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1,1,2,2-Tetrabromethan

1,1,2,2-Tetrabromoethane

HCID 6588
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Grundinformationen

CAS
79-27-6
Standard-SMILES
BrC(Br)C(Br)Br
InChIKey
QXSZNDIIPUOQMB-UHFFFAOYSA-N
Summenformel
C2H2Br4
Durchschnittliche Molmasse
345,65 g/mol
Monoisotopische Masse
341,689

Überblick

Acetylene tetrabromide appears as a yellowish liquid with a pungent odor, much like camphor. Irritates skin. Ingestion or inhalation may produce irritation or a narcotic effect. Chronic exposure may damage liver. Noncombustible, but decomposes at 374 °F, releasing flammable and toxic fumes. Much denser than water. Used as a solvent for fats, oils and waxes.

Namen und Bezeichner

Bevorzugter Name
1,1,2,2-Tetrabromoethane
IUPAC
1,1,2,2-tetrabromoethane
Lokaler Name
1,1,2,2-Tetrabromethan
Englischer Name
1,1,2,2-Tetrabromoethane
Summenformel
C2H2Br4
Molmasse
345.65

Namen und Synonyme

1,1,2,2-TETRABROMOETHANE79-27-6Acetylene tetrabromideMuthmann's liquidsym-TetrabromoethaneEthane, 1,1,2,2-tetrabromo-Tetrabromoacetylenes-Tetrabromoethane1,1,2,2-Tetrabromaethan1,1,2,2-Tetrabromoetano1,1,2,2-Tetrabroomethaan1,1,2,2-Tetrabromoethylene
Weitere Namen anzeigen
TBETETRABROMOETHANEKI822500001.1.2.2-TetrabMuthmans liquidMUTHMANNS LIQUIDETHANETETRABROMIDEbromured’acetylene
DTXSID1026083V00GKC584OAI3-08850NSC-406889DTXCID206083Symmetrical tetrabromoethaneRefChem:70874201-191-5

Datenbank-Bezeichner

CAS
79-27-6
PubChem CID
6588
DTXSID
DTXSID1026083
ChEMBL
CHEMBL1438332

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,6
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
6
Formalladung
0
Komplexität
26,5

Experimentelle und physikochemische Eigenschaften

Chemical ClassesReactive agents - 1st degree
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesBoiling point
LogP2.8
OdorOdor of camphor and iodoform
Density · 6 Einträge

2.9656 at 68 °F (NTP, 1992) - Denser than water; will sink

2.9656 @ 20 °C/4 °C

Relative density (water = 1): 2.96

2.97

2.9638 @25 °C

2.97

Color/Form · 3 Einträge

Yellowish, heavy liquid /SRP: technical grade/

Colorless to yellow liquid

Pale-yellow liquid [Note: A solid below 32 degrees F].

Solubility · 6 Einträge

less than 1 mg/mL at 68 °F (NTP, 1992)

0.065 g/100 ml water @ 30 °C

Soluble in acetone

Miscible in ethanol, ethyl ether, chloroform, aniline, acetic acid; soluble in benzene; slightly soluble in carbon tetrachloride.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P260, P264+P265, P271, P273, P280, P284, P304+P340, P305+P351+P338, P316, P320, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Ethane, 1,1,2,2-tetrabromo-

1,1,2,2-Tetrabromoethane: HSNO Approval: HSR002892 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Ethane, 1,1,2,2-tetrabromo-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 159 [Substances (Irritating)]:

· Some of these materials may burn, but none ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNon combustible.
Health Hazards · 2 Einträge

Excerpt from ERG Guide 159 [Substances (Irritating)]:

· Inhalation of vapors or dust is extremely irritating.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

1,1,2,2-Tetrabromo[U-14C]ethane ([14C]TBE) was used to study the metabolism of TBE in rats. Three graded doses of TBE (1.17, 13.6, and 123 mg/kg; 1 microCi 14C/rat at each dose) were administered by gavage to three groups of four rats each. Excreta samples were collected at various time intervals up to 96 hr. Following euthanization, 14C activity was measured in the excreta, tissues, and carcass. The fraction of the dose exhaled as volatile metabolites of TBE, excluding 14CO2, was approximately 9-10% higher in rats given the high dose of TBE compared to that in rats given either the low or the medium dose. The fraction excreted in the urine decreased with increasing TBE dosage. 1,2-Dibromoethylene and tribromoethylene were identified as exhaled metabolites at the high dose. Three major urinary metabolites were identified: dibromoacetic acid, glyoxylic acid, and oxalic acid. The results of this study indicate that the metabolism of TBE was linear up to a dose of 13.6 mg/kg, but the contribution of various TBE metabolic pathways was different at a dose of 123 mg/kg.

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)

Verwendung und Herstellung

Uses · 6 Einträge

Used as a solvent, ore flotation agent, catalyst, and flame-proofing additive; [ACGIH]

Metal Extraction and Refining [Category: Industry]

Separating minerals by specific gravity; solvent for fats, oils, and waxes; solvent in microscopy

Mercury substitute in gauges and balances.

ORE FLOTATION AGENT

CATALYST OR CATALYTIC INITIATOR IN SYNTHETIC FIBERS; POLYMER ADDITIVE IN FLAME-PROOF, FLAME-RETARDANT POLYSTYRENES, POLYURETHANES, AND POLYOLEFINS; AS REFRACTIVE INDEX LIQUID IN MICROSCOPY

U.S. Production · 2 Einträge

(1977) AT LEAST 4.54X10+8 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Methods of Manufacturing

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
V00GKC584O
EC Number
201-191-5
Nikkaji
J3.838E

0.28 g/100 g water @ 80 °C

In water, 678 mg/l @ 25 °C

Corrosivity... Will attack some forms of plastics, rubber, and coatings.
Flash Point · 2 Einträge

635 °F (NFPA, 2010)

-18 °C (closed cup)

Boiling Point · 5 Einträge

471 °F at 760 mmHg (NTP, 1992)

243.5 °C; 151 °C @ 54 mm Hg

243.5 °C

474 °F (decomposes)

474 °F (Decomposes)

Decomposition · 2 Einträge

NONCOMBUSTIBLE BUT DECOMPOSES @ 374 °F (190 °C) TO LIBERATE FLAMMABLE & HIGHLY TOXIC VAPORS. /SRP: EG, HYDROGEN BROMIDE AND CARBON MONOXIDE/

Toxic gases and vapors (such as ... carbonyl bromide, and brominated solvents) ... may be released when acetylene tetrabromide decomposes.

Physikochemische Eigenschaften

Schmelzpunkt
1 °C · 1 °C
Siedepunkt
244 °C · 244 °C
Dichte
2.967 g/mL · 2.967 g/mL at 25 °C(lit.)
Dampfdichte
11.9 · 11.9 (vs air)
Dampfdruck
0.1 mm · 0.1 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.637(lit.)
Flammpunkt
118 · 118-120°C/15mm
storage temp.
15 °C · Store at +15°C to +25°C.
Löslichkeit
alcohol: miscible
Aggregatzustand
Liquid
Farbe
Clear
Wasserlöslichkeit
0.63 g/L · 0.63 g/L (20 ºC)
Spezifische Wärmekapazität
0.48 J/ · Cp(liquid): 0.48 J/(g·K), at 25℃
Merck
14 · 14,9185
BRN
1098321 · 1098321
Henry's Law Constant
6.4 at · 6.40 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Dielectric constant
5.6 · 5.6(Ambient)
Stabilität
Stable. Incompatible with strong oxidizing agents, aluminium, magnesium, alkali metals.
InChI
1S/C2H2Br4/c3-1(4)2(5)6/h1-2H
InChIKey
QXSZNDIIPUOQMB-UHFFFAOYSA-N
SMILES
BrC(Br)C(Br)Br
Oberflächenspannung
49.7 mN/m · 49.7mN/m at 20°C
CAS Datenbank
79 · 79-27-6(CAS DataBase Reference)
NIST chemische Informationen
1 · 1,1,2,2-Tetrabromoethane(79-27-6)
EPA chemische Informationen
1 · 1,1,2,2-Tetrabromoethane (79-27-6)
Hazards Summary · 1 Eintrag

Some animals exposed at 4 ppm for 180 days show mild lung and liver injury. At an average exposure of 14 ppm for 100 to 106 days, tetrabromoethane produced some degree of pulmonary edema and slight fatty degeneration of the liver. One nearly fatal human case with prominent liver injury was reported. The exposure was estimated at 16 ppm for 10 minutes. Other chemicals may have been involved. Findings in another human case were that of solvent-induced encephalopathy. Direct skin contact can cause second degree burns. [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects and liver damage; [ICSC]

DOT ID and Guide · 2 Einträge

2504 159

2504 159

Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: T+; R: 26-36-52/53; S: (1/2)-24-27-45-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
OSHA StandardsPermissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 1 ppm (14 mg/cu m).

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch or walk through spilled material.

First Aid · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageSeparated from strong oxidants, strong bases and food and feedstuffs. Well closed. Ventilation along the floor.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 3 Einträge

To fight a fire /involving/ acetylene tetrabromide use dry chemical, carbon dioxide, water-foam, or fog.

If material involved in fire: Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)

Extinguish fire using agent suitable for surrounding fire. Use water spray to cool fire-exposed containers.

Storage Conditions · 2 Einträge

Store in a cool, dry, well-ventilated location. Separate from oxidizing materials and alkalies.

... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED ... .

Cleanup Methods · 2 Einträge

1. VENTILATE AREA OF SPILL OR LEAK. 2. COLLECT FOR RECLAMATION OR ABSORB IN VERMICULITE, DRY SAND, EARTH, OR A SIMILAR MATERIAL.

Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Approach release from upwind. Absorb in noncombustible material for proper disposal. Control runoff and isolate discharged material for proper disposal.

Nonfire Spill ResponseExcerpt from ERG Guide 159 [Substances (Irritating)]:
Disposal Methods · 2 Einträge

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Acetylene tetrabromide may be disposed of by absorbing it in vermiculite, dry sand, earth, or a similar material and disposing in a secured sanitary landfill.

Spillage Disposal · 1 Eintrag

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: self-contained breathing apparatus.

Toxikologische Informationen

Treatment · 1 Eintrag

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.

InteractionsClioquinol at a dose of 30-50 mg/kg, demonstrated a weak antagonistic action with tetrabromoethane (80 mg/kg).
Target OrgansEyes, respiratory system, liver, central nervous system
Health Effects · 1 Eintrag

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 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a water solubility of 678 mg/l(3) and a regression-derived equation(4), indicates that 1,1,2,2-tetrabromoethane is expected to have high mobility in soil(SRC). Volatilization of 1,1,2,2-tetrabromoethane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.34X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(2), and water solubility(3). The potential for volatilization of 1,1,2,2-tetrabromoethane from dry soil surfaces may exist(SRC) based upon its vapor pressure(2). 1,1,2,2-Tetrabromoethane, reached 29% of its theoretical BOD in 2 weeks using the Japanese MITI test(5), suggesting biodegradation in soil may be an important environmental fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a water solubility of 678 mg/l(3) and a regression-derived equation(4), indicates that 1,1,2,2-tetrabromoethane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.34X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(2), and water solubility, 678 mg/l(3). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5 and 43 days, respectively(SRC). However, hydrolysis half-lives of 20 and 2 hours at pH 7 and 8, respectively, have been calculated(5); therefore, under acidic or neutral conditions, hydrolysis will be the dominant removal process(SRC). According to a classification scheme(6), a BCF of <8.2(7), suggests that bioconcentration in aquatic organisms is low(SRC). A theoretical BOD of 29% was reported using an activated sludge inoculum at 30 mg/l and the Japanese MITI test over a 2 week test period(7), suggesting that biodegradation may occur in aquatic systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1,2,2-tetrabromoethane, which has a vapor pressure of 0.02 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,1,2,2-tetrabromoethane 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 115 days(SRC), calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 3 Einträge

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

inhalation, ingestion, skin and/or eye contact

Oral (L626) ; inhalation (L626) ; dermal (L626)

Toxicity Summary · 1 Eintrag

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 · 6 Einträge

Cough. Sore throat. Headache. Dizziness. Nausea. Abdominal pain.

Redness.

Redness.

See Inhalation.

irritation eyes, nose; anorexia, nausea; headache; abdominal pain; jaundice; leukocytosis (increased blood leukocytes); central nervous system depression

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)

Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=79-27-6]

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Medical Surveillance · 2 Einträge

Consider the eyes, upper respiratory system, and liver in preplacement and periodic physical examination.

... Workers exposed to concn of tetrabromoethane approaching ... /1 ppm and 15 mg/cu m (TLV)/ should be kept under medical surveillance.

Sicherheitsdaten

F
8
wgk
2
IDLA
8 ppm
tsca
TSCA listed
ridadr
UN 2504 6.1/PG 3
hs_code
29033036
RTECS-Nr.
KI8225000
risk_code
26-36-52/53
Toxizität
LD50 i.p. in mice: 443.3 mg/kg (Wolff)
hazard_code
T+,T
hazard_note
Toxic
safety_code
24-27-45-61-1/2
hazard_class
6.1
packing_group
III
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
79-27-6(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 2 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2
Selbstentzündungstemperatur
635 °F
· 2 Einträge

Interaction of acetylene and bromine and subsequent distillation.

Manuf by bromination of acetylene: Brit. pat. 889,649 (1962 to Associated Ethyl Co.)

Formulations/Preparations · 2 Einträge

Grades: Technical

Purity: Not less than 98%

General Manufacturing Information · 2 Einträge

Ethane, 1,1,2,2-tetrabromo-: ACTIVE

Method of purification: rectification.

Anwendungen

Verwenden1,1,2,2-Tetrabromoethane was used to prepare tribromoethene by dehydrohalogenation using sodium hydroxide in methanol.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Glass-lined reaction potCalciumacetylidBrom

Nachgelagerte Produkte

Benzol-1,2,4-tricarbonsure-1,2-anhydridTerephthalsureTribromethylen1,2-DibromethenHexabromoethane1,1'-Dibromoferrocene1,1-DiethoxyethanDimethylhydrogenphosphatBromethanBrommethan