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106-93-4

Basic Information
CAS No.: 106-93-4
Name: 1,2-Dibromoethane
Article Data: 109
Cas Database
Molecular Structure:
Molecular Structure of 106-93-4 (1,2-Dibromoethane)
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: ToxicT,DangerousN,FlammableF
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
Synthetic route
74-84-0

ethane

106-93-4

ethylene dibromide

Conditions
ConditionsYield
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%
74-85-1

ethene

106-93-4

ethylene dibromide

Conditions
ConditionsYield
With bromine; iodobis(N,N-diisopropyldithiocarbamato)iron(III) In dichloromethane at 20℃; under 760 Torr;98%
With bromine at -5℃;91%
With bromine
74-85-1

ethene

81373-35-5

di(neopentyloxy)thioxophosphoranesulphenyl bromide

A

74895-06-0

bis-(O,O-2,2-dimethylpropylthiophosphoryl)disulfide

B

106-93-4

ethylene dibromide

C

Dithiophosphoric acid S-(2-bromo-ethyl) ester O,O'-bis-(2,2-dimethyl-propyl) ester

Conditions
ConditionsYield
In toluene at 0 - 15℃;A 97%
B n/a
C 3%
107-21-1

ethylene glycol

106-93-4

ethylene dibromide

Conditions
ConditionsYield
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.
105089-47-2

N-bromo-1,8-naphthalenedicarboximide

71-43-2

benzene

A

6914-98-3

2-phenylbenzo[de]isoquinoline-1,3-dione

B

106-93-4

ethylene dibromide

Conditions
ConditionsYield
With ethene In dichloromethane at 70℃; Irradiation;A 79%
B 89%
6351-10-6

1-Indanol

A

83-33-0

inden-1-one

B

106-93-4

ethylene dibromide

Conditions
ConditionsYield
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

Tetracarbonyleisenkomplexe des Ethylens

Tetracarbonyleisenkomplexe des Ethylens

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
ConditionsYield
With bromine at -80℃; temperature up to 30 deg C;A 67%
B n/a
C n/a
D n/a
107-06-2

1,2-dichloro-ethane

A

107-04-0

1-Bromo-2-chloroethane

B

106-93-4

ethylene dibromide

Conditions
ConditionsYield
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h;A 38%
B 53%
107-21-1

ethylene glycol

A

106-93-4

ethylene dibromide

B

540-51-2

2-bromoethanol

Conditions
ConditionsYield
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
ConditionsYield
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

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 204.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 , 1977,p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (gavage); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-86 ,1978. ; NTP Carcinogenesis Bioassay (inhalation); Clear Evidence: mouse, rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-210 ,1982. . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 20 ppm; CL 30 ppm; Pk 50 ppm/5M/8H
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

For occupational chemical analysis use OSHA: #02 or NIOSH: Ethylene Dibromide, 1008.

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.


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 %.


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.