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I3750

3-Indoleacetic acid

98%

Synonym(s):

Heteroauxin, IAA

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5 g

Available to ship TODAYfromMILWAUKEE

$31.90
25 g

Available to ship TODAYfromMILWAUKEE

$114.00
100 g

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$283.00

About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-748-2
Beilstein/REAXYS Number:
143358
MDL number:
Assay:
98%

$31.90


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Quality Level

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

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.[1]

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assay

98%

assay

≥98%

assay

98%

assay

≥98.5%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

mp

165-169 °C (lit.)

mp

165-169 °C (lit.)

mp

160-162 °C (lit.)

mp

165-169 °C (lit.)


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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2



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Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Sulfoxonium Ylides for the Synthesis of alpha-Acetoxyl Ketones
Qiwen G, et al.
Organic Letters, 26, 5940-5945 (2024)
Microwave-assisted copper catalyzed decarboxylative reductive coupling of para-quinone methides with 3-indoleacetic acids: rapid access to polycyclic spiroindolequinone derivatives
Gui-Ting S, et al.
Inorganic chemistry frontiers, 10, 1512-1520 (2023)
Effects of exogenous 3-indoleacetic acid and cadmium stress on the physiological and biochemical characteristics of Cinnamomum camphora
Jihai Z, et al.
Ecotoxicology and Environmental Safety, 191, 109998-109998 (2020)



Global Trade Item Number

SKUGTIN
I3750-100MG04061833856277
I3750-500MG04061833856291
I3750-25MG04061835545742
I3750-1G04061826683576
I3750-5G-A04061835557295
I3750-25G-A04061833856284
I3750-100G-A04061833856260
I3750-2G04061835545759

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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