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121207-31-6

Basic Information
CAS No.: 121207-31-6
Name: 4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE
Article Data: 27
Molecular Structure:
Molecular Structure of 121207-31-6 (4,4-DIFLUORO-1,3,5,7,8-PENTAMETHYL-4-BORA-3A,4A-DIAZA-S-INDACENE)
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
Synthetic route
1414345-95-1

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

594-27-4

tetramethylstannane

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 5h; Stille Cross Coupling; Inert atmosphere; Reflux;97%
625-82-1

2,4-dimethyl-1H-pyrrole

109-63-7

trifluoroborane diethyl ether

75-36-5

acetyl chloride

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
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%
625-82-1

2,4-dimethyl-1H-pyrrole

109-63-7

boron trifluoride diethyl etherate

75-36-5

acetyl chloride

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
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 dichloromethane68%
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%
109-63-7

boron trifluoride diethyl etherate

4,4-diethyl-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.25h;70%
1031443-55-6

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

544-97-8

dimethyl zinc(II)

A

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

B

F2BN(C(CH3))3CC(CH3)C(C(CH3))3N

Conditions
ConditionsYield
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%
625-82-1

2,4-dimethyl-1H-pyrrole

109-63-7

boron trifluoride diethyl etherate

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
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%
625-82-1

2,4-dimethyl-1H-pyrrole

75-36-5

acetyl chloride

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
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;

(CH3C(C4HN(CH3)2)2)BF(NC5H4N(CH3)2)(1+)*CF3SO3(1-)*H2O=[((CH3)5C9H2N2)BF(NC5H4N(CH3)2)]CF3SO3*H2O

429-41-4

tetrabutyl ammonium fluoride

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
In chloroform-d1 detected by NMR;
130876-46-9

3,5,3',5',6-pentamethyldipyrrin hydrochloride

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
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
1380420-29-0

C14H17BF(18)FN2

121207-31-6

4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

Conditions
ConditionsYield
Heating;
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