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CAS No.: | 121207-31-6 |
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Name: | 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C14H17 B F2 N2 |
Molecular Weight: | 262.11 |
Synonyms: | Boron,[2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,5-dimethyl-1H-pyrrolato-N1,N2]difluoro-,(T-4)-; 1H-Pyrrole,2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene)ethyl]-3,5-dimethyl-, boron complex;4,4-Difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene; BODIPY493/503; PM 546; PMPBF2; Pyrromethene 546 |
Melting Point: | 257°C(lit.) |
PSA: | 13.32000 |
LogP: | 2.82650 |
10-chloro-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
tetramethylstannane
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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With tetrakis(triphenylphosphine) palladium(0) In toluene for 5h; Stille Cross Coupling; Inert atmosphere; Reflux; | 97% |
2,4-dimethyl-1H-pyrrole
trifluoroborane diethyl ether
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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With N(CH2CH3)3 In dichloromethane addn. of acetyl chloride to pyrrole deriv. in CH2Cl2 at room temp. over 30 min, refluxing for 1 h, cooling, addn. to hexane, evapn., dissolving in CH2Cl2, addn. of amine deriv., stirring for 10 min at room temp., addn. of boron compd., stirring for 1 h; washing with aq. satd. soln. of Na2CO3, drying over Na2SO4, evapn., chromy. (silica, n-pentane/CH2Cl2 (1:1)), evapn., recrystn. (CH2Cl2/methanol), NMR and MS; | 72% |
2,4-dimethyl-1H-pyrrole
boron trifluoride diethyl etherate
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane at 20℃; for 1.5h; Stage #2: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 20℃; for 1h; | 70% |
With triethylamine In dichloromethane | 68% |
Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane for 1.5h; Inert atmosphere; Reflux; Stage #2: With triethylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #3: boron trifluoride diethyl etherate In dichloromethane for 18h; Inert atmosphere; | 60% |
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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In dichloromethane at 25℃; for 0.25h; | 70% |
5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
dimethyl zinc(II)
A
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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With bis-triphenylphosphine-palladium(II) chloride In toluene at 20℃; for 0.666667h; Negishi Coupling; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | A 9% B 69% |
2,4-dimethyl-1H-pyrrole
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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Stage #1: 2,4-dimethyl-1H-pyrrole With acetyl chloride In dichloromethane at 20 - 50℃; for 1h; Stage #2: With triethylamine In hexane; dichloromethane at 20℃; for 0.166667h; Stage #3: boron trifluoride diethyl etherate In hexane; dichloromethane for 1h; | 58% |
2,4-dimethyl-1H-pyrrole
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane at 20℃; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate; triethylamine In dichloromethane | 40% |
With boron trifluoride diethyl etherate; triethylamine In dichloromethane | |
With boron trifluoride diethyl etherate; triethylamine In dichloromethane Inert atmosphere; |
tetrabutyl ammonium fluoride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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In chloroform-d1 detected by NMR; |
3,5,3',5',6-pentamethyldipyrrin hydrochloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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Stage #1: 3,5,3',5',6-pentamethyldipyrrin hydrochloride With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; | 4.924 g |
C14H17BF(18)FN2
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
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Heating; |