75-80-9

Usage

Uses

Used in Organic Synthesis:
2,2,2-Tribromoethanol is used as a reagent in the organic synthesis of beta-amino alcohols, which are important building blocks in the pharmaceutical industry for the development of various drugs.
Used in Pharmaceutical Preparation:
In the medical field, 2,2,2-Tribromoethanol serves as a basal anesthetic, particularly for small animals like rodents. Its anesthetic properties make it a valuable compound in veterinary medicine.
Used in Polymer Chemistry:
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). This application is significant in the polymer industry, as it allows for the creation of polymers with specific functional groups, which can enhance their properties and expand their potential applications.

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

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

Downstream Products

• 7511-97-9 Bis-<2,2,2-tribromoethyl>-fumarat 
• 17182-43-3 2,2,2-Tribromethoxycarbonylchlorid 
• 4998-93-0 2,2,2-tribromoethyl benzoate 
• 3078-13-5 glyoxal bis-(4-nitrophenylhydrazone) 
• 6093-24-9 3,5-dinitro-benzoic acid-(2,2,2-tribromo-ethyl ester) 
• 6263-68-9 Bis-(2,2,2-tribrom-ethyl)-formal 
• 46825-80-3 o-Hydroxyphenyl-2,2,2-tribromethylphosphat 
• 90224-92-3 4-nitro-benzoic acid-(2,2,2-tribromo-ethyl ester) 
• 53676-22-5 phosphorodichloridic acid 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 
• 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 

Relevant academic research and scientific papers

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.

Selektive Blockierung von primaeren oder sekundaeren Hydroxylgruppen mit elektroaktiven Schutzgruppen

In a diol such as 17, at first the primary OH-group is blocked with an electroactive protecting group (18).Then the secondary OH-group is protected with a second group (19), that is reduced at more negative potentials.Controlled potential electrolysis selectively deblocks the primary OH-group.As protecting groups the tritylone (= 9,10-dihydro-10-oxo-9-phenyl-9-anthracenyl-) and 4-cyanobenzyl residue were suitable.With the help of a combination of these groups 1-dodecyloxy-3-octadecyloxy-2-propanol (27) was prepared starting with 1,2-O-isopropylideneglycerol (21).