188813-05-0

Basic information

• Product Name: 3-BROMO-5-CHLORO-BENZALDEHYDE
• Synonyms: 3-BROMO-5-CHLORO-BENZALDEHYDE;3-Bromo-5-chlorobenzladehyde;5-Chloro-3-bromobenzaldehyde;3-BroMo-5-chlorobenzaldehyde, 98%+
• CAS NO: 188813-05-0
• Molecular Formula: C₇H₄BrClO
• Molecular Weight: 219.46
• Product Categories: C7Chemical Synthesis;Aldehydes;Carbonyl Compounds;New Products for Chemical Synthesis;Organic Building Blocks
• Mol File: 188813-05-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 68-73 °C
• Boiling Point: 264.044 °C at 760 mmHg
• Flash Point: 113.49 °C
• Appearance: white crystal powder
• Density: 1.698 g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-BROMO-5-CHLORO-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-CHLORO-BENZALDEHYDE(188813-05-0)
• EPA Substance Registry System: 3-BROMO-5-CHLORO-BENZALDEHYDE(188813-05-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 36/37/38-51/53-22
• Safety Statements: 26-36/37/39-61-53
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 188813-05-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystal powder

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

Synthetic route

1,3-dibromo-5-chlorobenzene (14862-52-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-bromo-5-chloro-benzaldehyde (188813-05-0)

Conditions	Yield
Stage #1: 1,3-dibromo-5-chlorobenzene With n-butyllithium In hexane; di-isopropyl ether at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In hexane; di-isopropyl ether at -78℃; Inert atmosphere;	67%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + ethylene glycol (107-21-1) → 2-(3-chloro-5-formylphenyl)-2-methylpropanenitrile (230642-94-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Inert atmosphere; Reflux;	100%
With toluene-4-sulfonic acid In toluene for 18h; Heating / reflux; Water removal;	85%
With toluene-4-sulfonic acid In toluene for 6h; Reflux; Dean-Stark;	6.05 g
With toluene-4-sulfonic acid In toluene at 140℃; for 2h; Inert atmosphere;

3-bromo-5-chloro-benzaldehyde (188813-05-0) + aniline (62-53-3) → C13H9BrClN

Conditions	Yield
In toluene at 111℃; for 18h; Inert atmosphere;	93%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + 9-phenanthrenylboronic acid (68572-87-2) → C21H13ClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	90%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + benzamidine monohydrochloride (1670-14-0) → 2-(3-bromo-5-chlorophenyl )-4,6-diphenyl-1,3,5-triazine (1073062-42-6)

Conditions	Yield
Stage #1: 3-bromo-5-chloro-benzaldehyde; benzamidine monohydrochloride With potassium phosphate In dimethyl sulfoxide at 90℃; for 1h; Stage #2: With magnesium sulfate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 0.166667h;	87%

biphenyl-4-acetaldehyde (92-91-1) + 3-bromo-5-chloro-benzaldehyde (188813-05-0) → C21H14BrClO

Conditions	Yield
With sodium methylate In ethanol for 5h;	80%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + trimethyl orthoformate (149-73-5) → 1-bromo-3-chloro-5-(dimethoxymethyl)benzene

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 12h; Reflux;	78%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + acetophenone (98-86-2) → C15H10BrClO

Conditions	Yield
With sodium methylate In methanol; ethanol for 5h;	77%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 4-(3-bromo-5-chloro-benzyl)piperazine-1-carboxylic acid tert-butyl ester (1460033-73-1)

Conditions	Yield
With sodium tris(acetoxy)borohydride; triethylamine In dichloromethane at 20℃; for 16h;	76%

2-thioxo-4-thiazolidinone (141-84-4) + 3-bromo-5-chloro-benzaldehyde (188813-05-0) → 5-(3-bromo-5-chlorobenzylidene)-2-thioxothiazolidin-4-one

Conditions	Yield
With sodium hydroxide In ethanol Reflux;	75%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + ((1-bromo-3-chloro-naphthalene-7-yl)methyl)triphenylphosphonium bromide → 1-bromo-7-(2-(3-bromo-5-chlorophenyl)vinyl)-3-chloronaphthalene

Conditions	Yield
Stage #1: ((1-bromo-3-chloro-naphthalene-7-yl)methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 5h; Inert atmosphere; Reflux; Stage #2: 3-bromo-5-chloro-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h;	70%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + ((1-bromo-4-chloro-naphthalene-7-yl)methyl)triphenylphosphonium bromide → 4-bromo-6-(2-(5-bromo-3-chlorophenyl)vinyl)-1-chloronaphthalene

Conditions	Yield
Stage #1: ((1-bromo-4-chloro-naphthalene-7-yl)methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 5h; Inert atmosphere; Reflux; Stage #2: 3-bromo-5-chloro-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; Reflux;	67%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + bis(pinacol)diborane (73183-34-3) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate In 1,4-dioxane for 12h; Reflux;	63%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + (6-bromopyridin-2-yl)boronic acid (440680-34-2) → 3-(6-bromopyridin-2-yl)-5-chlorobenzaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux;	62%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux;	62%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + C23H19N3 → C30H19BrClN3

Conditions	Yield
Stage #1: 3-bromo-5-chloro-benzaldehyde; C23H19N3 In ethanol at 20℃; for 0.5h; Stage #2: With [bis(acetoxy)iodo]benzene In ethanol at 20℃; for 3h;	61%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + 1,8-diazaspiro[4.5]decane-8-carboxylic acid tert butyl ester (937729-06-1) → tert-butyl 1-(3-bromo-5-chlorobenzyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

Conditions	Yield
Stage #1: 3-bromo-5-chloro-benzaldehyde; 1,8-diazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester In dichloromethane at 20℃; for 2h; Molecular sieve; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Time; Molecular sieve; Inert atmosphere;	60%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + (3-bromophenyl)boronic acid (89598-96-9) → 3'-bromo-5-chloro-[1,1'-biphenyl]-3-carbaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux;	60%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + N-phenylpent-4-enamide (58804-62-9) → 3-chloro-5-((5-oxo-1-phenylpyrrolidin-2-yl)methyl)benzaldehyde

Conditions	Yield
With Ir(dF(CF3)ppy)2(bpy)PF6; Ni(4,4'-dimethoxy-2,2'-bipyridine)(H2O)2Br2; dibutylphosphoric acid tetrabutylammonium salt In toluene; tert-butyl alcohol at 20℃; for 48h; Inert atmosphere; Sealed tube; Irradiation;	56%

4-Methoxystyrene (637-69-4) + 3-bromo-5-chloro-benzaldehyde (188813-05-0) → (E)-3-chloro-5-(4-methoxystyryl)benzaldehyde

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 100℃; for 16h; Inert atmosphere;	54%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 100℃; for 16h;	54%

morpholine (110-91-8) + 3-bromo-5-chloro-benzaldehyde (188813-05-0) → 3-chloro-5-morpholinobenzaldehyde (1446818-81-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; Inert atmosphere;	52%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + potassium ((4-(tert-butoxycarbonyl)piperidin-1-yl)methyl)trifluoroborate → tert-butyl 1-(3-chloro-5-formylbenzyl)piperidine-4-carboxylate

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In tetrahydrofuran; water at 80℃; Inert atmosphere;	47%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + p-aminoethylbenzoate (94-09-7) → 4-{[1-(3-bromo-5-chloro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (1343455-97-9)

Conditions	Yield
In ethanol for 2h; Reflux;	35%
In ethanol for 2h; Reflux;	35%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (141449-85-6) → tert-butyl 5-(3-chloro-5-formylphenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; Inert atmosphere;	32%

3-bromo-5-chloro-benzaldehyde (188813-05-0) + malonic acid (141-82-2) → ClBrC6H3CH(NH2)CH2COOH

Conditions	Yield
With ammonium acetate In isopropyl alcohol Heating;

3-bromo-5-chloro-benzaldehyde (188813-05-0) → ClBrC6H3CH(NH2)CH2COOC2H5

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium acetate / propan-2-ol / Heating 2: HCl View Scheme

3-bromo-5-chloro-benzaldehyde (188813-05-0) → ClBrC6H3CH(NH2)CH2COOC2H5 (792907-29-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium acetate / propan-2-ol / Heating 2: HCl 3: immobilized Pseudomonas cepacia lipase / various solvent(s) / 24 h / 20 °C View Scheme

3-bromo-5-chloro-benzaldehyde (188813-05-0) → ClBrC6H3CH(NH2)CH2COOH

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium acetate / propan-2-ol / Heating 2: HCl 3: immobilized Pseudomonas cepacia lipase / various solvent(s) / 24 h / 20 °C View Scheme

3-bromo-5-chloro-benzaldehyde (188813-05-0) → C22H22ClBrFN5O5C2H4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ammonium acetate / propan-2-ol / Heating 2.1: HCl 3.1: immobilized Pseudomonas cepacia lipase / various solvent(s) / 24 h / 20 °C 4.1: isobutyl chloroformate; N-methylmorpholine / N,N-dimethyl-acetamide / 0.25 h / 5 - 20 °C 4.2: N-methylmorpholine / N,N-dimethyl-acetamide / 20 °C View Scheme

3-bromo-5-chloro-benzaldehyde (188813-05-0) → C22H22ClBrFN5O5

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ammonium acetate / propan-2-ol / Heating 2.1: HCl 3.1: immobilized Pseudomonas cepacia lipase / various solvent(s) / 24 h / 20 °C 4.1: isobutyl chloroformate; N-methylmorpholine / N,N-dimethyl-acetamide / 0.25 h / 5 - 20 °C 4.2: N-methylmorpholine / N,N-dimethyl-acetamide / 20 °C 5.1: aq. NaOH / acetonitrile / 3 h / 20 °C View Scheme

Upstream product

• 14862-52-3 1,3-dibromo-5-chlorobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1541198-11-1 C₂₃H₃₄ClNO₆ 
• 1541198-03-1 (S)-ethyl 3-amino-3-(3-chloro-5-(4-(methoxymethyl)tetrahydro-2H-pyran-4-yl)phenyl)propanoate hydrochloride 
• 1541198-12-2 (R)-ethyl 3-amino-3-(3-chloro-5-(4-(methoxymethyl)tetrahydro-2H-pyran-4-yl)phenyl)propanoate hydrochloride 
• 1541198-14-4 C₁₅H₁₈ClFO₃ 
• 1541198-15-5 C₁₃H₁₄ClFO₂ 
• 1541198-16-6 C₁₇H₂₃ClFNO₃ 
• 1541198-17-7 C₂₂H₃₁ClFNO₅ 
• 1541198-18-8 C₂₂H₃₁ClFNO₅ 
• 1541198-19-9 C₂₂H₃₁ClFNO₅ 
• 1541198-13-3 (S)-ethyl 3-amino-3-(3-chloro-5-(4-(fluoromethyl)tetrahydro-2H-pyran-4-yl)phenyl)propanoate hydrochloride 
• 1541198-20-2 C₁₇H₂₃ClFNO₃*ClH 
• 1541198-22-4 C₁₅H₁₇ClO₄ 
• 1541198-23-5 C₁₄H₁₅ClO₄ 
• 1541198-24-6 C₁₄H₁₆ClNO₃ 

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