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TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER, also known as Boc-protected ethyl amino acetate, is an organic chemical compound that belongs to the carbamic acid and ester family. It is characterized by the presence of a carbonyl group (C=O) and an ester group (-COO-). TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER is a member of the protective reagents used in peptide synthesis, where it serves to protect the α-amino group of amino acids, preventing undesired side reactions. The protective group is removed after the intended reactions are complete, making it an essential tool in the fields of organic chemistry and biochemistry for efficient and precise peptide synthesis.

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  • 14719-37-0 Structure
  • Basic information

    1. Product Name: TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER
    2. Synonyms: N-Boc-glycine Ethyl Ester;Ethyl 2-(tert-butoxycarbonylaMino)acetate;Glycine, N-[(1,1-diMethylethoxy)carbonyl]-, ethyl ester;N-(tert-butoxycarbonyl)glycine ethyl ester;Ethyl [(tert-butoxycarbonyl)amino]acetate;EthylN-(tert-butoxycarbonyl)glycinate;2-(tert-butoxycarbonylamino)acetic acid ethyl ester;2-[(tert-butoxy-oxomethyl)amino]acetic acid ethyl ester
    3. CAS NO:14719-37-0
    4. Molecular Formula: C9H17NO4
    5. Molecular Weight: 203.24
    6. EINECS: 1533716-785-6
    7. Product Categories: N/A
    8. Mol File: 14719-37-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 97°C/0.7mmHg(lit.)
    3. Flash Point: 125.5oC
    4. Appearance: Colorless/Oily Liquid
    5. Density: 1.053g/cm3
    6. Vapor Pressure: 0.00306mmHg at 25°C
    7. Refractive Index: 1.4350 to 1.4390
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. PKA: 11.18±0.46(Predicted)
    11. CAS DataBase Reference: TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER(CAS DataBase Reference)
    12. NIST Chemistry Reference: TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER(14719-37-0)
    13. EPA Substance Registry System: TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER(14719-37-0)
  • 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: 14719-37-0(Hazardous Substances Data)

14719-37-0 Usage

Uses

Used in Organic Chemistry Research:
TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER is used as a protective reagent for [protecting the α-amino group of amino acids] in peptide synthesis for [preventing undesired side reactions].
Used in Biochemistry Research:
TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER is used as a protective reagent for [protecting the α-amino group of amino acids] in peptide synthesis for [ensuring efficient and precise synthesis of peptides].
Used in Pharmaceutical Industry:
TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER is used as a protective reagent for [protecting the α-amino group of amino acids] in the synthesis of bioactive peptides for [enhancing the stability and bioavailability of the final product].

Check Digit Verification of cas no

The CAS Registry Mumber 14719-37-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,1 and 9 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14719-37:
(7*1)+(6*4)+(5*7)+(4*1)+(3*9)+(2*3)+(1*7)=110
110 % 10 = 0
So 14719-37-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NO4/c1-5-13-7(11)6-10-8(12)14-9(2,3)4/h5-6H2,1-4H3,(H,10,12)

14719-37-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • TCI America

  • (B4782)  N-(tert-Butoxycarbonyl)glycine Ethyl Ester  >98.0%(GC)

  • 14719-37-0

  • 5g

  • 680.00CNY

  • Detail
  • TCI America

  • (B4782)  N-(tert-Butoxycarbonyl)glycine Ethyl Ester  >98.0%(GC)

  • 14719-37-0

  • 25g

  • 2,390.00CNY

  • Detail
  • Alfa Aesar

  • (H62611)  N-Boc-glycine ethyl ester, 95%   

  • 14719-37-0

  • 5g

  • 403.0CNY

  • Detail
  • Alfa Aesar

  • (H62611)  N-Boc-glycine ethyl ester, 95%   

  • 14719-37-0

  • 25g

  • 1613.0CNY

  • Detail

14719-37-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Boc-glycine Ethyl Ester

1.2 Other means of identification

Product number -
Other names Ethyl [(tert-butoxycarbonyl)amino]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:14719-37-0 SDS

14719-37-0Relevant articles and documents

Design and synthesis novel amide derivatives containing an 1,3,4-oxadiazole moiety as potential antibacterial agents

Chen, Jixiang,Chen, Yifang,Luo, Xin,Wang, Yu,Xing, Zhifu

supporting information, (2022/02/17)

To find new antibacterial agents, 25 novel amide derivatives containing an 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activity against Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas oryzae pv. oryzae (Xoo) were tested. Interestingly, all target compounds showed excellent antibacterial activities against Xoc and Xoo. The EC50 values of compounds 1–25 against Xoc and Xoo were 1.2–4.0?mg/L and 0.5–2.3?mg/L, respectively, which were significantly superior to those of the thiodiazole copper (95.1 and 89.0?mg/L) and bismerthhibol (73.8 and 68.8?mg/L). For example, the EC50 values of compound 16 against Xoc and Xoo were 1.7 and 0.5?mg/L, respectively. Meanwhile, the curative and protection activity of compound 16 against rice bacterial leaf blight were 42.4% and 42.1%, respectively, which were superior to the control of jiahuangxianjunzuo (34.1% and 32.6%) and thiodiazole copper (33.0% and 27.1%). In addition, compound 16 might suppress the cell growth of Xoo by inhibiting the production of extracellular polysaccharide, the formation of biofilm, changes the cell membrane permeability, and cell surface morphology.

ANTIBIOTICS EFFECTIVE FOR GRAM-NEGATIVE PATHOGENS

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Page/Page column 53; 54; 66; 69, (2019/10/04)

Disclosed herein are antibacterial compounds that accumulate in Gram-negative bacteria, methods of preparing the compounds, and methods of using the compounds to inhibit or kill microbes, and methods of treating microbial infections, such as Gram-negative

IONIZABLE CATIONIC LIPID FOR RNA DELIVERY

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Paragraph 0029; 0487-0491, (2018/07/04)

What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons; R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons; L1 and L2 are the same or different, each a linear alkylene of 1 to 20 carbons or a linear alkenylene of 2 to 20 carbons; X1 is S or O; R3 is a linear or branched alkylene consisting of 1 to 6 carbons; and R4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

IONIZABLE CATIONIC LIPID FOR RNA DELIVERY

-

Paragraph 0529; 0530; 0531; 0532; 0533, (2018/07/05)

What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons;R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons, or a branched chain alkyl consisting of 10 to 31 carbons;L1 and L2 are the same or different, each a linear alkane of 1 to 20 carbons or a linear alkene of 2 to 20 carbons;X1 is S or O;R3 is a linear or branched alkylene consisting of 1 to 6 carbons; andR4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

BICYCLIC AMINES AS NOVEL JAK KINASE INHIBITORS

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Page/Page column 42, (2018/08/12)

The present invention relates to a compound according to formula (I) wherein R1 represents alkyl; n is 1 or 2; R2 is selected from the group consisting of hydrogen, cyano, -SO2Ra, -SO2NRbR

New reagent for the introduction of Boc protecting group to amines: Boc-OASUD

Maheswara Rao, B. Leela,Nowshuddin, Shaik,Jha, Anjali,Divi, Murali K.,Rao

supporting information, p. 2127 - 2132 (2017/10/31)

A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.

Facile synthesis of hexahydropyrazino[2,3-e]pyrazines from 3-aminomethyl-1,2,4-triazoles

Khomenko, Dmytro M.,Doroschuk, Roman O.,Trachevskii, Vladimir V.,Shova, Sergiu,Lampeka, Rostyslav D.

, p. 990 - 992 (2016/02/18)

The cyclocondensation of aminomethyl-1,2,4-triazoles and glyoxal gives hexahydropyrazino[2,3-e]pyrazines in good yields. 1H and 13C NMR spectra of the title compounds are described and the molecular structure of 4a,5,6,10a,11,12-hexa

Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs

Howarth, Nicola M.,Ricci, Jennyfer

experimental part, p. 9588 - 9594 (2011/12/14)

Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment.

Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles

Woodard, Scott S.,Jerome, Kevin D.

experimental part, p. 132 - 137 (2012/04/18)

Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.

Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile

Zheng, Jianlong,Yin, Biaolin,Huang, Wenming,Li, Xiaopeng,Yao, Hequan,Liu, Zhaogui,Zhang, Jiancun,Jiang, Sheng

scheme or table, p. 5094 - 5097 (2009/12/01)

Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst.

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