7,9,10-pentamethyl-2,8-dithiocyanato-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6031 - 6038
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6031 - 6038

30
[ 75-75-2 ]
[ 121207-31-6 ]
(2Z)-2-[1-(3,5-dimethyl-1H-pyrrol-2-yl)ethylidene]-3,5-di-methyl-2H-pyrrolium methanesulfonate [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 68676 - 68680

31
4NO₃^(1-)*4C₅₃H₄₆N₂O₆*2Pt⁽²⁺⁾ [ No CAS ]
[ 121207-31-6 ]
4NO₃^(1-)*C₁₄H₁₇BF₂N₂*4C₅₃H₄₆N₂O₆*2Pt⁽²⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9266 - 9269

32
[ 121207-31-6 ]
2,4,4-trifluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]ChemPhysChem,2016,vol. 17,p. 433 - 442
[2]ChemPhysChem,2016,vol. 17,p. 433 - 442

33
[ 121207-31-6 ]
2-bromo-5,5-difluoro-1,3,7,9,10-pentamethyl-5H-5λ⁴,6λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 5168 - 5172
Angew. Chem.,2021,vol. 133,p. 5228 - 5232,5
[2]ChemPhysChem,2016,vol. 17,p. 433 - 442

34
[ 1031443-55-6 ]
[ 544-97-8 ]
[ 121207-31-6 ]
F₂BN(C(CH₃))3CC(CH₃)C(C(CH₃))3N [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 3700 - 3710

35
[ 141-82-2 ]
[ 121207-31-6 ]
C₁₇H₁₉BN₂O₄ [ No CAS ]

Reference： [1]Advanced Functional Materials,2016,vol. 26,p. 2756 - 2769

36
[ 112-54-9 ]
[ 121207-31-6 ]
2,6-di((E)-docen-1-enyl)-1,3,5,7,8-pentamethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
2-((E)-docen-1-enyl)-1,3,5,7,8-pentamethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
6,6’-(dodecane-1,1-diyl)bis-(2-((E)-docen-1-enyl)-1,3,5,7,8-pentamethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 10320 - 10325

37
[ 98-29-3 ]
[ 121207-31-6 ]
C₂₄H₂₉BN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Intermediate (1) obtained in the above example (1) step (1) 1.3 g(5 mmol) and aluminum chloride (AlCl3) 1.3 g(10 mmol) were added in 100 ml of dichloromethane was stirred for 5 minutes at room temperature, 4-tert- butylcatechol 4.2 g (25 mmol) was added and the mixture was stirred for 30 minutes at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give an orange solid of compound 1b 1.7 g (Yield: 87%).

Reference： [1]Patent: KR2015/131807,2015,A .Location in patent: Paragraph 0081-0083

38
[ 92-44-4 ]
[ 121207-31-6 ]
C₂₄H₂₃BN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		Intermediate (1) obtained in the above example (1) step (1) 1.3 g(5 mmol) and aluminum chloride (AlCl3) 1.3 g(10 mmol) were added in 100 ml of dichloromethane was stirred for 5 minutes at room temperature, 2,3-dihydroxy-naphthalene 4.0 g (25 mmol) was added and the mixture was stirred for 30 minutes at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give an orange solid of compound 1c 1.5 g (Yield: 77%).

Reference： [1]Patent: KR2015/131807,2015,A .Location in patent: Paragraph 0084-0086

39
[ 120-80-9 ]
[ 121207-31-6 ]
C₂₀H₂₁BN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		Intermediate (1) obtained in the above step (1) 1.3 g(5 mmol) and aluminum chloride (AlCl3) 1.3 g(10 mmol) were added in 100 ml of dichloromethane was stirred for 5 minutes at room temperature, 1,2-dihydroxy-benzene 2.8 g (25 mmol) was added and the mixture was stirred for 30 minutes at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give an orange solid of compound 1a 1.4 g (Yield: 83%).

Reference： [1]Patent: KR2015/131807,2015,A .Location in patent: Paragraph 0074; 0078-0080

40
[ 75-09-2 ]
[ 124-40-3 ]
[ 121207-31-6 ]
C₁₇H₂₄BF₂N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.1%	In tetrahydrofuran; for 72h;Reflux;	Compound 3 (82.0 mg, 0.314 mmol)Was dissolved in 3 mL of deionized dichloromethane,Followed by addition of dimethylamine(3.14 mL, 2M solution in THF, 6.28 mmol). The reaction solution was refluxed under nitrogen for 3 days with stirringDiluted with dichloromethane, and washed with saturated aqueous ammonium chloride and brine to give the crude product. Purification of the intermediate 4 by column chromatography(60.0 mg, 60.1%).

Reference： [1]Patent: CN105503921,2016,A .Location in patent: Paragraph 0106; 0107; 0108

41
[ 33513-42-7 ]
[ 121207-31-6 ]
[ 198149-19-8 ]
C₁₉H₂₂BF₂N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%; 60%		A mixture of DMF (100-150 equiv.) and POCl3(50-100 equiv.) was stirred at 0 C under argon atmosphere for 5 min, allowed to warm up to r.t., and stirred for further 30 mim.Then, a solution of the corresponding BODIPY (1 equiv.) in 1,2-dichloroethane (DCE; 20 mL) was added over, and the resulting mixture warmed up to 60 C and stirred for further 30-500 min. Finally, the solution was cooled down to r.t., and carefully treated with cooled (0 C) saturated aq. NaHCO3. The resulting mixture was extracted with CH2Cl2, and the obtained solution washed with H2O, dried over MgSO4, filtered and concentrated to dryness. The obtained crude product was purified by flash chromatography on silica gel.
60%; 10%		A mixture of DMF (100-150 equiv.) and POCl3(50-100 equiv.) was stirred at 0 C under argon atmosphere for 5 min, allowed to warm up to r.t., and stirred for further 30 mim.Then, a solution of the corresponding BODIPY (1 equiv.) in 1,2-dichloroethane (DCE; 20 mL) was added over, and the resulting mixture warmed up to 60 C and stirred for further 30-500 min. Finally, the solution was cooled down to r.t., and carefully treated with cooled (0 C) saturated aq. NaHCO3. The resulting mixture was extracted with CH2Cl2, and the obtained solution washed with H2O, dried over MgSO4, filtered and concentrated to dryness. The obtained crude product was purified by flash chromatography on silica gel.

Reference： [1]Dyes and Pigments,2017,vol. 141,p. 286 - 298
[2]Dyes and Pigments,2017,vol. 141,p. 286 - 298

42
[ 33513-42-7 ]
[ 121207-31-6 ]
C₁₇H₂₂BF₂N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With acetic anhydride; In N,N-dimethyl acetamide; for 3h;	BODIPY 4a (50 mg, 0.19 mmol) and DMF-DMA (0.5 mL, 3.8 mmol) in Ac2O (3 mL) were reacted for 3 h. Flash chromatography, by using neutral activated aluminium oxide and hexane/EtOAc (95:5), afforded 7a (38 mg, 63%) as a red solid; mp: 168-169 C. 7a: 1H NMR (700 MHz, CDCl3) δ 6.83 (d, J 11.9 Hz, 1H, CH ),5.93 (s, 2H, 2CH), 5.56 (d, J 11.9 Hz, 1H, CH ), 3.01 (s, 6H,(CH3)2N), 2.44 (s, 6H, 2CH3), 2.19 (s, 6H, 2CH3) ppm. 13C NMR(176 MHz CDCl3) δ 155.1 (CH), 147.6, 146.3, 135.1, 129.4, 118.9 (CH),93.9 (CH), 41.1 (CH3N), 17.1 (CH3), 14.3 (CH3) ppm. FTIR ν 2920, 1610,1554, 1477, 1460, 1365, 1254, 1157, 978 cm-1. HRMS-EI (m/z) M+ 317.1873 (calcd for C17H22BF2N3: 317.1875).

Reference： [1]Dyes and Pigments,2017,vol. 141,p. 286 - 298

43
[ 104-92-7 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-((4-methoxyphenyl)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

44
[ 623-00-7 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-((4-cyanophenyl)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

45
[ 1122-91-4 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-((4-aldehydephenyl)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

46
[ 19524-06-2 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-(4-pyridinemethyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

47
[ 402-43-7 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-((4-trifluoromethylphenyl)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

48
[ 2367-76-2 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-((1,3,5-trifluorophenyl)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

49
[ 16518-62-0 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-(3-(N,N-dimethylaniline)methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

50
[ 108-86-1 ]
[ 121207-31-6 ]
1,3,5,7-tetramethyl-8-phenylmethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 4687 - 4699

51
[ 121207-31-6 ]
[ 609-09-6 ]
C₂₁H₂₇BF₂N₂O₅ [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2090 - 2093

52
[ 516-12-1 ]
[ 121207-31-6 ]
[ 1031443-55-6 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 2296 - 2308
[2]ChemPlusChem,2021,vol. 86,p. 87 - 94

53
[ 7553-56-2 ]
[ 121207-31-6 ]
[ 1031443-55-6 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 2170 - 2178

54
[ 121207-31-6 ]
4,4-difluoro-1,3,5,7,8-pentamethyl-2-nitro-4-bora-3a,4adiaza-s-indecene [ No CAS ]

Reference： [1]Photochemical and Photobiological Sciences,2017,vol. 16,p. 499 - 506

55
3-(6-methyl-1,2,4,5-tetrazin-3-yl)propan-1-ol [ No CAS ]
[ 121207-31-6 ]
C₂₀H₂₆BFN₆O [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

56
C₇H₁₂N₄O [ No CAS ]
[ 121207-31-6 ]
C₂₁H₂₈BFN₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: A preparation method of a fluoroboron fluoran-tetrazine bioorthogonal probe, the reaction structure is as follows,As shown in Figure 18, the specific operation method is: 5 mmol of TMSOTf was added to 9 ml of an anhydrous acetonitrile solution containing 1 mmol of BODIPY1-2, and the reaction was stirred at 0 C for 30 min to activate BODIPY1-2.4mmol t-BuOH was added and then quenched with TMSOTf,5 mmol of 2,6-lutidine and 5 mmol of tetrazine Tza-Tzg mixed anhydrous acetonitrile solution were quickly added, and the reaction was further stirred at 0 C for 10 min.The reaction was quenched with water and the reaction product was extracted with DCM.The organic phase was dried over anhydrous sodium sulfate and dried.The fluoroboron fluoran-tetrazine bioorthogonal probe is separated by separating the silica gel column.The reaction equation and yield are as follows.

Reference： [1]Patent: CN108997402,2018,A .Location in patent: Paragraph 0041-0044; 0090-0094
[2]ChemBioChem,2018,vol. 19,p. 530 - 534

57
C₈H₁₄N₄O [ No CAS ]
[ 121207-31-6 ]
C₂₂H₃₀BFN₆O [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

58
C₁₂H₂₂N₄O [ No CAS ]
[ 121207-31-6 ]
C₂₆H₃₈BFN₆O [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

59
C₁₂H₂₁N₅O₃ [ No CAS ]
[ 121207-31-6 ]
C₂₆H₃₇BFN₇O₃ [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

60
C₁₀H₁₁N₅O [ No CAS ]
[ 121207-31-6 ]
C₂₄H₂₇BFN₇O [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

61
C₇H₁₂N₄O₂ [ No CAS ]
[ 121207-31-6 ]
C₂₁H₂₈BFN₆O₂ [ No CAS ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 530 - 534

62
[ 1204518-02-4 ]
[ 121207-31-6 ]
[ 1268614-82-9 ]
5,5-difluoro-1,3,7,9,10-pentamethyl-2,8-di-p-tolyl-5H-4^λ,5^λ-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine [ No CAS ]