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56990-02-4

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56990-02-4 Usage

Description

3,5-Dibromobenzaldehyde is a white or beige solid with a melting point of 84-88 °C. Its boiling point and density are estimated to be 287.2±20.0 °C and 1.977±0.06 g/cm3, respectively. It is insoluble in water.

Synthesis

1,3,5-tribromobenzene (3.01 g, 9.6 mmol) in diethyl ether (80 mL) was cooled to -78°C followed by the addition of one equivalent of n-BuLi dropwise (2.5 M, 3.8 mL). The reaction was stirred for 30 minutes then DMF (740 μL, 9.6 mmol) was added dropwise to the reaction and stirred at -78°C for one hour. The vessel was then placed in an ice bath and stirred for 30 minutes. A 10% HCl solution (100 mL) was added to quench the reaction followed by CHCl3 (150 mL). The organic layer was collected and the aqueous layer washed with CHCl3 (80 mL). The organic layers where combined and dried over MgSO4 and the solvent removed. The crude product was purified by column chromatography eluting with 10% EtOAc in hexanes. Spectral data for the title compound was not reported in the literature reference. Yield: 1.93 g of the title compound (77%). 1H NMR (CDCl3, 300 MHz): δ = 9.90 (s, 1H), 7.92 (d, 2H), 7.60 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ = 189.3, 139.7, 139.0, 131.37, 124.1; GC-MS [M+H]+ 262.8709, calcd 262.8707

Uses

3,5-Dibromobenzaldehyde is a dibrominated benzaldehyde that is a very useful building block for the preparation of a wide range of biologically active compounds such as a antibacterials

Application

Reactant involved in:Suzuki-Miyaura cross-coupling reactionsSynthesis of blue fluorescent dye derivatives for organic light emitting diodesSharpless kinetic resolution for the formation of Baylis-Hillman enal adductsSynthesis of podophyllotoxin mimetic pyridopyrazoles as anticancer agentsAllylic alkylationSynthesis of C2-symmetric biphosphine ligand I

Check Digit Verification of cas no

The CAS Registry Mumber 56990-02-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,9,9 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 56990-02:
(7*5)+(6*6)+(5*9)+(4*9)+(3*0)+(2*0)+(1*2)=154
154 % 10 = 4
So 56990-02-4 is a valid CAS Registry Number.

56990-02-4 Well-known Company Product Price

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  • TCI America

  • (D2832)  3,5-Dibromobenzaldehyde  >97.0%(GC)

  • 56990-02-4

  • 5g

  • 790.00CNY

  • Detail
  • TCI America

  • (D2832)  3,5-Dibromobenzaldehyde  >97.0%(GC)

  • 56990-02-4

  • 25g

  • 2,990.00CNY

  • Detail
  • Alfa Aesar

  • (B25495)  3,5-Dibromobenzaldehyde, 98%   

  • 56990-02-4

  • 1g

  • 157.0CNY

  • Detail
  • Alfa Aesar

  • (B25495)  3,5-Dibromobenzaldehyde, 98%   

  • 56990-02-4

  • 5g

  • 597.0CNY

  • Detail
  • Alfa Aesar

  • (B25495)  3,5-Dibromobenzaldehyde, 98%   

  • 56990-02-4

  • 25g

  • 2501.0CNY

  • Detail

56990-02-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,5-Dibromobenzaldehyde

1.2 Other means of identification

Product number -
Other names 3,5-Dibrom-benzaldehyd

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:56990-02-4 SDS

56990-02-4Synthetic route

1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1,3,5-trisbromobenzene With magnesium In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Large scale;
Stage #2: With methylmagnesium chloride In tetrahydrofuran for 3.5h; Reflux; Inert atmosphere; Large scale;
Stage #3: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 10℃; for 2h; Temperature; Reagent/catalyst; Inert atmosphere; Large scale;
95%
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃;
Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78 - 0℃; Further stages.;
94%
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃;
Stage #2: N,N-dimethyl-formamide In diethyl ether for 1h;
Stage #3: With hydrogenchloride In diethyl ether; water
70%
3,5-dibromobenzyl bromide
56908-88-4

3,5-dibromobenzyl bromide

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide In tetrahydrofuran for 12h; Reflux;92%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3,5-dibromophenyllithium

3,5-dibromophenyllithium

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
In diethyl ether at -78℃; for 1h;86%
3,5-dibromotoluene
1611-92-3

3,5-dibromotoluene

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With C15H11ClN4SZn; p-benzoquinone In tert-butyl alcohol for 8h; Reagent/catalyst;83%
With bromine at 180 - 200℃; Erwaermen des Reaktionsprodukts mit konz. Schwefelsaeure auf 70-80grad;
Multi-step reaction with 2 steps
1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 24 h / Reflux
2: 4-methylmorpholine N-oxide / tetrahydrofuran / 12 h / Reflux
View Scheme
C13H9Br2NO

C13H9Br2NO

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride In water; N,N-dimethyl-formamide at 50℃; for 1h;82%
With hydrogenchloride; water at 50℃; for 1h;82%
3,5-dibromophenylboronic acid

3,5-dibromophenylboronic acid

Glyoxilic acid
298-12-4

Glyoxilic acid

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With 1,2,3,4-tetrahydroisoquinoline In acetonitrile at 20℃; Green chemistry;50%
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With magnesium In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide45%
With magnesium In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide
1,3-dibromo-5-iodobenzene
19752-57-9

1,3-dibromo-5-iodobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-iodobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃;
28%
4-amino-3,5-dibromo-benzaldehyde
42460-62-8

4-amino-3,5-dibromo-benzaldehyde

A

3,5-dibromonitrobenzene
6311-60-0

3,5-dibromonitrobenzene

B

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With potassium disulphite; nitric acid Erwaermen der mit Eiswasser verd. Diazoniumsalz-Loesung mit Alkohol in Gegenwart von Kupfersulfat;
3,5-dibromotoluene
1611-92-3

3,5-dibromotoluene

acetic anhydride
108-24-7

acetic anhydride

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid; acetic acid anschl. Erhitzen mit wss. H2SO4;
diazotized 3.5-dibromo-4-amino-benzaldehyde

diazotized 3.5-dibromo-4-amino-benzaldehyde

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With ethanol
4-amino-3,5-dibromo-benzaldehyde
42460-62-8

4-amino-3,5-dibromo-benzaldehyde

nitric acid
7697-37-2

nitric acid

K2S2O5

K2S2O5

A

3,5-dibromonitrobenzene
6311-60-0

3,5-dibromonitrobenzene

B

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
at 0℃; anschliessend Erwaermen mit waessrig-alkoholischer Kupfersulfat-Loesung.Diazotization;
(3,5-dibromophenyl)methanol
145691-59-4

(3,5-dibromophenyl)methanol

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 40℃;
3,5-dibromonitrobenzene
6311-60-0

3,5-dibromonitrobenzene

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C
2.1: H2SO4; NaNO2 / 2 h / 0 °C
2.2: 70 percent / KI / 0.25 h / 80 °C
3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C
3.2: 28 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
3,5-dibromoaniline
626-40-4

3,5-dibromoaniline

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: H2SO4; NaNO2 / 2 h / 0 °C
1.2: 70 percent / KI / 0.25 h / 80 °C
2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C
2.2: 28 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
2,6-dibromo-4-nitroaniline
827-94-1

2,6-dibromo-4-nitroaniline

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 80 percent / H2SO4; NaNO2 / ethanol / 36 h / 90 °C
2.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C
3.1: H2SO4; NaNO2 / 2 h / 0 °C
3.2: 70 percent / KI / 0.25 h / 80 °C
4.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C
4.2: 28 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
4-nitro-aniline
100-01-6

4-nitro-aniline

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / Br2 / acetic acid / 4 h / 65 °C
2.1: 80 percent / H2SO4; NaNO2 / ethanol / 36 h / 90 °C
3.1: 89 percent / SnCl2*2H2O / ethanol; tetrahydrofuran / 20 h / 20 °C
4.1: H2SO4; NaNO2 / 2 h / 0 °C
4.2: 70 percent / KI / 0.25 h / 80 °C
5.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C
5.2: 28 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
3,5-dibromobenzoic acid
618-58-6

3,5-dibromobenzoic acid

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H3B*S(CH3)2 / tetrahydrofuran / 70 °C
2: PCC / CH2Cl2 / 40 °C
View Scheme
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

(3,5-dibromophenyl)methanol
145691-59-4

(3,5-dibromophenyl)methanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; dichloromethane at 20℃; for 3h;100%
With sodium tetrahydroborate In methanol at 0 - 20℃;95%
With sodium tetrahydroborate In ethanol; dichloromethane at 20℃; for 3h;93%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

ethylene glycol
107-21-1

ethylene glycol

2-(3,5-dibromophenyl)-1,3-dioxolane
773094-77-2

2-(3,5-dibromophenyl)-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1h; Heating / reflux;100%
With toluene-4-sulfonic acid In benzene Heating;98%
With toluene-4-sulfonic acid In toluene at 110℃; for 4h; Inert atmosphere;83.6%
With toluene-4-sulfonic acid In benzene for 5h; Heating;
With toluene-4-sulfonic acid In toluene for 5h; Reflux; Dean-Stark;6.27 g
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

2-(3,5-Dibromo-phenyl)-5,5-dimethyl-[1,3]dioxane
213622-10-7

2-(3,5-Dibromo-phenyl)-5,5-dimethyl-[1,3]dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran for 8h; Reflux;100%
With toluene-4-sulfonic acid In benzene for 48h; Reflux; Inert atmosphere;97%
With toluene-4-sulfonic acid In benzene Dean-Stark;97%
With toluene-4-sulfonic acid In tetrahydrofuran for 8h; Reflux;
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

p-toluidine
106-49-0

p-toluidine

(E)-N-(3,5-dibromobenzylidene)-4-methylaniline

(E)-N-(3,5-dibromobenzylidene)-4-methylaniline

Conditions
ConditionsYield
In neat (no solvent) at 20℃; Green chemistry;99%
In dichloromethane at 27℃; for 0.0833333h;
biphenyl-4-acetaldehyde
92-91-1

biphenyl-4-acetaldehyde

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

1-[1,10-biphenyl]-4-yl-3-(3,5-dibromophenyl)-2-propen-1-one

1-[1,10-biphenyl]-4-yl-3-(3,5-dibromophenyl)-2-propen-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 2h;99%
In ethanol; water at 20℃; for 2h;98%
With sodium t-butanolate In ethanol at 25℃; Inert atmosphere;98.49%
sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate

sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate

bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II)
225931-80-6

bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II)

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C59H72Br2O11P2Pd2S2(2-)*2Na(1+)

C59H72Br2O11P2Pd2S2(2-)*2Na(1+)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;99%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C23H37N2OP

C23H37N2OP

C30H41Br2N2O2P

C30H41Br2N2O2P

Conditions
ConditionsYield
In toluene at 20℃; for 3h;99%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

3,5-di(3-nitrophenyl)-benzaldehyde

3,5-di(3-nitrophenyl)-benzaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Schlenk technique; Inert atmosphere;99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Inert atmosphere;80%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

[1,1′:3′,1″-terphenyl]-5′-carbaldehyde
220955-80-6

[1,1′:3′,1″-terphenyl]-5′-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water; toluene at 105℃; for 120h; Suzuki-Miyaura cross-coupling reaction;98%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; Suzuki Coupling; Inert atmosphere;98%
With palladium diacetate; sodium carbonate; triphenylphosphine In ethanol; toluene at 100℃; for 24h; Suzuki Coupling; Inert atmosphere; Sealed tube;93%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

phenylacetylene
536-74-3

phenylacetylene

(-)-(1S)-1-(3,5-dibromophenyl)-3-phenylprop-2-yn-1-ol

(-)-(1S)-1-(3,5-dibromophenyl)-3-phenylprop-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With (-)-N-methylephedrine; triethylamine; zinc trifluoromethanesulfonate In toluene for 0.25h;
Stage #2: 3,5-dibromobenzaldehyde In toluene Further stages.;
98%
2-acetylpyridine
1122-62-9

2-acetylpyridine

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C14H9Br2NO

C14H9Br2NO

Conditions
ConditionsYield
In ethanol; water at 20℃; for 2h;98%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

4,5-dimethoxybenzene-1,2-diamine
27841-33-4

4,5-dimethoxybenzene-1,2-diamine

C15H12Br2N2O2

C15H12Br2N2O2

Conditions
ConditionsYield
With sodium hydrogensulfite In ethanol; water for 48h; Reflux;98%
2-methoxyisobutanol
22665-67-4

2-methoxyisobutanol

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

2-(3,5-Dibromo-phenyl)-5,5-dimethyl-[1,3]dioxane
213622-10-7

2-(3,5-Dibromo-phenyl)-5,5-dimethyl-[1,3]dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;97%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

1-ethynyl-4-(n-pentyl)benzene
79887-10-8

1-ethynyl-4-(n-pentyl)benzene

3,5-bis-(4-pentyl-phenylethynyl)-benzaldehyde
496043-84-6

3,5-bis-(4-pentyl-phenylethynyl)-benzaldehyde

Conditions
ConditionsYield
With 4 A molecular sieve; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 7h; Sonogashira coupling;97%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

3,5-di(naphthalen-2-yl)benzaldehyde

3,5-di(naphthalen-2-yl)benzaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 19h; Inert atmosphere;97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 120℃; Inert atmosphere;95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

malononitrile
109-77-3

malononitrile

[1-(3,5-dibromophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester

[1-(3,5-dibromophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester

Conditions
ConditionsYield
With 1,4-diazabicyclo[2.2.2]octane hydroacetate In neat (no solvent) at 25℃; for 0.666667h; Green chemistry;97%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

pinacol homoallenylboronate

pinacol homoallenylboronate

(1S,2R)-1-((1-(3,5-dibromophenyl)-2-methylenebut-3-en-1-yl)amino)-2,3-dihydro-1H-inden-2-ol

(1S,2R)-1-((1-(3,5-dibromophenyl)-2-methylenebut-3-en-1-yl)amino)-2,3-dihydro-1H-inden-2-ol

Conditions
ConditionsYield
Stage #1: 3,5-dibromobenzaldehyde; (1S,2R)-1-amino-2-indanol In methanol; dimethyl sulfoxide at 20℃; for 2h; Petasis Reaction; Schlenk technique;
Stage #2: pinacol homoallenylboronate In methanol; dimethyl sulfoxide at 20℃; for 48h; Petasis Reaction; Schlenk technique; regioselective reaction;
97%
C72H110O4

C72H110O4

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C151H222O9

C151H222O9

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine; copper(l) iodide In tetrahydrofuran at 65℃; Sonogashira reaction;96%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3,5‐bis((trimethylsilyl)ethynyl)benzaldehyde
153390-73-9

3,5‐bis((trimethylsilyl)ethynyl)benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; diisopropylamine; triphenylphosphine In 1,4-dioxane at 20℃; Inert atmosphere;95%
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; diisopropylamine; triphenylphosphine In 1,4-dioxane at 20℃;95%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling;95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

5-dibromomethyl-1,3-dibromobenzene
256386-08-0

5-dibromomethyl-1,3-dibromobenzene

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 24h; Inert atmosphere;95%
With boron tribromide In dichloromethane at 20℃; for 24h;80%
With boron tribromide In dichloromethane at 20℃; Substitution;
carbon tetrabromide
558-13-4

carbon tetrabromide

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C8H4Br4

C8H4Br4

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 20℃; for 24h;
Stage #2: 3,5-dibromobenzaldehyde In dichloromethane at 0 - 20℃; Further stages.;
95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

2-propenoic acid, 3-(3,5-dibromophenyl)-methyl ester

2-propenoic acid, 3-(3,5-dibromophenyl)-methyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 7h; Inert atmosphere;95%
morpholine
110-91-8

morpholine

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

phenylacetylene
536-74-3

phenylacetylene

C19H17Br2NO

C19H17Br2NO

Conditions
ConditionsYield
With catena-poly[di-μ-iodido-bis[(1,2-bis(4-chlorophenylthio)propane)copper(I)]] In neat (no solvent) at 80℃; for 4h;95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine
74258-81-4

3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine

acetylacetone
123-54-6

acetylacetone

1-[7-(3,5-dibromophenyl)-5-methyl-2-(3,4,5-trimethoxyphenyl)-1,7-dihydro-[1,2,4]triazolo [1,5-a]pyrimidin-6-yl]ethanone

1-[7-(3,5-dibromophenyl)-5-methyl-2-(3,4,5-trimethoxyphenyl)-1,7-dihydro-[1,2,4]triazolo [1,5-a]pyrimidin-6-yl]ethanone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90℃; for 12h;95%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

2-indanone
615-13-4

2-indanone

C16H10Br2O

C16H10Br2O

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 3h;94%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine
74258-81-4

3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-amine

9-(3,5-dibromophenyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,9-tetrahydro-1H-[1,2,4]triazolo [5,1-b]quinazolin-8-one

9-(3,5-dibromophenyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,9-tetrahydro-1H-[1,2,4]triazolo [5,1-b]quinazolin-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90℃; for 12h;94%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

C14H10Br4O2

C14H10Br4O2

Conditions
ConditionsYield
With isonicotinate tert-butyl ester; bis(pinacol)diborane for 6h; Reflux;94%
1-Pentyne
627-19-0

1-Pentyne

3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

3,5-bis(pentynyl)benzaldehyde
618119-37-2

3,5-bis(pentynyl)benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 48h; Sonogashira coupling;93%
3,5-dibromobenzaldehyde
56990-02-4

3,5-dibromobenzaldehyde

1,3-dibromo-5-[(diethylphosphonyl)methyl]benzene
363622-48-4

1,3-dibromo-5-[(diethylphosphonyl)methyl]benzene

(E)-1,2-bis(3,5-dibromophenyl)ethene

(E)-1,2-bis(3,5-dibromophenyl)ethene

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Wittig reaction; Inert atmosphere;93%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;81%

56990-02-4Relevant articles and documents

Alkyl-thiophene Functionalized D-π-A Porphyrins for Mesoscopic Solar Cells

Lu, Jianfeng,Liu, Shuangshuang,Shen, Yan,Xu, Jie,Cheng, Yibing,Wang, Mingkui

, p. 187 - 196 (2015)

An alkyl-thiophene functionalized D-π-A porphyrin (LW16) is designed and synthesized for dye-sensitized solar cells (DSSCs). Two hexyl-thiophene groups are attached to the meta-position of each meso-phenyl with a motivation to increase the light-harvesting ability as well as retarding the aggregation of porphyrins dyes. For comparison, none-alkyl substituted (LW14) and octyloxy substituted (LW15) porphyrin dyes are also synthesized to fully investigate the influence of porphyrin chromophore modification. These porphyrins present similar spectrum while the oxidation potentials vary as the functionalized group changes from the meta-position to ortho-position. The DSSCs based on the alkyl-thiophene functionalized (LW16), none-alkyl substituted (LW14), and octyloxy substituted (LW15) porphyrins can be achieved a power conversion efficiency of 8.5%, 6.9%, and 8.2% using I-/I3-redox electrolyte under full sunlight irradiation (AM 1.5 G, 100 mW cm-2), respectively. It is found that by tailoring the porphyrin chromophore with hexyl-thiophenes, the photocurrent of the corresponding devices could be increased without sacrifice the photovoltage. Detailed investigation, including spectroscopy, electrochemical and transient photovoltage decay measurement, provides general influence of π-conjugation extension at the meso-position onto the optoelectronic features of porphyrins dyes.

Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs

Liu, Hao,Su, Huan,Chen, Zhiyuan,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun

, p. 1697 - 1705 (2021/07/10)

In this work, we depict the synthesis and characterization of a series of meso-substituted boron-dipyrromethene (BODIPY) compounds. Their optical and electrochemical properties were investigated systematically. All these compounds exhibited intense absorption bands in the ultraviolet (UV) and visible regions, which arise from the π–π* transitions based on their BODIPY core segments. By comparing electron-withdrawing substituents and electron-donating substituents, we found that these compounds exhibited some similar photophysical properties but exhibited different fluorescence in the solid state. All compounds were highly emissive in dichloromethane at room temperature (λem = 512–523 nm, ΦPL > 0.9). When these compounds were applied in blue-driven light-emitting diodes (LEDs) as light-emitting materials, the devices showed luminescence efficiency ranging from 1.09 to 34.13 lm/W. Their luminescence and electrochemical properties could be used for understanding the structure–property relationship of BODIPY compounds and developing functional fluorescent materials.

Stable and efficient phosphorescent organic light-emitting device utilizing a δ-carboline-containing host displaying thermally activated delayed fluorescence

Liu, Shihao,Wang, Hui,Xie, Wenfa,Zang, Chunxiu,Zhang, Letian,Zhao, Hongyu

, p. 3800 - 3806 (2020/03/31)

Materials displaying thermally activated delayed fluorescence (TADF) can when used as hosts alleviate the serious efficiency roll-off of phosphorescent organic light-emitting devices (PHOLEDs). However, the stability of the device remains challenging due to the unstable moiety in the TADF molecule. Here, a stable and efficient yellow PHOLED based on a δ-carboline-containing TADF host and bis(4-phenyl-thieno[3,2-c]pyridinato-C2′) (acetylacetonato) iridium(iii) (PO-01) guest was demonstrated. Compared to the lifetime of the PHOLED with a 4,4′-bis(N-carbazolyl)-2,2′-biphenyl host, a greater than twenty times enhancement of the lifetime of the PO-01-based device was achieved. The LT50 lifetime (time to 50% of initial luminance of 1000 cd m-2) of an unpackaged DCb-BPP-based PHOLED reached 424 h, and was accompanied by a maximum external quantum efficiency of 21.5% and an impressive low efficiency roll-off of 17.7% at a high luminance of 10 000 cd m-2. These values are among the best of those reported for PO-01-based yellow PHOLEDs.

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