1462-37-9

Basic information

• Product Name: BENZYL 2-BROMOETHYL ETHER
• Synonyms: BENZYL 2-BROMOETHYL ETHER;1-BROMO-2-BENZYLOXYETHANE;1-BENZYLOXY-2-BROMOETHANE;2-BENZYLOXY-1-BROMOETHANE;Benzyl 2-bromoethyl ether, 97 % (GC);(2-Bromoethoxymethyl)benzene;Benzyloxyethyl Bromide;2-(Benzyloxy)ethyl bromide
• CAS NO: 1462-37-9
• Molecular Formula: C₉H₁₁BrO
• Molecular Weight: 215.09
• EINECS: 1592732-453-0
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;C9;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;alkyl bromide
• Mol File: 1462-37-9.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 254 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow liquid
• Density: 1.36 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: n20/D 1.541(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: BENZYL 2-BROMOETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-BROMOETHYL ETHER(1462-37-9)
• EPA Substance Registry System: BENZYL 2-BROMOETHYL ETHER(1462-37-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• RIDADR: UN 3334
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 1462-37-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 1462-37-9 differently. You can refer to the following data:
1. Alkylation reagent for synthesis of a macrocyclic antifungal antibiotic.1
2. Benzyl 2-broMoethyl ether is a reactant used in the preparation of muscarinic antagonist.
3. Building block used to prepare a copper phthalocyanine discotic liquid crystal.

General Description

Benzyl 2-bromoethyl ether is an organic building block. Its enthalpy of vaporization at boiling point (527.15K) has been reported to be 46.499kjoule/mol.

InChI:InChI=1/C9H11BrO/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5H,6-8H2

Synthetic route

2-Benzyloxyethanol (622-08-2) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	98%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -78 - 20℃; Inert atmosphere; Darkness;	98%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 13h;	89%

2,4,6-tris(benzyloxy)-1,3,5-triazine (7285-83-8) + 2-bromoethanol (540-51-2) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5h; Inert atmosphere;	98%

2-bromoethanol (540-51-2) + benzyl alcohol (100-51-6) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold (I) at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation;	98%

2-(Benzyloxy)ethyl p-toluenesulfonate (4981-83-3) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With lithium bromide In acetonitrile at 70 - 80℃; for 2.5h; Reagent/catalyst; Solvent; Temperature;	94.3%

Pyridine-2-sulfonic acid 2-benzyloxy-ethyl ester (123455-81-2) → bromoethyl-2-benzyl ether (1462-37-9) + C5H4NO3S(1-)*Br(1-)*Mg(2+)

Conditions	Yield
With magnesium bromide ethyl etherate In diethyl ether; dichloromethane at 0℃; for 0.5h;	A 94% B n/a

2-(benzyloxy)ethyl methanesulfonate (58841-52-4) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With sodium bromide In dimethyl sulfoxide at 80 - 100℃; for 1h;	93.5%

2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine + 2-bromoethanol (540-51-2) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 0.0166667h; Molecular sieve; Inert atmosphere;	89%

2-Benzyloxyethanol (622-08-2) + triphenylphosphine (603-35-0) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
In hexane; dichloromethane	85%
In N-Bromosuccinimide; hexane; dichloromethane	85%

2-Benzyloxyethanol (622-08-2) → bromoethyl-2-benzyl ether (1462-37-9) + benzyl bromide (100-39-0)

Conditions	Yield
With bromine In acetonitrile at 0℃; for 0.5h; Bromination;	A 77% B n/a

carbon tetrabromide (558-13-4) + 2-Benzyloxyethanol (622-08-2) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With pyridine; triphenylphosphine In methanol; dichloromethane; ethyl acetate	76%

ethylene dibromide (106-93-4) + benzyl alcohol (100-51-6) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With potassium hydroxide; tetrafluoroboric acid; mercury(II) oxide In dichloromethane 1.) room temp., 1 h;	70%

oxirane (75-21-8) + benzyl bromide (100-39-0) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
With copper

1-bromo-2-(chloromethoxy)ethane (1462-35-7) + phenylmagnesium bromide → bromoethyl-2-benzyl ether (1462-37-9)

benzyl bromide (100-39-0) + polymer-bound NMe3(1+)*SCN(1-) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / NaH / tetrahydrofuran / 3 h / Heating 2: 89 percent / NBS; PPh3 / CH2Cl2 / 13 h / 20 °C View Scheme

benzyl bromide (100-39-0) + sodium compound of cyclohexanol → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH 2: Br2, Ph3P View Scheme

benzyl bromide (100-39-0) → bromoethyl-2-benzyl ether (1462-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 16 h / 0 - 23 °C 2: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 1 h / -10 - 23 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 12 h / 0 - 20 °C 2.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 1 h / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 1 h / -78 - 20 °C View Scheme

bromoethyl-2-benzyl ether (1462-37-9) → benzyl vinyl ether (935-04-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 8h;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 8h;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 68℃; for 12h;	97%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	70%
With potassium tert-butylate

bromoethyl-2-benzyl ether (1462-37-9) → benzyl iodoethyl ether (54555-84-9)

Conditions	Yield
With sodium iodide In acetone Reflux;	100%
With sodium iodide In acetone for 48h; Reflux;	85%
With sodium iodide In acetone for 3h; Reflux;	73%
With sodium iodide In acetone for 16h; Reflux;	60%
With sodium iodide In acetone for 6h; Reflux;

bromoethyl-2-benzyl ether (1462-37-9) + triethyl phosphite (122-52-1) → diethyl <2-(benzyloxy)ethyl>phosphonate (727-18-4)

Conditions	Yield
at 200℃; for 3h; Arbuzov Reaction; Inert atmosphere;	98%
at 165 - 170℃; for 3h;	76%
at 165 - 170℃;	76%
at 170℃; for 2h;	71%

piperidin-2-one (675-20-7) + bromoethyl-2-benzyl ether (1462-37-9) → 1-(2-(benzyloxy)ethyl)piperidin-2-one (157399-43-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) 0 deg C; 2.) heating;	97%

C27H24N2O3 (1057644-00-4) + bromoethyl-2-benzyl ether (1462-37-9) → C36H34N2O4 (1057644-06-0)

Conditions	Yield
With sodium hydroxide In water; acetone Reflux;	97%

bromoethyl-2-benzyl ether (1462-37-9) + 2-fluoro-4-hydroxybenzonitrile (82380-18-5) → 4-(2-benzyloxy-ethoxy)-2-fluoro-benzonitrile (1409990-80-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;	97%

3,5-dicarbomethoxypyrazole (4077-76-3) + bromoethyl-2-benzyl ether (1462-37-9) → 3,5-dimethyl 1-[2-(benzyloxy)ethyl]-1H-pyrazole-3,5-dicarboxylate (1200497-52-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃; for 4h; Inert atmosphere;	96.22%
With potassium carbonate In acetonitrile at 90℃; for 4h; Inert atmosphere;	96.22%
With potassium carbonate In acetonitrile at 85℃; for 1.5h;
With potassium carbonate In acetonitrile for 4.5h; Inert atmosphere; Reflux;
With potassium carbonate In acetonitrile for 4.5h; Reflux; Inert atmosphere;

bromoethyl-2-benzyl ether (1462-37-9) + Diethyl methylmalonate (609-08-5) → diethyl 2-(2-(benzyloxy)ethyl)-2-methylmalonate (172644-58-5)

Conditions	Yield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran Stage #2: bromoethyl-2-benzyl ether In tetrahydrofuran at 90℃; for 5h;	96%

bromoethyl-2-benzyl ether (1462-37-9) + 4-(5-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile (33469-11-3) → 4-(1-(2-(benzyloxy)ethyl)-4-(trifluoromethyl)-1H-imidazol-2-yl)benzonitrile

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 18h;	96%

bromoethyl-2-benzyl ether (1462-37-9) → 1-(ethoxymethyl)benzene (539-30-0)

Conditions	Yield
With tris-(trimethylsilyl)silane In acetonitrile at 50℃; for 24h;	95%

bromoethyl-2-benzyl ether (1462-37-9) + 2-bromo-4-fluoro-phenol (496-69-5) → 1-(2-(benzyloxy)ethoxy)-2-bromo-4-fluorobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;	95%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrochloride → Umeclidinium bromide

Conditions	Yield
In propan-1-ol; water for 2h; Solvent; Reflux;	94.01%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrobromide → Umeclidinium bromide

Conditions	Yield
In 2-methyltetrahydrofuran; water for 2.5h; Reflux;	93.25%

bromoethyl-2-benzyl ether (1462-37-9) + meta-hydroxybenzaldehyde (100-83-4) → 3-(2-(benzyloxy)ethoxy)benzaldehyde (1141781-75-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Large scale;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Large scale;	93%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol sulfuric acid → Umeclidinium bromide

Conditions	Yield
In water; acetonitrile for 3h; Reflux;	92.87%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol formic acid → Umeclidinium bromide

Conditions	Yield
In isopropyl alcohol for 2.5h; Reflux;	92.05%

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) + bromoethyl-2-benzyl ether (1462-37-9) → 2-(2-benzyloxyethyl)-allylmalonate (188125-31-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 12h; Alkylation; Heating;	92%

bromoethyl-2-benzyl ether (1462-37-9) + 2-nitro-4-phenylmethoxy-phenol (96315-18-3) → 4-(benzyloxy)-1-[2-(benzyloxy)ethoxy]-2-nitrobenzene (1257408-27-7)

Conditions	Yield
Stage #1: 2-nitro-4-phenylmethoxy-phenol With potassium carbonate In N,N-dimethyl-formamide for 0.333333h; Williamson alkylation; Stage #2: bromoethyl-2-benzyl ether In N,N-dimethyl-formamide at 110℃; for 14h; Williamson alkylation; Inert atmosphere;	92%

4-iodopyrazole (3469-69-0) + bromoethyl-2-benzyl ether (1462-37-9) → 1-(2-(benzyloxy)ethyl)-4-iodo-1H-pyrazole (1562305-17-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	91.7%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	91.7%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	20 g

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol nitric acid → Umeclidinium bromide

Conditions	Yield
In 1,4-dioxane for 2h; Reflux;	90.85%

diethyl <1-14C>malonate (23178-23-6) + bromoethyl-2-benzyl ether (1462-37-9) → diethyl <2-(benzyloxy)ethyl><1-14C>malonate

Conditions	Yield
With sodium hydride In tetrahydrofuran for 9h; Heating;	90%

bromoethyl-2-benzyl ether (1462-37-9) + 4,5-bis(hydroxy)phthalic acid dimethyl ester (66323-03-3) → 4,5-bis(benzyloxyethoxy)phthalic acid dimethyl ester (264871-01-4)

Conditions	Yield
With potassium carbonate In acetone for 48h; Etherification; Heating;	90%

C25H20N2O3 (263141-91-9) + bromoethyl-2-benzyl ether (1462-37-9) → C34H30N2O4 (263141-92-0)

Conditions	Yield
With sodium hydroxide In water; acetone for 14h; Reflux;	90%

bromoethyl-2-benzyl ether (1462-37-9) + 3-hydroxy-5-methoxy-benzoic acid methyl ester (19520-74-2) → methyl 3-(2-(benzyloxy)ethoxy)-5-methoxybenzoate (203803-61-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	90%
With potassium carbonate In N,N-dimethyl-formamide	90%
Stage #1: 3-hydroxy-5-methoxy-benzoic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: bromoethyl-2-benzyl ether In N,N-dimethyl-formamide at 160℃; for 2h;

Upstream product

• 146237-62-9 sodium 2-tert-butylpyrimidin-5-ol 
• 14623-75-7 carbonic acid, cerium salt 
• 14623-68-8 2-(p-amino-N-ethylanilino)ethanol sulphate 
• 14623-60-0 5-amino-1H-pyrimidine-2,4-dithione 
• 14623-58-6 4,5-DIAMINO-2-MERCAPTOPYRIMIDINE 
• 14623-57-5 2,4-dithio-5-nitropyrimidine 
• 1462-35-7 1-BROMO-2-CHLOROMETHOXY-ETHANE 
• 146235-53-2 (2S,9S)-2,9-diamino-5-[(2S,3R)-3-{[(2Z,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-2,4,6-trienoyl](butanoyl)amino}-2-methyl-3-(methylamino)-4-oxobutyl]-5-[(diaminomethylidene)amino]-4,6-dioxodecanedioic acid 
• 14623-54-2 3-MERCAPTOPICOLINIC ACID HYDROCHLORIDE 
• 146235-30-5 Methyl (S)-4-acetoxy-2-oxo-1-pyrrolidineacetate 
• 14623-50-8 8-methoxy-5,6-dihydrobenzo[h]quinazoline-2(1H)-thione 
• 14623-49-5 8-METHOXY-5,6-DIHYDROBENZO[H]QUINAZOLIN-2-AMINE 
• 14623-39-3 ethyl [(1-cyano-6-methoxynaphthalen-2-yl)amino](oxo)acetate 
• 1462-33-5 2-Chloromethoxyethylchloride 

Downstream Products

• 1462383-16-9 tert-Butyl 4,7-diazaspiro[2.5]octane-7-carboxylate hydrochloride 
• 1462-39-1 3-(2-CHLORO-ETHOXY)-PROPENE 
• 146239-76-1 Lumi-Phos 530 
• 146239-82-9 nefloxacin 
• 146240-19-9 sakacin P 
• 146240-37-1 zooxanthellatoxin A 
• 14624-13-6 aluminium tri(octanolate) 
• 14624-15-8 aluminium tridodecanolate 
• 1462470-54-7 Ivabradine Impurity 5 
• 14624-85-2 1,3-DIETHYL-2-OXO-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBALDEHYDE 
• 14624-88-5 BIO-FARMA BF002424 
• 14624-97-6 1-BENZYL-2-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE 
• 14625-01-5 4-[(2,5-dioxoimidazolidin-4-ylidene)methyl]benzaldehyde 
• 14625-03-7 1H-Benzimidazole,2-(2-propenyl)-(9CI) 

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