tert-Amyl alcohol

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.Historically tert-Amyl alcohol has been used an anesthetic[3] and more recently used as a recreational drug.[4] TAA is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol.[5] The effects of tert-Amyl alcohol and ethanol are similar.

CAS NO:75-85-4
EC NO:200-908-9

IUPAC NAMES:
2-Methyl-2-butanol
2-Methyl-butan-2-ol
2-methyl-butan-2-ol
2-Methylbutan-2-ol
2-methylbutan-2-ol
2-methylbutan-2-ol
2-methylbutan-2-ol;
tert-Amyl Alcohol
tert-Amyl Alcohol
tert-pentanol

Other names;
2-Methyl-2-butanol
tert-Amyl alcohol
t-Amylol
TAA
tert-Pentyl alcohol
2-Methyl-2-butyl alcohol
t-Pentylol
Amylene hydrate
Dimethylethylcarbinol

SYNONYMS:
2-METHYL-2-BUTANOL;tert-Amyl alcohol;2-Methylbutan-2-ol;Amylene hydrate;75-85-4;tert-Pentyl alcohol;tert-Pentanol;t-Amyl alcohol;2-Butanol, 2-methyl-;Dimethylethylcarbin;Ethyldimethylcarbinol;tert-Isoamyl alcohol;t-Pentyl alcohol;3-Methylbutan-3-ol;Dimethyl ethyl carbinol;Ethyl dimethyl carbinol;2-Methyl butanol-2;1,1-Dimethyl-1-propan;tert-n-Amyl alcohol;tert-amylalcohol;Amylenum hydratum;Amylalkohol, tertiaerer;3-Methyl-butanol-(3);NSC 25498;tertiary amyl alcohol;Methyl-2 butanol;Methyl-3 butanol-3;UNII-69C393R11Z;Amylene hydrate (NF);Amylene hydrate [NF];2-Methyl-butan-2-ol;MFCD00004478;2-BUTANOL,2-METHY
;2-ETHYL-2-PROPANOL;C2H5C(CH3)2OH;69C393R11Z;2-Methyl-2-butanol, 99%, pure;;Amylene hydrate [USAN];HSDB 5005;3-Methyl-butanol-(3) [German];EINECS 200-908-9;BRN1361351;tertpentanol;Amylenhydrat;tertamylalcohol;AI3-24191;tert-amyl-alcohol;tert. amylalcohol;tert.-amylalcohol;tert.-amyl alcohol;tertiary amylalcohol;2-methyl-2butanol;t-AmOH;1,1-dimethylpropanol;Amylene hydrate, USAN;ACMC-1BKTB;methyl-tert-butyl alcohol;EC 200-908-9;3-Hydroxy-3-methyl butane;DSSTox_CID_21436;DSSTox_RID_79732;DSSTox_GSID_41436;4-01-00-01668 (BeilsteinHandbookReference);CHEMBL44658;2M2B;DTXSID0041436;CHEBI:132750;WLN:QX2&1&1;HMS3264I17;Pharmakon1600-01301017;NSC25498;ZINC1481970;Tox21_302356;7338AF;ANW-36689;NSC-25498;NSC760354;AKOS000119037;CCG-213670;MCULE-7894262803;NSC-760354;CAS-75-85-4;tert-Pentylalcohol2-Methyl-2-butanol;2-methyl-2-butanol(tert-amylalcohol);2-Methyl-2-butanol,analyticalstandard;NCGC00166208-01;;NCGC00255665-01;2-Methyl-2-butanol, anhydrous, >=99%;2-Methyl-2-butanol, ReagentPlus(R), 99%;FT-0612915;P0059;2-Methyl-2-butanol,ReagentPlus(R),>=99%;C21401;D02931;28290-EP2380568A1;AB01563165_01;A838528;Q209428;2-Methyl-2-butanol 100 microg/mL in Acetonitrile;J-510046;F0001-1906;5A800302-5F41-4E10-9197-D3B0BD85C237;t-Amyl Alchohol, Pharmaceutical Secondary Standard; Certified Reference Material;25-85-4

tert-Amyl alcohol

tert-Amyl alcohol is a colorless liquid with a burning flavor[6] and an unpleasant odor[7] similar to paraldehyde with a hint of camphor.[8] tert-Amyl alcohol remains as a liquid at room temperature making it a useful alternative solvent to tert-butyl alcohol.
Production
tert-Amyl alcohol is primarily made by the hydration of 2-methyl-2-butene in the presence of an acidic catalyst.[9][3]

Natural occurrence
Fusel alcohols like tert-Amyl alcohol are grain fermentation byproducts and therefore trace amounts of TAA are present in many alcoholic beverages.[10] Traces of tert-Amyl alcohol have been detected in other foods, like fried bacon,[11] cassava[12] and rooibos tea.[13]

History
From about 1880s to 1950s, tert-Amyl alcohol was used as an anesthetic with the contemporary name of amylene hydrate, but was rarely used solely because of the existence of more efficient drugs.[3] In the 1930s, tert-Amyl alcohol was mainly used as a solvent for the primary anesthetic tribromoethanol (TBE). Like chloroform, TBE is toxic for the liver, so the use of such solutions declined in the 1940s in humans. TBE-TAA-solutions remained in use as short-acting anesthetics for laboratory mice and rats. Such solutions are sometimes called Avertin, which was a brand name for the now discontinued tert-Amyl alcohol and TBE solution with a volume ratio of 0.5:1 made by the Winthrop Laboratories.[14] Nowadays tert-Amyl alcohol has found use as a recreational drug.[4]

Use and effects
Ingestion or inhalation of tert-Amyl alcohol causes euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol.[15] When ingested, the effects of tert-Amyl alcohol may begin in about 30 minutes and can last up to 1–2 days.[16] 2–4 grams of tert-Amyl alcohol causes unconsciousness. About 100 g of ethanol induces a similar level of unconsciousness.[7]

Uses at industrial sites
tert-Amyl alcohol is used in the following products: pharmaceuticals and laboratory chemicals.
tert-Amyl alcohol has an industrial use resulting in manufacture of another substance (use of intermediates).
tert-Amyl alcohol is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and in the production of articles.

Formula    C5H12O
CAS no.    75-85-4
Gas Response Factor, 11.7 eV    1.01
Gas Response Factor, 10.6 eV    1.5
Gas Response Factor, 10.0 eV    2.8
ppm per mg/m⁻³, (20 °C, 1 bar)    0.273

tert-Amyl alcohol [CASRN 75-85-4, also known as amylene hydrate or
2-methyl-2-butanol (NLM, 2011a)], is used as a solvent for resins and gums and in the
production of plastics, and other chemicals such as arylpyruvic acids. It is also used as a frothing and flotation agent (e.g., in ore-flotation processes) and in some pharmaceutical applications as a sedative-hypnotic drug (NLM, 2011b). tert-Amyl alcohol has been shown to be a major metabolite of tert-amyl methyl ether in rats, mice, rabbits, and humans (NLM, 2011b). The molecular formula of tert-amyl alcohol is C5H12O (see Figure 1), and a table of physicochemical properties for tert-amyl alcohol is provided below.

Features:
Balanced composition
Soluble with water and organic solvents
Non hazardous
Highly effective

tert-amyl alcohol by Research Lab Fine Chem Industries is a high grade reagent. Also known as 2-methylbutan-2-ol, this organic compound is a branched pentanol, one of the different isomers of amyl alcohol. This reagent is available as a colourless liquid with a pungent aroma which is slightly soluble in water and miscible in organic solvents. It has a melting point of 9 C and a boiling point of 101 - 103 C. tert-amyl alcohol can be synthesized by hydroformylation. CAS No.: 75-85-4 Molecular Formula: C5H12O Molecular Weight: 88.15 Assay: Minimum 99.5 % Liquid density: 0.806 Analytical grade reagent tert-amyl alcohol has a variety of applications in chemical and biological sectors. This compound is primarily used as a pharmaceutical or pigment solvent. Tertamyl alcohol finds applications as organic solvents, chemical intermediates for gasoline fuel additives, food flavour, pharmaceutical peroxy esters, ink composition, and stabilizer in rubber productions. It produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation. Tertamyl alcohol has been used in the preparation of 2-chloro-2-methylbutane by reaction with concentrated hydrochloric acid. This reagent is suitable for industrial synthesis of products and research applications.

Tert.-Amyl alcohol special solvent for coatings. Tert.-Amyl alcohol is suitable for two-components (2K) polyurethane coatings (automotive repair coatings, plastic coatings). It increases the pot-life of two-component (2K) coatings.

Chemical Properties
colourless liquid with a camphor-like odour

Chemical Properties
Amyl alcohol is produced during the fermentation of grains, potatoes, and beets. It is also produced during the acid hydrolysis of petroleum fraction. Amyl alcohol is widely used in industry. For example, in the manufacturing of lacquers, paints, varnishes, perfumes, pharmaceuticals, plastics, rubber, explosives, hydraulic fl uids, for the extraction of fats, is also used in the petroleum refi nery industries

Chemical Properties
Amyl alcohols (pentanols) have eight isomers. All are flammable, colorless liquids, except the isomer 2,2- dimethyl-1-propanol, which is a crystalline solid.

Chemical Properties
tert-Amyl alcohol is a volatile liquid.2-Methyl-2-butanol has a sour odor, a threshold value of 8.2 mg/m3 (2.3 ppm), an absolute perception limit of 0.04 ppm, and a 100% recognition level of 0.23 ppm .

Uses
Pharmaceutic aid (solvent).

Definition
ChEBI: A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.

Production Methods
tert-Amyl alcohol is prepared by hydrating 2-methyl-2- butenes. It can also be prepared by reducing pivalic acid.

General Description
A clear, colorless liquid with an odor of camphor. Flash point 70°F. Density 0.81 g / cm3. 
Slightly soluble in water.

Air & Water Reactions
Highly flammable. Slightly soluble in water.

Reactivity Profile
2-Methyl-2-butanol attacks plastics [Handling Chemicals Safely 1980. p. 236]. Reacts violently with acetyl bromide [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

tert-Amyl Alcohol, Reagent is a colorless liquid with a pungent odor of camphor, and soluble with water and other organic solvents. It is used primarily as a pharmaceutical or pigment solvent. The Reagent grade denotes that this chemical is the highest quality commercially available and that the American Chemical Society has not officially set any specifications for this material. Spectrum Chemical manufactured Reagent grade products meet the toughest regulatory standards for quality and purity.

Items    Specifications
Appearance    colorless and transparent liquid
Active Content    ≥99%
Density    0.806~0.810
Water    ≤0.1%
Color APHA    ≤10

It is widely used in industries such as synthetic perfume, medicine and color film.

In the presence of a strong acid, alcohols will protonate. This turns a bad leaving group (hydroxide) into a good leaving group (water). After protonation of a tertiary alcohol, a water molecule leaves with a pair of electrons creating a carbocation.

Tert-Amyl alcohol is an isomer of amyl alcohol and has been used in solubilization and extraction cytoplasmic bound membrane enzymes and synthesis of ginsenoside Rb1 esters. The compound has also been utilized in anaerobic biotransformation studies as well as the affects it has on the structure and function of microbial communities in soil.
An organic solvent used for organic synthesis and biotransformation.

tert-Amyl alcohol (TAA), systematic name: 2-methyl-2-butanol (2M2B), is a branched pentanol used primarily as a pharmaceutical or pigment solvent. It remains liquid at room temperature making it a useful alternative to tert-butyl alcohol.

tert-Amyl alcohol is used as a solvent in flavors, pharmaceuticals, corrosion inhibitors, resins, gums, coating materials and in organic synthesis. It acts as a frothing agent (ore flotation), surfactant (petroleum recovery) and stabilizing agent. Further, it is used in processing aids.

tert-Amyl alcohol is an isomer of amyl alcohol and has been used in solubilization and extraction cytoplasmic bound membrane enzymes and synthesis of ginsenoside Rb1 esters. The compound has also been utilized in anaerobic biotransformation studies as well as the affects it has on the structure and function of microbial communities in soil.

Description
Colorless liquid with an odor of camphor; [Hawley]

Sources/Uses
Used as a solvent in flavors, pharmaceuticals, corrosion inhibitors, resins, gums, coating materials, and other chemicals; Also used in organic synthesis and as a frothing agent (ore flotation), surfactant (petroleum recovery), and stabilizing agent;

USES
*Includes spices, extracts, colorings, flavors, etc added to food for human consumption    
*General flavoring agents used in foods, including condiments and seasonings        
*General term used only when the only information known from the source is 'chemical,' typically related to manufacturing of chemicals, or laboratory chemicals     
*Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet if indicated by source
*Accelerators, activators, oxidation agents, reducing agents, etc    
*Paint removers, graffiti removers, or general solvents    
*General stabilizers, application unknown
*Used as a solvent in synthetic flavoring, pharmaceuticals, corrosion inhibitors, and making plastics and other chemicals.

Industry Uses    
Processing aids, not otherwise listed
Industry Processing Sectors
All other basic organic chemical manufacturing
Pharmaceutical and medicine manufacturing
Wholesale and retail trade
General description
tert-Amyl alcohol is a sterically hindered alcohol.

Application
tert-Amyl alcohol may be used as a solvent in the following processes:
• Palladium (II)-catalyzed ortho-C–H olefination of phenylacetic acids.
• Rhodium-catalyzed direct C-H functionalization at the C7 position of N-pivaloylindoles.

It may also be used in the preparation of 2-chloro-2-methylbutane by reacting with concentrated hydrochloric acid.

properties
Physical Properties
tert-Amyl alcohol is a colorless substance that melts at room temperature but is mostly still solid and has a characteristic camphor-like smell. The substance is a tertiary alcohol, which means that the carbon atom to which the hydroxyl group is bound is itself bound to three other carbon atoms. Like all butanols, tert-Amyl alcohol is also flammable.

Chemical properties
Like all aliphatic alcohols, the hydroxyl group ofter t-Amyl alcohol can be deprotonated and the tert-butoxide anion is obtained. A well-known salt that is often used in synthetic organic chemistry is potassium tert-butoxide, which z. B. is accessible by reaction of tert-Amyl alcohol with elemental potassium.

This strongly basic salt is used as a sterically demanding but only weakly nucleophilic base, for example in deprotonations in which the base must not attack nucleophilically. Oftenter t-Amyl alcohol is also used as a solvent.