77771-02-9

Usage

Uses

Used in Pest Control:
3-Bromo-4-fluorobenzaldehyde is used as an active ingredient in the pest control industry for its ability to effectively manage and control various types of pests. Its chemical structure allows it to target specific pests, making it a valuable component in the development of new and improved pest control solutions.
Used in Chemical Synthesis:
3-Bromo-4-fluorobenzaldehyde is used as a key intermediate in the synthesis of various organic compounds. For instance, it has been utilized in the synthesis of 4-fluoro-3-phenoxybenzoic acid-glycine, a compound with potential applications in pharmaceuticals and other industries.
Additionally, 3-Bromo-4-fluorobenzaldehyde has been employed in the synthesis of Schiff bases of 4-nitroaniline, 2,4-dinitroaniline, 3,4-dichloroaniline, and 4-methoxy-3-nitroaniline through an ultrasound irradiation method. These Schiff bases are important in the development of new materials and compounds with a range of applications, including pharmaceuticals, dyes, and sensors.

InChI:InChI=1/C7H4BrClO/c8-6-3-5(4-10)1-2-7(6)9/h1-4H

Synthetic route

4-fluorobenzaldehyde (459-57-4) → 3-bromo-4-fluorobenzaldehyde (77771-02-9)

Conditions	Yield
With sulfuric acid; sulfur trioxide; bromine; iodine; zinc dibromide at 30 - 40℃; for 5.91667h; Product distribution / selectivity; Inert atmosphere;	97%
With hydrogenchloride; sodium hypochlorite solution; sodium bromide In dichloromethane; water at 20 - 25℃; for 1.5h; Irradiation;	91.9%
With bromine; aluminium trichloride In dichloromethane

3-bromo-4-fluoro-benzyl alcohol (77771-03-0) → 3-bromo-4-fluorobenzaldehyde (77771-02-9)

Conditions	Yield
With dipotassium peroxodisulfate at 55℃; for 0.25h; Ionic liquid;	87%
With pyridine; hydrogenchloride In dichloromethane
With potassium dichromate; sulfuric acid In dichloromethane; water
With sodium hydroxide; nitric acid In water; toluene

3-bromo-4-hydroxybenzylaldehyde (2973-78-6) → 3-bromo-4-fluorobenzaldehyde (77771-02-9)

Conditions	Yield
With Cl(1-)*C27H36ClN2(1+)*Cs(1+)*F(1-) In toluene at 23 - 110℃; for 24h; Inert atmosphere;	61%

2-bromo-1-fluoro-4-vinyl-benzene (701914-09-2) → 2-azido-1-(3-bromo-4-fluorophenyl)ethanone + 3-bromo-4-fluorobenzaldehyde (77771-02-9)

Conditions	Yield
With trimethylsilylazide; oxygen; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 18h; Overall yield = 75 %Spectr.;	A 54% B n/a

4-fluorobenzaldehyde (459-57-4) + 1,2-dichloro-ethane (107-06-2) → 3-bromo-4-fluorobenzaldehyde (77771-02-9)

Conditions	Yield
With bromine; aluminium trichloride

3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-fluorobenzoic acid (1007-16-5)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 3h;	100%
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	96%
With sodium chlorite In tetrahydrofuran; water at 50℃; for 5h;	91%

copper(l) cyanide + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 2-fluoro-5-formylbenzonitrile (218301-22-5)

Conditions	Yield
Stage #1: copper(l) cyanide; 3-bromo-4-fluorobenzaldehyde In 1-methyl-pyrrolidin-2-one at 170℃; for 24h; Stage #2: With celite In 1-methyl-pyrrolidin-2-one at 80℃; for 1h;	100%
In 1-methyl-pyrrolidin-2-one at 170℃; for 24h;	100%
In 1-methyl-pyrrolidin-2-one at 170℃;	65.4%
In 1-methyl-pyrrolidin-2-one at 170℃; for 24h;	52%
In 1-methyl-pyrrolidin-2-one at 25 - 170℃;

3-bromo-4-fluorobenzaldehyde (77771-02-9) + 2,2-dimethoxyethylamine (22483-09-6) → N-[(3-bromo-4-fluoro-phenyl)methyl]-2,2-dimethoxy-ethanamine (1036712-61-4)

Conditions	Yield
Stage #1: 3-bromo-4-fluorobenzaldehyde; 2,2-dimethoxyethylamine In toluene at 20℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2h; Inert atmosphere;	100%

acetoacetamido (5977-14-0) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 6-(3-bromo-4-fluorophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (464192-73-2)

Conditions	Yield
With urea	99%

3-fluorobenzene-1,2-diamine (18645-88-0) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → C14H9BrF2N2

Conditions	Yield
With C23H3BF16N2O In toluene at 25℃; for 3h; Green chemistry;	99%

4-Chloro-1,2-phenylenediamine (95-83-0) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → C14H9BrClFN2

Conditions	Yield
With C23H3BF16N2O In toluene at 25℃; for 3h; Green chemistry;	99%

3-bromo-4-fluorobenzaldehyde (77771-02-9) + 5-(aminomethyl)-2-chloropyridine (97004-04-1) → C13H11BrClFN2

Conditions	Yield
Stage #1: 3-bromo-4-fluorobenzaldehyde; 5-(aminomethyl)-2-chloropyridine In methanol at 20℃; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.333333h;	98.1%

di-tert-butyl dicarbonate (24424-99-5) + 2-(tributylstannyl)furan (118486-94-5) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 4-fluoro-3-(furan-2-yl)-benzaldehyde (359867-36-0)

Conditions	Yield
tetrakis(triphenylphosphine)palladium (0) In diethyl ether; N,N-dimethyl-formamide	98%
tetrakis(triphenylphosphine)palladium (0) In diethyl ether; N,N-dimethyl-formamide	98%

1.3-propanedithiol (109-80-8) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 2-(3-bromo-4-fluorophenyl)-1,3-dithiane (1035267-53-8)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1.5h;	98%

3-bromo-4-fluorobenzaldehyde (77771-02-9) + phosphonic acid diethyl ester (762-04-9) + 4-amino-4'-chlorodiphenyl ether (101-79-1) → C23H23BrClFNO4P

Conditions	Yield
With ZnBr2/SiO2 In neat (no solvent) for 0.0833333h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry; chemoselective reaction;	98%

3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-fluorobenzonitrile (79630-23-2)

Conditions	Yield
With ammonium hydroxide; iodine In tetrahydrofuran at 5 - 20℃; Solvent; Reagent/catalyst;	97.5%

ethane-1,2-dithiol (540-63-6) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 2-(3-bromo-4-fluorophenyl)-1,3-dithiolane (1262048-10-1)

Conditions	Yield
With iodine In dichloromethane at 20℃; for 1h;	97%

dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate (61260-15-9) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 2-fluoro-5-(3-oxo-3H-isobenzofuran-1-ylmethylene)-1-bromobenzene (63964-50-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 30℃; for 6h; Solvent;	97%
With triethylamine In dichloromethane at 6 - 20℃; for 4h;	95%
With triethylamine In tetrahydrofuran at 0 - 20℃;	78.5%

2-(2,5-dimethylthiazol-4-yl)acetohydrazide + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → (E)-N'-(3-bromo-4-fluorobenzylidene)-2-(2,5-dimethyl-1,3-thiazol-4-yl)acetohydrazide

Conditions	Yield
With acetic acid In ethanol	97%

S-tert-butylsulfinimide (146374-27-8) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → (E)-N-tert-butanesulfinyl 3-bromo-4-fluorophenyl-aldimine

Conditions	Yield
With titanium(IV) tetraethanolate In tetrahydrofuran at 65℃; for 12h;	96%
With titanium(IV) tetraethanolate In tetrahydrofuran at 65℃; for 12h;	96%

4,4-ethylenedioxy-piperidine (177-11-7) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde

Conditions	Yield
With potassium carbonate In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; acetonitrile	96%

3-bromo-4-fluorobenzaldehyde (77771-02-9) + phosphonic acid diethyl ester (762-04-9) + malononitrile (109-77-3) → [1-(3-bromo-4-fluorophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester (1537917-45-5)

Conditions	Yield
With 1,4-diazabicyclo[2.2.2]octane hydroacetate In neat (no solvent) at 25℃; for 0.416667h; Green chemistry;	96%

N-methoxylamine hydrochloride (593-56-6) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-fluorobenzaldehyde O-methyloxime (646051-34-5)

Conditions	Yield
	95%

sodium chlorite (7758-19-2) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-fluoroaniline (656-64-4)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sulfuric acid In tetrahydrofuran; chloroform; water; ethyl acetate	95%

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) + malononitrile (109-77-3) → 2-amino-4-(3-bromo-4-fluorophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile (1019060-10-6)

Conditions	Yield
With triethylamine In ethanol for 0.833333h; Heating;	95%

2,4-difluorophenol (367-27-1) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-(2,4-difluorophenoxy)benzaldehyde

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 1h; Temperature;	95%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 1h;	95%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 1h; Inert atmosphere;	95%

2.6-dimethylphenol (576-26-1) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-(2,6-dimethylphenoxy)benzaldehyde

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃;	95%
With caesium carbonate In dimethyl sulfoxide at 90℃; Inert atmosphere;	7 g

(E)-3,3-diisopropyl-1-(phenylethynyl)triaz-1-ene + 4-methoxy-aniline (104-94-9) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) + benzoic acid (65-85-0) → (E)-N-(1-(3-bromo-4-fluorophenyl)-3-(3,3-diisopropyltriaz-1-en-1-yl)-3-oxo-2-phenylpropyl)-N-(4-methoxyphenyl)benzamide

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; Molecular sieve; Schlenk technique; diastereoselective reaction;	95%

3-o-chlorobenzyl-4-amino-4,5-dihydro-1H-1,2,4-triazole-5-one (877315-80-5) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 5-(o-chlorobenzyl)-4-m-bromo-4-fluorobenzyliden amino-2,4-dihydro-2H-1,2,4-triazol-3-one (1470364-72-7)

Conditions	Yield
With acetic acid at 115℃; for 0.0666667h; Time; Microwave irradiation;	94%

3-bromo-4-fluorobenzaldehyde (77771-02-9) + malononitrile (109-77-3) + triethyl phosphite (122-52-1) → [1-(3-bromo-4-fluorophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester (1537917-45-5)

Conditions	Yield
With HCNC-4 In neat (no solvent) at 20℃; for 0.416667h; UV-irradiation; Green chemistry;	94%

4-chloro-2-iodo phenol (71643-66-8) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-(4-chloro-2-iodophenoxy)benzaldehyde

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 90℃;	94%
With caesium carbonate In dimethyl sulfoxide at 90℃; for 18h; Inert atmosphere;	94%

2-benzofuran-1(3H)-one (87-41-2) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 2-fluoro-5-(3-oxo-3H-isobenzofuran-1-ylmethylene)-1-bromobenzene (63964-50-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;	94%
With sodium hydride In tetrahydrofuran at 20℃; for 2.5h; Solvent; Inert atmosphere;	92%

1,3-cylohexanedione (504-02-9) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) + 3-aminohex-2-enoic acid methyl ester → 4-(3-bromo-4-fluoro-phenyl)-5-oxo-2-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester (927669-87-2)

Conditions	Yield
In ethanol at 80℃; for 16h;	93%

3-bromo-4-fluorobenzaldehyde (77771-02-9) → 3-bromo-4-fluoro-benzyl alcohol (77771-03-0)

Conditions	Yield
With methanol; sodium tetrahydroborate at 20℃;	93%
With sodium tetrahydroborate In ethanol for 2h;
With sodium tetrahydroborate In ethanol for 2h;

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 107-06-2 1,2-dichloro-ethane 
• 701914-09-2 2-bromo-1-fluoro-4-vinyl-benzene 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 77771-03-0 3-bromo-4-fluoro-benzyl alcohol 

Downstream Products

• 145438-90-0 1-(3-Bromo-4-fluoro-phenyl)-propan-1-ol 
• 145438-90-0 1-(3-Bromo-4-fluoro-phenyl)-propan-1-ol 
• 77771-04-1 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane 
• 165803-94-1 methyl 2-fluoro-5-formylbenzoate 
• 311808-49-8 3-bromo-4-[(2,4-dichlorophenyl)thio]benzaldehyde 
• 359867-36-0 4-fluoro-3-(furan-2-yl)-benzaldehyde 

Relevant academic research and scientific papers

A 3 - bromo -4 - fluoro benzaldehyde synthetic method

The present invention relates to the technical field of agricultural chemicals or pharmaceutical intermediate synthesis, in particular to a 3 - bromo - 4 - fluoro benzaldehyde synthetic method, comprises the following steps: (1) the 4 - fluorophenyl formaldehyde dissolved in methylene chloride, to obtain solution A; (2) the sodium bromide is dissolved in pure water, stirring while adding 35% hydrochloric acid, to obtain solution B; (3) the solution and the solution after mixing A B, opening ultrasonic, dropping sodium hypochlorite aqueous solution; (4) [...], ultrasonic, thermal insulation under stirring, then standing; (5) split-phase, dichloromethane phase washed to neutral, drying desolvation; (6) it is crude, 31 °C body melt crystallization, to get the pure product. The synthetic method does not require the use of a catalyst, in the process does not involve the precursor chemicals or toxic chlorine bromine; raw materials are easy, low-risk; high yield; process green, easy operation, and environmental protection.

Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes

The copper(II)-promoted free-radical oxidative difunctionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by 18O-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.

PhenoFluorMix: Practical chemoselective deoxyfluorination of phenols

A practical deoxyfluorination with novel deoxyfluorinating reagent PhenoFluorMix, a mixture of N,N'-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF, is presented. PhenoFluorMix overcomes the challenges associated with hydrolysis of PhenoFluor. PhenoFluorMix does not hydrolyze, is readily available on decagram scale, and is storable in air. In this paper, we demonstrate the practicality of the reagent and exhibit the deoxyfluorination of a variety of phenols and heterocycles.

PROCESS FOR THE PREPARATION OF 3-BROMO - 4 - FLUOROBENZALDEHYDE

The invention relates to a process of manufacturing 3-bromo-4- fluorobenzaldehyde using zinc bromide as a catalyst.

Solvent-free oxidation of alcohols with potassium persulphate in the presence of bronsted acidic ionic liquids

An efficient conversion of alcohols to aldehydes was achieved using potassium persulphate and 3-methylimidazolinium methane sulfonate. Copyright Taylor & Francis Group, LLC.

Isoquinoline compound melanocortin receptor ligands and methods of using same

The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.

Insecticidal ethers

This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.

Fluorobenzyl esters

A compound of formula: STR1 wherein R is selected from hydrogen, cyano, methyl, and ethynyl, and X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol. The compounds are useful as insecticides and acaricides.

Insecticidal alkenes

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