6-azidohexanoic Acid

Base Information

• Chemical Name: 6-azidohexanoic Acid
• CAS No.: 79598-53-1
• Molecular Formula: C6H11N3O2
• Molecular Weight: 157.172
• Hs Code.: 29270000
• European Community (EC) Number: 633-038-7
• DSSTox Substance ID: DTXSID90452913
• Nikkaji Number: J1.303.575J
• Wikidata: Q72444583
• Mol file: 79598-53-1.mol

Synonyms:6-azidohexanoic Acid;79598-53-1;6-azido-hexanoic acid;epsilon-Azidocaproic acid;Hexanoic acid, 6-azido-;MFCD12406156;6-Azido- hexanoic acid;6-Azidohexanoicacid;-Azidocaproic acid;LCZC427;6-Azidohexanoic acid, >=95%;SCHEMBL13913078;DTXSID90452913;JCORXJUUSVCJEP-UHFFFAOYSA-N;AMY21582;AKOS024438820;AT15139;CS-7003;BP-25446;PD018365;SY031646;CS-0181306;FT-0685276;EN300-7061900;A897884

Chemical Property of 6-azidohexanoic Acid

Chemical Property:

• Density: 1.074 g/mL
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 157.085126602
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-AzidohexanoicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)O)CCN=[N+]=[N-]
• Description: 6-Azido-hexanoic acid is a linker containing an azide group and a terminal carboxylic acid. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.
• Uses: 6-Azidohexanoic acid is a six-carbon saturated fatty acid with an ω-terminal azide group. This building block can be reacted with primary amine groups in the presence of activators (e.g. EDC, or DCC), forming a stable amide bond. The terminal azide group allows conjugation with compounds containing alkyne groups through a copper(I)-catalyzed cycloaddition reaction, also known as click chemistry. 6-Azidohexanoic acid is useful for crosslinking, synthesis of chemical probes, and other bioconjugation strategies.

Technology Process of 6-azidohexanoic Acid

There total 2 articles about 6-azidohexanoic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

6-chlorohexanoic acid (4224-62-8) → 6-azidohexanoic acid (79598-53-1) + 4-azido-1-butylacetate (172468-38-1)

Guidance literature:

With sodium azide; In water; N,N-dimethyl-formamide;

Reference yield: 75.0%

C8H13N3O3 → 6-azidohexanoic acid (79598-53-1) + acetic acid (64-19-7,77671-22-8)

Guidance literature:

With ammonium hydroxide;

DOI:10.1016/S0040-4039(00)95723-X

Reference yield: 100.0%

6-azidohexanoic acid (79598-53-1) + diphenylphosphaneylmethanethiol borane complex (613688-05-4) → N3(CH2)5C(O)SCH2P(C6H5)2BH3 (613688-06-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.200351930

upstream raw materials:

6-chlorohexanoic acid

Downstream raw materials:

6-aminohexanoic acid

6-Azido-hexanethioic acid S-phenyl ester

N₃(CH₂)5C(O)SCH₂P(C₆H₅)2BH₃

6-azidohexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Refernces

• 1、 Garcia, Jordi,Vilarrasa, Jaume. "NEW SYNTHETIC "TRICKS". FROM ALIPHATIC AMINES AND AMIDES TO AZIDES AND/OR HOW TO CONVERT RNHCOR' INTO RNHCOR" AVOIDING DRASTIC HYDROLYSES". . p. 341 - 342. Retrieved 2007/10/02.