6-Bromo-2-naphthaldehyde supplier

Name
6-bromonaphthalene-2-carbaldehyde
EINECS
CAS No. 170737-46-9
Article Data30
CAS DataBase
Density 1.552 g/cm³
Solubility
Melting Point 125.0 to 130.0 °C
Formula C₁₁H₇BrO
Boiling Point 355.8 °C at 760 mmHg
Molecular Weight 235.08
Flash Point 125.9 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Naphthalenecarboxaldehyde, 6-bromo-;
PSA 17.07000
LogP 3.41480

Synthetic route

: 100751-63-1
(6-bromo-2-naphthy)methanol

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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%

: 13720-06-4
2,6-dibromonaphthalene

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

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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

: 33626-98-1
methyl 6-bromo-2-naphthoate

A: 100751-63-1
(6-bromo-2-naphthy)methanol

B: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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

: 5111-65-9
2-Bromo-6-methoxynaphthalene

A: 3453-33-6
6-methoxynaphthalene-2-carbaldehyde

B: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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%)

: 5773-80-8
6-bromo-2-naphthoic acid

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

Conditions

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

: 1017593-93-9
C9H15NO5

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1017594-45-4
C20H20BrNO5

Conditions

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%

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 504-63-2
trimethyleneglycol

: 1129491-95-7
6-bromo-2-(1,3-dioxan-2-yl)naphthalene

Conditions

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

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 100751-63-1
(6-bromo-2-naphthy)methanol

Conditions

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

: 158813-39-9
2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (R,Z)-1-(6-bromonaphthalen-2-yl)-4-chlorobut-3-en-1-ol

Conditions

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

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (R,Z)-1-(6-bromonaphthalen-2-yl)-5,5,5-trifluoropent-3-en-1-ol

Conditions

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

: 107-21-1
ethylene glycol

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 935473-01-1
2-(6-bromonaphthalen-2-yl)-1,3-dioxolane

Conditions

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%

: 38186-51-5
diethyl (4-bromobenzyl)phosphonate

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (E)-2-bromo-6-(4-bromostyryl)naphthalene

Conditions

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

: 1017593-93-9
C9H15NO5

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1017594-71-6
C20H20BrNO5

Conditions

Conditions	Yield
With magnesium sulfate In methanol; dichloromethane	91%

: 24350-54-7
diisopropyl trimethylsily phosphite

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (R)-diisopropyl ((6-bromonaphthalen-2-yl)(hydroxy)methyl)phosphonate

Conditions

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%

: 141-82-2
malonic acid

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (E)-3-(6-bromonaphthalen-2-yl)acrylic acid

Conditions

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

: 18292-38-1
2-methallyltrimethylsilane

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1448863-14-6
(1R)-1-(6-bromonaphth-2-yl)-3-methyl-3-buten-1-ol

Conditions

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%

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1066-54-2
trimethylsilylacetylene

: 6-[(trimethylsilyl)ethynyl]-2-naphthaldehyde

Conditions

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

: 62-53-3
aniline

: 84-11-7
9,10-phenanthrenequinone

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 2-(6-bromonaphthalen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

Conditions

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%

...Expand

: 459423-02-0
3-(1-adamantyl)-4,5-methylenedioxy-1-phenyl boronic acid

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde

Conditions

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

: 84418-43-9
9-fluorenylmethyl carbamate

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 762-72-1
allyl-trimethyl-silane

: (R)-(9H-fluoren-9-yl)methyl (1-(6-bromonaphthalen-2-yl)but-3-en-1-yl)carbamate

Conditions

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

...Expand

: 110-91-8
morpholine

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1114962-61-6
6-morpholin-4-yl-naphthalene-2-carbaldehyde

Conditions

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

: 109-01-3
1-methyl-piperazine

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1290035-73-2
6-(4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde

Conditions

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

: 558-43-0
2-Methyl-1,2-propanediol

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (S)-2-(6-bromonaphthalen-2-yl)-4,4-dimethyl-1,3-dioxolane

Conditions

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

: 2234-82-4
1-propylmagnesium chloride

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1-(6-bromonaphthalen-2-yl)butan-1-ol

Conditions

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

: 110-89-4
piperidine

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1208971-02-1
6-(piperidin-1-yl)naphthalene-2-carbaldehyde

Conditions

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%

: 84468-17-7
N-(2-aminomethyl)-5-isoquinolinesulfonamide

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: N-(2-(((6-bromonaphthalen-2-yl)methyl)amino)ethyl)isoquinoline-5-sulfonamide

Conditions

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

: 22924-18-1
2′,4′-diethoxyacetophenone

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: C35H34BrNO4

Conditions

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

: 1530-32-1
ethyltriphenylphosphonium bromide

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: C13H11Br

Conditions

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%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 170737-47-0
C12H9Br

Conditions

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%

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1208971-02-1
6-(piperidin-1-yl)naphthalene-2-carbaldehyde

Conditions

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

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: 1-(6-bromonaphthalen-2-yl)-2,2,2-trifluoroethanol

Conditions

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

: 170737-46-9
6-bromo-naphthalene-2-carboxaldehyde

: (E)-4-(2-(6-bromonaphthalene-2-yl)-1-phenylvinyl)-N,N-diphenylaniline

Conditions

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%

6-Bromo-2-naphthaldehyde Specification

The CAS registry number of 6-Bromo-2- aphthalenecarboxaldehyde is 170737-46-9. This chemical is also named as 2-Naphthalenecarboxaldehyde, 6-bromo-. In addition, its molecular formula is C₁₁H₇BrO and molecular weight is 235.08. Its systematic name is called 6-bromonaphthalene-2-carbaldehyde.

Physical properties about this chemical are: (1)ACD/LogP: 3.64; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.64; (4)ACD/LogD (pH 7.4): 3.64; (5)ACD/BCF (pH 5.5): 345.31; (6)ACD/BCF (pH 7.4): 345.31; (7)ACD/KOC (pH 5.5): 2282.71; (8)ACD/KOC (pH 7.4): 2282.71; (9)#H bond acceptors: 1#H bond donors: 0; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.7; (12)Molar Refractivity: 58.53 cm³; (13)Molar Volume: 151.3 cm³; (14)Surface Tension: 52 dyne/cm; (15)Density: 1.552 g/cm³; (16)Flash Point: 125.9 °C; (17)Enthalpy of Vaporization: 60.1 kJ/mol; (18)Boiling Point: 355.8 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1ccc2cc(Br)ccc2c1
(2)InChI: InChI=1/C11H7BrO/c12-11-4-3-9-5-8(7-13)1-2-10(9)6-11/h1-7H
(3)InChIKey: DLLDUYJRQNTEOR-UHFFFAOYAQ

Product Name

6-bromonaphthalene-2-carbaldehyde

Synthetic route

6-Bromo-2-naphthaldehyde Specification

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