Indoline

Iupac Name：2,3-dihydro-1H-indole

Molecular Weight：119.167

Modify Date.: 2022-11-29 12:26

Introduction: As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists. View more+

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1. Names and Identifiers

1.1 Name: Indoline
1.2 Synonyms: 1-Azaindan 1H-Indole, 2,3-dihydro- 2,3-dihydro-1H-1-indole 2,3-dihydro-1h-indol 2,3-DIHYDRO-1H-INDOLE 2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE 2,3-DIHYDROINDOLE Dihydroindole EINECS 207-816-8 IDN Indoline in stock Factory LABOTEST-BB LT01605668 MFCD00005705 TIMTEC-BB SBB004291 trans-dihydroindole

1.3 CAS No.: 496-15-1

1.4 CID: 10328

1.5 EINECS(EC#): 207-816-8

1.6 Molecular Formula: C8H9N (isomer)

1.7 Inchi: InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2

1.8 InChkey: LPAGFVYQRIESJQ-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CNC2=CC=CC=C21

1.10 Isomers Smiles: C1CNC2=CC=CC=C21

2. Properties

2.1 Density: 1.063

2.1 Melting point: -21℃

2.1 Boiling point: 228-230℃

2.1 Refractive index: 1.592-1.594

2.1 Flash Point: 92℃

2.1 Precise Quality: 119.07300

2.1 PSA: 12.03000

2.1 logP: 1.79260

2.1 Solubility: 5g/l

2.2 Appearance: clear to yellow liquid

2.3 Storage: Light Sensitive. Ambient temperatures.

2.4 Chemical Properties: Clear colorless to slightly brown liquid

2.5 Color/Form: clear dark brown

2.6 pKa: 5.20±0.20(Predicted)

2.7 Water Solubility: H2O: 5 g/L (20 oC)

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Keep in dark place,Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 8 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 8 companies. For more detailed information, please visit ECHA C&L website

Of the 5 notification(s) provided by 6 of 8 companies with hazard statement code(s):

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (83.33%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (83.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (66.67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H412 (16.67%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.2 Usage: As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H302

4.1 Caution Statement: P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: NL6906300

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NO_x.
Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-37/39-26?
S23:Do not breathe vapour.?
S24/25:Avoid contact with skin and eyes.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: NL6906300
Hazard Note of Indoline (CAS NO.496-15-1): Irritant

4.3 Sensitive: Light Sensitive

4.4 Specification: ? Indoline (CAS NO.496-15-1), its Synonyms are 1-Azaindan ; 2,3-Dihydro-1H-indole ; 2,3-Dihydroindole ; 1H-Indole, 2,3-dihydro- . Indoline is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound is based on the indole structure, but the 2-3 bond is saturated. It is clear colorless to slightly brown liquid.

4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 238mg/kg (238mg/kg)	?	Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1620, 1974.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : liquid film

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

496-15-1Total: 75 Synthesis Route

61-71-2 1 Suppliers

496-15-1 182 Suppliers

Literatures:
Sakurai Bulletin of the Chemical Society of Japan, 1942 , vol. 17, p. 269,272
Yield: null

91-56-5 206 Suppliers

496-15-1 182 Suppliers

Literatures:
Sakurai Bulletin of the Chemical Society of Japan, 1942 , vol. 17, p. 269,272
Yield: null

88-72-2 80 Suppliers

496-15-1 182 Suppliers

Literatures:
Minin, Patricia L.; Walton, John C. Journal of Organic Chemistry, 2003 , vol. 68, # 7 p. 2960 - 2963
Yield: null

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8. Precursor and Product

precursor:

5670-66-6

3192-06-1

496-30-0

935-07-9

2039-85-2

120-72-9

587-65-5

88-72-2

91-56-5

61-71-2

59-48-3

5339-85-5

480-93-3

7633-57-0

100-63-0

View all

product :

80166-90-1

3433-54-3

25658-80-4

32692-19-6

5192-03-0

6872-06-6

27158-79-8

6019-39-2

4769-96-4

824-21-5

1670-83-3

4993-96-8

54698-11-2

16078-34-5

7075-68-5

19727-83-4

16078-30-1

22949-08-2

578-54-1

4170-68-7

7633-56-9

7633-57-0

20538-21-0

2861-59-8

3289-82-5

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9. Other Information

9.0 Mesh Entry Terms: 2,3-dihydro-1H-indole

9.1 Manufacturing Info: 1H-Indole, 2,3-dihydro-: ACTIVE

9.2 BRN: 111915

9.3 Chemical Properties: Clear colorless to slightly brown liquid

9.4 Uses: As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists.

9.5 Uses

Reactant for preparation of:

Inhibitors of NOD1-Induced Nuclear Factor-κB Activation
Sphingosine-1-phosphate 4(S1P4) receptor antagonists
Cytotoxic cell cycle inhibitors
2-Aminopyridines
PET agent for imaging of protein kinase C (PKC)
Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes
α4β2-Nicotinic acetylcholine receptor-selective partial agonists
mGlu4 positive allosteric modulators
Bacterial biofilm inhibitors
Serotonin 5-HT6 receptor antagonists

9.6 Usage: Indole is used in perfumery and in preparing tryptophan, one of the 20 amino acids commonly found in animal proteins. It has important application in the industry of plant growth. It is used to prepare indoleacetic acid (auxin) and other plant growth substances which help the development of roots in plant. Indole and its derivatives are widely used in making perfumes, dyes, agrochemicals and medicines.

10. Computational chemical data

Molecular Weight: 119.167g/mol
Molecular Formula: C₈H₉N
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 119.073499291
Monoisotopic Mass: 119.073499291
Complexity: 101
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 12
Heavy Atom Count: 9
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: AAADccByAAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgBAAAAHAAQAAAADAjBGAQwwILAAACAAiRCQACCAAAhAgAIiIAIZIgIICLAkZGEIAhgkADIyAcQgIAOAAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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Indoline