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Epibromohydrin

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Identification
Molecular formula
C3H5BrO
CAS number
3132-64-7
IUPAC name
2-(bromomethyl)oxirane
State
State

Epibromohydrin is a liquid at room temperature.

Melting point (Celsius)
-57.00
Melting point (Kelvin)
216.15
Boiling point (Celsius)
136.50
Boiling point (Kelvin)
409.65
General information
Molecular weight
136.98g/mol
Molar mass
136.9920g/mol
Density
1.7147g/cm3
Appearence

Epibromohydrin is a colorless to pale yellow liquid. It may exhibit a sharp, pungent odor.

Comment on solubility

Solubility of 2-(bromomethyl)oxirane

2-(bromomethyl)oxirane, also known as an epoxide, exhibits interesting solubility characteristics due to its unique chemical structure. The presence of the bromomethyl group attached to the epoxide ring can significantly influence its interactions with solvents and other substances. Here are some key points regarding its solubility:

  • Polar Solvents: 2-(bromomethyl)oxirane is generally more soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and acetone. This is due to the polar nature of the epoxide ring which enhances interactions with polar solvents.
  • Nonpolar Solvents: In nonpolar solvents, solubility may be considerably lower. Compounds like hexane or benzene may not effectively solvate 2-(bromomethyl)oxirane, resulting in limited solubility.
  • Hydrolysis: It's important to note that 2-(bromomethyl)oxirane can undergo hydrolysis in the presence of water, which can change its solubility profile as it reacts to form other products.

The solubility of this compound is therefore influenced by:

  1. The polarity of the solvent
  2. Presence of functional groups capable of hydrogen bonding
  3. Temperature and pressure conditions

Understanding the solubility of 2-(bromomethyl)oxirane is crucial for applications in organic synthesis and industrial processes, making it an interesting subject for further investigation.

Interesting facts

Interesting Facts about 2-(bromomethyl)oxirane

2-(bromomethyl)oxirane, commonly known as an epoxide, is a fascinating compound that is significant in the field of organic chemistry due to its unique structure and reactivity. Here are some intriguing highlights about this compound:

  • Epoxide Structure: The epoxide functional group (a three-membered cyclic ether) contributes to the compound's high strain energy, making it highly reactive. This characteristic is what allows epoxides to serve as excellent intermediates in chemical synthesis.
  • Applications in Synthesis: 2-(bromomethyl)oxirane is often employed as a building block for various chemical reactions. It can undergo ring-opening reactions with both nucleophiles and acids, which allows for the synthesis of diverse organic compounds, including pharmaceuticals and agrochemicals.
  • Biological Activity: Compounds containing epoxide groups have been observed to exhibit interesting biological activities. They can act as electrophiles that can modify biomolecules, potentially leading to therapeutic effects or toxicity, depending on the context.
  • Chirality: Depending on the specific substituents, 2-(bromomethyl)oxirane can exist as different stereoisomers. This chirality is essential in developing enantiomerically pure compounds that are critical for the pharmaceutical industry.
  • Historical Significance: The study of epoxides began in the early 20th century, and they have since become a staple in synthetic organic chemistry, showcasing the evolution of how chemists understand and utilize reactive intermediates.

As a versatile and reactive molecule, 2-(bromomethyl)oxirane exemplifies the beauty of organic chemistry, offering both challenges and opportunities for synthetic chemists. Its ability to participate in various chemical transformations makes it a compound of great interest across multiple areas of research.

Synonyms
Epibromohydrin
1-Bromo-2,3-epoxypropane
2-(Bromomethyl)oxirane
Epibromohydrine
Epibromhydrin
(Bromomethyl)oxirane
Oxirane, (bromomethyl)-
(Bromomethyl)ethylene oxide
1,2-Epoxy-3-bromopropane
3-Bromo-1,2-epoxypropane
3-bromopropylene oxide
Epibromhydrine
ALPHA-EPIBROMOHYDRIN
Propane, 1-bromo-2,3-epoxy-
Epibromhidrina
Propane, 3-bromo-1,2-epoxy-
Epibromhydrine [French]
Epibromhidrina [Spanish]
NSC 630
(RS)-3-bromo-1,2-epoxypropane
Oxirane, 2-(bromomethyl)-
CCRIS 2620
2,3-epoxypropyl bromide
HSDB 2717
EINECS 221-525-3
OXIRANYLMETHYL BROMIDE
2-bromomethyloxiran
UN2558
BRN 0079786
DTXSID5025237
UNII-8E89677I6B
CHEBI:18718
AI3-03546
NSC-630
EPOXY BROMOPROPANE
8E89677I6B
EPIBROMOHYDRIN [HSDB]
DTXCID605237
(.+/-.)-(Bromomethyl)oxirane
UN 2558
Epibromhydrine (French)
Epibromhidrina (Spanish)
alphaEpibromohydrin
2(Bromomethyl)oxirane
1,2Epoxy3bromopropane
1Bromo2,3epoxypropane
3Bromo1,2epoxypropane
Oxirane, (bromomethyl)
Oxirane, 2(bromomethyl)
BROMOMETHYL OXIRANE
Propane, 1bromo2,3epoxy
Propane, 3bromo1,2epoxy
(+-)-EPIBROMOHYDRIN
(.+-.)-EPIBROMOHYDRIN
EPIBROMOHYDRIN, (+-)-
(+-)-(BROMOMETHYL)OXIRANE
(.+-.)-(BROMOMETHYL)OXIRANE
(BROMOMETHYL)OXIRANE, (+-)-
Propane, 1-bromo-2,3-epoxy-(8CI)
(+-)-3-BROMO-1,2-EPOXYPROPANE
(.+-.)-3-BROMO-1,2-EPOXYPROPANE
3-BROMO-1,2-EPOXYPROPANE, (+-)-
5-17-01-00023 (beilstein handbook reference)
gkipxfaanltwbm-uhfffaoysa-n
3132-64-7
(R)-Epibromohydrine
51594-57-1
27815-35-6
Bromohydrin
Propane,2-epoxy-
2-bromomethyloxirane
2-bromomethyl-oxirane
racemic epibromohydrine
Epibromohydrin, 98%
(+/-)-epibromohydrin
2-(bromomethyl) oxirane
2-(bromomethyl)-oxirane
WLN: T3OTJ B1E
1-bromo-2,3-epoxypropane-
SCHEMBL78600
(r/s)-2-bromomethyl-oxirane
NSC630
CHEMBL3183066
EPIBROMOHYDRIN, (+/-)-
Tox21_202607
BR1167
AKOS002664702
AKOS016043519
Epibromohydrin [UN2558] [Poison]
(BROMOMETHYL)OXIRANE, (+/-)-
Epibromohydrin;1-Bromo-2,3-epoxypropane
NCGC00260155-01
BP-21061
Epibromohydrin, purum, >=97.5% (GC)
LS-12953
PD195014
CAS-3132-64-7
NS00029059
EN300-55586
3-BROMO-1,2-EPOXYPROPANE, (+/-)-
Q27109087