Indole-3-acetamide (HCID 397)

Overview

Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a plant metabolite, a fungal metabolite and a bacterial metabolite. It is a member of indoles, a monocarboxylic acid amide and a N-acylammonia. It is functionally related to an acetamide.

Names & identifiers

Preferred name: Indole-3-acetamide
IUPAC: 2-(1H-indol-3-yl)acetamide
English name: 3-Indoleacetamide
Molecular formula: C10H10N2O
Molecular weight: 174.2

Names & synonyms

indole-3-acetamide879-37-82-(1H-Indol-3-yl)acetamide3-IndoleacetamideIndoleacetamide(indol-3-yl)acetamideO9SEW65XW3DTXSID60236686NSC-1969CHEBI:16031RefChem:148193DTXCID90159177

Show more names

BRN08735433-IndoleaceBRN 0873543BRN-0873543ACETAMIDOINDOZE

212-904-41H-Indole-3-acetamide3-IndolylacetamideMFCD000056411H-Indol-3-ylacetamide2-(3-Indolyl)acetamide1-Indole-3-acetamideNSC 1969

Database identifiers

CAS: 879-37-8
PubChem CID: 397
DTXSID: DTXSID60236686
ChEBI: CHEBI:16031
UNII: O9SEW65XW3
EC Number: 212-904-4
Nikkaji: J128.124K

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 58.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 205

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Melting Point150 - 151 °C

Physical DescriptionSolid

Collision Cross Section · 2 items

135.5 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

136.2 Å² [M+H]+

Physicochemical properties

Melting point: 148 · 148-150 °C(lit.)
Boiling point: 469.7 · 469.7±28.0 °C(Predicted)
Density: 1.285 · 1.285±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Slightly)
form: Solid
pka: 16.37 · 16.37±0.40(Predicted)
color: White to Off-White
InChI: InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
InChIKey: ZOAMBXDOGPRZLP-UHFFFAOYSA-N
SMILES: N1C2=C(C=CC=C2)C(CC(N)=O)=C1
CAS DataBase Reference: 879 · 879-37-8(CAS DataBase Reference)
FDA UNII: 9 SEW65XW3 · O9SEW65XW3
NIST Chemistry Reference: 3 · 3-Indoleacetamide(879-37-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
WGK Germany: 3 · 3
Hazard Note: Irritant
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (37 of 37) of all reports.

Not Classified

Aggregated GHS information provided per 37 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29339900
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications · 2 items

UsesIndole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid.Reactant for the synthesis of:PET agent for imaging of protein kinase CA potential agent against Prion DiseaseProtein kinase C (PKC) inhibitor bisindolylmaleimide IVGlycogen synthase kinase-3 (GSK-3) inhibitorsInhibitors of CaMKIIdA VEGF inhibitorJAK3 inhibitorsInhibitors of NAD+-Dependent Histone DeacetylasesInhibitors of human adipocyte fatty acid-binding proteinCyclin-dependent kinase inhibitors

General DescriptionIndole-3-acetamide is an auxin precursor.

Upstream & downstream products

Upstream raw materials

Downstream products

Tryptophol 3-Indoleacetonitrile

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a fungal metabolite, a bacterial metabolite and a plant metabolite. It is a N-acylammonia, a monocarboxylic acid amide and a member of indoles. It is functionally related to an acetamide.