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CAS No.: | 75-80-9 |
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Name: | 2,2,2-Tribromoethanol |
Molecular Structure: | |
Formula: | C2H3Br3O |
Molecular Weight: | 282.757 |
Synonyms: | 2,2,2-Tribromoethyl alcohol;Avertin;Basibrol;Bromethol;Ethobrom;Ethobrome;NSC 2189;Narcolan;Narcotyl;Narkolan;Rectanol;Tribromoethanol;b-Tribromoethanol; |
EINECS: | 200-903-1 |
Density: | 2.866 g/cm3 |
Melting Point: | 73-79 °C(lit.) |
Boiling Point: | 199 °C at 760 mmHg |
Flash Point: | 99.7 °C |
Solubility: | Soluble in alcohol, ether, benzene and warmpetroleum ether. Partially soluble in water. |
Appearance: | almost white to beige crystalline powder |
Hazard Symbols: | Xn |
Risk Codes: | 22-36/37/38 |
Safety: | 26-36 |
PSA: | 20.23000 |
LogP: | 1.81720 |
Conditions | Yield |
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With potassium tert-butylate; ammonia at -75 - -65℃; for 0.5h; | 46% |
bromal
ethylmagnesium bromide
A
2,2,2-tribromoethanol
B
1,1,1-tribromo-butan-2-ol
Conditions | Yield |
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With diethyl ether |
Conditions | Yield |
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With magnesium methanolate | |
With aluminum isopropoxide | |
With zirconium(IV) tetraisopropoxide |
Conditions | Yield |
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With carbon disulfide; aluminum tri-bromide | |
With bromine; aluminium; 1,2-dibromomethane at 40℃; | |
With carbon disulfide; aluminum tri-bromide | |
With bromine; aluminium; 1,2-dibromomethane at 40℃; |
Conditions | Yield |
---|---|
bei der Einw. von gaerender Hefe; |
tert-butylchlorodiphenylsilane
tert-Butyl-diphenyl-(2,2,2-tribromo-ethoxy)-silane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 25℃; for 18h; | 98% |
2,2,2-tribromoethanol
triisopropylsilyl chloride
Triisopropyl-(2,2,2-tribromo-ethoxy)-silane
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 25℃; | 97% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; 4-methoxy-benzaldehyde In acetonitrile at 25℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; | 94% |
With 2,6-diiodo-4,4-difluoro-1,3,5,7-tetramethyl-8-phenyl-4-bora-3a,4a-diaza-s-indacene; sodium L-ascorbate; lithium bromide In water; N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; Schlenk technique; Irradiation; | 63% |
Conditions | Yield |
---|---|
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature; | 93.7% |
The IUPAC name of this chemical is 2,2,2-Tribromoethanol. With the CAS registry number 75-80-9 and EINECS registry number 200-903-1, it is also named as Ethanol,2,2,2-tribromo-. In addition, the molecular formula is C2H3Br3O and the molecular weight is 282.76. It is a kind of almost white to beige crystalline powder and belongs to the class of Halogen Compounds.
Physical properties about this chemical are: (1)ACD/LogP: 2.30; (2)ACD/LogD (pH 5.5): 2.3; (3)ACD/LogD (pH 7.4): 2.3; (4)ACD/BCF (pH 5.5): 32.94; (5)ACD/BCF (pH 7.4): 32.94; (6)ACD/KOC (pH 5.5): 424.66; (7)ACD/KOC (pH 7.4): 424.66; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 9.23 Å2; (12)Index of Refraction: 1.65; (13)Molar Refractivity: 36.01 cm3; (14)Molar Volume: 98.6 cm3; (15)Polarizability: 14.27 ×10-24cm3; (16)Surface Tension: 64.8 dyne/cm; (17)Density: 2.866 g/cm3; (18)Flash Point: 99.7 °C; (19)Enthalpy of Vaporization: 50.64 kJ/mol; (20)Boiling Point: 199 °C at 760 mmHg; (21)Vapour Pressure: 0.0879 mmHg at 25°C.
Preparation of 2,2,2-Tribromoethanol: it can be prepared by formaldehyde and tribromomethane. This reaction will need reagents liq. NH3 and t-BuOK. The reaction time is 30 minutes at reaction temperature of -75- -65 °C. And the yield is about 46%.
Uses of 2,2,2-Tribromoethanol: it can be used in organic synthesis and also can be used as anesthetic in medicine. In addition, it can react with benzoyl chloride to get benzoic acid-(2,2,2-tribromo-ethyl ester). This is a kind of esterification reaction. And the reaction will need reagent NEt3 and solvent tetrahydrofuran. The reaction time is 6 hours at reaction temperature of 20 °C by heating. Moreover, the yield is about 80%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. Whenever you will contact it, please wear suitable protective clothing. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: BrC(Br)(Br)CO
(2)InChI: InChI=1/C2H3Br3O/c3-2(4,5)1-6/h6H,1H2
(3)InChIKey: YFDSDPIBEUFTMI-UHFFFAOYAI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 930mg/kg (930mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of Pharmaceutical Sciences. Vol. 56, Pg. 920, 1967. |
rabbit | LDLo | intraperitoneal | 450mg/kg (450mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 132, Pg. 214, 1928. |
rabbit | LDLo | oral | 1100mg/kg (1100mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 132, Pg. 214, 1928. |
rabbit | LDLo | rectal | 300mg/kg (300mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 55, Pg. 1, 1935. | |
rat | LDLo | intraperitoneal | 300mg/kg (300mg/kg) | GASTROINTESTINAL: OTHER CHANGES LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" | Laboratory Animal Science. Vol. 49, Pg. 665, 1999. |
rat | LDLo | oral | 1gm/kg (1000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 63, Pg. 183, 1938. | |
rat | LDLo | subcutaneous | 530mg/kg (530mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936. |