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a flammable colorless gaseous alkene; obtained from petroleum and natural gas and used in manufacturing many other chemicals; sometimes used as an anesthetic (同)ethene

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エチレン(引火性の気体;吸入麻酔薬に用いる)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/05 02:22:43」(JST)

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1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH₂Br)₂. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant.^[2]

Preparation and use[edit]

It is produced by the reaction of ethylene with bromine, in a classic halogen addition reaction:

CH₂=CH₂ + Br₂ → BrCH₂CH₂Br

Historically, 1,2-dibromoethane was used as an anti-knock additive in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine.^[3]

Pesticide[edit]

It has been used as a pesticide in soil and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP).^[2] Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for termites and beetles, for control of moths in beehives.^[4]

Reagent[edit]

Ethylene bromide has wider applications in the preparation of other organic compounds. It is used to make vinyl bromide, a precursor to some fire retardants.^[2]

In the laboratory, 1,2-dibromoethane is used in organic synthesis as a source of bromine, e.g., to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.^[5]

Health effects[edit]

The effects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain. Changes in the brain and behavior were also seen in young rats whose male parents had breathed 1,2-dibromoethane, and birth defects were observed in the young of animals that were exposed while pregnant. 1,2-Dibromoethane is not known to cause birth defects in humans.^[6] Swallowing has caused death at 40 mL doses^[4]

It is a known carcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.^[7]

References[edit]

^ "Ethylene Dibromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 19 June 2012.
^ ^a ^b ^c Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. (2005), "Bromine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a04_405
^ Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics 22 (25): 5154–5178. doi:10.1021/om030621b.
^ ^a ^b "Toxicological Profile for 1,2-Dibromoethane". Archived from the original on 2009-11-22. Retrieved 2009-11-22.
^ Maynard, G. D. (2004). "1,2-Dibromoethane". In L. Paquette. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289.
^ http://www.atsdr.cdc.gov/mmg/mmg.asp?id=1062&tid=131
^ "Ranking Possible Cancer Hazards on the HERP Index". Retrieved 2010-10-14.

External links[edit]

National Pollutant Inventory 1,2-Dibromoethane Fact Sheet
Congressional Research Service (CRS) Reports regarding Ethylene Dibromide
ATSDR ToxFAQs

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Use of X-Chromosome Inactivation Pattern to Analyze the Clonality of 14 Female Cases of Kaposi Sarcoma.

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PMID 26246995

Bromine enrichment in marsh sediments as a marker of environmental changes driven by Grand Solar Minima and anthropogenic activity (Caminha, NW of Portugal).

Moreno J1, Fatela F2, Leorri E3, Araújo MF4, Moreno F4, De la Rosa J5, Freitas MC2, Valente T6, Corbett DR3.
The Science of the total environment.Sci Total Environ.2015 Feb 15;506-507:554-66. doi: 10.1016/j.scitotenv.2014.11.062. Epub 2014 Nov 26.
A sediment core collected in Caminha tidal marsh, NW Portugal, was used to assess bromine (Br) signal over the last ca. 1,700 years. The Br temporal variability reflects its close relationship with soil/sediment organic matter (OM) and also alterations in Br biogeochemical recycling in marsh environ
PMID 25433387

Japanese Journal

Novel Artificial Co-enzyme Based on Reduced Form of Diquat for Formate Dehydrogenase in the Catalytic Conversion of CO2 to Formic Acid

Chemistry Letters advpub(0), 2016
NAID 130005156590

飼料中のEPTC及び二臭化エチレンのガスクロマトグラフ質量分析計による定量法

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NAID 40016132984

Role of Bipyridinium Salts in Generation of Photocurrent by Rhodospirillum rubrum Cells.

Bulletin of the Chemical Society of Japan 68(6), 1545-1550, 1995
NAID 130004149210

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リンク元	「二臭化エチレン」「エチレンジブロマイド」
関連記事	「ethylene」

「二臭化エチレン」

1,2-Dibromoethane
	IUPAC name 1,2-Dibromoethane
	Other names Ethylene bromide[citation needed]; Ethylene dibromide[citation needed]; Glycol bromide[citation needed];
Identifiers
Abbreviations	EDB[citation needed]
CAS number	106-93-4
PubChem	7839
ChemSpider	7551
EC number	203-444-5
UN number	1605
KEGG	C11088
MeSH	Ethylene+Dibromide
ChEBI	CHEBI:28534
ChEMBL	CHEMBL452370
RTECS number	KH9275000
Beilstein Reference	605266
Jmol-3D images	Image 1
	SMILES BrCCBr ;
	InChI InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2 ; Key: PAAZPARNPHGIKF-UHFFFAOYSA-N ;
Properties
Molecular formula	C2H4Br2
Molar mass	187.86 g mol−1
Appearance	Colorless liquid
Density	2.18 g mL−1
Melting point	9-10 °C, 282.5-283.3 K, 49-50 °F
Boiling point	129-133 °C, 402-406 K, 264-271 °F
Vapor pressure	1.56 kPa
kH	14 μmol Pa kg−1
Refractive index (nD)	1.539
Thermochemistry
Std enthalpy of; combustion ΔcHo298	−1.2419–−1.2387 MJ mol−1
Standard molar; entropy So298	223.30 J K−1 mol−1
Specific heat capacity, C	134.7 J K−1 mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H311, H315, H319, H331, H335, H350, H411
GHS precautionary statements	P261, P273, P280, P301+310, P305+351+338
EU Index	602-010-00-6
EU classification	T N
R-phrases	R45, R23/24/25, R36/37/38, R51/53
S-phrases	S45
NFPA 704	0 3 0
Flash point	>104 °C
LD50	55.0 mg kg−1 (oral, rabbit); 79.0 mg kg−1 (oral, chicken); 110.0 mg kg−1 (oral, guinea pig); 130.0 mg kg−1 (oral, quail); 300.0 mg kg−1 (dermal, rabbit);
Related compounds
Related alkanes	Dibromomethane; Bromoform; Tetrabromomethane; 1,1-Dibromoethane; Tetrabromoethane; 1,2-Dibromopropane; 1,3-Dibromopropane; 1,2,3-Tribromopropane;
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: ethylene dibromide
関: エチレンジブロマイド

「エチレンジブロマイド」

　　[★]

英: ethylene dibromide
関: 二臭化エチレン

「ethylene」

　　[★]

エチレン

関: C2H4

[1] "Ethylene Dibromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 19 June 2012.

[Ullmann-2] Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. (2005), "Bromine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a04_405

[Seyferth-3] Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics 22 (25): 5154–5178. doi:10.1021/om030621b.

[www.atsdr.cdc.gov-4] "Toxicological Profile for 1,2-Dibromoethane". Archived from the original on 2009-11-22. Retrieved 2009-11-22.

[5] Maynard, G. D. (2004). "1,2-Dibromoethane". In L. Paquette. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289.

[atsdr.cdc.gov-6] ttp://www.atsdr.cdc.gov/mmg/mmg.asp?id=1062&tid=131

[7] "Ranking Possible Cancer Hazards on the HERP Index". Retrieved 2010-10-14.

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案内

ethylene dibromide