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4-Acetoxyindole

HCID 583934
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
5585-96-6
Standard SMILES
CC(=O)Oc1cccc2[nH]ccc12
InChIKey
ZXDMUHFTJWEDEF-UHFFFAOYSA-N
Molecular formula
C10H9NO2
Average molar mass
175.18 g/mol
Monoisotopic mass
175.06332853

Names & identifiers

Preferred name
4-Acetoxyindole
IUPAC
1H-indol-4-yl acetate
English name
4-Acetoxyindole
Molecular formula
C10H9NO2
Molecular weight
175.18

Names & synonyms

4-Acetoxyindole5585-96-6DTXSID70342707RefChem:1070205DTXCID90293787881-373-41H-Indol-4-yl acetate4-Indolyl acetateMFCD00010678acetic acid 1H-indol-4-yl ester4-Acetoxy indole4-Indolyl acetate, 99%
Show more names
ACETOXYINDOLE4-Acetoxy-1H-indole2-(1H-indol-4-yl)acetate4-acacetoxyindole4-Acetoxyindole 98%
1H-Indol-4-yl acetate #SCHEMBL594038AKOS015837973AB01042AS-31131SY004859A-03004-Indoxyl acetate

Database identifiers

CAS
5585-96-6
PubChem CID
583934
DTXSID
DTXSID70342707
EC Number
881-373-4
Nikkaji
J236.466B

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
42.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
13
Formal charge
0
Complexity
205

Physicochemical properties

Melting point
100 · 100-102°C
Boiling point
339.1 · 339.1±15.0 °C(Predicted)
Density
1 · 1+-.0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
16.38 · 16.38±0.30(Predicted)
color
Off-White to Beige
InChI
InChI=1S/C10H9NO2/c1-7(12)13-10-4-2-3-9-8(10)5-6-11-9/h2-6,11H,1H3
InChIKey
ZXDMUHFTJWEDEF-UHFFFAOYSA-N
SMILES
N1C2=C(C(OC(=O)C)=CC=C2)C=C1
CAS DataBase Reference
5585 · 5585-96-6(CAS DataBase Reference)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
hs_code
2933998090
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
P280-P305+P351+P338-P310

Chemistry & industry

Applications · 4 items

Description4-acetoxylindole is also known as 4-Indolyl acetate. It can be used as standards of the reverse phase HPLC during separation of small molecules. It can also be used as reactant during the preparation of inhibitors of HIV-attachment, prostanoid EP3 antagonist, indolyl-nitroalkanes and psilocybin.

UsesReactant for preparation of:Inhibitors of HIV-1 attachmentProstanoid EP3 receptor antagonist, as a novel antiplatelet agentIndolyl-nitroalkanes via N-bromosuccinimide catalyzed synthesisPsilocybin as a medicinal agent

Uses4-Acetoxyindole is a useful intermediate for organic synthesis of Psilocine and Psilocine analogs.

General Description4-Acetoxyindole is a chromophore that belongs to the pyrrole family of compounds. It has been shown to react with an ionic liquid under acidic conditions to form a protonated intermediate, which can be deprotonated by a nucleophile. This reaction yields an acetate anion and a fluorescing product. 4-Acetoxyindole also reacts with deuterium gas, yielding an acetate, a deuterium atom, and fluorescing product. The reaction is reversible and the yield of the product depends on the concentration of the reactants. 4-Acetoxyindole has strong carbonyl groups that make it reactive towards other functional groups. These reactions are useful for synthesizing heterocycles such as indoles and isoquinolines.

Upstream & downstream products

Downstream products

4-HO-MiPT

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海策嵘生物科技有限公司[email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]

Related reactions

11 records
New reaction record
HRID 8989 reaction equation
HRID 8989As reactantuspto-grants-2006_08
HRID 257612 reaction equation
HRID 257612As productuspto-grants-1993_11
HRID 550143 reaction equation
HRID 550143As reactantuspto-grants-2011_05
HRID 643414 reaction equation
HRID 643414As reactantuspto-grants-2010_04
HRID 1640617 reaction equation
HRID 1640617As reactantuspto-grants-2012_02
HRID 1878884 reaction equation
HRID 1878884As reactantuspto-grants-2012_11
HRID 1993216 reaction equation
HRID 1993216As reactantuspto-grants-2010_01
HRID 2042308 reaction equation
HRID 2042308As reactantuspto-grants-2013_11
Page 1 of 2

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Hazard statements
302 · H302-H315-H319-H332-H335
Precautionary statements
280 · P280-P305+P351+P338-P310
Hazard Codes
Xi
WGK Germany
3 · 3
Hazard Note
Irritant
HS Code
2933998090 · 2933998090
Storage Class
11 · 11 - Combustible Solids
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Accela ChemBio Inc.+1(858) 699-3322 · [email protected]
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