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Safety Information

I3750

Sigma-Aldrich

3-Indoleacetic acid

98%

Synonym(s):

Heteroauxin, IAA

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
87-51-4
Molecular Weight:
175.18
Beilstein:
143358
EC Number:
201-748-2
MDL number:
MFCD00005636
UNSPSC Code:
12352100
PubChem Substance ID:
24896043
NACRES:
NA.22

Assay

98%

mp

165-169 °C (lit.)

SMILES string

OC(=O)Cc1c[nH]c2ccccc12

InChI

1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)

InChI key

SEOVTRFCIGRIMH-UHFFFAOYSA-N

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General description

3-Indoleacetic acid (IAA) is a naturally occurring hydrophilic organic compound consists of an unsaturated aromatic ring that is commonly used in the synthesis of indolylated diarylmethanes, α-acetoxyl ketones, and Indolmethyl-Chromones via copper catalyzed coupling reactions.

Application

3-Indoleacetic acid (IAA) can be used as a building block to synthesize ,(±) harmacine using 4,4-diethoxybutan-1-amine via an acid-catalyzed acyl iminium ion cyclization reaction.
(±)-Harmacine is a vital step in the synthesis of a variety of indole alkaloids and dopamine/serotonin receptor ligands. IAA can also be used in the preparation of alkaloid (±)-19-hydroxyibogamine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

I3750-100G-A:
I3750-25G-A:
I3750-BULK-A:
I3750-5G-A:
I3750-VAR-A:

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’.

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