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2,2,2-Tribromoethanol

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Name

2,2,2-Tribromoethanol

EINECS 200-903-1
CAS No. 75-80-9 Density 2.866 g/cm3
PSA 20.23000 LogP 1.81720
Solubility Soluble in alcohol, ether, benzene and warmpetroleum ether. Partially soluble in water. Melting Point 73-79 °C(lit.)
Formula C2H3Br3O Boiling Point 199 °C at 760 mmHg
Molecular Weight 282.757 Flash Point 99.7 °C
Transport Information N/A Appearance almost white to beige crystalline powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 75-80-9 (2,2,2-Tribromoethanol) Hazard Symbols HarmfulXn
Synonyms

2,2,2-Tribromoethyl alcohol;Avertin;Basibrol;Bromethol;Ethobrom;Ethobrome;NSC 2189;Narcolan;Narcotyl;Narkolan;Rectanol;Tribromoethanol;b-Tribromoethanol;

 

2,2,2-Tribromoethanol Synthetic route

50-00-0

formaldehyd

75-25-2

Bromoform

75-80-9

2,2,2-tribromoethanol

Conditions
ConditionsYield
With potassium tert-butylate; ammonia at -75 - -65℃; for 0.5h;46%
115-17-3

bromal

75-80-9

2,2,2-tribromoethanol

115-17-3

bromal

925-90-6

ethylmagnesium bromide

A

75-80-9

2,2,2-tribromoethanol

B

58577-58-5

1,1,1-tribromo-butan-2-ol

Conditions
ConditionsYield
With diethyl ether
115-17-3

bromal

75-80-9

2,2,2-tribromoethanol

Conditions
ConditionsYield
With magnesium methanolate
With aluminum isopropoxide
With zirconium(IV) tetraisopropoxide
115-20-8

1,1,1-trichloroethanol

75-80-9

2,2,2-tribromoethanol

Conditions
ConditionsYield
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℃;
507-42-6

bromal hydrate

75-80-9

2,2,2-tribromoethanol

Conditions
ConditionsYield
bei der Einw. von gaerender Hefe;
2,2,2-tribromoethanol

2,2,2-tribromoethanol

58479-61-1

tert-butylchlorodiphenylsilane

122760-58-1

tert-Butyl-diphenyl-(2,2,2-tribromo-ethoxy)-silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 25℃; for 18h;98%
75-80-9

2,2,2-tribromoethanol

13154-24-0

triisopropylsilyl chloride

122760-59-2

Triisopropyl-(2,2,2-tribromo-ethoxy)-silane

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 25℃;97%
821-41-0

5-Hexen-1-ol

75-80-9

2,2,2-tribromoethanol

2,2,4-tribromooctane-1,8-diol

Conditions
ConditionsYield
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%
75-80-9

2,2,2-tribromoethanol

C64H51Cl3N8O15P2*C6H15N

C66H52Br3Cl3N8O15P2

Conditions
ConditionsYield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;93.7%

2,2,2-Tribromoethanol Standards and Recommendations

assay: 97%

2,2,2-Tribromoethanol Specification

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%.

2,2,2-Tribromoethanol can be prepared by formaldehyde and tribromomethane

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%.

2,2,2-Tribromoethanol can react with benzoyl chloride to get benzoic acid-(2,2,2-tribromo-ethyl ester).

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.

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