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2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE is a chemical compound characterized by its molecular formula C6H10N2O2. It is a highly reactive substance with potential hazardous properties, particularly due to its azide functional group. 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE is utilized in organic synthesis and pharmaceutical research, where its reactivity is harnessed for click chemistry, a method for efficiently linking molecules together. Given its potential explosive nature, careful handling is imperative for researchers working with this compound. It also holds promise for the development of innovative pharmaceuticals and materials.

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  • 85820-82-2 Structure
  • Basic information

    1. Product Name: 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE
    2. Synonyms: 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE
    3. CAS NO:85820-82-2
    4. Molecular Formula: C6H11N3O2
    5. Molecular Weight: 157.17
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 85820-82-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE(85820-82-2)
    11. EPA Substance Registry System: 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE(85820-82-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 85820-82-2(Hazardous Substances Data)

85820-82-2 Usage

Uses

Used in Organic Synthesis:
2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE is used as a reactive intermediate for the synthesis of complex organic molecules. Its azide group facilitates click chemistry reactions, allowing for the efficient and selective formation of new molecular structures.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE is used as a key building block in the development of new drugs. Its reactivity enables the creation of novel molecular entities with potential therapeutic applications.
Used in Click Chemistry:
2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE is employed as a reactant in click chemistry processes, which are characterized by their high yield, selectivity, and compatibility with a wide range of functional groups. This makes it a valuable tool for the rapid assembly of complex molecules and the modification of existing compounds.
Used in Material Science:
2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE also finds applications in material science, where its unique reactivity can be leveraged to create new materials with specific properties. These materials could have uses in various fields, including electronics, coatings, and advanced composites.

Check Digit Verification of cas no

The CAS Registry Mumber 85820-82-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,8,2 and 0 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 85820-82:
(7*8)+(6*5)+(5*8)+(4*2)+(3*0)+(2*8)+(1*2)=152
152 % 10 = 2
So 85820-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H11N3O2/c1-6(2)10-4-5(11-6)3-8-9-7/h5H,3-4H2,1-2H3/t5-/m0/s1

85820-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2-DIMETHYL-4(S)-4-AZIDOMETHYL-1,3-DIOXALANE

1.2 Other means of identification

Product number -
Other names 2-(1-benzylpyrrolidin-2-yl)-propan-2-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:85820-82-2 SDS

85820-82-2Relevant articles and documents

Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

Martins, Rafaela de S.,Pereira, Mathias P.,de Castro, Pedro P.,Bombonato, Fernanda I.

, (2019/12/24)

The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.

Synthesis and cytotoxicity evaluation of aryl triazolic derivatives and their hydroxymethine homologues against B16 melanoma cell line

Kalhor-Monfared, Shiva,Beauvineau, Claire,Scherman, Daniel,Girard, Christian

supporting information, p. 436 - 441 (2016/07/15)

In this manuscript we describe synthesis and cytotoxicity evaluation of some triazolic derivatives against B16 melanoma cell line. For this purpose, we transformed a set of aromatic aldehydes into terminal alkynes, using Besthmann-Ohira reagent, and we made the corresponding hydroxymethyl homologated alkynes by an acetylene Grignard reagent. These generated two sets of alkynes were then subjected to a copper(I)-catalyzed alkyne-azide cycloaddition reaction (CuAAC) using a solid-supported catalyst (Amberlyst A-21?CuI), with a third set composed of organic azides. Synthesized triazoles were then tested in?vitro against B16 melanoma cell line. Amongst them, compounds a1b1 (R1?=?p-nitrophenyl, R2?=?benzyl), a4b1 (R1?=?naphthyl, R2?=?benzyl) and a4b5 (R1?=?naphthyl, R2?=?(R/S)- dioxolane) showed the best activity against B16 melanoma cells, with IC50of 5.12, 3.89 and 6.60?μM respectively.

Synthesis of phosphonoglycine backbone units for the development of phosphono peptide nucleic acids

Doboszewski, Bogdan,Groaz, Elisabetta,Herdewijn, Piet

, p. 4804 - 4815 (2013/08/23)

A series of phosphono-modified backbone mimics based on achiral and chiral N-(dihydroxypropyl)glycine units were obtained by sequential addition of phosphonate and nucleobase moieties to suitably protected dihydroxypropylamines. Simple synthetic strategies enabled the preparation of various target derivatives that will be useful as building blocks for the preparation of new synthetic polymers containing a phosphonate internucleotide linkage in place of the standard phosphodiester bond. Copyright

Synthesis of β-hydroxyphosphonate and 1,2-dihydroxy acyclic nucleoside analogs via 1,3-dipolar cycloaddition strategy

Ganesan,Muraleedharan

, p. 91 - 96 (2011/08/02)

A convenient synthetic approach toward nucleoside analogs where β-hydroxyphosphonate- or 1,2-dihydroxy units are connected to the nucleic acid base through a triazole spacer is discussed.

Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition 'click-chemistry' in water

Kumar, Indresh,Rana, Sravendra,Cho, Jae Whan,Rode, Chandrashekhar V.

scheme or table, p. 352 - 355 (2010/06/16)

The synthesis of a new class of hybrid 1,2,3-triazozlo-δ-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition 'click-chemistry' reaction of various organic azides with an activated alkyne in water, followed by cyclization.

COMPOUNDS AND METHODS FOR TREATING TOLL-LIKE RECEPTOR 2-RELATED DISEASES AND CONDITIONS

-

Page/Page column 78, (2008/06/13)

The present invention relates to compounds and methods useful in the prevention or treatment of diseases or conditions associated with Toll-like receptor 2 activation.

Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

Lépine, Renaud,Carbonnelle, Anny-Claude,Zhu, Jieping

, p. 1455 - 1458 (2007/10/03)

Synthesis of orthogonally protected (2S, 4R)- and (2S, 4S)-4-hydroxyornithine was reported featuring an asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester (6) by (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine (7). Double stereoselection was examined using chiral ammonium salts as phase transfer catalysts and a substrate-directed chiral induction is documented.

Design, Synthesis, and Evaluation of Phospholipid Analogues as Inhibitors of the Bacterial Phospholipase C from Bacillus cereus

Martin, Stephen F.,Wong, Yue-Ling,Wagman, Allan S.

, p. 4821 - 4831 (2007/10/02)

Enzymes belonging to the phospholipase C (PLC) family hydrolyze the phosphodiester bond of phospholipids to give a diacylglycerol and a phosphorylated head group.The bacterial phospholipase C from Bacillus cereus (PLCBc) has been studied extensively, and there is a wealth of information regarding those structural features that are important for substrate activity.In contrast, there is virtually no data available regarding structure-activity relationships for inhibitors of this enzyme.To address this shortcoming, a series of optically pure analogues of 1,2-dihexanoyl-sn-glycero-3-phosphocholine (2) containing different replacements of the phosphate group were first synthesized including the phosphoramidates 4 and 8, the phosphonate 5, the (difluoromethylene)phosphonate 6, the thiophosphate 7, the diastereomeric phosphorothioates 9 and 10, and the phosphorodithioate 11.Each of these phosphatidylcholine derivatives was tested for inhibitor or substrate activity with PLCBc using the water-soluble phosphatidylcholine 2 as the monomeric substrate.The measurements were conducted below the critical micellar concentrations of both 2 and the inhibitor.Of the analogues, only 7 and 9 underwent observable enzymatic hydrolysis under the assay conditions used.The kcat of the (Sp)-phosphorothioate 9 was approximately one-fifth that of 2, and when compared to 2, 7 was hydrolyzed only very slowly by the enzyme.Kinetic studies indicated that the phospholipid analogues tested were competitive inhibitors with increasing Ki's as follows: 7 ca. 11 ca. 10 4 ca. 8 5 ca. 6.

The Synthesis of Biphenomycin B

Schmidt, Ulrich,Meyer, Regina,Leitenberger, Volker,Lieberknecht, Albrecht,Griesser, Helmut

, p. 275 - 277 (2007/10/02)

Biphenomycin B, a highly potent antibiotic against Gram-negative, β-lactam-resistant bacteria, which was previously isolated from culture filtrates of Streptomyces griseorubiginosus No. 43708, has now been synthesized.

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