75-80-9

Basic information

• Product Name: 2,2,2-Tribromoethanol
• Synonyms: NARKOLAN;TRIBROMOETHYL ALCOHOL;2,2,2-TRIBROMOETHANOL;ETHOBROM;BETA-TRIBROMOETHYL ALCOHOL;B-TRIBROMOETHYL ALCOHOL;BROMETHOL;2,2,2-Tribromoethanol, GC 99%
• CAS NO: 75-80-9
• Molecular Formula: C₂H₃Br₃O
• Molecular Weight: 282.76
• EINECS: 200-903-1
• Product Categories: Halogen compounds
• Mol File: 75-80-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 73-79 °C(lit.)
• Boiling Point: 92-93 °C10 mm Hg(lit.)
• Flash Point: 92-93°C/10mm
• Appearance: almost white to beige crystalline powder
• Density: 2.5731 (rough estimate)
• Vapor Pressure: 0.0879mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 13.41±0.10(Predicted)
• Water Solubility: Soluble in alcohol, ether, benzene and warmpetroleum ether. Partially soluble in water.
• Sensitive: Light Sensitive
• BRN: 1733249
• CAS DataBase Reference: 2,2,2-Tribromoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Tribromoethanol(75-80-9)
• EPA Substance Registry System: 2,2,2-Tribromoethanol(75-80-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KM3675000
• F: 8-23
• TSCA: Yes
• Hazardous Substances Data: 75-80-9(Hazardous Substances Data)

Usage

Chemical Properties

White crystals or powder; slight aromatic odor and taste. Unstable in air and light. Slightly soluble in water; soluble in alcohol, ether, benzene, and amylene hydrate; aqueous and alcoholic solutions decompose on exposure to light. Combustible.

Uses

Different sources of media describe the Uses of 75-80-9 differently. You can refer to the following data:
1. 2,2,2-Tribromoethanol is utilized in organic synthesis of beta-amino alcohols. The pharmaceutical preparation of tribromoethanol serves as an anesthetic in medicine.
2. 2,2,2-Tribromoethanol can be used as a functional initiator for the introduction of α-hydroxyl groups to poly(methyl methacrylate) and poly(n-butyl acrylate).
3. Medicine (basal anesthetic).

General Description

2,2,2-Tribromoethanol is generally used as an anesthetic drug for rodents.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and other routes. Dangerous when heated; see also BROMIDES.

InChI:InChI=1/C2H3Br3O/c3-2(4,5)1-6/h6H,1H2

Synthetic route

formaldehyd (50-00-0) + Bromoform (75-25-2) → 2,2,2-tribromoethanol (75-80-9)

Conditions	Yield
With potassium tert-butylate; ammonia at -75 - -65℃; for 0.5h;	46%

bromal (115-17-3) + magnesium methanolate (109-88-6, 16436-83-2, 16436-85-4) → 2,2,2-tribromoethanol (75-80-9)

bromal (115-17-3) + ethylmagnesium bromide (925-90-6) → 2,2,2-tribromoethanol (75-80-9) + 1,1,1-tribromo-butan-2-ol (58577-58-5)

Conditions	Yield
With diethyl ether

bromal (115-17-3) → 2,2,2-tribromoethanol (75-80-9)

Conditions	Yield
With magnesium methanolate
With aluminum isopropoxide
With zirconium(IV) tetraisopropoxide

1,1,1-trichloroethanol (115-20-8) → 2,2,2-tribromoethanol (75-80-9)

Conditions	Yield
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℃;

bromal hydrate (507-42-6) → 2,2,2-tribromoethanol (75-80-9)

Conditions	Yield
bei der Einw. von gaerender Hefe;

2,2,2-tribromoethanol + tert-butylchlorodiphenylsilane (58479-61-1) → tert-Butyl-diphenyl-(2,2,2-tribromo-ethoxy)-silane (122760-58-1)

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

2,2,2-tribromoethanol (75-80-9) + triisopropylsilyl chloride (13154-24-0) → Triisopropyl-(2,2,2-tribromo-ethoxy)-silane (122760-59-2)

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

5-Hexen-1-ol (821-41-0) + 2,2,2-tribromoethanol (75-80-9) → 2,2,4-tribromooctane-1,8-diol

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%

2,2,2-tribromoethanol (75-80-9) + C64H51Cl3N8O15P2*C6H15N → C66H52Br3Cl3N8O15P2

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

2,2,2-tribromoethanol (75-80-9) + C73H68Cl2N10O16P2*C6H15N → C75H69Br3Cl2N10O16P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	93.2%

2,2,2-tribromoethanol (75-80-9) + Di-tert-butylmethylsilyl Trifluoromethanesulfonate (105866-92-0) → Di-tert-butyl-methyl-(2,2,2-tribromo-ethoxy)-silane (122760-57-0)

Conditions	Yield
With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene at 0 - 25℃;	93%

L-N-Boc-Ala (15761-38-3) + 2,2,2-tribromoethanol (75-80-9) → N-(tert-butoxycarbonyl)-L-alanine 2,2,2-tribromoethyl ester

Conditions	Yield
With dmap; dacarbazine; 4-N,N-dimethylaminopyridine trifluoroacetate In dichloromethane at 20℃; for 17.5h; Esterification;	86%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate	78%

2,2,2-tribromoethanol (75-80-9) + N,N-diisopropylcarbamoyl chloride (19009-39-3) → 2,2,2-tribromoethyl N,N-diisopropylcarbamate

Conditions	Yield
In pyridine at 70℃; for 16h;	86%
With pyridine at 70℃; for 16h;	74%

2,2,2-tribromoethanol (75-80-9) + C68H60Cl2N8O16P2*C6H15N → C70H61Br3Cl2N8O16P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	85%

2,2,2-tribromoethanol (75-80-9) + C63H52Cl2N6O16P2*C6H15N → C65H53Br3Cl2N6O16P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	84.5%

2,2,2-tribromoethanol (75-80-9) + C51H46Cl2N4O16P2*C6H15N (79275-85-7) → C53H47Br3Cl2N4O16P2 (79535-70-9)

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	84%

2,2,2-tribromoethanol (75-80-9) + C57H49Cl2N5O16P2*C6H15N → C59H50Br3Cl2N5O16P2 (79526-65-1)

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	84%

2,2,2-tribromoethanol (75-80-9) + Cyclohexanecarboxylic acid (98-89-5) → 2,2,2-tribromoethyl cyclohexanecarboxylate (221887-36-1)

Conditions	Yield
With dmap; dacarbazine; 4-N,N-dimethylaminopyridine trifluoroacetate In dichloromethane at 20℃; for 6h; Esterification;	83%

2,2,2-tribromoethanol (75-80-9) + C62H57Cl2N7O16P2*C6H15N → C64H58Br3Cl2N7O16P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	82.7%

BOC-glycine (4530-20-5) + 2,2,2-tribromoethanol (75-80-9) → C9H14Br3NO4

Conditions	Yield
With dicyclohexyl-carbodiimide	82.1%

2,2,2-tribromoethanol (75-80-9) + 7,7-dimethoxybicyclo<2.2.1>hept-2-ene (875-04-7) → 7-(2,2,2-tribromoethoxy)-7-methoxybicyclo<2.2.1>hept-2-ene

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	82%

2,2,2-tribromoethanol (75-80-9) + dimethyl sulfate (77-78-1) → 1,1,1-tribromo-2-methoxy-ethane (126015-45-0)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In chloroform at 95 - 100℃; for 0.5h;	82%

2,2,2-tribromoethanol (75-80-9) + C58H48Cl3N7O15P2*C6H15N → C60H49Br3Cl3N7O15P2 (79535-65-2)

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	80.6%

2,2,2-tribromoethanol (75-80-9) + C69H59Cl3N10O14P2*C6H15N → C71H60Br3Cl3N10O14P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	80%

2,2,2-tribromoethanol (75-80-9) + C64H51Cl3N8O15P2*C6H15N → C66H52Br3Cl3N8O15P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	79.5%

2,2,2-tribromoethanol (75-80-9) + C65H50Cl4N10O14P2*C6H15N → C67H51Br3Cl4N10O14P2

Conditions	Yield
With pyridine; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole for 0.75h; Ambient temperature;	79%

Upstream product

• 57-55-6 propylene glycol 
• 17182-43-3 2,2,2-Tribromethoxycarbonylchlorid 
• 115-17-3 bromal 
• 555-75-9 aluminum ethoxide 
• 50-00-0 formaldehyd 
• 75-25-2 Bromoform 
• 60-29-7 diethyl ether 
• 100-52-7 benzaldehyde 
• 25016-92-6 aluminium triisopentylate 
• 507-42-6 bromal hydrate 
• 115-20-8 1,1,1-trichloroethanol 
• 925-90-6 ethylmagnesium bromide 
• 109-88-6 magnesium methanolate 

Downstream Products

• 7511-97-9 Bis-<2,2,2-tribromoethyl>-fumarat 
• 28049-05-0 3-Phenylpropionsaeure-tribromethylester 
• 593-92-0 vinylidene dibromide 
• 79535-65-2 C₆₀H₄₉Br₃Cl₃N₇O₁₅P₂ 
• 80817-55-6 Phosphoric acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2-diphenylacetylamino-6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 2,2,2-tribromo-ethyl ester 
• 80817-56-7 Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 2,2,2-tribromo-ethyl ester 
• 80817-54-5 Phosphoric acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-[4-(4-methoxy-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 2,2,2-tribromo-ethyl ester 

Relevant articles and documents

PRODUCTION OF 1,1,1-TRIHALOGENO-2-ALKANOLS AND SOME OF THEIR PROPERTIES

The reaction of acyclic and carbocyclic carbonyl compounds with haloforms was studied in liquid ammonia and dimethylformamide in the presence of basic catalysts (t-BuOK, KOH).As a result of the reaction 1,1,1-trihalogeno-2-alkanols were obtained.They were used for the synthesis of 1,1,1-trihalogeno-2-methoxyalkanes, 1,1-dibromoalkenes, 1,1-dichloro-2-methoxyalkenes, and alkyl mono- and dichloromethyl ketones.