PRODUCTS

TERT-AMYL ALCOHOL

CAS Number: 75-85-4
EC Number: 200-908-9
IUPAC name: 2-Methylbutan-2-ol
Chemical formula: C5H12O

Tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.
Historically Tert-Amyl alcohol has been used an anesthetic and more recently used as a recreational drug.
Tert-Amyl alcohol is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol.

The psychotropic effects of Tert-Amyl alcohol and ethanol are similar, though distinct.
Impact on coordination and balance are proportionately more prominent with Tert-Amyl alcohol, which is significantly more potent by weight than ethanol.

Tert-Amyl alcohol is a colorless liquid with a burning flavor and an unpleasant odor similar to paraldehyde with a hint of camphor.
TAA remains as a liquid at room temperature making it a useful alternative solvent to tert-butyl alcohol.

Production of Tert-Amyl alcohol:
Tert-Amyl alcohol is primarily made by the hydration of 2-methyl-2-butene in the presence of an acidic catalyst.
On the other hand, it could be product from acetone and acetylene by Favorskii reaction to give 2-Methylbut-3-yn-2-ol, then hydrogenation with Raney nickel catalyst to give Tert-Amyl alcohol.

Natural occurrence of Tert-Amyl alcohol:
Fusel alcohols like Tert-Amyl alcohol are grain fermentation byproducts and therefore trace amounts of Tert-Amyl alcohol are present in many alcoholic beverages.
Traces of Tert-Amyl alcohol have been detected in other foods, like fried bacon, cassava and rooibos tea.
Tert-Amyl alcohol is also present in rabbit milk and seems to play a role of pheromone inducing suckling in the newborn rabbit.

History of Tert-Amyl alcohol:
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.
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 TAA and TBE solution with a volume ratio of 0.5:1 made by the Winthrop Laboratories.
Nowadays Tert-Amyl alcohol has found use as a recreational drug.

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

Overdose and toxicity of Tert-Amyl alcohol:
The smallest known dose of Tert-Amyl alcohol that has killed a person is 30 mL.

An overdose produces symptoms similar to alcohol poisoning and is a medical emergency due to the sedative/depressant properties which manifest in overdose as potentially lethal respiratory depression.
Sudden loss of consciousness, simultaneous respiratory and metabolic acidosis, fast heartbeat, increased blood pressure, pupil constriction, coma, respiratory depression and death may follow from an overdose.
The oral LD50 in rats is 1 g/kg. The subcutaneous LD50 in mice is 2.1 g/kg.

Metabolism of Tert-Amyl alcohol:
In rats, Tert-Amyl alcohol is primarily metabolized via glucuronidation, as well as by oxidation to 2-methyl-2,3-butanediol.
It is likely that the same path is followed in humans, though older sources suggest Tert-Amyl alcohol is excreted unchanged.

The use of Tert-Amyl alcohol cannot be detected with general ethanol tests or other ordinary drug tests.
Tert-Amyl alcohol's use can be detected from a blood or a urine sample by using gas chromatography–mass spectrometry for up to 48 hours after consumption.

Widespread uses by professional workers:
Other release to the environment of Tert-Amyl alcohol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use as processing aid.

Formulation or re-packing of Tert-Amyl alcohol:
Tert-Amyl alcohol is used in the following products: laboratory chemicals and pharmaceuticals. Release to the environment of Tert-Amyl alcohol can occur from industrial use: formulation of mixtures.

Uses at industrial sites of Tert-Amyl alcohol:
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 Tert-Amyl alcohol 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.

Appearance: Colorless liquid
Odor: Camphorous
Density: 0.805 g/cm3
Melting point: −9 °C

Boiling point: 101 to 103 °C
Solubility in water: 120 g·dm−3
log P: 1.0950.5:1 volume ratio
Vapor pressure: 1.6 kPa (at 20 °C)

Refractive index (nD): 1.405
Viscosity: 4.4740 mPa·s
Molecular Weight: 88.15
XLogP3: 0.9

Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 1
Exact Mass: 88.088815002

Monoisotopic Mass: 88.088815002
Topological Polar Surface Area: 20.2 Å²
Heavy Atom Count: 6
Complexity: 39.2

Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0

Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Tert-Amyl alcohol (TAA) or amylene hydrate, belongs to the class of organic compounds known as tertiary alcohols.
Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H).
2-Methyl-2-butanol is a pungent tasting compound. 2-methyl-2-butanol has been detected, but not quantified, in several different foods, such as red bell peppers, pepper (c. annuum), fruits, yellow bell peppers, and orange bell peppers.

This could make 2-methyl-2-butanol a potential biomarker for the consumption of these foods.
In 1930's TAA was mainly used as a solvent for tribromoethanol (TBE), forming Avertin at a 0.5:1 volume ratio of TAA to TBE. When ingested, the effects of TAA may begin in about 30 minutes and can last up to 2 days.
The oral LD50 in rats is 1 g/kg.

Tert-Amyl alcohol or 2m2b, belongs to the class of organic compounds known as tertiary alcohols.
Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H).
Tert-Amyl alcohol is a pungent tasting compound.
Tert-Amyl alcohol is found, on average, in the highest concentration within grape wine.

Tert-Amyl alcohol has also been detected, but not quantified in, several different foods, such as evergreen blackberries (Rubus laciniatus), orange bell peppers (Capsicum annuum), blackberries (Rubus), green bell peppers (Capsicum annuum), and celeriacs (Apium graveolens var. rapaceum).
This could make 2-methyl-2-butanol a potential biomarker for the consumption of these foods.
Based on a literature review a significant number of articles have been published on 2-Methyl-2-butanol.

Tert-Amyl alcohol system name 2-methyl-2-butanol, colorless transparent liquid, slightly soluble in water, with water can form an azeotropic mixture, the boiling point of 87.4 deg C, and ethanol, ether, benzene, chloroform, glycerol and other miscible.
As a chemical raw material, tert-amyl alcohol is widely used in synthetic perfume, medicine and color film industries.

In the mid-Seventy's, Japan's research on the synthesis of the intermediate of the tert-amyl alcohol as the raw material was successful, so that a number of high value-added extension products were available, and the deep processing of tert-amyl alcohol was pushed to a new height.

Use
Used as raw materials for the synthesis of spices and pesticides, and also an excellent solvent
mainly used for the production of new pesticides, and can be used for the synthesis of indane Musk, as well as color couplers for color films. Production of tert-amyl alcohol intermediate methyl butynol is also useful pharmaceutical intermediates and terpene perfume intermediates, and used in the manufacture of acid etching inhibitor, viscosity stabilizer, viscosity reducer, and used in the manufacture of nickel plating, copper plating polishing agent, chlorinated hydrocarbon stabilizer, etc.

Production method
acetone and acetylene are used as raw materials, which are obtained by alkynylation and hydrogenation. Acetylene is dissolved in liquid ammonia, mixed with acetone and catalyst, and then sent to the alkynylation reactor. The reaction solution is flash evaporated to separate unreacted acetylene and ammonia, and the unreacted acetone is distilled off, the obtained methyl butynol enters the hydrogenation reactor for reaction to generate tert-amyl alcohol, and the product is obtained by dehydration and purification.

It is formed by adding water to isopentene.
Obtained by fractional distillation of a mixed alcohol formed by chlorination and hydrolysis of pentane.
The raw material pentane was dehydrated with anhydrous hydrogen chloride, evaporated and mixed with chlorine gas into the reactor, and the reaction temperature was 250-300 °c.
The reaction product was separated by four distillation columns to obtain chloropentane.
In the hydrolyzer, sodium oleate is used as catalyst, and the chloropentane is hydrolyzed with sodium hydroxide aqueous solution.

The pentanol containing 59% primary alcohol, 36% secondary alcohol and 5% tertiary alcohol can be obtained by separating and distilling crude pentanol from water.
Using acetone and acetylene as raw materials, the purity of the product was 99%. Raw material consumption quota: acetone 1040kg/t, calcium carbide 1500kg/t, hydrogen (99.5%)650, liquid ammonia 135kg/t, potassium carbonate 340kg/t.

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.

Tert-Amyl alcohol 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;

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.

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

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.

Other names:
2-METHYL-2-BUTANOL
75-85-4
2-Methylbutan-2-ol
Amylene hydrate
tert-Pentyl alcohol
tert-Pentanol
t-Amyl alcohol
2-Butanol, 2-methyl-
Dimethylethylcarbinol
Ethyldimethylcarbinol
tert-Isoamyl alcohol
t-Pentyl alcohol
3-Methylbutan-3-ol
1,1-Dimethyl-1-propanol
Dimethyl ethyl carbinol
Ethyl dimethyl carbinol
tert-amylalcohol
2-Methyl butanol-2
tert-n-Amyl alcohol
Amylenum hydratum
Amylalkohol, tertiaerer
3-Methyl-butanol-(3)
NSC 25498
tertiary amyl alcohol
Methyl-2 butanol-2
Methyl-3 butanol-3
Amylene hydrate
2-Methyl-butan-2-ol
NSC-2549
2-BUTANOL,2-METHYL
C2H5C(CH3)2OH
69C393R11Z
25-85-4
HSDB 5005
EINECS 200-908-9
BRN 1361351
tertpentanol
Amylenhydrat
amylene-hydrate
tertamyl alcohol
AI3-24191
UNII-69C393R11Z
tert-amyl-alcohol
tert. amylalcohol
tert.-amylalcohol
tert.-amyl alcohol
tertiary amylalcohol
2-methyl-2butanol
t-AmOH
MFCD00004478
1,1-dimethylpropanol
methyl-tert-butyl alcohol
EC 200-908-9
3-Hydroxy-3-methyl butane
DSSTox_CID_21436
DSSTox_RID_79732
2-ETHYL-2-PROPANOL
DSSTox_GSID_41436
CHEMBL44658
PENTYL ALCOHOL, TERT-
2M2B
DTXSID0041436
1,1-Dimethyl-1-propanol-[d6]
CHEBI:132750
WLN: QX2&1&1
HMS3264I17
Pharmakon1600-01301017
AMY11089
NSC25498
ZINC1481970
Tox21_302356
NSC760354
AKOS000119037
CCG-213670
NSC-760354
CAS-75-85-4
NCGC00166208-01
NCGC00255665-01
FT-0612915
P0059
EN300-19309
C21401
D02931
E80408
AB01563165_01
A838528
Q209428
J-510046
F0001-1906
Z104473496