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

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

Relevant articles and documents

METHODS OF DETECTING NEUROLOGICAL DISORDERS VIA BINDING TO PHOSPHORYLATED TAU PROTEIN

Provided herein are methods and compositions for determining whether a patient suffers from a neurological disease or disorder is provided, comprising detecting the presence of a phosphorylated tau protein in a tissue of the patient, wherein the detecting comprises contacting the phosphorylated tau protein with a compound described herein.

COMPOSITIONS AND METHODS FOR DETECTION OF TRAUMATIC BRAIN INJURY

The present disclosure relates generally to compositions and methods for determining whether a patient suffers from a traumatic brain injury (TBI) by detecting the presence of an amyloid beta protein in an eye of the patient. Also provided are compositions and methods for preparing a patient for diagnosis and treatment of traumatic brain injury (TB).

Photoactuators based on the dynamic molecular crystals of naphthalene acrylic acids driven by stereospecific [2+2] cycloaddition reactions

The photomechanical effects of the dynamic molecular crystals of halogen-substituted naphthalene acrylic acids (1FNaAA, 1ClNaAA, 1BrNaAA, 1INaAA and 6BrNaAA) have been investigated. Upon UV irradiation, the needle-like crystal of 1FNaAA curls away from the light source, while the slice-like crystal of 6BrNaAA bends towards the light source. Moreover, the light-induced bending, flipping and bursting are observed for the elongated needle-like crystals of 1FNaAA, and the slice-like crystals of 1ClNaAA and 1BrNaAA show bending, cracking, coiling, rotating and twisting triggered by 365 nm light. It is found that stereospecific [2+2] cycloaddition reactions take place in the crystals to afford one stereoisomer of β-type cyclobutanes, since 1FNaAA, 1ClNaAA, 1BrNaAA and 6BrNaAA pack in a head-to-head mode, which satisfies the Schmidt's topo-photochemical criteria. The strain can be generated and accumulated during the photodimerization, and the release of the strain leads to the photomechanical effects. This provides new clues for the development of photomechanical molecular crystals based on acrylic acids bearing halogen-substituted aromatic units.