molecular formula C4H8 B012930 3,3,3-Trideuterio-2-methylprop-1-ene CAS No. 110597-10-9

3,3,3-Trideuterio-2-methylprop-1-ene

Cat. No.: B012930
CAS No.: 110597-10-9
M. Wt: 59.12 g/mol
InChI Key: VQTUBCCKSQIDNK-BMSJAHLVSA-N
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Description

This compound is a colorless gas used in various industrial applications, including the production of synthetic rubber, plastics, and fuel additives.

Preparation Methods

Synthetic Routes and Reaction Conditions

The synthesis of 3,3,3-Trideuterio-2-methylprop-1-ene typically involves the deuteration of 2-methylpropene. This process can be achieved through the catalytic exchange of hydrogen atoms with deuterium atoms using deuterium gas (D2) in the presence of a suitable catalyst, such as palladium on carbon (Pd/C). The reaction conditions often include elevated temperatures and pressures to facilitate the exchange process.

Industrial Production Methods

In an industrial setting, the production of this compound may involve continuous flow reactors to ensure efficient deuteration. The use of deuterium gas in large quantities and the recycling of unreacted deuterium are common practices to optimize the yield and reduce costs.

Chemical Reactions Analysis

Types of Reactions

3,3,3-Trideuterio-2-methylprop-1-ene undergoes various chemical reactions, including:

    Oxidation: The compound can be oxidized to form corresponding alcohols, aldehydes, or carboxylic acids.

    Reduction: Reduction reactions can convert it into saturated hydrocarbons.

    Substitution: It can participate in substitution reactions where deuterium atoms are replaced by other functional groups.

Common Reagents and Conditions

    Oxidation: Common oxidizing agents include potassium permanganate (KMnO4) and chromium trioxide (CrO3).

    Reduction: Catalytic hydrogenation using hydrogen gas (H2) and a catalyst such as palladium on carbon (Pd/C).

    Substitution: Halogenation reactions using halogens like chlorine (Cl2) or bromine (Br2) under controlled conditions.

Major Products

    Oxidation: Formation of deuterated alcohols, aldehydes, or carboxylic acids.

    Reduction: Formation of deuterated alkanes.

    Substitution: Formation of deuterated halides.

Scientific Research Applications

3,3,3-Trideuterio-2-methylprop-1-ene is used in various scientific research applications, including:

    Chemistry: As a deuterated compound, it is used in nuclear magnetic resonance (NMR) spectroscopy to study reaction mechanisms and molecular structures.

    Biology: It serves as a tracer in metabolic studies to understand biochemical pathways.

    Medicine: Used in the development of deuterated drugs to improve pharmacokinetic properties.

    Industry: Employed in the production of deuterated polymers and materials with unique properties.

Mechanism of Action

The mechanism by which 3,3,3-Trideuterio-2-methylprop-1-ene exerts its effects involves the replacement of hydrogen atoms with deuterium atoms. This isotopic substitution can alter the compound’s physical and chemical properties, such as bond strength and reaction rates. The molecular targets and pathways involved depend on the specific application, such as its role as a tracer in metabolic studies or its use in NMR spectroscopy.

Comparison with Similar Compounds

Similar Compounds

    2-Methylpropene (Isobutylene): The non-deuterated form of 3,3,3-Trideuterio-2-methylprop-1-ene.

    3,3,3-Trideuterio-2-methylpropane: A fully saturated deuterated derivative.

    Deuterated Ethylene: Another deuterated hydrocarbon used in similar applications.

Uniqueness

This compound is unique due to its specific deuteration pattern, which makes it particularly useful in NMR spectroscopy and as a tracer in metabolic studies. Its deuterium atoms provide distinct advantages in studying reaction mechanisms and improving the stability and efficacy of deuterated drugs.

Properties

IUPAC Name

3,3,3-trideuterio-2-methylprop-1-ene
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C4H8/c1-4(2)3/h1H2,2-3H3/i2D3
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

VQTUBCCKSQIDNK-BMSJAHLVSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CC(=C)C
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Isomeric SMILES

[2H]C([2H])([2H])C(=C)C
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C4H8
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Weight

59.12 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Synthesis routes and methods I

Procedure details

In another aspect, the invention comprises a process for the recovery of methacrylic acid and acetic acid produced by the oxidation of isobutylene or tertiary butyl alcohol into methacrolein, followed by the recovery of methacrolein, and thereafter oxidation of the methacrolein to form methacrylic acid. The methacrylic acid and acetic acid are recovered by cooling and condensing the effluent from the second oxidation (of methacrolein) and then passing the condensed effluent directly, and without preliminary extraction, into an azeotropic distillation carried out in the presence of a solvent, preferably methyl n-propyl ketone. Substantially dry crude methacrylic acid is withdrawn as a bottoms product from the azeotropic distillation, along with impurities and acetic acid. Separation and recovery of methacrylic acid and acetic acid may be carried out in conventional distillation facilities.
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Synthesis routes and methods II

Procedure details

The apparatus as shown in FIG. 2 was employed in this Example. Reactor I employed had a 120 ml reaction zone and two separation zones, one at the upper portion of the reaction zone and the other at the lower portion of the reaction zone and the reaction zone was divided into 7 compartments and each compartment was stirred with a flat stirring paddle. The same so-called spent B-B fraction as in Example 3 was fed at a rate of 50 ml per hour to the lowest compartment of reactor I through line 1 and at the same time a recycling liquid containing water and 12-tungstophosphoric acid having an atomic ratio of P to W of 1 to 12 in a weight ratio of 1 to 2 coming from distillation column II through line 2 was fed at a rate of 442 g per hour to the highest compartment of reactor I. In reactor I the so-called spent B-B fraction and the mixture of the recycling liquid and the additional water was countercurrently contacted with each other at 70° C. and 10 atms. The remaining hydrocarbon mixture was collected from the upper separation zone of reactor I through line 5 while an aqueous solution containing tert-butanol formed and the 12-tungstophosphoric acid was transferred from the lower separation zone of reactor I through line 4 to distillation column II. Then, the tert-butanol formed was collected by distillation from the top of distillation column II through line 6 and an aqueous solution containing the 12 -tungstophosphoric acid was recycled from the bottom of distillation column II through line 2 to the highest compartment of reactor I together with additional water through line 3 in an amount corresponding to the amount reduced in the reaction and escaped from the reaction system. The conversion of isobutylene was 95.4% and the amount of isobutylene polymers such as diisobutylene formed was at most 1,000 ppm based on the weight of tert-butanol produced and the selectivity of isobutylene to tert-butanol was quantitative.
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Synthesis routes and methods III

Procedure details

Into a 300 ml pressure-resistant glass autoclave were charged 10 g of isobutylene, 10 g of 1-butene, 50 g of sulfuric acid and 50 g of water, and the mixture was stirred at 60° C. at a pressure of 8.5 atms for one hour. As a result, isobutylene was hydrated to form tert-butanol with the conversion of 90% and the selectivity to tert-butanol of 92%. At the same time, diisobutylene and the trimer of isobutylene were produced at a yield of 2% and 6%, respectively, and 1-butene was hydrated to form sec-butanol at a yield of 4%.
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pressure-resistant glass
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Synthesis routes and methods IV

Procedure details

An apparatus for the production of (meth)acrylic acid which is preferred according to the invention comprises the (meth)acrylic acid reactor and a quench absorber during the synthesis of (meth)acrylic acid by catalytic gaseous phase reaction of C4 starting compounds with oxygen. (Meth)acrylic acid may be obtained particularly preferably by catalytic gaseous phase oxidation of isobutene, isobutane, tert.-butanol, iso-butyraldehyde, methacrolein or meth-tert.-butylether. Further details on the production of (meth)acrylic acid are disclosed in EP 0 092 097 B1, EP 0 058 927 and EP 0 608 838.
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(meth)acrylic acid
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C4
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Synthesis routes and methods V

Procedure details

The alkylation process results in the substitution of an alkyl group for a hydrogen atom in the sulfur-containing starting material and causes a corresponding increase in molecular weight over that of the starting material. The higher molecular weight of such an alkylation product is reflected by a higher boiling point relative to that of the starting material. For example, the conversion of thiophene to 2-t-butylthiophene by alkylation with 2-methylpropene results in the conversion of thiophene, which has a boiling point of 84° C., to a product which has a boiling point of 164° C. and can be easily removed from lower boiling material in the feedstock by fractional distillation. Conversion of thiophene to di-t-butylthiophene by dialkylation with 2-methylpropene results in a product which has an even higher boiling point of about 224° C. Alkylation with alkyl groups that add a large rather than a small number of carbon atoms is preferred since the products will have higher molecular weights and, accordingly, will usually have higher boiling points than products which are obtained through alkylation with the smaller alkyl groups.
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Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

Reactant of Route 1
3,3,3-Trideuterio-2-methylprop-1-ene
Reactant of Route 2
3,3,3-Trideuterio-2-methylprop-1-ene
Reactant of Route 3
3,3,3-Trideuterio-2-methylprop-1-ene
Reactant of Route 4
3,3,3-Trideuterio-2-methylprop-1-ene
Reactant of Route 5
3,3,3-Trideuterio-2-methylprop-1-ene
Reactant of Route 6
3,3,3-Trideuterio-2-methylprop-1-ene

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.