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121207-31-6

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  • Boron,[2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene-kN)ethyl]-3,5-dimethyl-1H-pyrrolato-kN]difluoro-, (T-4)- 121207-31-6

    Cas No: 121207-31-6

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121207-31-6 Usage

Uses

Pyrromethene 546 is a hydrophobic compound that adsorbed strongly to the PDMS (poly(dimethylsiloxane)), indicating the hydrophobicity of the channel walls is clearly problematic for CZE analysis of hydrophobic analytes.

General Description

Difluoro{2-(1-(3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl)-3,5-dimethyl-1H-pyrrolato-N}boron is an organoboron composed of dipyrromethene with a boron in the center. It is a fluorescent dye with a high quantum yield and an ability to absorb small molecules with sharp peaks in the ultraviolet region.

Check Digit Verification of cas no

The CAS Registry Mumber 121207-31-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,2,0 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 121207-31:
(8*1)+(7*2)+(6*1)+(5*2)+(4*0)+(3*7)+(2*3)+(1*1)=66
66 % 10 = 6
So 121207-31-6 is a valid CAS Registry Number.

121207-31-6 Well-known Company Product Price

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  • Aldrich

  • (790389)  Difluoro{2-[1-(3,5-dimethyl-2H-pyrrol-2-ylidene-N)ethyl]-3,5-dimethyl-1H-pyrrolato-N}boron  99% (HPLC)

  • 121207-31-6

  • 790389-500MG

  • 1,559.61CNY

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121207-31-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4-Difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene

1.2 Other means of identification

Product number -
Other names Pyrromethene 546

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121207-31-6 SDS

121207-31-6Synthetic route

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
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

tetramethylstannane
594-27-4

tetramethylstannane

4,4-difluoro-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
With tetrakis(triphenylphosphine) palladium(0) In toluene for 5h; Stille Cross Coupling; Inert atmosphere; Reflux;97%
2,4-dimethyl-1H-pyrrole
625-82-1

2,4-dimethyl-1H-pyrrole

trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

acetyl chloride
75-36-5

acetyl chloride

4,4-difluoro-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
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
625-82-1

2,4-dimethyl-1H-pyrrole

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

acetyl chloride
75-36-5

acetyl chloride

4,4-difluoro-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
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%
boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

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

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

4,4-difluoro-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%
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
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

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

A

4,4-difluoro-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

B

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

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%
2,4-dimethyl-1H-pyrrole
625-82-1

2,4-dimethyl-1H-pyrrole

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

4,4-difluoro-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
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
625-82-1

2,4-dimethyl-1H-pyrrole

acetyl chloride
75-36-5

acetyl chloride

4,4-difluoro-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
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

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

tetrabutyl ammonium fluoride
429-41-4

tetrabutyl ammonium fluoride

4,4-difluoro-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 chloroform-d1 detected by NMR;
3,5,3',5',6-pentamethyldipyrrin hydrochloride
130876-46-9

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

4,4-difluoro-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
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
1380420-29-0

C14H17BF(18)FN2

4,4-difluoro-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
Heating;
1,1-bis-(3,5-dimethyl-pyrrol-2-yl)-ethane

1,1-bis-(3,5-dimethyl-pyrrol-2-yl)-ethane

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

4,4-difluoro-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
With triethylamine In dichloromethane at 20℃; for 0.166667h;
2,4-dimethyl-1H-pyrrole
625-82-1

2,4-dimethyl-1H-pyrrole

4,4-difluoro-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
Multi-step reaction with 2 steps
1: dichloromethane
2: triethylamine / dichloromethane
View Scheme
Multi-step reaction with 5 steps
1.1: toluene; diethyl ether / 1 h / 0 °C
2.1: potassium hydroxide; dihydrogen peroxide / ethanol; water / 0.08 h / Heating; Cooling with ice
3.1: phosgene / chloroform; toluene / 1 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h
4.2: 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 1 h / Reflux
2: triethylamine / dichloromethane / 0.17 h / 20 °C
View Scheme
boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

C14H18N2*ClH

C14H18N2*ClH

4,4-difluoro-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
With triethylamine In dichloromethane
bis-(3,5-dimethyl-1H-pyrrol-2-yl)methanone
859188-06-0

bis-(3,5-dimethyl-1H-pyrrol-2-yl)methanone

4,4-difluoro-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
Multi-step reaction with 3 steps
1.1: phosgene / chloroform; toluene / 1 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h
2.2: 20 °C
3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux
View Scheme
bis(3,5-dimethyl-1H-pyrrol-2-yl)methanethione
1379003-11-8

bis(3,5-dimethyl-1H-pyrrol-2-yl)methanethione

4,4-difluoro-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
Multi-step reaction with 4 steps
1.1: potassium hydroxide; dihydrogen peroxide / ethanol; water / 0.08 h / Heating; Cooling with ice
2.1: phosgene / chloroform; toluene / 1 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h
3.2: 20 °C
4.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux
View Scheme
5-chloro-1,3,7,9-tetramethyldipyrromethene hydrochloride

5-chloro-1,3,7,9-tetramethyldipyrromethene hydrochloride

4,4-difluoro-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
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h
1.2: 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux
View Scheme
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

4,4-difluoro-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

(CH3C(C4HN(CH3)2)2)BF(OSO2CF3)
1082830-07-6

(CH3C(C4HN(CH3)2)2)BF(OSO2CF3)

Conditions
ConditionsYield
In toluene100%
In chloroform-d1 monitored by NMR;
In toluene -25 °C;
In dichloromethane; acetonitrile at 20℃; for 0.0166667h;
20°C, 1 min;
4,4-difluoro-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

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
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

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at 25℃; for 12h;100%
With N-iodo-succinimide at 25℃; for 0.0166667h; Green chemistry; regioselective reaction;93%
With N-iodo-succinimide; choline chloride at 25℃; for 0.25h; Green chemistry;92%
4NO3(1-)*4C53H46N2O6*2Pt(2+)

4NO3(1-)*4C53H46N2O6*2Pt(2+)

4,4-difluoro-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

4NO3(1-)*C14H17BF2N2*4C53H46N2O6*2Pt(2+)

4NO3(1-)*C14H17BF2N2*4C53H46N2O6*2Pt(2+)

Conditions
ConditionsYield
In water-d2 at 80℃; for 1h;100%
4,4-difluoro-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

Diethyl ketomalonate
609-09-6

Diethyl ketomalonate

C21H27BF2N2O5

C21H27BF2N2O5

Conditions
ConditionsYield
With piperidine; acetic acid In toluene at 60℃;100%
2-(2-fluoropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
1469887-23-7

2-(2-fluoropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide

4,4-difluoro-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

2,8-bis(2,2-bis((trifluoromethyl)sulfonyl)ethyl)-5,5-difluoro-1,3,7,9,10-pentamethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

2,8-bis(2,2-bis((trifluoromethyl)sulfonyl)ethyl)-5,5-difluoro-1,3,7,9,10-pentamethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h; Inert atmosphere;99.8%
bromobenzene
108-86-1

bromobenzene

4,4-difluoro-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

1,3,5,7-tetramethyl-8-phenylmethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

1,3,5,7-tetramethyl-8-phenylmethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,4-dioxane at 100℃; Reagent/catalyst; Inert atmosphere;99%
methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate
956833-12-8

methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate

4,4-difluoro-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

C25H27BF2N2O2

C25H27BF2N2O2

Conditions
ConditionsYield
With Cinchonidin In chloroform at 20℃; enantioselective reaction;99%
methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate
1132641-29-2

methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate

4,4-difluoro-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

C25H26BClF2N2O2

C25H26BClF2N2O2

Conditions
ConditionsYield
With Cinchonidin In chloroform at 20℃; enantioselective reaction;98%
methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate
1132641-29-2

methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate

4,4-difluoro-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

C25H26BClF2N2O2

C25H26BClF2N2O2

Conditions
ConditionsYield
With Cinchonin In chloroform at 20℃; enantioselective reaction;98%
4,4-difluoro-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

1,1'-bi-2-naphthol
602-09-5

1,1'-bi-2-naphthol

C34H29BN2O2

C34H29BN2O2

Conditions
ConditionsYield
Stage #1: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene With aluminum (III) chloride In dichloromethane Reflux; Cooling with ether-dry ice;
Stage #2: 1,1'-bi-2-naphthol In dichloromethane; acetonitrile at 20℃; for 18h; Inert atmosphere;
97%
4,4-difluoro-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

2,6-dibromo-4,4-difluoro-1,3,5,7-tetramethyl-8-methyl-4-bora-3a,4a-diaza-s-indacene
134382-52-8

2,6-dibromo-4,4-difluoro-1,3,5,7-tetramethyl-8-methyl-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
With N-Bromosuccinimide at 25℃; for 0.0833333h; Green chemistry; regioselective reaction;95%
With N-Bromosuccinimide; choline chloride at 25℃; Green chemistry;94%
With bromine In dichloromethane at 20℃; Inert atmosphere;88%
With bromine In dichloromethane at 20℃; for 3h; Inert atmosphere;88%
methanesulfonic acid
75-75-2

methanesulfonic acid

4,4-difluoro-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

(2Z)-2-[1-(3,5-dimethyl-1H-pyrrol-2-yl)ethylidene]-3,5-di-methyl-2H-pyrrolium methanesulfonate

(2Z)-2-[1-(3,5-dimethyl-1H-pyrrol-2-yl)ethylidene]-3,5-di-methyl-2H-pyrrolium methanesulfonate

Conditions
ConditionsYield
In dichloromethane at 40℃; for 24h;92%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4,4-difluoro-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

5,5-difluoro-1,3,7,9,10-pentamethyl-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2-carbaldehyde
198149-19-8

5,5-difluoro-1,3,7,9,10-pentamethyl-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.583333h; Inert atmosphere;
Stage #2: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene In 1,2-dichloro-ethane at 20 - 50℃; Inert atmosphere;
89%
With trichlorophosphate In 1,2-dichloro-ethane at 50℃; for 4h; Inert atmosphere;60%
With trichlorophosphate In 1,2-dichloro-ethane at 60℃;
trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4,4-difluoro-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

4,4-bis(trimethylsilylethynyl)-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene

4,4-bis(trimethylsilylethynyl)-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene In tetrahydrofuran; hexane at 20℃; for 0.166667h; Inert atmosphere;
89%

121207-31-6Relevant articles and documents

Bright solid-state red-emissive BODIPYs: facile synthesis and their high-contrast mechanochromic properties

Duan, Chong,Zhou, Yibin,Shan, Guo-Gang,Chen, Yuncong,Zhao, Weijun,Yuan, Dandan,Zeng, Lintao,Huang, Xiaobo,Niu, Guangle

, p. 3471 - 3478 (2019)

Organic compounds with bright solid-state emission are emerging as versatile materials in many fields. However, traditional fluorescent dyes generally show high-emissive fluorescence in solution but faint or quenched emission in the solid state. Therefore, it remains a great challenge to develop bright solid-state emissive materials based on traditional fluorescent dyes. Herein, we report several solid-state emissive meso-substituted BODIPYs (PhMe3-BODIPY, PhMe-BODIPY, Ph-BODIPY and Me-BODIPY) obtained by using a simple two-step synthesis. Interestingly, these BODIPYs exhibit bright dual-state emission (DSE) with green fluorescence (512-520 nm, fluorescence quantum yield ΦF is up to 85%) in THF and solid-state red emission (601-632 nm, ΦF is up to 32.2%) in the crystalline state. The highly emissive fluorescence in the crystalline state is demonstrated to be due to the formation of J-aggregation. More importantly, the single crystals of the meso-aryl-substituted BODIPYs exhibit an unusual high-contrast mechanochromic property, which displays remarkable fluorescence color changes from red to yellow upon gentle grinding due to the transition from single crystals to microcrystals. Furthermore, strong grinding completely destroys the J-aggregation and leads to the transformation from microcrystals to a free state, hence the fluorescence color becomes green after strong grinding.

Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes

Palao, Eduardo,Duran-Sampedro, Gonzalo,De La Moya, Santiago,Madrid, Miriam,García-López, Carmen,Agarrabeitia, Antonia R.,Verbelen, Bram,Dehaen, Wim,Boens, N?el,Ortiz, María J.

, p. 3700 - 3710 (2016)

The generality of the palladium-catalyzed C-C coupling Negishi reaction when applied to haloBODIPYs is demonstrated on the basis of selected starting BODIPYs, including polyhalogenated and/or asymmetrical systems, and organozinc reagents. This reaction is an interesting synthetic tool in BODIPY chemistry, mainly because it allows a valuable regioselective postfunctionalization of BODIPY chromophores with different functional groups. In this way, functional patterns that are difficult to obtain by other procedures (e.g., asymmetrically functionalized BODIPYs involving halogenated positions) can now be made. The regioselectivity is achieved by controlling the reaction conditions and is based on almost-general reactivity preferences, and the nature of the involved halogens and their positions. This ability is exemplified by the preparation of a series of new BODIPY dyes with unprecedented substitution patterns allowing noticeable lasing properties.

Synthesis of [18F]BODIPY: Bifunctional reporter for hybrid optical/positron emission tomography imaging

Hendricks, J. Adam,Keliher, Edmund J.,Wan, Dongpeng,Hilderbrand, Scott A.,Weissleder, Ralph,Mazitschek, Ralph

, p. 4603 - 4606 (2012)

The best of both worlds: BODIPY-based imaging probes can be tracelessly transformed into hybrid PET/fluorescence imaging reagents by direct 19F/18F exchange without the need for redesign. This approach has the potential to accelerate

Modulating absorption and charge transfer in bodipy-carbazole donor-acceptor dyads through molecular design

Strahan, John,Popere, Bhooshan C.,Khomein, Piyachai,Pointer, Craig A.,Martin, Shea M.,Oldacre, Amanda N.,Thayumanavan,Young, Elizabeth R.

, p. 8488 - 8501 (2019)

Three bodipy-based (BDP = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) donor-acceptor dyads were designed and synthesized, and their ground-state and photophysical properties were systematically characterized. The electronic coupling between the BDP chromophore and an electron-donating carbazole (Carb) moiety was tuned by attachment via the meso and the beta positions on the BDP core, and through the use of various chemical linkers (phenyl and alkynyl) to afford mesoBDP-Carb, mesoBDP-phen-Carb, and betaBDP-alk-Carb. meso-Substituted dyads were found to retain ground-state absorption features of the unsubstituted BDP. However, variation of the linkage between the donor and acceptor moieties modulated the photophysical behavior of excited-state deactivation by controlling the rate of photoinduced internal charge transfer (ICT). The beta-substituted dyad dramatically tuned (red shifted) the absorption spectrum, while retaining desired features of the BDP, specifically stability and high extinction coefficients, however the ICT kinetics were accelerated compared to the meso-substituted dyads. Density functional theory (DFT) and time-dependent DFT (TDDFT) were carried out on the six potential dyads formed between BDP and Carb (attachment using the beta and meso positions for all three connections: direct, phenyl and alkynyl) to support the experimental observations. DFT and TDDFT showed molecular orbital density spread across the HOMO level only when attachment occurred through the beta position of BDP. In the meso-substituted BDP-Carb dyads, the molecular orbitals resembled those of the unsubstituted BDP. This work reveals several possible synthetic paradigms to tune photophysical properties with directed synthetic modifications and provides a mechanistic understanding of the ground- and excited- state behavior in these small-molecule donor-acceptor dyads.

Fine-Tuning Plasmon-Molecule Interactions in Gold-BODIPY Nanocomposites: The Role of Chemical Structure and Noncovalent Interactions

Kumar, P. P. Praveen,Rahman, Atikur,Goswami, Tanmay,Ghosh, Hirendra N.,Neelakandan, Prakash P.

, p. 87 - 94 (2020/10/19)

Strong coupling between localized surface plasmons and molecular absorptions leads to remarkable changes in the photophysical properties of dye-loaded metal nanoparticles. Here, we report supramolecular nanocomposites consisting of BODIPY, tryptophan, and gold nanoparticles, and investigate the effect of structural variations on their photophysical properties. Our results indicate that the photostability and photosensitization properties of the nanocomposites depend on the chemical composition of the BODIPY molecules. The singlet oxygen quantum yield of the nanocomposites NC1 (BODIPY, B1 bearing a single methyl group) and NC3 (BODIPY, B3 with 5 methyl and 2 iodo groups) were 0.46 and 0.42, respectively, which were significantly higher compared to their individual components. Ultrafast spectroscopy studies revealed that the migration of photoexcited BODIPY electrons to the plasmonic photoexcitation allowed electron transfer into the singlet oxygen states, thereby leading to efficient generation of singlet oxygen.

Design and synthesis of perfluoroalkyl decorated BODIPY dye for random laser action in a microfluidic device

Maity, Apurba,Sarkar, Anirban,Bhaktha B.n, Shivakiran,Patra, Sanjib K.

supporting information, p. 14650 - 14661 (2020/10/02)

New and highly emissive 2,6-diacetynyl and 2,6-bis-(phenylacetynyl) functionalized pentamethyldifluoroboron-dipyrromethane (BODIPY) derivatives (FBDP1-2) with perfluorinated pendant groups at the boron center have been synthesized successfully by the combination of two strategies: extending the π-conjugation and functionalization at the boron centre. The newly synthesized dyes have been characterized unambiguously by using various analytical tools such as multinuclear NMR, MALDI-TOF, and single crystal XRD analysis. The dyes (FBDP1-2) exhibit excellent photophysical properties in the yellow to red spectral region (λabs = 530 nm and 555 nm, and λem = 555 nm and 596 nm, respectively) with relatively good Stokes shifts (849 cm-1 and 1240 cm-1), high quantum efficiency (?F = 0.72 and 0.61) and excellent brightness (2.95 × 104 and 2.38 × 104 M-1 cm-1). Most importantly, under a transverse pumping condition at 532 nm, the dyes show efficient and stable laser action, having a good tunable range (20 nm and 13 nm) with a maximum lasing efficiency of 45% and 38% for FBDP1 and FBDP2, respectively. Moreover, the random lasing behavior of FBDP1 has been investigated in a dye-circulated polydimethylsiloxane (PDMS) based disordered microfluidic device. The appearance of randomly positioned sharp spikes with a full width at half maximum (FWHM) of less than 0.3 nm around 555 nm indicates the random laser (RL) emission. The relationship between input pump energy and output random lasing intensity has also been demonstrated, with the random lasing threshold of 0.5 mJ.

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