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2,2'-Dibromodiethyl ether
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Name

2,2'-Dibromodiethyl ether

 EINECS 226-504-2
CAS No. 5414-19-7 Density 1.821 g/cm3
PSA 9.23000 LogP 1.79280
Solubility immiscible in water Melting Point N/A
Formula C4H8Br2O Boiling Point 216.3 °C at 760 mmHg
Molecular Weight 231.915 Flash Point 85 °C
Transport Information N/A Appearance colourless liquid
Safety 53-26-36/37/39-45 Risk Codes 61-37/38-41
Molecular Structure Molecular Structure of 5414-19-7 (2,2'-Dibromodiethyl ether) Hazard Symbols ToxicT,IrritantXi
Synonyms

Ether,bis(2-bromoethyl) (6CI,7CI,8CI);1,1'-Oxybis[2-bromoethane];1,5-Dibromo-3-oxapentane;1-(2-Bromoethoxy)-2-bromoethane;1-Bromo-2-(2-bromoethoxy)ethane;2-(2-Bromoethoxy)ethyl bromide;2-Bromoethyl ether;3-Oxa-1,5-dibromopentane;Bis(2-bromoethyl) ether;Bis(b-bromoethyl) ether;Di(2-bromoethyl) ether;NSC 8025;b,b'-Dibromodiethyl ether;

Article Data 30

2,2'-Dibromodiethyl ether Synthetic route

1,4-oxathiane-4,4-dioxide

1,4-oxathiane-4,4-dioxide

5414-19-7

1,1'-oxybis(2-bromo-ethane)

Conditions
ConditionsYield
With hydrogen bromide at 20℃; for 12h; Temperature;82.1%
111-46-6

diethylene glycol

5414-19-7

1,1'-oxybis(2-bromo-ethane)

Conditions
ConditionsYield
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%
799296-23-4

ethyl (2S)-2-[(diisopropylsilyl)oxy]propanoate

540-51-2

2-bromoethanol

A

5414-19-7

1,1'-oxybis(2-bromo-ethane)

B

1202570-30-6

ethyl (2S)-2-{[(2-bromoethoxy)(diisopropyl)silyl]oxy}propanoate

Conditions
ConditionsYield
With bromopentacarbonylmanganese(I) In dichloromethane at 20℃; for 2h;A n/a
B 68%
111-44-4

3-oxa-1,5-dichloropentane

5414-19-7

1,1'-oxybis(2-bromo-ethane)

Conditions
ConditionsYield
With potassium bromide In ethylene dibromide; N,N-dimethyl-formamide for 24h; Reflux;65%
34604-52-9

diethylene glycol dimesylate

5414-19-7

1,1'-oxybis(2-bromo-ethane)

Conditions
ConditionsYield
With lithium bromide In acetone for 20h; Heating / reflux;50%
With lithium bromide In acetone for 20h; Heating;
75-21-8

oxirane

74-85-1

ethene

5414-19-7

1,1'-oxybis(2-bromo-ethane)

Conditions
ConditionsYield
With bromine
With bromine In tetrachloromethane
616-47-7

1-methyl-1H-imidazole

5414-19-7

1,1'-oxybis(2-bromo-ethane)

3,3′-(oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] dibromide

Conditions
ConditionsYield
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;
5414-19-7

1,1'-oxybis(2-bromo-ethane)

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
ConditionsYield
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%
5414-19-7

1,1'-oxybis(2-bromo-ethane)

trans-4-(tert-butoxycarbonylamino)cyclohexylamine

tert-butyl ((1,4-trans)-4-morpholinocyclohexyl)carbamate

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 75℃; for 48h;100%
With triethylamine In N,N-dimethyl-formamide at 70℃; for 16h;
5414-19-7

1,1'-oxybis(2-bromo-ethane)

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

2,2'-Dibromodiethyl ether Specification

The Ethane,1,1'-oxybis[2-bromo-, with the cas registry number 5414-19-7, has the IUPAC name of 1-bromo-2-(2-bromoethoxy)ethane. Being a kind of colourless liquid, it is combustible and incompatible with oxidizing agents, acid chlorides, chloroformates, reducing agents, halogens. And its product categories are various, including Aliphatics; Halides; Ethers; Organic Building Blocks; Oxygen Compounds.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.87; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.87; (4)ACD/LogD (pH 7.4): 1.87; (5)ACD/BCF (pH 5.5): 15.64; (6)ACD/BCF (pH 7.4): 15.64; (7)ACD/KOC (pH 5.5): 249.2; (8)ACD/KOC (pH 7.4): 249.2; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 9.23; (13)Index of Refraction: 1.505; (14)Molar Refractivity: 37.78 cm3; (15)Molar Volume: 127.2 cm3; (16)Polarizability: 14.98 ×10-24 cm3; (17)Surface Tension: 37.6 dyne/cm; (18)Density: 1.821 g/cm3; (19)Flash Point: 85 °C; (20)Enthalpy of Vaporization: 43.42 kJ/mol; (21)Boiling Point: 216.3 °C at 760 mmHg; (22)Vapour Pressure: 0.207 mmHg at 25°C; (23)Exact Mass: 231.892143; (24)MonoIsotopic Mass: 229.89419; (25)Topological Polar Surface Area: 9.2; (26)Heavy Atom Count: 7; (27)Formal Charge: 0; (28)Complexity: 28.9.

When you are dealing with this chemical, you should be much more careful. For being a kind of irritant chemical to respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. If inadequately used, it may have risk of serious damage to eyes and may cause harm to the unborn child. Then it is toxic which may at low levels cause damage to health. Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Then remember to avoid exposure - obtain special instructions before use.

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C(CBr)OCCBr
(2)InChI: InChI=1S/C4H8Br2O/c5-1-3-7-4-2-6/h1-4H2
(3)InChIKey: FOZVXADQAHVUSV-UHFFFAOYSA-N 

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