1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole

• ChemBase ID: 148524
• Molecular Formular: C12H15N
• Molecular Mass: 173.2542
• Monoisotopic Mass: 173.12044949
• SMILES: CC1(c2ccccc2N(C1=C)C)C
• Canonical SMILES: CN1c2ccccc2C(C1=C)(C)C
• InChI: InChI=1S/C12H15N/c1-9-12(2,3)10-7-5-6-8-11(10)13(9)4/h5-8H,1H2,2-4H3
• InChIKey: ZTUKGBOUHWYFGC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole
• IUPAC Traditional name: 1,3,3-trimethyl-2-methylideneindole
• Synonyms: NSC 66176; 2-Methylene-1,3,3-trimethylindoline; Fischer base; 1,3,3-Trimethyl-2-methyleneindoline; Fischer's Base; 2-亚甲基-1,3,3-三甲基吲哚啉; Fischer 碱; 1,3,3-三甲基-2-亚甲基吲哚啉

Database IDs

• CAS Number: 118-12-7
• EC Number: 204-235-1
• MDL Number: MFCD00005813
• Beilstein Number: 131162
• PubChem SID: 162242699; 24889678; 24896929
• PubChem CID: 8351

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.0841491
• LogD (pH = 7.4): 3.084355
• Log P: 3.0843577
• Molar Refractivity: 57.4286 cm^3
• Polarizability: 21.59455 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: red liquid
• Melting Point: -10°C
• Boiling Point: 247-248°C; 248 °C(lit.)
• Flash Point: 101°C(213°F); 145.4 °F; 63 °C
• Density: 0.979; 0.979 g/mL at 25 °C(lit.)
• Refractive Index: 1.5780; n20/D 1.577; n20/D 1.577(lit.)

Safety Information

• RTECS: NM1926500
• European Hazard Symbols: Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 3082
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-38-50/53; 36/37/38
• Safety Statements: 26-37; 28-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H400; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P273
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3

Product Information

• Purity: ≥96.0%; ≥96.0% (GC); 95%; 97%
• Grade: for paper chromatography
• Empirical Formula (Hill Notation): C12H15N

DETAILS

Sigma Aldrich - M46209

Packaging
5, 100 g in glass bottle
Application
Reactant for:
• Cycloaddition reactions1
• Preparation of red photochromic dyes2
• Synthesis of photochromic homopolymers via ring-opening metathesis polymerization3

Sigma Aldrich - 92550

Other Notes
Lit.1

REFERENCES

• Reacts with salicylaldehydes to form N,O-spiroacetals, providing a means of protection. The group is cleaved by ozonolysis: Tetrahedron Lett., 41, 3915 (2000):