2,5-Dimethyl-1H-indole (HCID 70965)

Names & identifiers

Preferred name: 2,5-Dimethyl-1H-indole
IUPAC: 2,5-dimethyl-1H-indole
English name: 2,5-Dimethylindole
Molecular formula: C10H11N
Molecular weight: 145.2

Names & synonyms

2,5-Dimethyl-1H-indole2,5-Dimethylindole1196-79-8ETU94V283MEINECS 214-816-1DTXSID30152521RefChem:444510DTXCID1075012214-816-11H-Indole, 2,5-dimethyl-Indole, 2,5-dimethyl-MFCD00005621

Show more names

2,5-Dimethylindole>Indole, 2,5-dimethyl-2,5-Dimethylindole 97%2,5-Dimethylindole,97%8. 2,5-Dimethylindole -

UNII-ETU94V283M2,5-dimethyl indoleSCHEMBL755812,5-Dimethyl-1H-indole #BIDD:GT02992,5-Dimethyl-Indole2,5-Dimethylindole, 97%orb3030183

Database identifiers

CAS: 1196-79-8
PubChem CID: 70965
DTXSID: DTXSID30152521
UNII: ETU94V283M
EC Number: 214-816-1
Nikkaji: J45.615B

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 15.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 144

Experimental & physicochemical properties

LogP3.02

Physicochemical properties

Melting point: 112 · 112-113 °C (lit.)
Boiling point: 254.33 °C · 254.33°C (rough estimate)
Density: 1.0353 · 1.0353 (rough estimate)
refractive index: 1.5 · 1.5000 (estimate)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: soluble in Methanol
form: Solid
pka: 17.75 · 17.75±0.30(Predicted)
color: Off-white to pale pink or light brown
InChI: 1S/C10H11N/c1-7-3-4-10-9(5-7)6-8(2)11-10/h3-6,11H,1-2H3
InChIKey: ZFLFWZRPMDXJCW-UHFFFAOYSA-N
SMILES: Cc1ccc2[nH]c(C)cc2c1
CAS DataBase Reference: 1196 · 1196-79-8(CAS DataBase Reference)
FDA UNII: 94 V283M · ETU94V283M
NIST Chemistry Reference: 1 H-indole, · 1H-indole, 2,5-dimethyl-(1196-79-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 315 · H315-H318-H335
Precautionary statements: 280 · P280-P302+P352-P305+P351+P338+P310
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 37 · 37/38-41
Safety Statements: 26 · 26-39
WGK Germany: 3 · 3
Hazard Note: Irritant
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 Skin · Eye Dam. 1Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: 3
hs_code: 29339900
risk_code: 37/38-41
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H318-H335
Hazard Classifications: Eye Dam. 1Skin Irrit. 2STOT SE 3
Precautionary statements: P280-P302+P352-P305+P351+P338+P310

Chemistry & industry

Applications · 2 items

Description2, 5-Dimethylindole is a kind of carbazole-system derived indole compound, which is valuable in the manufacturing of perfume. It is also a useful chemical intermediate. It is usually used as reactant in the following reaction: stereoselective synthesis of indolines via palladium-catalyzed asymmetric hydrogenation of unprotected indoles; stereoselective preparation of substituted indoles via rhodium-catalyzed enantioselective coupling reaction of indoles with diazo compounds; enantioselective synthesis of fluorene derivatives via Friedel-Crafts reactions; preparation of bis-indolyldihydroxybenzoquinones by addition indoles to dichlorobenzoquinone promoted by Bronsted acid; Reaction with hydroxypyrazolines.

UsesReactant in stereoselective preparation of substituted indoles via rhodium-catalyzed enantioselective coupling reaction of indoles with diazo compoundsReactant in stereoselective synthesis of indolines via palladium-catalyzed asymmetric hydrogenation of unprotected indolesReactant in enantioselective synthesis of fluorene derivatives via Friedel-Crafts reactionsReactant in preparation of bis-indolyldihydroxybenzoquinones by addition indoles to dichlorobenzoquinone promoted by Bronsted acidReactant in reaction with hydroxypyrazolines