5414-19-7

Basic information

• Product Name: 2,2'-Dibromodiethyl ether
• Synonyms: 1,1’-oxybis[2-bromo-ethan;2-bromoethyl;beta,beta'-Dibromodiethyl ether;Ethane, 1,1'-oxybis*2-bromo-;Ethane, 1,1'-oxybis[2-bromo-;Ether, bis(2-bromoethyl);2,2'-DIBROMODIETHYL ETHER;2,2' DIBROMOETHYL ETHER
• CAS NO: 5414-19-7
• Molecular Formula: C₄H₈Br₂O
• Molecular Weight: 231.91
• EINECS: 226-504-2
• Product Categories: Aliphatics;Halides;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 5414-19-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 92-93 °C12 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: colourless liquid
• Density: 1.845 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.207mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible or difficult to mix with water.
• Stability: This product may also contain 2-chloroethyl ether (CAS 111-44-4) or N,N-dimethylformamide (CAS 68-12-2) MSDS data for these mate
• BRN: 1098335
• CAS DataBase Reference: 2,2'-Dibromodiethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dibromodiethyl ether(5414-19-7)
• EPA Substance Registry System: 2,2'-Dibromodiethyl ether(5414-19-7)

Safety Data

• Hazard Codes: T,Xi
• Statements: 61-37/38-41
• Safety Statements: 53-26-36/37/39-45
• RIDADR: 2810
• WGK Germany: 3
• TSCA: Y
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5414-19-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5414-19-7 differently. You can refer to the following data:
1. 2,2'-dibromodiethyl ether is an important organic intermediate (building block) to synthetize substituted diethyl ether products.
2. 2-Bromoethyl ether (2,2′-Dibromodiethyl ether) may be used in the preparation of 1,4,7-trioxa-10-19-dithia-13,16-diaza-12,17-dioxo-8,9,14,15,20,21-tribenzoheneicosane.

Description

Bis(2-bromoethyl) ether is an either compound with two terminal bromine atoms. Bis(2-bromoethyl) ether can be used as a building block for variety of pharmaceutical compounds and mateials.

Chemical Properties

colourless liquid

General Description

2-Bromoethyl ether (2,2′-Dibromodiethyl ether) is a halogen containing ether. 2,2′-Dibromodiethyl ether has been prepared by reacting dioxane with anhydrous, bromine free hydrogen bromide.

InChI:InChI=1/C4H8Br2O/c5-1-3-7-4-2-6/h1-4H2

Synthetic route

1,4-oxathiane-4,4-dioxide → 1,1'-oxybis(2-bromo-ethane) (5414-19-7)

Conditions	Yield
With hydrogen bromide at 20℃; for 12h; Temperature;	82.1%

diethylene glycol (111-46-6) → 1,1'-oxybis(2-bromo-ethane) (5414-19-7)

Conditions	Yield
With phosphorus tribromide at 0 - 60℃; for 13h;	80%
With phosphorus tribromide at 50 - 60℃; for 12h;	80%
With phosphorus tribromide for 9.5h;	33%

ethyl (2S)-2-[(diisopropylsilyl)oxy]propanoate (799296-23-4) + 2-bromoethanol (540-51-2) → 1,1'-oxybis(2-bromo-ethane) (5414-19-7) + ethyl (2S)-2-{[(2-bromoethoxy)(diisopropyl)silyl]oxy}propanoate (1202570-30-6)

Conditions	Yield
With bromopentacarbonylmanganese(I) In dichloromethane at 20℃; for 2h;	A n/a B 68%

3-oxa-1,5-dichloropentane (111-44-4) → 1,1'-oxybis(2-bromo-ethane) (5414-19-7)

Conditions	Yield
With potassium bromide In ethylene dibromide; N,N-dimethyl-formamide for 24h; Reflux;	65%

diethylene glycol dimesylate (34604-52-9) → 1,1'-oxybis(2-bromo-ethane) (5414-19-7)

Conditions	Yield
With lithium bromide In acetone for 20h; Heating / reflux;	50%
With lithium bromide In acetone for 20h; Heating;

oxirane (75-21-8) + ethene (74-85-1) → 1,1'-oxybis(2-bromo-ethane) (5414-19-7)

Conditions	Yield
With bromine
With bromine In tetrachloromethane

1-methyl-1H-imidazole (616-47-7) + 1,1'-oxybis(2-bromo-ethane) (5414-19-7) → 3,3′-(oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] dibromide

Conditions	Yield
In toluene Reflux; Inert atmosphere;	100%
In toluene at 90℃; for 48h;	99%
In acetonitrile for 48h; Reflux;	95%
at 80℃; for 16h;
In 1,1,1-trichloroethane at 80℃; for 24h;

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + cis-(+/-)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one → cis-2-[2-(2-bromoethoxy)ethyl]-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one

Conditions	Yield
Stage #1: cis-(+/-)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: 1,1'-oxybis(2-bromo-ethane) In N,N-dimethyl-formamide; mineral oil for 0.25h;	100%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + trans-4-(tert-butoxycarbonylamino)cyclohexylamine → tert-butyl ((1,4-trans)-4-morpholinocyclohexyl)carbamate

Conditions	Yield
With sodium carbonate In acetonitrile at 75℃; for 48h;	100%
With triethylamine In N,N-dimethyl-formamide at 70℃; for 16h;

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (3S)-4-[2-chloro-6-(methanesulfonylmethyl)pyrimidin-4-yl]-3-ethylmorpholine → (3S)-4-[2-chloro-6-(4-methanesulfonyloxan-4-yl)pyrimidin-4-yl]-3-ethylmorpholine

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 90℃; for 2.25h; Sealed tube;	100%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + borane-THF (14044-65-6) + methylphenylphosphine (6372-48-1) → 2,2'-oxybis(ethane-2,1-diyl)bis(methylphenylphosphine-borane) (1147564-62-2, 1147564-78-0)

Conditions

Yield

With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-DIFLUORPHOS)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate), NMR and MS;

99%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + trimethylamine (75-50-3) → (5-bromo-3-oxapentyl)trimethylammonium bromide

Conditions	Yield
In tetrahydrofuran for 24h; Ambient temperature;	98%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + diethyl malonate (105-53-3) → (1-ethoxy-ethyl)-malonic acid diethyl ester (91368-89-7)

Conditions	Yield
With sodium In ethanol; hexane	98%
With sodium In ethanol; hexane	98%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 2-[3,5-bis(1-ethoxyethoxy)phenyl]acetonitrile → 4-[3,5-bis(1-ethoxyethoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Conditions	Yield
Stage #1: 2-[3,5-bis(1-ethoxyethoxy)phenyl]acetonitrile With potassium hexamethylsilazane In tetrahydrofuran at -16℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,1'-oxybis(2-bromo-ethane) In tetrahydrofuran at -16℃; for 1h; Inert atmosphere;	98%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine (77421-68-2) → 5'-O-acetyl-3-N-[2-(2-bromoethoxy)ethyl]-2',3'-didehydro-2',3'-dideoxythymidine (514213-69-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h;	97%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) → 1,5-diazido-3-oxapentane (24345-74-2)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h;	97%
With sodium azide In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	95%
With sodium azide In N,N-dimethyl-formamide at 55℃; for 3h;

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 2-(((1R,3R)-3-(benzyloxy)cyclohexyl)oxy)-5-bromopyridin-3-amine → 4-(2-(((1R,3R)-3-(benzyloxy)cyclohexyl)oxy)-5-bromopyridin-3-yl)morpholine

Conditions	Yield
Stage #1: 2-(((1R,3R)-3-(benzyloxy)cyclohexyl)oxy)-5-bromopyridin-3-amine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 25℃; for 0.5h; Stage #2: 1,1'-oxybis(2-bromo-ethane) In N,N-dimethyl-formamide; mineral oil at 80℃; for 11.5h;	97%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + methyl salicylate (119-36-8) → 1,7-bis(2-(methoxycarbonyl)phenyl)-1,4,7-trioxaheptane (161724-78-3)

Conditions	Yield
With potassium carbonate In acetone for 168h; Heating;	96%
With potassium carbonate In acetone for 168h; Heating;	90%
With potassium carbonate In acetone for 168h; Reflux;	55%
With potassium carbonate In acetone Heating;

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 3-(2-imidazolin-1-yl)propyltriethoxysilane (63365-92-4) → 3-[3-(triethoxysilyl)propyl]-1-[2-(2-{1-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium-3-yl}ethoxy)ethyl]-1H-imidazol-3-ium dibromide

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 4h;	96%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 4-chloro-7-fluoro-7-deazapurine (582313-57-3) → 7-(2-[2-bromoethoxy]ethyl)-4-chloro-5-fluoro-7H-pyrrolo-[2,3-d]pyrimidine

Conditions	Yield
Stage #1: 4-chloro-7-fluoro-7-deazapurine With sodium hydride In mineral oil at 0 - 22℃; for 0.166667h; Stage #2: 1,1'-oxybis(2-bromo-ethane) In N,N-dimethyl-formamide; mineral oil at 60℃; for 2h;	96%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 6-hydroxy-2-chloroquinoline (577967-89-6) → C22H18Cl2N2O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	95.8%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + ethyl (6-chloro-pyridin-3-yl)acetate (197376-47-9) → ethyl 4-(6-chloropyridin-3-yl)tetrahydro-2H-pyran-4-carboxylate

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	95%
Stage #1: ethyl (6-chloro-pyridin-3-yl)acetate With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.666667h; Cooling with ice; Stage #2: 1,1'-oxybis(2-bromo-ethane) In N,N-dimethyl-formamide; mineral oil at 0℃; for 3h;	0.82 g

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 2-(2-(difluoro(trifluoromethoxy)methoxy)-1,1,2,2-tetrafluoroethoxy)-N-(3-(dimethylamino)propyl)-2,3,3,3-tetrafluoropropanamide → N,N'-(oxybis(ethane-2,1-diyl))bis(1,1,1,3,3,5,5,6,6,8-decafluoro-N,N-dimethyl-9-oxo-8-(trifluoromethyl)-2,4,7-trioxa-10-azatridecan-13-aminium) bromide

Conditions	Yield
In acetonitrile at 80℃; for 12h; Schlenk technique;	95%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + N,N',N'',N'''-tetratosyl-1,10-diamino-4,7-diazadecane (74676-47-4) → 4,8,11,15-tetrakis(p-tolylsulphonyl)-1-oxa-4,8,11,15-tetraazacycloheptadecane (120808-61-9)

Conditions	Yield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;	94%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;	94%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (1S,2S,3R,5S)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (69363-09-3) → (1S,2S,3R,5S)-2,6,6-trimethyl-3-morpholinobicyclo[3.1.1]heptan-2-ol

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	94%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 2-bromo-5-((4-(3-hydroxyphenyl)pyrimidin-2-yl)amino)phenol → C20H18BrN3O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 20h;	94%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) → diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With silver nitrate In acetonitrile at 70℃; for 16h; Darkness;	93.4%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (1S,2R)-(+)-norphedrine (37577-28-9) → (1S,2R)-2-(morpholin-4-yl)-1-phenylpropanol

Conditions	Yield
With sodium hydrogencarbonate In toluene for 22.5h; Heating;	93%
Stage #1: 1,1'-oxybis(2-bromo-ethane); (1S,2R)-(+)-norphedrine With sodium hydrogencarbonate In toluene at 115℃; for 22.5h; Stage #2: With sodium hydroxide In water pH=13;	93%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 1-(6-chloropyridin-3-yl)cyclohexanamine → 4-(1-(6-chloropyridin-3-yl)cyclohexyl)morpholine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; Sealed tube;	93%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (3-bromophenyl)acetonitrile (31938-07-5) → 4-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (245439-36-5)

Conditions	Yield
Stage #1: (3-bromophenyl)acetonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1,1'-oxybis(2-bromo-ethane) In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	93%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on (485-72-3) → 7-(2-(2-bromoethoxy)-ethoxy)-3-(4-methoxyphenyl)-4H-chromen-4-one

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 10h;	93%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 3'-azido-2',3'-deoxythymidine (30516-87-1) → 3'-azido-3-N-(5-bromoethyl ether)-3'-deoxythymidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone for 24h; Alkylation; Heating;	92%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 4,4'-bis(hydroxy)-3,3'-oxybis(ethyleneoxy)dibenzaldehyde (486395-57-7) → 6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin-2,14-dicarbaldehyde (90265-03-5)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 43.5h; Williamson macrocyclization;	92%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + p-aminophenylacetonitrile (3544-25-0) → 2-[4-(morpholin-4-yl)phenyl]acetonitrile (1000512-72-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;	92%
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;	92%
With N-ethyl-N,N-diisopropylamine In toluene for 20h; Reflux;

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + (R)-Phenylglycinol (56613-80-0) → (R)-2-morpholino-2-phenylethan-1-ol

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 24h;	92%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + tert-butyl {[5-(4-butoxyphenyl)thien-2-yl]sulfonyl}acetate (701270-40-8) → tert-butyl 4-{[5-(4-butoxyphenyl)thien-2-yl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate (701270-41-9)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In DMF (N,N-dimethyl-formamide) at 65℃; for 15h;	91%

Upstream product

• 75-21-8 oxirane 
• 74-85-1 ethene 
• 123-91-1 1,4-dioxane 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 10035-10-6 hydrogen bromide 
• 7726-95-6 bromine 
• 34604-52-9 diethylene glycol dimesylate 
• 799296-23-4 ethyl (2S)-2-[(diisopropylsilyl)oxy]propanoate 
• 540-51-2 2-bromoethanol 
• 107-61-9 1,4-oxathiane-4,4-dioxide 
• 107-21-1 ethylene glycol 
• 3741-38-6 ethylene sulfite 
• 111-46-6 diethylene glycol 

Downstream Products

• 92221-61-9 Propyl-2-oxo-1,3,6-trioxa-2-phospha-cyclooctan 
• 31191-40-9 1-[2-(2-Bromo-ethoxy)-ethoxy]-2-chloro-4-nitro-benzene 
• 16192-66-8 C₁₈H₂₂O₅S₄ 
• 16186-52-0 C₂₀H₂₆O₅S₄ 
• 16192-67-9 C₁₆H₁₆Br₂O₅S₄ 
• 60147-28-6 4,7,10-tris(p-tolylsulphonyl)-1-oxa-4,7,10-triazacyclododecane 
• 74461-32-8 4,8,12-tris(p-tolylsulphonyl)-1-oxa-4,8,12-triazacyclotetradecane 
• 75953-71-8 N,N'-diphenyl-1,5-diamino-3-oxapentane 
• 75953-68-3 N,N'-dibenzyl-1,5-diamino-3-oxapentane dihydrochloride 
• 120808-61-9 4,8,11,15-tetrakis(p-tolylsulphonyl)-1-oxa-4,8,11,15-tetraazacycloheptadecane 
• 52601-77-1 4,10-bis(p-tolylsulphonyl)-1,7-dioxa-4,10-diazacyclododecane 
• 74461-33-9 7,13-bis(p-tolylsulphonyl)-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 74461-34-0 10,16-bis(p-tolylsulphonyl)-1,4,7,13-tetraoxa-10,16-diazacyclo-octadecane 
• 54533-65-2 1,5-bis(o-nitrophenoxy)-3-oxapentane 

Relevant articles and documents

Solubility of 3,3′-(Oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] Dihexafluorophosphate in Water, Methanol, Ethanol, Acetone, and Acetonitrile and Binary Mixtures (Water + DMF) from (283.00 to 323.00) K

3,3′-(Oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] dihexafluorophosphate ([C4O(mim)2][PF6]2) was synthesized and confirmed with 1H NMR and FT-IR. The thermal stability of [C4O(mim)2][PF6]2 was studied with differential scanning calorimetry and thermogravimetric analyses. Using the dynamic method, the solubility of [C4O(mim)2][PF6]2 in five different pure solvents (water, methanol, ethanol, acetone, and acetonitrile) and binary mixtures (water + DMF) was measured at the temperature range from (283.00 to 323.00 K) at atmospheric pressure. The solubility of [C4O(mim)2][PF6]2 in those selected solvents increased with increasing temperature and DMF contents, but the rate of solubility is different. The experimental data were correlated with the modified Apelblat equation. Also, the solubility of [C4O(mim)2][PF6]2 and [C6O2(mim)2][PF6]2 was been compared in the same solvent. (Graphical Presented).

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COMPOUND, DECORATIVE MATERIAL, DECORATED ARTICLE, AND INK COMPOSITION

To provide a compound exhibiting golden glossiness and providing a film having flexibility.SOLUTION: There is provided a compound represented by the formula (1). Rand Rare each independently a substituted or unsubstituted C1 to 12 alkyl group, -(CH)-COO-R, -(CH)-O-R, -(CH)-CONH-R, -(CH)-CONH-(CH)-OH or the like; Rto Rare each independently a C1 to 6 alkyl group; nis an integer of 2 to 10; and mto mare integer of 1 to 6.SELECTED DRAWING: None

Double (2-haloethyl) ether synthesis method

The invention relates to the synthesis of fine chemical intermediates, in particular to a synthesis method of di(2-halogenated ethyl) ether. According to the synthesis method, 1,4-thioxane-1,1-dioxo and a hydrogen halide water solution react with each other to obtain the target product, namely di(2-halogenated ethyl) ether. The synthesis method is simple and convenient in technical route, good in selectivity, high in yield, less in pollution and simple in post-processing, conforms to the tendency of the green chemical industry nowadays, and has great industrial value.