Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide at 45℃; for 0.666667h; Temperature; Reagent/catalyst; | 96.11% |
With bromine | |
With hypobromous acid | |
With water; bromine | |
With N-Bromosuccinimide; ammonium acetate; water In acetone at 40℃; under 4654.46 Torr; for 0.5h; Flow reactor; |
2-(tert-butyldimethylsilyloxy)ethyl bromide
2-bromoethanol
Conditions | Yield |
---|---|
With potassium hydrogensulfate In methanol at 20℃; for 1.5h; | 96% |
1-bromo-2-propanol
2-bromoethanol
Conditions | Yield |
---|---|
61% |
Conditions | Yield |
---|---|
With phosphorus tribromide for 3h; Cooling with ice; Reflux; | 60% |
With phosphorus tribromide for 3h; Cooling with ice; Reflux; | 60% |
With hydrogen bromide for 8h; Heating; | 49% |
4-Bromo-1-butanol
2-bromoethanol
Conditions | Yield |
---|---|
58% |
oxirane
p-bromo-n-propylbenzene
A
2-(4-propylphenyl)ethanol
B
rac-1-(4-propylphenyl)ethanol
C
2-bromoethanol
Conditions | Yield |
---|---|
Stage #1: p-bromo-n-propylbenzene With magnesium In diethyl ether Heating; Stage #2: oxirane In diethyl ether | A 55% B n/a C n/a |
Conditions | Yield |
---|---|
With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation; | A 50% B 45% |
Conditions | Yield |
---|---|
Zers. des entstandenen Additionsproduktes mit Wasser; |
oxirane
3-buten-1-ynylmagnesium bromide
A
hex-5-en-3-yn-1-ol
B
2-bromoethanol
Conditions | Yield |
---|---|
With hydrogen bromide | |
With hydrogen bromide in der Gasphase; |
Conditions | Yield |
---|---|
With bromine |
ethylene sulfite
diethyl ether
A
1,1'-sulfinylbisbenzene
B
2-bromoethanol
bromal hydrate
A
2,2-dibromoethanol
B
2,2,2-tribromoethanol
C
2-bromoethanol
Conditions | Yield |
---|---|
bei der Einw. von gaerender Hefe; |
2-bromoethanol
Conditions | Yield |
---|---|
bei der thermischen Zersetzung; |
bis-(1,2-dibromo-ethyl) ether
ethylene glycol
A
2-bromomethyl-1,3-dioxolane
B
2-bromoethanol
ethylene glycol
ethylene dibromide
A
1,4-dioxane
B
2-(2′-(2″-bromoethoxy)ethoxy)ethanol
C
2-(2-bromoethoxy)ethan-1-ol
D
2-bromoethanol
Conditions | Yield |
---|---|
at 160℃; |
Conditions | Yield |
---|---|
With ethylene glycol; potassium bromide |
morpholine
1-bromo-2-nitrosooxy-ethane
A
N-nitrosomorpholine
B
2-bromoethanol
Conditions | Yield |
---|---|
With sodium docusate In 2,2,4-trimethylpentane; water Rate constant; | |
In 1,4-dioxane; water at 25℃; Rate constant; solvent isotope effect (kH/kD); |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; Equilibrium constant; acetylcholinesterase, pH 7.8; |
1-bromo-2-nitrosooxy-ethane
2-bromoethanol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium perchlorate at 25℃; Rate constant; acetate buffer pH 2; |
Conditions | Yield |
---|---|
With water reaction with water corroborated the structure of the starting compound; |
piperazine
1-bromo-2-nitrosooxy-ethane
A
N-nitrosopiperazine
B
2-bromoethanol
Conditions | Yield |
---|---|
With sodium docusate In 2,2,4-trimethylpentane; water Rate constant; |
1-bromo-2-nitrosooxy-ethane
benzyl-methyl-amine
A
Benzylmethylnitrosamin
B
2-bromoethanol
Conditions | Yield |
---|---|
With sodium docusate In 2,2,4-trimethylpentane; water Rate constant; |
1-bromo-2-nitrosooxy-ethane
malononitrile
A
2-(hydroxyimino)malononitrile
B
2-bromoethanol
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; Rate constant; |
Conditions | Yield |
---|---|
at 0℃; |
2-bromoethanol
2-bromoethanol
Conditions | Yield |
---|---|
With methanol |
3,4-dihydro-2H-pyran
2-bromoethanol
2-(2-bromoethoxy)tetrahydropyran
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane | 100% |
With cerium(III) chloride heptahydrate In dichloromethane at 20℃; for 2h; | 95.1% |
With Amberlyst H15 In hexane for 2h; Ambient temperature; | 90% |
2-bromoethanol
2-bromoethyl nitrate
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0℃; for 2h; | 100% |
With sulfuric acid; nitric acid at 0℃; for 1h; | 94% |
With sulfuric acid; nitric acid In dichloromethane at -5℃; for 3h; | 91% |
2-bromoethanol
2-(nitrooxy)ethan-1-ol
Conditions | Yield |
---|---|
With silver nitrate In acetonitrile for 24h; Ambient temperature; | 100% |
With silver nitrate In acetonitrile for 3h; Heating; | 90% |
With silver nitrate In acetonitrile for 8h; Reflux; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
at 120℃; for 6h; | 100% |
In toluene at 70℃; for 24h; | 92% |
at 70 - 80℃; | 78% |
1-methyl-1H-imidazole
2-bromoethanol
1-methyl-3-(2-hydroxyethyl)imidazolium bromide
Conditions | Yield |
---|---|
In acetonitrile for 80h; Reflux; | 100% |
microwave irradiation; | 99% |
at 20℃; for 24h; Inert atmosphere; | 99% |
tert-butyldimethylsilyl chloride
2-bromoethanol
2-(tert-butyldimethylsilyloxy)ethyl bromide
Conditions | Yield |
---|---|
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromoethanol In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
With dmap; triethylamine In dichloromethane at 20℃; for 15h; | 100% |
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃; | 98.3% |
tert-butylchlorodiphenylsilane
2-bromoethanol
(2-bromoethoxy)(tert-butyl)diphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; | 98% |
With 1H-imidazole for 12h; | 97% |
D-glucose pentaacetate
2-bromoethanol
2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere; diastereoselective reaction; | 100% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 18h; Inert atmosphere; | 80% |
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 21.5h; Substitution; | 61% |
With boron trifluoride diethyl etherate In dichloromethane for 1h; | 42% |
With boron trifluoride diethyl etherate In dichloromethane at 0 - 35℃; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Reflux; Inert atmosphere; | 100% |
With toluene-4-sulfonic acid In toluene for 3h; Dean-Stark; Reflux; Inert atmosphere; | 98% |
With sulfuric acid In toluene at 20 - 60℃; for 3.5h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With thionyl chloride Ambient temperature; | 100% |
L-phenylalanine
2-bromoethanol
L-phenylalanine 2-bromoethyl ester hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride Ambient temperature; | 100% |
With hydrogenchloride at 40℃; for 21h; | 87% |
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine
2-bromoethanol
2-cyanoethyl-2-bromoethyl-(N,N-di-i-propylamino)phosphoramidite
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; Ambient temperature; | 100% |
With triethylamine In dichloromethane for 1h; Ambient temperature; | |
With triethylamine In tetrahydrofuran for 1h; Ambient temperature; |
2-bromoethanol
Conditions | Yield |
---|---|
With sodium carbonate In ethanol Heating; | 100% |
With sodium carbonate In ethanol for 18h; Heating; | 100% |
2-bromoethanol
β-D-glucose pentaacetate
2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; | 100% |
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 85% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2.5h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With sodium azide In water at 80℃; Inert atmosphere; | 100% |
With sodium azide In water for 12h; Reflux; | 99% |
With sodium azide; tetrabutylammomium bromide at 110℃; for 15h; | 95% |
2-bromoethanol
6-(2-hydroxyethoxycarbonyl)-4-methoxycarbonyl-2,2,4-trimethylhept-6-enoic acid 2-hydroxyethyl ester
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 4.5h; | 100% |
(piperidin-4-yl)carbamic acid tert-butyl ester
2-bromoethanol
[1-(2-hydroxyethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 5h; Inert atmosphere; Reflux; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere; | 97% |
With potassium carbonate In acetonitrile for 5h; Heating; | 94% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 22℃; for 19.5h; | 100% |
4-methyl-2-nitrophenol
2-bromoethanol
2-(4-methyl-2-nitro-phenoxy)-ethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 6h; Heating / reflux; | 100% |
(1R,3S,5S)-8-azabicyclo[3.2.1]octan-3-ol hydrochloride
2-bromoethanol
8-(2-hydroxy-ethyl)-8-aza-bicyclo[3.2.1]octanol
Conditions | Yield |
---|---|
With sodium carbonate In ethanol at 20℃; for 15.3333h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In ethyl bromide; acetonitrile for 16h; Reflux; | 100% |
With potassium carbonate In acetonitrile for 6h; Reflux; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; | 98.6% |
(10,11-dihydro-5H-benzo[e]pyrido[2,3-b]azepin-10-ylmethyl)-methyl-amine
2-bromoethanol
(10,11-dihydro-5H-benzo[e]pyrido[2,3-b]azepin-10-ylmethyl)(2-hydroxyethyl)-methylamine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux; | 100% |
With potassium carbonate In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux; | 100% |
1,4-bis(4-nitrophenyl)[1,4,7]triazonane
2-bromoethanol
2-[4,7-bis(4-nitrophenyl)[1,4,7]triazonan-1-yl]ethanol
Conditions | Yield |
---|---|
With triethylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 7h; | 100% |
1-Methylhomopiperazine
2-bromoethanol
2-(4-methyl-1,4-diazepan-1-yl)ethanol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 100℃; | 100% |
6-bromo-7-hydroxy-2,2,4,4-tetramethyl-1,2,3,4-tetrahydroquinolin-3-one
2-bromoethanol
6-bromo-7-(2-hydroxyethoxy)-2,2,4,4-tetramethyl-1,2,3,4-tetrahydroquinolin-3-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; | 100% |
isocyanate de chlorosulfonyle
2-bromoethanol
2‐oxo‐1,3‐oxazolidine‐3‐sulfonyl chloride
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 0.5h; | 100% |
In dichloromethane at 0 - 10℃; Inert atmosphere; | |
In dichloromethane at 0℃; for 0.5h; |
di-tert-butyl phosphoric acid tetra-n-butylammonium salt
2-bromoethanol
di-tert-butyl (2-hydroxyethyl) phosphate
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 80 - 85℃; for 3h; | 100% |
2-(5'-bromo-2'-hydroxyphenyl)indole
2-bromoethanol
2-(5-bromo-2-(2-bromoethoxy)phenyl)-1H-indole
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 1h; | 100% |
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; |
tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate
2-bromoethanol
tert-butyl 2-(5-(N-(2-hydroxyethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile at 110℃; for 3h; Microwave irradiation; | 100% |
With potassium carbonate In acetonitrile at 110℃; for 3h; Microwave irradiation; |
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 13h; Inert atmosphere; | 100% |
The 2-Bromoethanol, with the CAS registry number 540-51-2, is also known as Ethylene bromohydrin. It belongs to the product categories of Pharmaceutical Intermediates; Omega-Bromoalkanols; Omega-Functional Alkanols, Carboxylic Acids, Amines & Halides; ASTM 5578: Analysis of Ethylene Oxide in AirAlphabetic; A-BMethod Specific; Alpha Sort; ASTM Air Monitoring; B; BI - BZChemical Class; Bromo; Halogenated; Volatiles/ Semivolatiles. Its EINECS registry number is 208-748-1. This chemical's molecular formula is C2H5BrO and molecular weight is 124.96. What's more, its IUPAC name is the same with its product name. It should be stored in a cool, dry and well-ventilated place.
Physical properties about 2-Bromoethanol are: (1)ACD/LogP: 0.263; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.26; (4)ACD/LogD (pH 7.4): 0.26; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 33.12; (8)ACD/KOC (pH 7.4): 33.12; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.482; (14)Molar Refractivity: 20.581 cm3; (15)Molar Volume: 72.237 cm3; (16)Polarizability: 8.159×10-24cm3; (17)Surface Tension: 39.06 dyne/cm; (18)Density: 1.73 g/cm3; (19)Flash Point: 57.134 °C; (20)Enthalpy of Vaporization: 43.53 kJ/mol; (21)Boiling Point: 136.21 °C at 760 mmHg; (22)Vapour Pressure: 3.178 mmHg at 25 °C.
Preparation of 2-Bromoethanol: this chemical can be prepared by ethane-1,2-diol. The reaction occurs with reagent HBr and other condition of heating for 8 hours. The yield is 49 %.
Uses of 2-Bromoethanol: (1) it is used as a solvent and organic synthetic raw material; (2) it is used to produce other chemicals. For example, it can react with piperidine to get 2-piperidin-1-yl-ethanol. This reaction needs reagent benzene at temperature of 80 °C. The reaction time is 72 hours. The yield is 85 %.
When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health at low levels and it may cause inflammation to the skin or other mucous membranes. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it is toxic by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell you should seek medical advice immediately.
You can still convert the following datas into molecular structure:
(1) SMILES: BrCCO
(2) InChI: InChI=1S/C2H5BrO/c3-1-2-4/h4H,1-2H2
(3) InChIKey: LDLCZOVUSADOIV-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 80mg/kg (80mg/kg) | Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972. |
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