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161810

Sigma-Aldrich

5-Chloro-2-methylene-1,3,3-trimethylindoline

technical grade, 95%

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About This Item

Empirical Formula (Hill Notation):
C12H14ClN
CAS Number:
Molecular Weight:
207.70
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Assay

95%

form

liquid

refractive index

n20/D 1.594 (lit.)

density

1.083 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

CN1C(=C)C(C)(C)c2cc(Cl)ccc12

InChI

1S/C12H14ClN/c1-8-12(2,3)10-7-9(13)5-6-11(10)14(8)4/h5-7H,1H2,2-4H3

InChI key

VDMXGJJMPKAYQP-UHFFFAOYSA-N

General description

5-Chloro-2-methylene-1,3,3-trimethylindoline undergoes regiospecific 1,3-dipolar cycloaddition reaction with arylnitriloxydes and N-phenylarylnitrilimines.

Application

5-Chloro-2-methylene-1,3,3-trimethylindoline was used in the synthesis of 5′,6-dichloro-1′,3′,3′-trimethyl­spiro­[2H-1-benzopyran-2,2′-indoline].

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Naoual Laghrib et al.
Acta crystallographica. Section E, Structure reports online, 65(Pt 2), o374-o374 (2009-01-01)
Two diastereoisomers of the title compound, C(25)H(26)N(2)O, have been prepared by cyclo-addition between 1,3,3-trimethyl-2-methyl-eneindoline and C-phenyl-N-phenyl-nitrone. The stereochemistry of the major diastereoisomer, viz. S,R/R,S, is confirmed by the X-ray analysis. The oxazole and the pyrole rings have envelope conformations. The
Nameer Alhashimy et al.
Acta crystallographica. Section E, Structure reports online, 64(Pt 8), o1430-o1431 (2008-01-01)
In the crystal structure of the title compound, C(19)H(17)Cl(2)NO, the indoline and benzopyran ring systems are approximately perpendicular to each other. The indoline ring is in an envelope conformation with the spiro C atom as the flap. The N atom

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