Tetramethylazodicarboxamide

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Tetramethylazodicarboxamide [1]
Tetramethylazodicarboxamide Structural Formula V.1.svg
Names
IUPAC name
3-(Dimethylcarbamoylimino)-1,1-dimethylurea
Other names
Diamide; Tetramethyldiazenedicarboxamide; N,N,N,N-Tetramethylazoformamide 1,1'-Azobis(N,N-dimethylformamide); N,N,N,N-Tetramethylazobisformamide; Azodicarboxylic acid bis(dimethylamide); 1,1'-Azobis(N,N-dimethylformamide)
Identifiers
3D model (JSmol)
AbbreviationsTMAD
ChEBI
ChemSpider
ECHA InfoCard 100.030.852
EC Number 233-951-7
PubChem CID
UNII
Properties
C6H12N4O2
Molar mass 172.188 g·mol−1
AppearanceYellow crystalline solid
Melting point 113 to 115 °C (235 to 239 °F; 386 to 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetramethylazodicarboxamide (also known as TMAD and diamide) is a reagent used in biochemistry for oxidation of thiols in proteins to disulfides. [2] It has also been used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate. [1]

Organic redox reaction redox reaction that takes place with organic compounds

Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemical sense of the word. Instead the relevant criterion for organic oxidation is gain of oxygen and/or loss of hydrogen

Thiol any organic compound having a sulfanyl group

Thiol is an organosulfur compound of the form R-SH, where R represents an alkyl or other organic substituent. Thiols are the sulfur analogue of alcohols, and the word is a portmanteau of "thion" + "alcohol," with the first word deriving from Greek θεῖον (theion) = "sulfur". The –SH functional group itself is referred to as either a thiol group or a sulfhydryl group.

Mitsunobu reaction chemical reaction

The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). The alcohol undergoes an inversion of stereochemistry. It was discovered by Oyo Mitsunobu (1934–2003).

Related Research Articles

Grignard reaction Organometallic coupling reaction

The Grignard reaction is an organometallic chemical reaction in which alkyl, vinyl, or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is an important tool for the formation of carbon–carbon bonds. The reaction of an organic halide with magnesium is not a Grignard reaction, but provides a Grignard reagent.

Organolithium reagent organometallic compound with a direct bond between a carbon and a lithium atom

Organolithium reagents are organometallic compounds that contain carbon – lithium bonds. They are important reagents in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C-Li bond is highly ionic. Owing to the polar nature of the C-Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless whereas technical grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging degraded samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is a derivative of formamide, the amide of formic acid. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Appel reaction organic reaction that converts an alcohol into an alkyl chloride

The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbon tetraiodide, methyl iodide or iodine gives alkyl iodides. The reaction is credited to and named after Rolf Appel, it had however been described earlier. The use of this reaction is becoming less common, due to carbon tetrachloride being restricted under the Montreal protocol.

The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel, who first posited the synthesis with the aid of his partner, James Dornbush.

Metalation is a chemical reaction which involves the bonding of a metal atom to what is typically an organic molecule to form a new compound. This reaction usually involves the replacement of a halogen atom in an organic molecule with a metal atom to form an organometallic compound. In the laboratory, metalation is commonly used to activate organic molecules during the formation of C—X bonds, which are necessary for the synthesis of many organic molecules.

Diethyl azodicarboxylate chemical compound

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2O2CN=NCO2CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.

Aziridines are organic compounds containing the aziridine functional group, a three-membered heterocycle with one amine group (-NH-) and two methylene bridges. The parent compound is aziridine, with molecular formula C
2
H
5
N
.

Lawessons reagent chemical compound

Lawesson's reagent, or LR, is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it. Lawesson's reagent was first made in 1956 during a systematic study of the reactions of arenes with P4S10.

Carbonyldiimidazole chemical compound

1,1'-Carbonyldiimidazole (CDI) is an organic compound with the molecular formula (C3H3N2)2CO. It is a white crystalline solid. It is often used for the coupling of amino acids for peptide synthesis and as a reagent in organic synthesis.

Diisopropyl azodicarboxylate chemical compound

Diisopropyl azodicarboxylate (DIAD) is the diisopropyl ester of azodicarboxylic acid. It is used as a reagent in the production of many organic compounds. It is often used in the Mitsunobu reaction where it serves as an oxidizer of triphenylphosphine to triphenylphosphine oxide. It has also been used to generate aza-Baylis-Hillman adducts with acrylates. It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.

Weinreb ketone synthesis

The Weinreb–Nahm ketone synthesis is a chemical reaction used in organic chemistry to make carbon–carbon bonds. It was discovered in 1981 by Steven M. Weinreb and Steven Nahm as a method to synthesize ketones. The original reaction involved two subsequent nucleophilic acyl substitutions: the conversion of an acid chloride with N,O-Dimethylhydroxylamine, to form a Weinreb–Nahm amide, and subsequent treatment of this species with an organometallic reagent such as a Grignard reagent or organolithium reagent. Nahm and Weinreb also reported the synthesis of aldehydes by reduction of the amide with an excess of lithium aluminum hydride.

Sulfur tetrafluoride chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless gas. It is a corrosive species that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

Picolinic acid chemical compound

Picolinic acid is an organic compound with the formula C5H4N(CO2H). It is a derivative of pyridine with a carboxylic acid substituent at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a white solid that is soluble in water.

The Yamaguchi esterification is the chemical reaction of an aliphatic carboxylic acid and 2,4,6-trichlorobenzoyl chloride to form a mixed anhydride which, upon reaction with an alcohol in the presence of stoichiometric amount of DMAP, produces the desired ester. It was first reported by Masaru Yamaguchi et al. in 1979.

Phosphoramidite salt or ester of any amidophosphorous acid

A phosphoramidite (RO)2PNR2 is a monoamide of a phosphite diester. The key feature of phosphoramidites is their markedly high reactivity towards nucleophiles catalyzed by weak acids e.c., triethylammonium chloride or 1H-tetrazole. In these reactions, the incoming nucleophile replaces the NR2 moiety.

Naloxol is an opioid antagonist closely related to naloxone. It exists in two isomeric forms, α-naloxol and β-naloxol.

2-Methyl-6-nitrobenzoic anhydride chemical compound

2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent, having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina. The compound is often abbreviated MNBA.

Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH3)3COC(O)]2NH. It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides. It was popularized as an alternative to the Gabriel synthesis for the same conversion. Amines can also be prepared from alcohols by dehydration using the Mitsunobu reaction.

References

  1. 1 2 Tetsuto Tsunoda, Hiroto Kaku, N,N,N,N-Tetramethylazodicarboxamide, in Encyclopedia of Reagents for Organic Synthesis, 2003, John Wiley & Sons, Ltd, doi:10.1002/047084289X.rn00274
  2. CID 4278 from PubChem

Further reading

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In computing, a Digital Object Identifier or DOI is a persistent identifier or handle used to uniquely identify objects, standardized by the International Organization for Standardization (ISO). An implementation of the Handle System, DOIs are in wide use mainly to identify academic, professional, and government information, such as journal articles, research reports and data sets, and official publications though they also have been used to identify other types of information resources, such as commercial videos.