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N-(Diphenylmethylene)glycerine tert-butyl ester is an organic compound that serves as a valuable intermediate in various chemical reactions and applications. It is characterized by its diphenylmethylene group attached to a glycerine backbone with a tert-butyl ester functional group, which contributes to its unique chemical properties and reactivity.

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  • 81477-94-3 Structure
  • Basic information

    1. Product Name: N-(Diphenylmethylene)glycerine tert-butyl ester
    2. Synonyms: N-(Diphenylmethylene)glycine tert-butyl ester;N-(DIPHENYLMETHYLENE)GLYCINE TERT-BUTYL ESTER;N-(DIPHENYLMETHYLENE)GLYCERINE TERT-BUTYL ESTER;(N,N-DIPHENYLMETHYLENE)GLYCINE ETHYL ESTER;DIPHENYLMETHYLENE GLYCINE TERT-BUTYL ESTER;N-(DIPHENYLMETHYLENE)GLYCINE TERT- &;N-(Diphenylmethylene)glycine;DIPHENYLMETHYLENE-GLYCINE BUTYL ESTER
    3. CAS NO:81477-94-3
    4. Molecular Formula: C19H21NO2
    5. Molecular Weight: 295.38
    6. EINECS: 1533716-785-6
    7. Product Categories: Amino Acids 13C, 2H, 15N;Glycine Equivalents;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Amino Acids & Derivatives
    8. Mol File: 81477-94-3.mol
  • Chemical Properties

    1. Melting Point: 51-53 °C(lit.)
    2. Boiling Point: 377.5 °C at 760 mmHg
    3. Flash Point: 134.5 °C
    4. Appearance: white solid
    5. Density: 1 g/cm3
    6. Vapor Pressure: 6.7E-06mmHg at 25°C
    7. Refractive Index: 1.529
    8. Storage Temp.: 2-8°C
    9. Solubility: Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 2.31±0.50(Predicted)
    11. Water Solubility: Insoluble in water.
    12. Stability: Moisture Sensitive
    13. CAS DataBase Reference: N-(Diphenylmethylene)glycerine tert-butyl ester(CAS DataBase Reference)
    14. NIST Chemistry Reference: N-(Diphenylmethylene)glycerine tert-butyl ester(81477-94-3)
    15. EPA Substance Registry System: N-(Diphenylmethylene)glycerine tert-butyl ester(81477-94-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. F: 10-21
    7. TSCA: No
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 81477-94-3(Hazardous Substances Data)

81477-94-3 Usage

Uses

Used in Suzuki Reaction:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as a reactant in the Suzuki reaction, a widely employed cross-coupling process in organic synthesis. This reaction allows for the formation of carbon-carbon bonds between an organoboron compound and an organic halide or triflate, facilitated by a palladium catalyst. The use of N-(Diphenylmethylene)glycerine tert-butyl ester in this reaction enables the synthesis of various complex organic molecules with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Organic Synthesis:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as an intermediate in organic synthesis for the preparation of a range of compounds. Its unique structure allows for further functionalization and modification, making it a versatile building block for the synthesis of target molecules with specific properties and applications.
Used in Pharmaceuticals:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as a key intermediate in the synthesis of pharmaceutical compounds. Its reactivity and structural features make it suitable for the development of new drugs with potential therapeutic applications.
Used in Agrochemicals:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as a starting material in the production of agrochemicals, such as pesticides and herbicides. Its involvement in the synthesis of these compounds contributes to the development of effective solutions for crop protection and management.
Used in Dye Industry:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as a dye in the dye industry. Its unique chromophoric properties make it suitable for the development of dyes with specific color characteristics and applications in various industries, such as textiles, plastics, and printing.
Used in Biological Research:
N-(Diphenylmethylene)glycerine tert-butyl ester is used as a dye for biological research purposes. Its ability to bind and stain specific biological structures makes it a valuable tool for researchers in the study of cellular and molecular processes.

Check Digit Verification of cas no

The CAS Registry Mumber 81477-94-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,4,7 and 7 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 81477-94:
(7*8)+(6*1)+(5*4)+(4*7)+(3*7)+(2*9)+(1*4)=153
153 % 10 = 3
So 81477-94-3 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO2/c1-19(2,3)22-17(21)14-20-18(15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-13H,14H2,1-3H3

81477-94-3 Well-known Company Product Price

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  • Alfa Aesar

  • (H32709)  N-(Diphenylmethylene)glycine tert-butyl ester, 99%   

  • 81477-94-3

  • 1g

  • 443.0CNY

  • Detail
  • Alfa Aesar

  • (H32709)  N-(Diphenylmethylene)glycine tert-butyl ester, 99%   

  • 81477-94-3

  • 5g

  • 1478.0CNY

  • Detail

81477-94-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(Diphenylmethylene)glycerine tert-butyl ester

1.2 Other means of identification

Product number -
Other names tert-butyl 2-(benzhydrylideneamino)acetate

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:81477-94-3 SDS

81477-94-3Relevant articles and documents

Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis

Fanelli, Roberto,Salah, Khoubaib Ben Haj,Inguimbert, Nicolas,Didierjean, Claude,Martinez, Jean,Cavelier, Florine

, p. 4498 - 4501 (2015)

A concise synthetic pathway yielding to hydrophobic α,α-disubstituted disilylated amino acids based on a hydrosilylation reaction is described. As a first example of utilization in solid-phase peptide synthesis, TESDpg was introduced in replacement of Aib in an alamethicin sequence, leading to analogues with modified physicochemical properties and conserved helical structures. This study highlights the potential of these new amino acids as tools for peptide modulation.

Preparation method of benzophenone imine glycine ester

-

Paragraph 0024-0026; 0043-0045, (2021/06/09)

The invention relates to a preparation method of benzophenone imine glycine ester, and belongs to the technical field of chemical organic synthesis. The preparation method comprises the following step: by taking benzophenone imine as an initial raw material, reacting benzophenone imine with halogenated acetate in the presence of alkali to obtain benzophenone imine glycine ester. The structure of the halogenated acetate is shown as a formula 3 in the specification, wherein X is chlorine or bromine, and R is methyl, ethyl, isopropyl or tertiary butyl. By starting from simple and easily available raw materials, the invention provides a simple and convenient method for synthesizing benzophenone imine glycine ester.

Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines

Hirazawa, Yoshinobu,Kadota, Tetsuya,Kondo, Yuta,Morimoto, Hiroyuki,Morisaki, Kazuhiro,Ohshima, Takashi

supporting information, p. 120 - 125 (2020/02/20)

N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis of N-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the corresponding N-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation of N-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.

Methylation of geometrically constrained lysine analogues by histone lysine methyltransferases

Al Temimi, Abbas H. K.,White, Paul B.,Mulders, Marcus J. M.,Van Der Linden, Nicole G. A.,Blaauw, Richard H.,Wegert, Anita,Rutjes, Floris P. J. T.,Mecinovi?, Jasmin

supporting information, p. 3039 - 3042 (2020/03/18)

We report synthesis and enzymatic assays on human histone lysine methyltransferase catalysed methylation of histones that possess lysine and its geometrically constrained analogues containing rigid (E)-alkene (KE), (Z)-alkene (KZ) and alkyne (Kyne) moieties. Methyltransferases G9a and GLP do have a capacity to catalyse methylation in the order K ? KE > KZ ~ Kyne, whereas monomethyltransferase SETD8 catalyses only methylation of K and KE,.

Enantio- and Diastereoselective Synthesis of β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones

Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng

supporting information, (2019/02/07)

A fully stereoselective synthesis of unnatural chiral β-aryl-β-pyrazolyl α-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded β-1H-pyrazol-5-ol-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

Enantio- And diastereoselective synthesis of b-Aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed reaction of azomethine ylides with benzylidenepyrazolones

Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng

supporting information, p. 1389 - 1393 (2019/10/28)

A fully stereoselective synthesis of unnatural chiral b-aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded b-1H-pyrazol-5-ol-a-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor

Meng, Kaicheng,Shim, Paul,Wang, Qingtin,Zhao, Shuai,Gu, Ting,Kahsai, Alem W.,Ahn, Seungkirl,Chen, Xin

, p. 2320 - 2330 (2018/03/29)

The β2-adrenergic receptor (β2AR), a G protein-coupled receptor, is an important therapeutic target. We recently described Cmpd-15, the first small molecule negative allosteric modulator (NAM) for the β2AR. Herein we report in details the design, synthesis and structure-activity relationships (SAR) of seven Cmpd-15 derivatives. Furthermore, we provide in a dose-response paradigm, the details of the effects of these derivatives in modulating agonist-induced β2AR activities (G-protein-mediated cAMP production and β-arrestin recruitment to the receptor) as well as the binding affinity of an orthosteric agonist in radio-ligand competition binding assay. Our results show that some modifications, including removal of the formamide group in the para-formamido phenylalanine region and bromine in the meta-bromobenzyl methylbenzamide region caused dramatic reduction in the functional activity of Cmpd-15. These SAR results provide valuable insights into the mechanism of action of the NAM Cmpd-15 as well as the basis for future development of more potent and selective modulators for the β2AR based on the chemical scaffold of Cmpd-15.

Expedient Synthesis of Fmoc-(S)-γ-Fluoroleucine and Late-Stage Fluorination of Peptides

Fanelli, Roberto,Martinez, Jean,Cavelier, Florine

, p. 1403 - 1407 (2016/05/24)

A concise synthesis of (S)-γ-fluoroleucine is described in five steps from commercially available compounds, with an overall yield of 57%. The Markovnikov hydrofluorination reaction of the unsaturated amino acid precursor as last step of the synthesis pro

Effect of α-Methyl versus α-Hydrogen Substitution on Brain Availability and Tumor Imaging Properties of Heptanoic [F-18]Fluoroalkyl Amino Acids for Positron Emission Tomography (PET)

Bouhlel, Ahlem,Alyami, Wadha,Li, Aixiao,Yuan, Liya,Rich, Keith,McConathy, Jonathan

, p. 3515 - 3531 (2016/05/19)

Two [18F]fluoroalkyl substituted amino acids differing only by the presence or absence of a methyl group on the α-carbon, (S)-2-amino-7-[18F]fluoro-2-methylheptanoic acid ((S)-[18F]FAMHep, (S)-[18F]14) and (S)-2-amino-7-[18F]fluoroheptanoic acid ((S)-[18F]FAHep, (S)-[18F]15), were developed for brain tumor imaging and compared to the well-established system L amino acid tracer, O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET), in the delayed brain tumor (DBT) mouse model of high-grade glioma. Cell uptake, biodistribution, and PET/CT imaging studies showed differences in amino acid transport of these tracer by DBT cells. Recognition of (S)-[18F]15 but not (S)-[18F]14 by system L amino acid transporters led to approximately 8-10-fold higher uptake of the α-hydrogen substituted analogue (S)-[18F]15 in normal brain. (S)-[18F]15 had imaging properties similar to those of (S)-[18F]FET in the DBT tumor model while (S)-[18F]14 afforded higher tumor to brain ratios due to much lower uptake by normal brain. These results have important implications for the future development of α-alkyl and α,α-dialkyl substituted amino acids for brain tumor imaging.

AZAINDOLINE COMPOUNDS AS GRANZYME B INHIBITORS

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Page/Page column 56, (2016/03/12)

Azaindoline compounds as granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. Methods for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are provided.

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