Indole-3-Carboxaldehyde

HCID 10256
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Substructure searchFind similar structures

Basic information

CAS
487-89-8
Standard SMILES
O=Cc1c[nH]c2ccccc12
InChIKey
OLNJUISKUQQNIM-UHFFFAOYSA-N
Molecular formula
C9-H7-N-O
Average molar mass
145.16 g/mol
Monoisotopic mass
145.05276384

Overview

Indole-3-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group. It has a role as a marine metabolite, a plant metabolite, a human xenobiotic metabolite and a bacterial metabolite. It is a member of indoles, an indole alkaloid and a heteroarenecarbaldehyde.

Names & identifiers

Preferred name
Indole-3-Carboxaldehyde
IUPAC
1H-indole-3-carbaldehyde
English name
Indole-3-carboxaldehyde
Molecular formula
C9H7NO
Molecular weight
145.16

Names & synonyms

INDOLE-3-CARBOXALDEHYDE487-89-83-Formylindole1H-Indole-3-carboxaldehydeIndole-3-carbaldehydeIndole-3-aldehydebeta-Indolylaldehyde3-indolemethanal7FN04C32UODTXSID5060069CHEBI:28238NSC-10118
Show more names
3-IndolecarboxaldehydeNSC 269470INDOL-3-ALDEHYDE
RefChem:148197DTXCID8040640207-665-81H-Indole-3-carbaldehyde3-IndolecarbaldehydeINDOLE-3-CARBOXYALDEHYDEIndol-3-carboxaldehyde3-Indolealdehyde

Database identifiers

CAS
487-89-8
PubChem CID
10256
DTXSID
DTXSID5060069
ChEMBL
CHEMBL147741
ChEBI
CHEBI:28238
UNII
7FN04C32UO
EC Number
207-665-8
Nikkaji
J26.057F

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
32.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Indoles
SpringerMaterials PropertiesChemical shift
PesticidesBiocide
LogP1.68
Melting Point197 - 199 °C
Vapor Pressure0.00043 [mmHg]

Physicochemical properties

Melting point
193 · 193-198 °C(lit.)
Boiling point
264.27 °C · 264.27°C (rough estimate)
Density
1.1555 · 1.1555 (rough estimate)
bulk density
200 · 200-300kg/m3
refractive index
1.45 · 1.4500 (estimate)
Flash point
240 °C · 240 °C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.9% (1 of 34) of reports.

Warning

H315 (97.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 34 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1H-Indole-3-carboxaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses smooth muscle relaxation and changes in motor activity in intraperitoneal lethal-dose studies of mice (LDLo = 600 mg/kg); [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (97.1%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

2.6 [ppm]

29 [ppm]

170 [ppm]

Safety data

F
9-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
NL5993600
hs_code
29339990

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing Information1H-Indole-3-carboxaldehyde: ACTIVE
Applications · 2 items

UsesIndole-3-carboxaldehyde is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group. It was also used as the starting material for the synthesis of higher order indoles including isoindolo[2,1-a]indoles, aplysinopsins, and 4-substituted-tetrahydrobenz[cd]indoles.

General DescriptionIndole-3-carboxaldehyde can undergo Schiff bases condensation to form multifunctional silica nano-vehicles and magnetic nanoparticles.

Upstream & downstream products

Suppliers100 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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.

Related reactions

242 records
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Compound notes

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