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| CAS No.: | 106-93-4 |
|---|---|
| Name: | 1,2-Dibromoethane |
| Article Data: | 109 |
| Molecular Structure: | |
|
|
|
| Formula: | C2H4Br2 |
| Molecular Weight: | 187.862 |
| Synonyms: | Soilfume;alpha,omega-dibromoethane;Iscobrome D;Soil-borne wheat mosaic virusSoilbrom;DBE;Aadibroom;EDB;Dowfume W 85;1,2-Dibromoethane(Ethylene bromide);Nefis;sym-Dibromoethane;ethylene bromide;alpha,beta-dibromoethane;Sanhyuum;1,2-dibromo- Ethane;1,2- Dibromoethane;Ethylene Dibromide;Ethane,1,2-dibromo-;Edabrom; |
| EINECS: | 203-444-5 |
| Density: | 2.173 g/cm3 |
| Melting Point: | 9 °C |
| Boiling Point: | 130.2 °C at 760 mmHg |
| Flash Point: | 12.6 °C |
| Solubility: | 4 g/L (20 °C) in water |
| Appearance: | Colorless to light yellow liquid |
| Hazard Symbols: |
 T, N, F
|
| Risk Codes: | 45-23/24/25-36/37/38-51/53-34-39/23/24/25-11 |
| Safety: | 53-45-61-36/37/39-26-36/37-16-7 |
| Transport Information: | UN 1605 6.1/PG 1 |
| PSA: | 0.00000 |
| LogP: | 1.77620 |
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| Conditions | Yield |
|---|---|
| With 2AlBr3*CBr4; bromine at 55 - 65℃; for 18h; | 100% |
| With 2AlBr3*CBr4; bromine at 55 - 65℃; for 18h; Product distribution; Mechanism; different times; | 100% |
| Conditions | Yield |
|---|---|
| With bromine; iodobis(N,N-diisopropyldithiocarbamato)iron(III) In dichloromethane at 20℃; under 760 Torr; | 98% |
| With bromine at -5℃; | 91% |
| With bromine |
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ethene
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A
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bis-(O,O-2,2-dimethylpropylthiophosphoryl)disulfide
B
- 106-93-4
ethylene dibromide
| Conditions | Yield |
|---|---|
| In toluene at 0 - 15℃; | A 97% B n/a C 3% |
| Conditions | Yield |
|---|---|
| With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation; | 96% |
| With phosphorus; phosphorous; bromine | |
| With sulfuric acid; hydrogen bromide | |
| bromination; | |
| With tetrabutylammomium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; | 78 % Chromat. |
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N-bromo-1,8-naphthalenedicarboximide
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benzene
A
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2-phenylbenzo[de]isoquinoline-1,3-dione
B
- 106-93-4
ethylene dibromide
| Conditions | Yield |
|---|---|
| With ethene In dichloromethane at 70℃; Irradiation; | A 79% B 89% |
| Conditions | Yield |
|---|---|
| With air; bromine; sodium carbonate; adogen 464; palladium dichloride Product distribution; multistep reaction: 1.) 1,2-dichloroethane, reflux, 15 h, 2.) CCl4; reactions under var. conditions, reactions of derivatives; | A 88% B n/a |
- 67-56-1
methanol
A
- 3395-91-3
Methyl 3-bromopropionate
B
- 3852-09-3
methyl 3-methoxypropionate
C
- 106-93-4
ethylene dibromide
D
- 6482-24-2
2-Bromoethyl methyl ether
| Conditions | Yield |
|---|---|
| With bromine at -80℃; temperature up to 30 deg C; | A 67% B n/a C n/a D n/a |
| Conditions | Yield |
|---|---|
| With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h; | A 38% B 53% |
| 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% |
- 74-85-1
ethene
- 7182-86-7
tetrabutylammonium p-toluenesulfonate
A
- 19263-21-9
2-bromoethyl p-toluenesulfonate
B
- 106-93-4
ethylene dibromide
| Conditions | Yield |
|---|---|
| With bromine In dichloromethane at 20℃; Product distribution; Mechanism; | A 34% B 51 % Spectr. |
| With bromine In dichloromethane at 20℃; | A 34% B 51 % Spectr. |
| With bromine In dichloromethane Ambient temperature; |
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Consensus Reports
Standards and Recommendations
ACGIH TLV: Animal Carcinogen
DFG MAK: DFG TRK: Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (EDB) 0.045 ppm; CL 1 mg/m3/15M
DOT Classification: 6.1; Label: Poison
Analytical Methods
Specification
The IUPAC name of 1,2-Dibromoethane is 1,2-dibromoethane. With the CAS registry number 106-93-4, it is also named as Aadibroom; Celmide. The product's categories are organics and bromine chemicals. It is colorless to light yellow liquid with a sweetish odor. And it is slightly soluble in water, and soluble in most organic solvents and thinners. In addition, this chemical slowly decomposes in the presence of light and heat, so it may turn brown upon exposure to light. It is corrosive to iron and other metals and may decompose upon contact with alkalis. Furthermore, it is incompatible with oxidizing agents. Reacts with sodium, potassium, calcium, powdered aluminum, zinc, magnesium and liquid ammonia.
The other characteristics of 1,2-Dibromoethanecan be summarized as:
(1)ACD/LogP: 2.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.08; (4)ACD/LogD (pH 7.4): 2.08; (5)ACD/BCF (pH 5.5): 22.42; (6)ACD/BCF (pH 7.4): 22.42; (7)ACD/KOC (pH 5.5): 322.43; (8)ACD/KOC (pH 7.4): 322.43; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.521; (13)Molar Refractivity: 26.77 cm3; (14)Molar Volume: 87.9 cm3; (15)Polarizability: 10.61×10-24 cm3; (16)Surface Tension: 36.4 dyne/cm; (17)Enthalpy of Vaporization: 34.77 kJ/mol; (18)Vapour Pressure: 12 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 187.865929; (21)MonoIsotopic Mass: 185.867975; (22)Heavy Atom Count: 4.
Preparation of 1,2-Dibromoethane:
It can be obtained by ethene petroleum ether and bromine under Geschwindigkeit der Reaktion at -80 - -100°C.
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Uses of 1,2-Dibromoethane:
It can be used as ethyl reagents and solvents.In agriculture, it is used as a nematicide and synthetic plant growth regulator. And it is also used as intermediate in synthesis of diethyl-bromophenyl acetonitrile, and fire retardant of vinyl bromide in medicine. In addition, it is used in gasoline to eliminate lead in seismic liquid agent, metal surface treatment agent and fire-fighting agent. It reacts with 2,4,5-tribromo-1H-imidazole to get 2,4,5-tribromo-1-vinylimidazole. This reaction needs reagent aq. tetrabutylammonium bromide and aq. NaOH by heating. The reaction time is 3 hours. The yield is 90 %.
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Safety informationg of 1,2-Dibromoethane:
When you are using this chemical, please be cautious about it as the following:It is highly flammable, so it is toxic by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause cancer and is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES:BrCCBr;
(2)Std. InChI:InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2;
(3)Std. InChIKey:PAAZPARNPHGIKF-UHFFFAOYSA-N.
The following are the toxicity data of 1,2-Dibromoethane:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| chicken | LD50 | oral | 79mg/kg (79mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
| guinea pig | LCLo | inhalation | 400ppm/3H (400ppm) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
| guinea pig | LCLo | inhalation | 400ppm/3H (400ppm) | LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. |
| guinea pig | LD50 | oral | 110mg/kg (110mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
| man | TDLo | oral | 43uL/kg (0.043mL/kg) | LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Human & Experimental Toxicology. Vol. 19, Pg. 152, 2000. |
| mouse | LD50 | intraperitoneal | 220mg/kg (220mg/kg) | Journal fuer Praktische Chemie. Vol. 320, Pg. 133, 1978. | |
| mouse | LD50 | unreported | 146mg/kg (146mg/kg) | "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 38, 1971. | |
| mouse | LDLo | oral | 250mg/kg (250mg/kg) | Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972. | |
| quail | LD50 | oral | 130mg/kg (130mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | British Poultry Science. Vol. 22, Pg. 355, 1981. |
| rabbit | LD50 | oral | 55mg/kg (55mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
| rabbit | LD50 | skin | 300mg/kg (300mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. | |
| rabbit | LD50 | skin | 300mg/kg (300mg/kg) | SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 6, Pg. 158, 1952. |
| rabbit | LDLo | rectal | 2500mg/kg (2500mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" | Journal of Pharmacology and Experimental Therapeutics. Vol. 34, Pg. 223, 1928. |
| rat | LC50 | inhalation | 14300mg/m3/30 (14300mg/m3) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Farmakologiya i Toksikologiya Vol. 8, Pg. 140, 1973. |
| rat | LD50 | oral | 108mg/kg (108mg/kg) | Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 17, 1978. | |
| rat | LD50 | skin | 300mg/kg (300mg/kg) | "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976. | |
| women | LDLo | oral | 90mg/kg (90mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 257, 1969. |