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496-12-8

496-12-8 Structure

496-12-8 Structure
IdentificationMore
[Name]

Isoindoline
[CAS]

496-12-8
[Synonyms]

2,3-DIHYDRO-1H-ISOINDOLE
DIHYDROISOINDOLE
ISOINDOLINE
1,3-Dihydroisoindole
1,3-Dihydro-2H-isoindole
o-Xyleneimine
[Molecular Formula]

C8H9N
[MDL Number]

MFCD00605324
[Molecular Weight]

119.16
[MOL File]

496-12-8.mol
Chemical PropertiesBack Directory
[Melting point ]

17 °C (lit.)
[Boiling point ]

221 °C (lit.)
[density ]

1.05 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.57(lit.)
[Fp ]

202 °F
[storage temp. ]

2-8°C
[form ]

Crystalline Powder, Crystals or Flakes, Darkening On Exposure To Light
[pka]

9.26±0.20(Predicted)
[color ]

White to off-white
[InChI]

1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2
[InChIKey]

GWVMLCQWXVFZCN-UHFFFAOYSA-N
[SMILES]

C1NCc2ccccc12
[CAS DataBase Reference]

496-12-8(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[HS Code ]

29339980
[Storage Class]

10 - Combustible liquids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

2H-Isoindole-->AKOS AUF2082-->2-(Hydroxymethyl)benzonitrile-->2-Iodobenzyl alcohol-->Phthalide
[Preparation Products]

2-cyano-2-[2,3-dihydro-3-(tetrahydro-2,4,6-trioxo-5(2H)-pyrimidinylidene)-1H-isoindol-1-ylidene]-N-methylacetamide-->Indobufen-->Pigment Yellow 139-->2-Benzyl-2,3-dihydro-1H-isoindole-->Isoindolin-5-amine hydrochloride-->benzyl 5-aminoisoindoline-2-carboxylate
Hazard InformationBack Directory
[Description]

Isoindoline can be considered as the “hydrogenated sister” of isoindole which is widespread in nature as heterocyclic core of alkaloids and antibiotics.
[Chemical Properties]

Isoindoline is a white to off-white solid at room temperature and pressure, poor solubility in water, it has a certain basicity, and can be nucleophilic substitution reaction with common alkyl halides.
[Uses]

Isoindoline is used to make a chiral diamine catalyst from L-proline for the asymmetric acylation of alcohols.1
[Uses]

Isoindolinone and isoindoline pigments are high quality products. They are used in general and high grade industrial paints including original automobile and automotive refinishes, in plastics and for spin dyeing, and in high grade printing inks, especially for metal deco, laminated plastic sheets, and in printing inks for bank notes and securities.
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 53, p. 5381, 1988 DOI: 10.1021/jo00257a041
Synthetic Communications, 18, p. 2055, 1988 DOI: 10.1080/00397918808068274
Spectrum DetailBack Directory
[Spectrum Detail]

Isoindoline(496-12-8)1HNMR
Isoindoline(496-12-8)1HNMR
Isoindoline(496-12-8)IR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

496-12-8(sigmaaldrich)
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