1-(Bromomethyl)naphthalene supplier

Name
1-(Bromomethyl)naphthalene
EINECS 801-817-2
CAS No. 3163-27-7
Article Data82
CAS DataBase
Density 1.444 g/cm³
Solubility Slightly soluble in water.
Melting Point 52-55 °C
Formula C₁₁H₉Br
Boiling Point 326 °C at 760 mmHg
Molecular Weight 221.096
Flash Point 151.8 °C
Transport Information
Appearance off-white powder
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Naphthalene, 1-(bromomethyl)-;1-Naphthylmethyl bromide;a-(Bromomethyl)naphthalene;(1-Naphtyl)bromomethane;
PSA 0.00000
LogP 3.73470

Synthetic route

: 4780-79-4
1-naphthalene methanol

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With bromocyane; triphenylphosphine In dichloromethane at 20℃; Inert atmosphere;	100%
With sulfurous dibromide In toluene for 7h;	99%
With ethyl 2,2-dibromoacetoacetate; triphenylphosphine In dichloromethane at 20℃; for 0.5h;	99%

: 90-12-0
1-Methylnaphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	96%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 80℃; for 2.5h; Inert atmosphere;	95%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; dibenzoyl peroxide In ethyl acetate for 4.5h; Reflux;	90%

: 33250-32-7
1-(dimethoxymethyl)naphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With triethylsilane; Acetyl bromide; tin(II) bromide In dichloromethane at 0℃; for 1h;	96%

: 50-00-0
formaldehyd

: 91-20-3
naphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With hydrogen bromide In acetic acid for 3h; bromomethylation; Irradiation;	92%
With hydrogen bromide; acetic acid at 55 - 60℃;
With hydrogen bromide; acetic acid at 60 - 65℃;

: 66-77-3
1-naphthaldehyde

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With isopinocampheyl-boron dibromide dimethylsulfide complex In hexane at 20℃; for 3h; Reduction; bromination;	75%
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: pyridine; benzene; PBr3 View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C 2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: acetic acid; hydrogen bromide / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: hydrogen bromide / acetic acid / 0.5 h / 0 °C View Scheme

: 90-12-0
1-Methylnaphthalene

A: 6627-78-7
1-bromo-4-methylnaphthalene

B: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In various solvent(s) at 90 - 95℃; for 1h; Wohl-Ziegler bromination;	A 73% B 3%
With N-Bromosuccinimide at 150℃; under 2625.26 Torr; for 0.0666667h; microwave irradiation;	A 18 % Chromat. B 53 % Chromat.

: 56-23-5
tetrachloromethane

: 128-08-5
N-Bromosuccinimide

: 90-12-0
1-Methylnaphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

...Expand

: 91-20-3
naphthalene

: 13057-17-5
bromethyl methyl ether

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With acetic acid

: 91-20-3
naphthalene

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With formaldehyd; sulfuric acid; acetic acid; sodium bromide

N-α-menaphthyl-benzamide: N-α-menaphthyl-benzamide

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With phosphorus pentabromide durch Verschmelzen und anschliessendes Destillieren im Vakuum;

N.N-di-α-menaphthyl-benzamide: N.N-di-α-menaphthyl-benzamide

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With phosphorus pentabromide durch Verschmelzen und anschliessendes Destillieren im Vakuum;

: 13686-51-6
2-bromoaceto-1-naphthone

A: 941-98-0
1'-naphthacetophenone

B: 90-12-0
1-Methylnaphthalene

C: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
In benzene Kinetics; Quantum yield; Product distribution; Further Variations:; Solvents; Photolysis;

...Expand

: 774197-63-6
3-(1-naphthylmethoxy)-3-bromoaziridine

A: 90-12-0
1-Methylnaphthalene

B: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With cyclohexa-1,4-diene In chloroform at 20℃; for 1h; Product distribution; Further Variations:; Reagents; UV-irradiation;	A 70 % Spectr. B 30 % Spectr.

: 86-55-5
1-naphthalenecarboxylic acid

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h; 2.) room temperature, 14 h 2: 91 percent / PBr3, pyridine / benzene / 6 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: pyridine; benzene; PBr3 View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 2 h / 65 °C 2: lithium borohydride / tetrahydrofuran / 4 h / 60 °C 3: phosphorus tribromide / tetrahydrofuran / 2 h / 0 - 10 °C View Scheme

: 558-13-4
carbon tetrabromide

: 4780-79-4
1-naphthalene methanol

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
With triphenylphosphine

: C16H17BrO4

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
at 30℃;

: 2459-24-7
methyl 1-naphthoate

: 3163-27-7
2-(bromomethyl)naphthalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium borohydride / tetrahydrofuran / 4 h / 60 °C 2: phosphorus tribromide / tetrahydrofuran / 2 h / 0 - 10 °C View Scheme

: 713530-56-4
6-bromo-2-methyl-4-nitro-1H-benzimidazole

: 3163-27-7
2-(bromomethyl)naphthalene

: 1372539-74-6
6-bromo-2-methyl-1-(naphthalen-1-ylmethyl)-4-nitro-1H-benzo[d]imidazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	100%

: 69555-14-2
ethyl N-diphenylmethylene glycine

: 3163-27-7
2-(bromomethyl)naphthalene

: 677005-00-4
(R)-2-(Benzhydrylidene-amino)-3-naphthalen-1-yl-propionic acid ethyl ester

Conditions

Conditions	Yield
With potassium hydroxide; 3,4,5-F3-C6H2-NAS-Br In toluene at 0℃; for 2h;	99%

: 2926-29-6
Langlois reagent

: 3163-27-7
2-(bromomethyl)naphthalene

: 1-naphthylmethyl trifluoromethyl sulfone

Conditions

Conditions	Yield
With propiononitrile Heating;	99%
In acetonitrile at 80℃; Inert atmosphere;

: 1185073-30-6
tetra{2-[bis(2-phenethyl)phosphanyl]ethoxy}neopentane

: 3163-27-7
2-(bromomethyl)naphthalene

: tetra{2-[bis(2-phenethyl)(1-naphthylmethyl)phosphonium]ethoxy}neopentane tetrabromide

Conditions

Conditions	Yield
In diethyl ether at 23 - 25℃; for 0.5h; Inert atmosphere;	99%

: 3163-27-7
2-(bromomethyl)naphthalene

: 105-53-3
diethyl malonate

: 2107-84-8
diethyl (1-naphthylmethyl)malonate

Conditions

Conditions	Yield
With sodium In ethanol for 3h;	98%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 2-(bromomethyl)naphthalene In tetrahydrofuran for 1h; Reflux; Schlenk technique; Inert atmosphere;

: 599177-26-1
2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-acetamide

: 3163-27-7
2-(bromomethyl)naphthalene

: 851596-59-3
2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide

Conditions

Conditions	Yield
With potassium hydroxide; N-spiro chiral quaternary ammonium bromide In toluene at 0℃; for 6h;	98%

: 3163-27-7
2-(bromomethyl)naphthalene

: 98-80-6
phenylboronic acid

: 611-45-0
1-Benzyl-naphthalene

Conditions

Conditions	Yield
With potassium fluoride; (R)-N-(2-methoxybenzylidene)-1-phenylethanamine; palladium diacetate In tetrahydrofuran at 0 - 35℃; for 3.5h; Suzuki-Miyaura coupling reaction; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide for 0.216667h; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere;	84%

: (R)-2-(dicyclohexylphosphinyl)-2'-hydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

: 3163-27-7
2-(bromomethyl)naphthalene

: (R)-2-(dicyclohexylphosphinyl)-2'-(1-naphthylmethyloxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

Conditions

Conditions	Yield
With potassium carbonate In acetone for 72h; Reflux; Inert atmosphere;	98%

: 1372540-68-5
methyl 2-(difluoromethyl)-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate

: 3163-27-7
2-(bromomethyl)naphthalene

: 1372540-70-9
methyl 2-(difluoromethyl)-6-morpholino-1-(naphthalen-1-ylmethyl)-1H-benzo[d]imidazole-4-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 18h;	98%

: 2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide

: 3163-27-7
2-(bromomethyl)naphthalene

: 2,4-dimethyl-N-(4-(1-(naphthalen-1-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide

Conditions

Conditions	Yield
Stage #1: 2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(bromomethyl)naphthalene In N,N-dimethyl-formamide; mineral oil at 20℃; for 2.5h;	98%

: 499-75-2
carvacrol

: 3163-27-7
2-(bromomethyl)naphthalene

: 1-((5-isopropyl-2-methylphenoxy)methyl)naphthalene

Conditions

Conditions	Yield
Stage #1: carvacrol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-(bromomethyl)naphthalene In N,N-dimethyl-formamide Inert atmosphere;	98%

: 80232-65-1, 68578-79-0
(E/Z)-1,2-bis-(4-hydroxyphenyl)-1,2-diphenylethylene

: 3163-27-7
2-(bromomethyl)naphthalene

: C48H36O2

Conditions

Conditions	Yield
With potassium tert-butylate In toluene at 105℃; for 12h;	97%

: 3163-27-7
2-(bromomethyl)naphthalene

: 66-77-3
1-naphthaldehyde

Conditions

Conditions	Yield
With dihydrogen peroxide In ethanol for 4h; Reflux; Green chemistry;	96%
With sodium periodate In dichloromethane at 40 - 50℃; Ionic liquid;	82%
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 0.583333h;	80%

: 3163-27-7
2-(bromomethyl)naphthalene

: 204064-81-3
4-(2-(diphenylmethoxy)ethyl]piperidine

: 4-[2-(diphenylmethoxy)ethyl]-1-(1-naphthylmethyl)piperidine

Conditions

Conditions	Yield
With potassium carbonate In ethanol for 1h; Heating;	96%

: 1666-13-3
diphenyl diselenide

: 3163-27-7
2-(bromomethyl)naphthalene

: 78808-31-8
(naphthalen-1-ylmethyl)(phenyl)selane

Conditions

Conditions	Yield
With indium iodide In dichloromethane at 20℃; for 0.116667h;	96%

: 1453863-93-8
C23H26N2O5

: 3163-27-7
2-(bromomethyl)naphthalene

: 1453863-99-4
(1S,3S)-ethyl 2-(naphthalen-1-ylmethyl)-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 81℃; for 5h;	96%

: 380895-64-7
methyl (1S,3S)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate

: 3163-27-7
2-(bromomethyl)naphthalene

: 1453864-02-2
(1S,3S)-methyl 1-(3,4-dimethoxyphenyl)-2-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 81℃; for 5h;	96%

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 3163-27-7
2-(bromomethyl)naphthalene

: tert-butyl (2S)-2-[(diphenylmethylene)amino]-3-(1-naphthyl)propanoate

Conditions

Conditions	Yield
With C30H32N3O(1+)*Br(1-); potassium hydroxide In water; toluene at -40℃; for 10h; Reagent/catalyst; enantioselective reaction;	96%
With 2Br(1-)*C59H64N4O3(2+); potassium hydroxide In dichloromethane; chloroform; water; toluene at 0℃; for 9h; Inert atmosphere; enantioselective reaction;	93%
With C37H37N2O(1+)*Br(1-); potassium hydroxide In chloroform; water; toluene at -40℃; for 72h; enantioselective reaction;	85%

: 73818-55-0, 15596-07-3
Bestmann ylide

: 3163-27-7
2-(bromomethyl)naphthalene

: <1-(1-Naphthylmethyl)-2,4-dioxo-3-(triphenylphosphoranyliden)cyclobutyl>triphenylphosphonium-bromid

Conditions

Conditions	Yield
In benzene at 60℃; for 24h;	95%

: 3163-27-7
2-(bromomethyl)naphthalene

: 479486-96-9
N,N-dimethyl (trimethylsilyl)methanamide

: 1140-52-9
α-Naphthylessigsaeure-N.N-dimethylamid

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene at 65℃; for 0.75h;	95%

: 132183-16-5
tert-butyldiphenylsilyl O-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 3163-27-7
2-(bromomethyl)naphthalene

: tert-butyldiphenylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-naphthylmethyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; for 6h;	95%

: 17356-08-0
thiourea

: 3163-27-7
2-(bromomethyl)naphthalene

: naphthalen-1-ylmethyl carbamimidothioate monohydrobromide

Conditions

Conditions	Yield
In ethanol for 2h; Reflux;	95%
In N,N-dimethyl-formamide at 60℃;

: 3163-27-7
2-(bromomethyl)naphthalene

: 171596-43-3
(1S,3S)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester

: 1453863-95-0
(1S,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-1-yl-methyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 81℃; for 5h;	95%

: 3163-27-7
2-(bromomethyl)naphthalene

: 238428-10-9
(1S,3S)-methyl 1-(4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

: 1453863-98-3
(1S,3S)-methyl 1-(4-fluorophenyl)-2-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 81℃; for 5h;	95%

: C28H30O5S

: 3163-27-7
2-(bromomethyl)naphthalene

: C39H38O5S

Conditions

Conditions	Yield
With sodium hydride In dichloromethane for 5h; Inert atmosphere;	95%

: 3163-27-7
2-(bromomethyl)naphthalene

: 485-71-2
Cinchonidin

: (2S,4S,5R)-2-((R)-hydroxy(quinolin-4-yl)methyl)-1-(naphthalen-1-ylmethyl)-5-vinylquinuclidin-1-ium bromide

Conditions

Conditions	Yield
In acetonitrile Inert atmosphere;	95%
In tetrahydrofuran Reflux;	80%

: 536-74-3
phenylacetylene

: 3163-27-7
2-(bromomethyl)naphthalene

: 1‐(naphthalen‐1‐yl)‐4‐phenyl‐1H‐1,2,3‐triazole

Conditions

Conditions	Yield
With sodium azide In water at 20℃; for 2h; Catalytic behavior; Green chemistry;	95%
With copper(l) iodide; sodium azide at 20℃; for 0.5h;	93%

1-(Bromomethyl)naphthalene Chemical Properties

IUPAC Name: 1-(Bromomethyl)naphthalene
Synonyms of 1-(Bromomethyl)naphthalene (CAS NO.3163-27-7): Naphthalene, 1-(bromomethyl)- ; 1-Bromomethyl naphthalene ; 1-Bromomethyl naphthalene 99.73% ; (1-Naphtyl)bromomethane ; 1-Naphtylmethyl bromide
CAS NO: 3163-27-7
Molecular Formula: C₁₁H₉Br
Molecular Weight: 221.0932
Molecular Structure:

Melting Point: 52-55°C
Index of Refraction: 1.663
Molar Refractivity: 56.74 cm³
Molar Volume: 153 cm³
Surface Tension: 46.6 dyne/cm
Density of 1-(Bromomethyl)naphthalene (CAS NO.3163-27-7): 1.444 g/cm³
Flash Point: 151.8 °C
Enthalpy of Vaporization: 54.56 kJ/mol
Boiling Point: 326 °C at 760 mmHg
Vapour Pressure: 0.000422 mmHg at 25°C

1-(Bromomethyl)naphthalene Safety Profile

Hazard Codes of 1-(Bromomethyl)naphthalene (CAS NO.3163-27-7): Harmful Xn
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.

Product Name

1-(Bromomethyl)naphthalene

Synthetic route

1-(Bromomethyl)naphthalene Chemical Properties

1-(Bromomethyl)naphthalene Safety Profile

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