Indole-3-carboxaldehyde

Iupac Name：1H-indole-3-carbaldehyde

Molecular Weight：145.15798

Modify Date.: 2022-11-29 12:21

Introduction:

Indole-3-carboxaldehyde (3-Formylindole), a cabbage extract, is the product of the oxidative degradation of indole-3-acetic acid (IAA) by crude enzyme preparations from etiolated pea seedlings. Indole-3-carboxaldehyde (3-Formylindole) is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin[1].

Solid

Indole-3-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.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

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1. Names and Identifiers

1.1 Name: Indole-3-carboxaldehyde
1.2 Synonyms: 1H-Indol-3-yl carboxaldehyde 1H-Indole-3-aldehyde 1H-Indole-3-carbaldehyde 1H-Indole-3-carboxaldehyde 1H-Indole-3-methanal 3-Formyl-1H-indole 3-Formylindole 3-Indolylformaldehyde I3CA INDOL-3-ALDEHYDE INDOLE-3-ALDEHYDE INDOLE-3-CARBALDEHYDE INDOLE-3-CARBOXYALDEHYDE INDOLE-3-CARBOXYBENZALDEHYDE Indole-3-carboxylaldehyde Indole-3-formaldehyde INDOLYL-3-ALDEHYDE NSC 10118 β-Indolylaldehyde

1.3 CAS No.: 487-89-8

1.4 CID: 10256

1.5 EINECS(EC#): 207-665-8

1.6 Molecular Formula: C9H7NO (isomer)

1.7 Inchi: InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H

1.8 InChkey: OLNJUISKUQQNIM-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C(=CN2)C=O

1.10 Isomers Smiles: C1=CC=C2C(=C1)C(=CN2)C=O

2. Properties

2.1 Density: 1.278

2.1 Melting point: 193-198℃

2.1 Boiling point: 339.1 °C at 760 mmHg

2.1 Refractive index: 1.4500 (estimate)

2.1 Flash Point: 240℃

2.1 Precise Quality: 145.05300

2.1 PSA: 32.86000

2.1 logP: 1.98040

2.1 Appearance: Off-white to beige-brown Crystalline Powder

2.2 Storage: Air Sensitive. Ambient temperatures.

2.3 Chemical Properties: off-white to beige-brown crystalline powder

2.4 Color/Form: Off-white to beige-brown

2.5 pKa: 15.50±0.30(Predicted)

2.6 Water Solubility: Insoluble in water.

2.7 Stability: Has not been fully evaluated.

2.8 StorageTemp: Keep Cold

3. Use and Manufacturing

3.1 Definition: ChEBI: A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Safety Statements: S24/25

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: NL5993600

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Safety Information of 3-Formylindole (CAS No.487-89-8):
Hazard Codes:?Xi
Safety Statements: 22-24/25?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: NL5993600
F: 9-23
Hazard Note: Irritant/Keep Cold
HazardClass: IRRITANT
HS Code: 29339990

4.3 Sensitive: Air Sensitive

4.4 Specification: ? 3-Formylindole (CAS No.487-89-8), it also can be called Indol-3-carboxaldehyde ; Indole-3-aldehyde ; beta-Indolylaldehyde ; 1H-Indole-3-carboxaldehyde .
? Storage of 3-Formylindole (487-89-8): Store in a cool dry place. Keep container closed.

4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	600mg/kg (600mg/kg)	AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" BEHAVIORAL: ANTICONVULSANT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Pharmaceutical Chemistry Journal Vol. 6, Pg. 33, 1972.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

487-89-8Total: 101 Synthesis Route

87-51-4 407 Suppliers

487-89-8 350 Suppliers

Literatures:
Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-baltork, Iraj; Sirjanian, Narges; Parand, Somayeh Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 9 p. 3394 - 3398
Yield: ~92%

83-34-1 212 Suppliers

487-89-8 350 Suppliers

Literatures:
Fonseca, I.; Martinez-Crrera, S.; Garcia-Blanco, S.; Rodriguez, J. G.; Subirats, J. B. Journal of Crystallographic and Spectroscopic Research, 1988 , vol. 18, # 3 p. 265 - 276
Yield: null

93-61-8 110 Suppliers

487-89-8 350 Suppliers

Literatures:
Shabica et al. Journal of the American Chemical Society, vol. 68>1946>1156
Yield: null

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8. Precursor and Product

precursor:

83-34-1

93-61-8

700-06-1

771-51-7

110-45-2

2591-98-2

771-50-6

120-72-9

5457-31-8

518-06-9

1477-49-2

54-12-6

22948-94-3

4299-70-1

87-52-5

87-51-4

2592-05-4

View all

product :

343-94-2

5379-88-4

1968-05-4

876-72-2

2731-00-2

700-06-1

771-51-7

771-50-6

118-48-9

1477-49-2

3156-51-2

526-32-9

4361-05-1

27092-42-8

1204-06-4

2592-05-4

830-96-6

4414-76-0

7042-71-9

1233-49-4

6336-32-9

73-22-3

5379-94-2

3766-02-7

4837-74-5

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9. Other Information

9.0 Usage: Indole-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.

9.1 Mesh Entry Terms: 3-indolemethanal

9.2 Manufacturing Info: 1H-Indole-3-carboxaldehyde: ACTIVE

10. Computational chemical data

Molecular Weight: 145.15798g/mol
Molecular Formula: C₉H₇NO
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 145.052763847
Monoisotopic Mass: 145.052763847
Complexity: 158
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 32.9
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYByIAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHgAQAAAADAjhngY8wPLJkACoAzx3xACCgCA1AiAI2aE4ZNgIIPrAlZGEIYhgkADIyccciMCOgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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