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1,1-Dibromoethane

HCID 11201
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Basic information

CAS
25620-62-6
Standard SMILES
CC(Br)Br
InChIKey
APQIUTYORBAGEZ-UHFFFAOYSA-N
Molecular formula
C2H4Br2
Average molar mass
187.86 g/mol
Monoisotopic mass
185.86797433

Overview

1,1-Dibromoethane is an organobromide compound. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (L625)

Names & identifiers

Preferred name
1,1-Dibromoethane
IUPAC
1,1-dibromoethane
English name
1,1-Dibromoethane
Molecular formula
C2H4Br2
Molecular weight
187.86

Names & synonyms

1,1-DIBROMOETHANE557-91-5DIBROMOETHANEEthylidene bromideEthylidene dibromideEthane, 1,1-dibromo-HSDB 7382KJ8ZJY72QQEINECS 209-184-9CCRIS 8552CH3CHBr2DIBROMOETHANE, 1,1-
Show more names
1,1-EDB1,1-Dibromethan1,1-dibromo-ethanEthane,1,1-dibromo-ethylidenedibromide1,1-DIBROMOETHANE STABILIZED 99%
DTXSID30603241,1-DIBROMOETHANE [HSDB]Ethane, 1,1dibromoRefChem:409764DTXCID9041944DTXCID301516055DTXSID801031002209-184-9

Database identifiers

CAS
25620-62-6、557-91-5
PubChem CID
11201
DTXSID
DTXSID3060324
UNII
KJ8ZJY72QQ
EC Number
209-184-9
Nikkaji
J2.663H

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
4
Formal charge
0
Complexity
11.5

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Aliphatics, Saturated
SpringerMaterials PropertiesBoiling point
Density2.0555 g/cu cm at 20 °C
Color/FormLiquid
SolubilitySoluble in ethanol, acetone, and benzene; slightly soluble in chloroform; very soluble in ether.
Boiling Point108.0 °C
DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen bromide/.
Melting Point-63 °C
Vapor Pressure · 2 items

25.6 [mmHg]

2.56X10+1 mm Hg at 25 °C

Refractive IndexIndex of refraction = 1.5128 at 20 °C
Physical Description

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (66.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards Summary · 1 item

A mutagen; [RTECS] Not mutagenic to Salmonella typhimurium (TA 102 and TA 2638) or two strains of Escherichia coli; Highly genotoxic and cytotoxic to Salmonella typhimurium tester strain NM5004, but not to original host strain TA 1535; Emergency medical treatment: see 1-Bromopropane. [HSDB] May cause irritation; [MSDSonline]

Hazard Classes and CategoriesAcute Tox. 3 (66.7%)
Hazardous Reactivities and IncompatibilitiesViolent reaction with magnisium.

Toxicology

Treatment · 1 item

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Uses & manufacturing

Uses · 2 items

Used as a research chemical; [HSDB]

Research chemical

General Manufacturing InformationEthane, 1,1-dibromo-: ACTIVE

Applications

Uses1,1-Dibromoethane is a useful reagent for setereoselective synthesis of (+)-phorboxazole A via Petasis-Ferrier rearrangement. It is also used for preparation of olefinic enol ether.

Upstream & downstream products

Upstream raw materials

2-BromopropionamideBromoethaneDibromomethaneIodomethaneAcetylene

Downstream products

4-Fluoro-2-methylbenzoic acid1,1,2-TribromoethaneVinyl bromide1,1-Dichloroethane

Related reactions

463 records
New reaction record
HRID 5325 reaction equation
HRID 5325As reactantuspto-grants-1993_09
HRID 5327 reaction equation
HRID 5327As reactantuspto-grants-1993_09
HRID 8528 reaction equation
HRID 8528As reactantuspto-grants-2006_08
HRID 15074 reaction equation
HRID 15074As reactantuspto-grants-2010_06
HRID 22039 reaction equation
HRID 22039As reactantuspto-grants-1995_06
HRID 22041 reaction equation
HRID 22041As reactantuspto-grants-1995_06
HRID 22134 reaction equation
HRID 22134As catalystuspto-grants-1995_06
HRID 22623 reaction equation
HRID 22623As reactantuspto-grants-2005_02
Page 1 of 58

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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Liquid; [HSDB] Clear, slightly brown liquid; Stabilized with potassium carbonate; [MSDSonline]
Other Experimental PropertiesHydroxyl radical reaction rate constant = 2.50X10-13 cu cm/molecule-sec at 25 °C

Physicochemical properties

Melting point
-63 °C · -63°C
Boiling point
107 °C · 107 °C
Density
2.06 · 2.06
refractive index
1.509 · 1.509-1.512
Water Solubility
Insoluble in water
solubility
Acetonitrile (Slightly), Chloroform (Soluble)
form
Liquid
color
Clear colorless to brown
Specific Gravity
2.1 · 2.1
Specific Heat Capacity
0.43 J/ · Cp(gas): 0.43 J/(g·K), at 25℃
Henry's Law Constant
7.6 · 7.6×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
CAS DataBase Reference
557 · 557-91-5(CAS DataBase Reference)
FDA UNII
8 ZJY72QQ · KJ8ZJY72QQ
EPA Substance Registry System
Ethylidene bromide (557-91-5)
Symbol(GHS)
6 · GHS06,GHS07
Signal word
Danger
Hazard statements
301 · H301+H311+H331-H315-H319
Precautionary statements
261 · P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501
Hazard Codes
Xn
Risk Statements
40 · 40-20/21/22
Safety Statements
45 · 45-36/37
RIDADR
2810 · 2810
RTECS
9000000 · KH9000000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29033990 · 29033990
Hazardous Substances Data
557 · 557-91-5(Hazardous Substances Data)
Health Effects · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from a structure estimation method(2), indicates that 1,1-dibromoethane is expected to have very high mobility in soil(SRC). Volatilization of 1,1-dibromoethane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,1-Dibromoethane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 25.6 mm Hg(4). Biodegradation data are not available for 1,1-dibromoethane(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from a structure estimation method(2), indicates that 1,1-dibromoethane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 6(SRC), from an estimated log Kow of 1.9(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The rate constant measured for the neutral hydrolysis reaction of 1,1-dibromoethane is 2.4X10-7 per minute at 25 °C which corresponds to a half-life of 5.5 years(7). Biodegradation data are not available for 1,1-dibromoethane(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1-dibromoethane, which has a vapor pressure of 25.6 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,1-dibromoethane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 64 days(SRC), calculated from its rate constant of 2.50X10-13 cu cm/molecule-sec at 25 °C(3). 1,1-Dibromoethane does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 item

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Signs and Symptoms · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

Effluent Concentrations1,1-Dibromoethane was detected (concentration <10 ug/L) in industrial effluent samples from only 1 out of 63 locations sampled across the United States(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,1-dibromoethane can be estimated to be 35(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,1-dibromoethane is expected to have very high mobility in soil.

Artificial Pollution Sources1,1-Dibromoethane's production and use as a research chemical(1) may result in its release to the environment through various waste streams(SRC).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 item

An estimated BCF of 6 was calculated for 1,1-dibromoethane(SRC), using an estimated log Kow of 35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Safety data

tsca
TSCA listed
rtecs
KH9000000
ridadr
2810
hs_code
29033990
risk_code
40-20/21/22
Signal word
Danger
Symbol(GHS)
GHS06,GHS07
hazard_code
Xn
safety_code
45-36/37
hazard_class
6.1(b)
packing_group
III
Hazard statements
H301+H311+H331-H315-H319
Precautionary statements
P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501
Hazardous Substances Data
557-91-5(Hazardous Substances Data)