Skip to Content
Merck
All Photos(2)

Documents

440914

Sigma-Aldrich

2,2′-Azobis(2-methylpropionamidine) dihydrochloride

powder or granules, 97%

Synonym(s):

α,α′-Azodiisobutyramidine dihydrochloride, AAPH

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
[=NC(CH3)2C(=NH)NH2]2·2HCl
CAS Number:
2997-92-4
Molecular Weight:
271.19
Beilstein:
3718854
EC Number:
221-070-0
MDL number:
MFCD00142725
UNSPSC Code:
12162002
PubChem Substance ID:
24867630
NACRES:
NA.23

Assay

97%

form

powder or granules

t1/2

10 hr(56 °C)

mp

175-177 °C (lit.)

solubility

acetone, dioxane, methanol, ethanol, DMSO and water: soluble

SMILES string

Cl.Cl.CC(C)(\N=N\C(C)(C)C(N)=N)C(N)=N

InChI

1S/C8H18N6.2ClH/c1-7(2,5(9)10)13-14-8(3,4)6(11)12;;/h1-4H3,(H3,9,10)(H3,11,12);2*1H/b14-13+;;

InChI key

LXEKPEMOWBOYRF-QDBORUFSSA-N

Related Categories

Application

Free radical initiator.
Polymerization initiator for acrylic, vinyl and allyl monomers.

Features and Benefits

Undergoes first order decomposition to a cationic radical. Decomposes on exposure to UV. Compatible with cationic surfactants. Decomposition rate is pH dependent

Signal Word

Danger

Hazard Statements

H251,H302,H317,H319,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Self-heat. 1 - Skin Sens. 1

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Olivier Mozziconacci et al.
Chemical research in toxicology, 25(9), 1842-1861 (2012-06-21)
Glutathione thiyl radicals (GS(•)) were generated in H(2)O and D(2)O by either exposure of GSH to AAPH, photoirradiation of GSH in the presence of acetone, or photoirradiation of GSSG. Detailed interpretation of the fragmentation pathways of deuterated GSH and GSH
Rong-Rong He et al.
PloS one, 8(3), e57732-e57732 (2013-03-08)
It is now well established that the developing embryo is very sensitive to oxidative stress, which is a contributing factor to pregnancy-related disorders. However, little is known about the effects of reactive oxygen species (ROS) on the embryonic cardiovascular system
A Nakajima et al.
Analytical and bioanalytical chemistry, 403(7), 1961-1970 (2012-05-01)
The characteristics of the spin-trapping reaction in the oxygen radical absorbance capacity (ORAC)-electron spin resonance (ESR) assay were examined, focusing on the kind of spin traps. 2,2-Azobis(2-amidinopropane) dihydrochloride (AAPH) was used as a free radical initiator. The spin adducts of
Ju-Young Ko et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 52, 113-120 (2012-11-14)
We investigated the effects of bioactive-peptides from hydrolysates of flounder fish muscle (FFM) on antioxidant activity. The hydrolysates were prepared by enzymatic reactions of FFM using eight commercial proteases such as papain, pepsin, trypsin, neutrase, alcalase, kojizyme, protamex, and α-chymotrypsin.
Chuan Xiao et al.
European journal of medicinal chemistry, 53, 159-167 (2012-04-24)
A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+•) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c
View All Related Papers

Articles

A Micro Review of Reversible Addition/Fragmentation Chain Transfer (RAFT) Polymerization

We presents an article about a micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization. RAFT (Reversible Addition/Fragmentation Chain Transfer) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteristics to radical polymerization.

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands

We presents an article about Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands, and the emergence of living radical polymerization mediated by transition metal catalysts in 1995, which was a seminal piece of work in the field of synthetic polymer chemistry.

Protocols

Concepts and Tools for RAFT Polymerization

Sigma-Aldrich presents an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

Typical Procedures for Polymerizing via RAFT

We presents an article featuring procedures that describe polymerization of methyl methacrylate and vinyl acetate homopolymers and a block copolymer as performed by researchers at CSIRO.

Typical Procedures for Polymerizing via ATRP

Sigma-Aldrich presents an article about the typical procedures for polymerizing via ATRP, which demonstrates that in the following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′s research group at the University of Warwick.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service