170737-46-9

Basic information

• Product Name: 6-bromonaphthalene-2-carbaldehyde
• Synonyms: 6-bromonaphthalene-2-carbaldehyde;2-NAPHTHALENECARBOXALDEHYDE, 6-BROMO-;6-BROMO-2-NAPHTHALDEHYDE;6-Bromonaphthalene-2-carbaldehyde ,98%;6-bromo-2-Naphthalenecarboxaldehyde
• CAS NO: 170737-46-9
• Molecular Formula: C₁₁H₇BrO
• Molecular Weight: 235.08
• Mol File: 170737-46-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 125.0 to 130.0 °C
• Boiling Point: 355.8 °C at 760 mmHg
• Flash Point: 125.9 °C
• Appearance: /
• Density: 1.552
• Vapor Pressure: 3.05E-05mmHg at 25°C
• Refractive Index: 1.7
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 6-bromonaphthalene-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromonaphthalene-2-carbaldehyde(170737-46-9)
• EPA Substance Registry System: 6-bromonaphthalene-2-carbaldehyde(170737-46-9)

Safety Data

• Hazardous Substances Data: 170737-46-9(Hazardous Substances Data)

Usage

General Description

6-Bromonaphthalene-2-carbaldehyde is a chemical compound characterized by its integration of bromine, naphthalene, and aldehyde functional groups. It is an aromatic bromoaldehyde, more specifically a member of the naphthalene family. The bromo group adds an element of reactivity, making it useful for various organic synthesis processes. In addition to being a reagent in organic chemistry, it may have potential application in making pharmaceutical intermediates, agrochemicals, and dyes. However, like other brominated compounds, it requires careful handling due to its potential as a health hazard and environmental pollutant.

InChI:InChI=1/C11H7BrO/c12-11-4-3-9-5-8(7-13)1-2-10(9)6-11/h1-7H

Synthetic route

(6-bromo-2-naphthy)methanol (100751-63-1) → 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 1h;	100%
With pyridinium chlorochromate In dichloromethane for 1h; Reflux;	98%
With pyridinium chlorochromate In dichloromethane for 5h; Reflux;	95%

methyl 6-bromo-2-naphthoate (33626-98-1) → 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
Stage #1: methyl 6-bromo-2-naphthoate With diisobutylaluminium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With pyridinium chlorochromate In dichloromethane at 60℃; for 6h; Inert atmosphere;	95%
Stage #1: methyl 6-bromo-2-naphthoate With diisobutylaluminium hydride In tetrahydrofuran at 0 - 20℃; for 12h; Stage #2: With pyridinium chlorochromate In dichloromethane for 5h; Reflux;	95%
With manganese dioxide; dibal In methanol; dichloromethane; toluene	61%

2,6-dibromonaphthalene (13720-06-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	78%

methyl 6-bromo-2-naphthoate (33626-98-1) → (6-bromo-2-naphthy)methanol (100751-63-1) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere;	A 35% B 57%

2-Bromo-6-methoxynaphthalene (5111-65-9) → 6-methoxynaphthalene-2-carbaldehyde (3453-33-6) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
With n-butyllithium; sodium chloride In tetrahydrofuran; hexanes on silica gel; hexane; ethyl acetate; N,N-dimethyl-formamide	A n/a B 2.86 g (91%)

6-bromo-2-naphthoic acid (5773-80-8) → 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 0 - 25 °C 2: pyridinium chlorochromate / dichloromethane / 25 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 7 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -10 - 0 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 0 - 20 °C 2: Dess-Martin periodane / dichloromethane / 0 - 20 °C View Scheme

C9H15NO5 (1017593-93-9) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → C20H20BrNO5 (1017594-45-4)

Conditions	Yield
Stage #1: C9H15NO5 With ytterbium(III) triflate In dichloromethane at 20℃; for 0.5h; Stage #2: 6-bromo-naphthalene-2-carboxaldehyde In dichloromethane at 20℃; Further stages.;	100%

6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) + trimethyleneglycol (504-63-2) → 6-bromo-2-(1,3-dioxan-2-yl)naphthalene (1129491-95-7)

Conditions	Yield
With zirconium(IV) chloride; orthoformic acid triethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere;	96%

6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (6-bromo-2-naphthy)methanol (100751-63-1)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃; for 4h; Inert atmosphere;	96%

2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane (158813-39-9) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (R,Z)-1-(6-bromonaphthalen-2-yl)-4-chlorobut-3-en-1-ol

Conditions	Yield
With methanol; (2S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-2-(3-hydroxyadamantan-1-yl) 1-(isoindolin-2-yl)ethan-1-one; zinc dimethoxide In toluene at 22℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; stereoselective reaction;	95%

(Z)-4,4,5,5-tetramethyl-2-(4,4,4-trifluorobut-2-en-1-yl)-1,3,2-dioxaborolane + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (R,Z)-1-(6-bromonaphthalen-2-yl)-5,5,5-trifluoropent-3-en-1-ol

Conditions	Yield
With methanol; C33H38N2O2Si; zinc dimethoxide In toluene at 4℃; for 2h; Glovebox; Inert atmosphere; Sealed tube; stereoselective reaction;	93%

ethylene glycol (107-21-1) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 2-(6-bromonaphthalen-2-yl)-1,3-dioxolane (935473-01-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Heating;	92%
With toluene-4-sulfonic acid for 48h; Heating;	92%
With toluene-4-sulfonic acid In toluene at 120℃; for 48h;	52%
With toluene-4-sulfonic acid In toluene for 48h; Reflux; Dean-Stark;	48%

diethyl (4-bromobenzyl)phosphonate (38186-51-5) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (E)-2-bromo-6-(4-bromostyryl)naphthalene

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 0 - 20℃; for 12h;	91%

C9H15NO5 (1017593-93-9) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → C20H20BrNO5 (1017594-71-6)

Conditions	Yield
With magnesium sulfate In methanol; dichloromethane	91%

diisopropyl trimethylsily phosphite (24350-54-7) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (R)-diisopropyl ((6-bromonaphthalen-2-yl)(hydroxy)methyl)phosphonate

Conditions	Yield
With 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide In diethyl ether at -50℃; for 96h; Abramov Phosphorylation; enantioselective reaction;	88%

malonic acid (141-82-2) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (E)-3-(6-bromonaphthalen-2-yl)acrylic acid

Conditions	Yield
With piperidine; pyridine at 90℃; for 8h; Knoevenagel Condensation;	88%

2-methallyltrimethylsilane (18292-38-1) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (1R)-1-(6-bromonaphth-2-yl)-3-methyl-3-buten-1-ol (1448863-14-6)

Conditions	Yield
Stage #1: 2-methallyltrimethylsilane; 6-bromo-naphthalene-2-carboxaldehyde With 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; (R)-3,3'-bis[4-methyl-3,5-dinitrophenyl]-1,1'-binaphthyl-2,2'-disulfonimide In toluene at -78℃; for 72h; Hosomi-Sakurai Reaction; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene at -78 - 20℃; enantioselective reaction;	82%

6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) + trimethylsilylacetylene (1066-54-2) → 6-[(trimethylsilyl)ethynyl]-2-naphthaldehyde

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃;	82%

aniline (62-53-3) + 9,10-phenanthrenequinone (84-11-7) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 2-(6-bromonaphthalen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

Conditions	Yield
With ammonium acetate; acetic acid for 24h; Reflux; Inert atmosphere;	82%
With ammonium acetate; acetic acid at 130℃; for 18h; Inert atmosphere;	70%

3-(1-adamantyl)-4,5-methylenedioxy-1-phenyl boronic acid (459423-02-0) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine)palladium (0) In 1,2-dimethoxyethane; water	81%

9-fluorenylmethyl carbamate (84418-43-9) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) + allyl-trimethyl-silane (762-72-1) → (R)-(9H-fluoren-9-yl)methyl (1-(6-bromonaphthalen-2-yl)but-3-en-1-yl)carbamate

Conditions	Yield
With (R)-3,3'-bis(4-nitrophenyl)-1,1'-binaphthyl-2,2'-disulfonimide In chloroform at 15℃; for 288h; enantioselective reaction;	80%

morpholine (110-91-8) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 6-morpholin-4-yl-naphthalene-2-carbaldehyde (1114962-61-6)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Reflux; Inert atmosphere;	79%

1-methyl-piperazine (109-01-3) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde (1290035-73-2)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Reflux; Inert atmosphere;	77%

2-Methyl-1,2-propanediol (558-43-0) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (S)-2-(6-bromonaphthalen-2-yl)-4,4-dimethyl-1,3-dioxolane

Conditions	Yield
With C80H73NO6P2 In toluene at 20℃; for 52h; Molecular sieve; enantioselective reaction;	77%

1-propylmagnesium chloride (2234-82-4) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 1-(6-bromonaphthalen-2-yl)butan-1-ol

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h;	76%

piperidine (110-89-4) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 6-(piperidin-1-yl)naphthalene-2-carbaldehyde (1208971-02-1)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 12h; Reflux;	75%
With caesium carbonate; tri-tert-butyl phosphine; palladium diacetate In toluene for 72h; Reflux;	70%
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Reflux; Inert atmosphere;	70%

N-(2-aminomethyl)-5-isoquinolinesulfonamide (84468-17-7) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → N-(2-(((6-bromonaphthalen-2-yl)methyl)amino)ethyl)isoquinoline-5-sulfonamide

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 19h;	74%

2′,4′-diethoxyacetophenone (22924-18-1) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → C35H34BrNO4

Conditions	Yield
With ammonium acetate; acetic acid at 120℃; for 6h;	73.6%

ethyltriphenylphosphonium bromide (1530-32-1) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → C13H11Br

Conditions	Yield
Stage #1: ethyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -40 - -30℃; for 2h; Inert atmosphere; Stage #2: 6-bromo-naphthalene-2-carboxaldehyde In tetrahydrofuran at -40 - -30℃; for 0.5h; Inert atmosphere;	71%

Methyltriphenylphosphonium bromide (1779-49-3) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → C12H9Br (170737-47-0)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Wittig Olefination; Inert atmosphere; Stage #2: 6-bromo-naphthalene-2-carboxaldehyde In tetrahydrofuran at -20 - 20℃; Inert atmosphere;	71%

6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 6-(piperidin-1-yl)naphthalene-2-carbaldehyde (1208971-02-1)

Conditions	Yield
With piperidine; tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Buchwald-Hartwig Coupling; Reflux;	70%
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 48 h / Reflux; Dean-Stark 2: tri-tert-butyl phosphine; caesium carbonate; palladium diacetate / toluene / 16 h / 110 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C View Scheme

(trifluoromethyl)trimethylsilane (81290-20-2) + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → 1-(6-bromonaphthalen-2-yl)-2,2,2-trifluoroethanol

Conditions	Yield
Stage #1: (trifluoromethyl)trimethylsilane; 6-bromo-naphthalene-2-carboxaldehyde With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h;	70%

N,N-diphenyl-4-(phenyl(trimethylsilyl)methyl)aniline + 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (E)-4-(2-(6-bromonaphthalene-2-yl)-1-phenylvinyl)-N,N-diphenylaniline

Conditions	Yield
Stage #1: N,N-diphenyl-4-(phenyl(trimethylsilyl)methyl)aniline With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 8h; Stage #2: 6-bromo-naphthalene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 24h;	66%

Upstream product

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 13720-06-4 2,6-dibromonaphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 5773-80-8 6-bromo-2-naphthoic acid 
• 100751-63-1 (6-bromo-2-naphthy)methanol 

Downstream Products

• 100751-63-1 (6-bromo-2-naphthy)methanol 
• 219873-03-7 6-(hydroxymethyl)-2-naphthonitrile 
• 1590-25-6 1-(6-bromonaphthalen-2-yl)ethanone 

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