3D Mol Similar

Indole-5-carboxaldehyde

: Iupac Name：1H-indole-5-carbaldehyde; CAS No.: 1196-69-6; Molecular Weight：145.161; Modify Date.: 2022-11-11 21:32; Introduction: Reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents 1 Reactant in preparation of analogs of botulinum neurotoxin serotype A protease inhibitors 2 Reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes 3 Reactant in synthesis of para-para stilbenophanes by McMurry coupling 4 Reactant in stereoselective synthesis of heteroaromatic (E)-α,β-unsaturated ketones from aldehydes 5 Reactant in structure-based drug design of aurora kinase A inhibitors. View more+

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1. Names and Identifiers

: 1.1 Name; Indole-5-carboxaldehyde; 1.2 Synonyms; 1H-indol-5-carbaldehyde 1H-INDOLE-5-CARBALDEHYDE 1H-INDOLE-5-CARBOXALDEHYDE 5-FORMYLINDOLE 5-INDOLE ALDEHYDE INDOLE-5-ALDEHYDE INDOLE-5-CARBALDEHYDE INDOLE-5-CARBOXALDEHYDE

1.3 CAS No.: 1196-69-6

1.4 CID: 589040

1.5 EINECS(EC#): 1312995-182-4

1.6 Molecular Formula: C9H7NO (isomer)

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

1.8 InChIkey: ADZUEEUKBYCSEY-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC2=C(C=CN2)C=C1C=O

1.10 Isomers Smiles: C1=CC2=C(C=CN2)C=C1C=O

2. Properties

2.1 Density: 1.278

2.1 Melting point: 100-103℃

2.1 Boiling point: 339.1 oC at 760 mmHg

2.1 Refractive index: 1.729

2.1 Flash Point: 166.8 oC

2.1 Precise Quality: 145.05300

2.1 PSA: 32.86000

2.1 logP: 1.98040

2.1 Appearance: Yellow Powder

2.2 Storage: Air Sensitive. Ambient temperatures.

2.3 Chemical Properties: Red Crystalline Powder

2.4 Color/Form: Liquid

2.5 pKa: 16.14±0.30(Predicted)

2.6 Water Solubility: Insoluble in water.

2.7 StorageTemp: Keep Cold

3. Safety and Handling

3.1 Symbol: GHS07;

3.1 Hazard Codes: Xi

3.1 Signal Word: Warning

3.1 Risk Statements: R36/37/38

3.1 Safety Statements: S26;S36/37/39

3.1 Hazard Class: IRRITANT

3.1 Hazard Declaration: H315; H319; H335

3.1 Caution Statement: P261; P305 + P351 + P338

3.1 WGK Germany: 3

3.1 Sensitive: Air Sensitive

4. 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

View all

5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

6. Synthesis Route

1196-69-6Total: 16 Synthesis Route

1075-25-8 50 Suppliers

1196-69-6 190 Suppliers

Literatures:
Cody, Wayne L.; Holsworth, Daniel D.; Powell, Noel A.; Jalaie, Mehran; Zhang, Erli; Wang, Wei; Samas, Brian; Bryant, John; Ostroski, Robert; Ryan, Michael J.; Edmunds, Jeremy J. Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 1 p. 59 - 68
Yield: ~96%

1011-65-0 133 Suppliers

1196-69-6 190 Suppliers

Literatures:
Chemical and Pharmaceutical Bulletin, , vol. 34, # 10 p. 4116 - 4125
Yield: null

1670-81-1 217 Suppliers

1196-69-6 190 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 64, # 6 p. 1823 - 1830
Yield: null

View all

7. Precursor and Product

precursor:

152879-74-8

68-12-2

1670-81-1

16066-91-4

594-19-4

105205-48-9

1011-65-0

1026678-47-6

1392050-82-6

1313-13-9

10075-50-0

24078-21-5

201230-82-2

52414-98-9

1075-25-8

148582-48-3

18515-67-8

View all

product :

671215-62-6

63263-88-7

1075-25-8

63232-11-1

944893-74-7

166670-56-0

889108-48-9

946077-36-7

21005-48-1

77132-99-1

90923-75-4

15861-24-2

8. Other Information

8.0 Chemical Properties: Red Crystalline Powder

8.1 Usage: Indole-5-carboxaldehyde is used as a reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents; and in synthesis of para-para stilbenophanes by McMurry coupling. It is also used as a reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes and in structure-based drug design of aurora kinase A inhibitors.

9. Computational chemical data

Molecular Weight: 145.161g/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: AAADcYByIAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHgAQAAAADAjhngY8wPLJkACoAzx3xACCgCA1AiAI2aE4ZNgIIPLAlZGEIQhgkADIyYcYicCeCAACAAACAAAQAAQAAAQAAAAAAAAAAA==