622-79-7 Usage
Description
BENZYL AZIDE is an aromatic azide compound, which is generally utilized in copper(I)-catalyzed azide-alkyne cycloaddition reactions. It is known for its ability to introduce a PhCH2N group into a molecule, making it a valuable reagent in chemical synthesis.
Uses
Used in Chemical Synthesis:
BENZYL AZIDE is used as a reagent for the synthesis of stable 1,2,3-triazole derivatives. It plays a crucial role in introducing a PhCH2N group into a molecule, which is essential for the formation of these derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZYL AZIDE is used as a key intermediate in the synthesis of various biologically active compounds. Its ability to form stable 1,2,3-triazole derivatives makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Material Science:
BENZYL AZIDE is also employed in the field of material science, where it is used to synthesize novel materials with unique properties. The introduction of the PhCH2N group into a molecule can lead to the development of new materials with enhanced characteristics, such as improved stability or reactivity.
Synthesis Reference(s)
Tetrahedron Letters, 16, p. 471, 1975 DOI: 10.1016/S0040-4039(00)71896-XJournal of the American Chemical Society, 91, p. 4323, 1969 DOI: 10.1021/ja01043a071
Safety Profile
A heat-sensitive explosive.Explosive reaction with bis(trifluoromethyl)nitroxide.Upon decomposition it emits toxic fumes of NOx. Seealso AZIDES.
Synthesis
Sodium azide (3.58 g, 55.0 mmol) was added to DMSO (120 mL) and stirred
vigorously until fully dissolved. Benzyl bromide 168 (6.54 mL, 55 mmol)
was added. The reaction mixture was stirred at RT overnight. The
colourless liquid was worked up with water (100 mL), and extracted with
diethyl ether (3 x 100 mL). The extractions were washed with water (2 x
80 mL) and brine (80 mL). The ether layer was dried over MgSO4 and after
filtration, it was evaporated to dryness, giving benzyl azide 73 as a
colourless oil (6.9 g, 51.8 mmol, 94%): IR (neat) νm a x / cm– 1 3455, 3028,
2970, 2946, 2093, 1605, 1586, 1496, 1454, 1349, 1252; 1H NMR (400 MHz,
CDCl 3 ) δ 7.44 – 7.28 (m, 5H), 4.33 (s, 2H); 1 3C NMR (100 MHz, CDCl 3 ) δ
135.55, 129.05, 128.52, 128.44, 55.00.
Check Digit Verification of cas no
The CAS Registry Mumber 622-79-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 2 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 622-79:
(5*6)+(4*2)+(3*2)+(2*7)+(1*9)=67
67 % 10 = 7
So 622-79-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N3/c8-10-9-6-7-4-2-1-3-5-7/h1-5,8H,6H2/q+1
622-79-7Relevant articles and documents
Mutagenicity of alkyl azides
Matsumura,Shiozawa,Matsushita,Terao
, p. 1805 - 1807 (1995)
Alkyl azides showed mutagenicity for S. typhimurium TA100 strain with S9 mix. However, no significant activity was observed for TA98 either with or without S9 mix or for TA100 without S9 mix. On the other hand, 3-azido-1,2- propanediol showed the enantios
Combinatorial synthesis of new fluorescent scaffolds using click chemistry
Cleemann, Felix,Karuso, Peter,Kum-Cheung, Wendy Loa
supporting information, (2021/12/08)
Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.
Alkylphosphinites as Synthons for Stabilized Carbocations
Ochmann, Lukas,Kessler, Mika L.,Schreiner, Peter R.
supporting information, p. 1460 - 1464 (2022/03/01)
We present a new acid-free method for the generation of carbocations based on a redox condensation reaction that enables SN1 reactions with a variety of nucleophiles. We utilize readily synthesized phosphinites that are activated by diisopropyl azodicarboxylate to form betaine structures that collapse upon adding a pronucleophile, thereby yielding reactive carbocation intermediates. We also employ this approach for the alkylation of some bioactive molecules.
NOVEL DIBENZOOXAPHOSPHININE OXIDE DERIVATIVE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE DISEASE COMPRISING THE SAME AS AN ACTIVE INGREDIENT
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Paragraph 0113-0116, (2021/03/23)
The present invention relates to a novel dibenzooxininin oxide derivative compound having various nitrogen-containing substituents introduced at 6-position of a dibenzooxaphosphorin oxide mononuclear, and to the use thereof. The present invention relates to a pharmaceutical composition for preventing or treating degenerative diseases and a health supplement food composition for preventing or treating degenerative diseases, comprising the dibenzooxaphosphorin oxide derivative compound of the present invention.