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Organic compounds containing the azide (N3) functional group
An organic azide is an organic compound that contains an azide (–N3) functional group. Because of the hazards associated with their use, few azides are
Organic_azide
Anion and chemical group (–N3)
acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant
Azide
Chemical compound
Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide. Methyl azide can be prepared by
Methyl_azide
Chemical compound
Imidazole-1-sulfonyl azide is an organic azide compound that can be used as an alternative organic synthesis reagent to trifluoromethanesulfonyl azide. It is an
Imidazole-1-sulfonyl_azide
1,3-dipolar cycloaddition
The azide-alkyne Huisgen cycloaddition is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole. Rolf
Azide-alkyne Huisgen cycloaddition
Azide-alkyne_Huisgen_cycloaddition
Chemical compound
Diphenylphosphoryl azide (DPPA) is an organic compound. It is widely used as a reagent in the synthesis of other organic compounds. DPPA undergoes pseudohalogen
Diphenylphosphoryl_azide
Chemical compound
Phenyl azide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent
Phenyl_azide
Carboxylic acid derivative
Acyl azides are carboxylic acid derivatives with the general formula RCON3. These compounds, which are a subclass of organic azides, are generally colorless
Acyl_azide
Chemical compound
Trifluoromethanesulfonyl azide or triflyl azide CF3SO2N3 is an organic azide used as a reagent in organic synthesis. Trifluoromethanesulfonyl azide is prepared by
Trifluoromethanesulfonyl azide
Trifluoromethanesulfonyl_azide
Chemical compound
Trimethylsilyl azide is the organosilicon compound with the formula (CH3)3SiN3. A colorless liquid, it is a reagent in organic chemistry, serving as the
Trimethylsilyl_azide
Chemical compound used in organic synthesis
Tosyl azide (systematic name: 4-methylbenzenesulfonyl azide; abbreviation: TsN3) is an organic compound with the formula CH3C6H4SO2N3. It is a widely used
Tosyl_azide
Chemical compound
hazard, sodium azide is of only limited value in industrial-scale organic synthesis. In the laboratory, it is used to introduce the azide functional group
Sodium_azide
Chemical compound
n-Propyl azide is an organic compound with the formula CH3CH2CH2N3. A white solid, it is a simple organic azide. n-Propyl azide has been used in the laboratory
N-Propyl_azide
Chemical reaction
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered
Staudinger_reaction
Modular approach to chemical synthesis
Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides". Journal of Organic Chemistry. 67 (9): 3057–3064. doi:10.1021/jo011148j. PMID 11975567
Click_chemistry
Chemical compounds and groups containing nitrogen with a lone pair (:N)
In chemistry, amines (/əˈmiːn, ˈæmiːn/, UK also /ˈeɪmiːn/) are organic compounds that contain carbon–nitrogen bonds. Amines are formed when one or more
Amine
Chemical reaction between an azide and a carbonyl derivative
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or
Schmidt_reaction
Chemical compound
Cyanogen azide is a chemical compound with the chemical formula CN4, or more precisely −N=N+=N−C≡N. It is an azide compound of carbon and nitrogen. It
Cyanogen_azide
Chemical compound
azide (IN3) is an explosive inorganic compound, which in ordinary conditions is a yellow solid. Formally, it is an inter-pseudohalogen. Iodine azide can
Iodine_azide
Chemical compound
combines with azide ions. In organic chemistry, ferric azide is a reagent in the one-pot conversion of alkenes to alkyl azide, such as n-butyl azide. The process
Iron(III)_azide
Chemical reaction
Curtius, T. (1894). "20. Hydrazide und Azide organischer Säuren I. Abhandlung" [Hydrazides and azides of organic acids I. paper]. Journal für Praktische
Curtius_rearrangement
Chemical compound
Methanesulfonyl azide is the azide of methanesulfonic acid. It is used as a reagent for the production of diazo compounds. Methanesulfonyl azide can be prepared
Methanesulfonyl_azide
Chemical compound
(thereafter referred to as OND) display unusually high reactivity towards organic azides and thiols. OND–thiol adducts are prone to retro-Diels–Alder fragmentation
Oxanorbornadiene
Chemical compound
system and skin. Ethyl azide is used for organic synthesis. Campbell, H. C.; Rice, O. K. (1935). "The Explosion of Ethyl Azide". Journal of the American
Ethyl_azide
Chemical reaction
of Bergmann and his close colleague Leonidas Zervas, combining the organic azide degradation of the Curtius rearrangement with the Bergmann-Zervas carbobenzoxy
Bergmann_degradation
Unstable and toxic chemical compound
Hydrazoic acid, also known as hydrogen azide or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive liquid
Hydrazoic_acid
Chemical compound
iodine azide. Co2(CO)8 + 4IN3 → 2Co(N3)2 + 8CO + 2I2 Aqueous solutions of cobalt(II) azide change in color when introduced to suitable organic solvents
Cobalt(II)_azide
Pericyclic chemical reaction
used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole). 1,3-dipolar cycloaddition
1,3-Dipolar_cycloaddition
Chemical element with atomic number 7 (N)
names of many nitrogen compounds, such as hydrazine and compounds of the azide ion. Finally, it led to the name "pnictogens" for the group headed by nitrogen
Nitrogen
Chemical compound
a reagent in organic synthesis. Tributyltin azide is synthesized by the salt metathesis reaction of tributyltin chloride and sodium azide. It is a reagent
Tributyltin_azide
Covalent bond
Y.; Arai, M.; Tamura, M. (2001). "Azidoacetamide, a neutral small organic azide". Acta Crystallogr. E. 57: o6–o8. doi:10.1107/S160053680001850X. Livingston
Carbon–nitrogen_bond
Chemical process
Staudinger ligation with organic azides, copper-catalyzed Huisgen cycloaddition of azides, and strain promoted Huisgen cycloaddition of azides. Bioconjugation
Bioconjugation
Chemical compound
Fluorosulfonyl azide is an inorganic compound with the chemical formula FN3O2S. This is a derivative of sulfuric acid containing a fluorine atom and an azide group
Fluorosulfonyl_azide
Chemical compound
is an unnatural amino acid derivative of L-phenylalanine, featuring an azide group at the para position of the phenyl ring. It is a bioorthogonal click-chemistry
Azidophenylalanine
Topics referred to by the same term
N3− may refer to: N−3, an azide anion in chemistry N3−, a nitride anion in chemistry N3- an organic azide group This disambiguation page lists articles
N3−
German chemist, winner of the 1953 Nobel Prize in Chemistry (1881–1965)
discoveries came in 1919, when he and colleague Meyer reported that organic azides react with triphenylphosphine to form an iminophosphorane (Figure 2)
Hermann_Staudinger
Chemical compound
Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic solvents. It is believed that the ligand promotes catalysis
Tris(benzyltriazolylmethyl)amine
Tris(benzyltriazolylmethyl)amine
Chemical compound
4-Chlorophenyl azide is an organic aryl azide compound with the chemical formula C6H4ClN3. The geometry between the nitrogen atoms in the azide functional
4-Chlorophenyl_azide
Chemical compound
2,4,6-Triisopropylbenzenesulfonyl azide (trisyl azide) is an organic chemical used as a reagent to supply azide for electrophilic amination reactions
2,4,6-Triisopropylbenzenesulfonyl azide
2,4,6-Triisopropylbenzenesulfonyl_azide
Organic compound or functional group containing a C=N bond
Reaction of organic azides with metal carbenoids (produced from diazocarbonyl compounds). The reaction of iminophosphoranes and organic azides in an aza-Wittig
Imine
Chemical compound
[CH3(CH2)10]2CO. With sodium azide, it reacts to give undecyl isocyanate via a Curtius rearrangement of the acyl azide. "Lauroyl chloride". pubchem.ncbi
Lauroyl_chloride
Chemical group (>C=N=N)
of Azides into Diazo Compounds Eddie L. Myers and Ronald T. Raines Angew. Chem. Int. Ed. 2009, 48, 2359 –2363 doi:10.1002/anie.200804689 Organic Syntheses
Diazo
Chemical compound
formula CO(N3)2. In terms of its structure, it can be described as two azide groups −N3 covalently attached to the carbonyl group −C(=O)− by single bonds
Carbonyl_diazide
Device used in chemical laboratories
This can also occur when taking certain unstable compounds, such as organic azides and acetylides, nitro-containing compounds, molecules with strain energy
Rotary_evaporator
Chemical coupling reaction
generated in situ. In this manifestation, the phosphine, carbonyl, and organic azide are combined Besides preparing imines from aldehydes and ketones, the
Aza-Wittig_reaction
Agents that emit light after excitation by light
carboxyl groups (carbodiimide), thiol (maleimide, acetyl bromide), and organic azide (via click chemistry or non-specifically (glutaraldehyde)). Additionally
Fluorophore
Isomers of chemical compounds that interconvert
bullvalene, and in open and closed forms of certain heterocycles, such as organic azides and tetrazoles, or mesoionic münchnone and acylamino ketene. Valence
Tautomer
Chemical compound
1‑Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4‑Cyano-1,2,3-triazoles". J. Org. Chem. 83 (9): 5092–5103
1,2,3-Triazole
Chemical compound
Potassium azide is the inorganic compound having the formula KN3. It is a white, water-soluble salt. It is used as a reagent in the laboratory. It has
Potassium_azide
Chemical compound
Calcium azide is a chemical compound with the formula Ca(N3)2. It can be obtained from a distilled reaction between hydrazoic acid and calcium hydroxide
Calcium_azide
Chemical compound
Ammonium azide is the chemical compound with the formula [NH4]N3, being the salt of ammonia and hydrazoic acid. Like other inorganic azides, this colourless
Ammonium_azide
Transition metal azide complexes are coordination complexes containing one or more azide (N3−) ligands. In addition to coordination complexes, this article
Transition metal azide complex
Transition_metal_azide_complex
the conventional Staudinger reaction is not applicable, i.e. when the organic azide is not available to generate the iminophosphorane. Thus, it is used
Kirsanov_reaction
Chemical compound
Magnesium azide is an inorganic chemical compound with the formula Mg(N3)2. It is composed of the magnesium cation (Mg2+) and the azide anions (N−3).
Magnesium_azide
Organosilicon compound with the formula (CH3)3SiCl
"Trimethylsilyl azide". Organic Syntheses. 50: 107; Collected Volumes, vol. 6, p. 1030. Brook, Michael A. (2000). Silicon in Organic, Organometallic,
Trimethylsilyl_chloride
Chemical compound
an organic azide, which is prepared by reacting the chloride of the corresponding alkyl-amine (in this case dimethyl ethylamine) with sodium azide: NaN3
2-Dimethylaminoethylazide
Functional group which gives an organic molecule explosive properties
The azo and azide groups respectively, connected to organic/inorganic compounds (e.g. silver azide AgN3, lead azide Pb(N3)2, ammonium azide NH4N3) III
Explosophore
Organic compounds with the tautomeric structures RC(S)OH or RC(O)SH
Thiocarboxylic acids react with various nitrogen functional groups, such as organic azide, nitro, and isocyanate compounds, to give amides under mild conditions
Thiocarboxylic_acid
Form of chemical synthesis
acetate-catalyzed reaction between the aryldiazoacetate (red) and the organic azide (blue) to form an imine. A Wolff rearrangement of the diazoacetoacetate
Staudinger_synthesis
Chemical reaction
ketone. Diazo-transfer reactions are commonly used methods, in which an organic azide, usually tosylazide, and an activated methylene (i.e. a methylene with
Wolff_rearrangement
Chemical compound
azide is prepared by passing chlorine gas over silver azide, or by an addition of acetic acid to a solution of sodium hypochlorite and sodium azide.
Chlorine_azide
Chemical compound
octahedral, depending on the nature of the reactant azide. One such product of a reaction with an organic azide is a unique pseudo-square planar iridium(III)
Trimesityliridium
Main group azido compounds are chemical compounds consisting of azide, N3− bonded to a main group element. Azido compounds are often shock sensitive.
Main_group_azido_compounds
Chemical compound
reduction). Similarly, it converts amide, nitro, nitrile, imine, oxime, and organic azides into the amines (see: amide reduction). It reduces quaternary ammonium
Lithium_aluminium_hydride
Substance that can explode
Lead(II) azide, Silver azide, Sodium azide, Rubidium azide, Selenium tetraazide, Silicon tetraazide, Tellurium tetraazide, Titanium tetraazide Organic: Cyanuric
Explosive
Any chemical compound having at least one nitrogen atom
However, the alkali metal azides NaN3 and KN3, featuring the linear N− 3 anion, are well-known, as are Sr(N3)2 and Ba(N3)2. Azides of the B-subgroup metals
Nitrogen_compounds
Chemical reaction in which one entity is inserted between bonded parts of another
dimeric dioxane being the major product. Organic azides also provide an example of an insertion reaction in organic synthesis and, like the above examples
Insertion_reaction
Reaction in organic chemistry
attack on the iminium ion. Stieglitz rearrangements can also proceed on organic azides with molecular nitrogen as a good leaving group. Those reactions proceed
Stieglitz_rearrangement
Chemical compound
sodium azide. This compound is used for bioconjugation. The target, which contains a terminal alkyne functional group, is treated with the organic azide in
3-Azidocoumarin
German chemist
years, his work broadened to include azide chemistry. In 2005, he reviewed the synthetic utility of organic azides, underlining their central role in cycloaddition
Stefan_Bräse
Chemical compound
Analogue of Pyridine Obtained by Ring Expansion of a Borole with an Organic Azide". Angewandte Chemie International Edition. 58 (1): 338–342. doi:10.1002/anie
Borole
Chemical compound
Bromine azide is an explosive inorganic compound with the formula BrN3. It has been described as a crystal or a red liquid at room temperature.[citation
Bromine_azide
Organic compound with at least one covalent carbon–phosphorus bond
agents, as illustrated in the Staudinger reduction for the conversion of organic azides to amines and in the Mitsunobu reaction for converting alcohols into
Organophosphorus_chemistry
Substance which explodes when exposed to small amounts of energy
that will eventually set off the secondary explosive. Compounds like lead azide are used to manufacture bullets that explode into shrapnel on impact. Flash
Contact_explosive
Chemical compound
prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. "methyl phenyl acetate". scentsandflavors.com.
Methyl_phenylacetate
The organic synthesis of the tetrafluoroborate salt of 2-quinuclidone is a six-step affair starting from norcamphor the final step being an azide - ketone
Quinuclidone
Chemical reaction
Banert cascade is an organic reaction in which an NH-1,2,3-triazole is prepared from a propargyl halide or sulfate and sodium azide in a dioxane- water
Banert_cascade
Class of chemical compounds
also illustrated in the Staudinger reduction for the conversion of organic azides to amines and in the Mitsunobu reaction for converting alcohols into
Organophosphine
Functional group made of a carbon-carbon-nitrogen heterocycle
{Rh2(CO2R)4}}]}}} aziridine Alternatively, photolysis or thermolysis of organic azides are good ways to generate nitrenes. The same conditions also contract
Aziridines
Type of sugar molecule
This can be achieved using azides with subsequent reduction yielding the amino sugar. One advantage of introducing azide moiety at C-2 lies in its non-participatory
Amino_sugar
Particle, atom or molecule with a net electrical charge
contain at least one carbon to hydrogen bond are called organic ions. If the charge in an organic ion is formally centred on a carbon, it is termed a carbocation
Ion
Compounds with similar properties to polyatomic halogens
groups in organic molecules, such as the nitrile group. Well-known pseudohalogen functional groups include cyanide, cyanate, thiocyanate, and azide. The pseudohalogen
Pseudohalogen
Overview of and topical guide to organic chemistry
following outline is provided as an overview of and topical guide to organic chemistry: Organic chemistry is the scientific study of the structure, properties
Outline_of_organic_chemistry
Various meanings of the terms
disfavored. As a chemical example, tetrazine reacts with transcyclooctene and azide reacts with cyclooctyne without any cross-reaction, so these are mutually
Orthogonality
Chemical compound
Heidenreich, K. (1895-09-12). "Hydrazide und Azide organischer Säuren. XI Abhandlung. 36. Die Hydrazide und Azide der Kohlensäure". Journal für Praktische
Oxalyldihydrazide
Chemical compound
amines, phosphines and pyridines. Azo, diazo, azido, hydrazine and organic azide compounds. esters, sulfate esters, phosphate esters, thiophosphate esters
Triazofos
Chemical compound
CH2=C=CHMgBr. Propargyl bromide and its ether derivatives participate in azide-based click reactions. Propargyl bromide is a lachrymator and an alkylating
Propargyl_bromide
Chemical compound
RCH(I)–CH(Cl)R′ When such reactions are conducted in the presence of sodium azide, the iodo-azide RCH(I)–CH(N3)R′ is obtained. The Wijs solution, iodine monochloride
Iodine_monochloride
Chemical group (>S(=O)2)
Fluorosulfonyl azide Sulfonyl halide Sulfonamide Sulfonate Methylsulfonylmethane (MSM) Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry
Sulfonyl_group
Chemical compound
synthesized using [Cp*Al]4 as a precursor through oxidative addition of an organic azide. [Cp*Al] is able to act as an atypical exotic ligand in donor-acceptor
(Pentamethylcyclopentadienyl)aluminium(I)
(Pentamethylcyclopentadienyl)aluminium(I)
Class of chemical compounds
literature. Nontrigonal phosphorus compounds can also be oxidized by organic azide to yield phosphazenes. These sterically constrained phosphorus compounds
Nontrigonal pnictogen compounds
Nontrigonal_pnictogen_compounds
Organic compound containing at least one covalent carbon-chlorine bond
in the Finkelstein reaction. Reaction with other pseudohalides such as azide, cyanide, and thiocyanate are possible as well. In the presence of a strong
Organochlorine_chemistry
Chemical compound
needed] to prepare some silver-based explosives, such as the fulminate, azide, or acetylide, through a precipitation reaction. Silver(I) salts are mild
Silver_nitrate
Any molecule with a cyano group (C≡N)
may be covalently bonded to atoms other than carbon, e.g., in cyanogen azide N3−C≡N, phosphorus tricyanide P(−C≡N)3 and trimethylsilyl cyanide (CH3)3Si−C≡N
Cyanide
Chemical compound
copolymer can then be made to undergo a cycloaddition with functional organic azides in order to create 1,2,3-triazoles. This process falls under the category
Diethyl_acetamidomalonate
Base-labile protecting group
N-hydroxysuccinimide. Reacting with 9-fluorenylmethyloxycarbonyl azide (itself made by reacting Fmoc-Cl with sodium azide) in sodium bicarbonate and aqueous dioxane is also
Fluorenylmethyloxycarbonyl protecting group
Fluorenylmethyloxycarbonyl_protecting_group
Polymerization after alignment of monomers by crystallisation
crystals based on [3+2] Topochemical Azide-Alkyne Cycloaddition (TAAC) reaction and [3+2] topochemical ene-azide cycloaddition (TEAC) reaction. The monomers
Topochemical_polymerization
Class of organometallic complexes
industrially relevant feedstock CO, aziridation catalysts to synthesize organic azide pharmaceutical precursor molecules and epoxidation catalysts to convert
Cyclic iron tetra N-heterocyclic carbenes
Cyclic_iron_tetra_N-heterocyclic_carbenes
Chemical group (–SO2CF3)
(trifluoromethanesulfonate) has the formula R−OSO2CF3, and is represented by –OTf. Triflyl azide, TfN3 Trioctylmethylammonium bis(trifluoromethylsulfonyl)imide, [MeN(C 8H
Triflyl_group
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
Mitsunobu_reaction
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