27333-50-2

Basic information

• Product Name: 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE]
• Synonyms: PHOTOROME II;5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE];5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIR O-(INDOLE-2,3'-(3H)NAPHTH(2,1-B)OXAZINE);Spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine],5-chloro-1,3-dihydro-1,3,3-trimethyl-;5-Chloro-1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]
• CAS NO: 27333-50-2
• Molecular Formula: C₂₂H₁₉ClN₂O
• Molecular Weight: 362.85
• Mol File: 27333-50-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 182-183 °C(lit.)
• Boiling Point: 568.4°Cat760mmHg
• Flash Point: 297.5°C
• Appearance: /
• Density: 1.27g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.87±0.40(Predicted)
• CAS DataBase Reference: 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE](CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE](27333-50-2)
• EPA Substance Registry System: 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE](27333-50-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 27333-50-2(Hazardous Substances Data)

Usage

General Description

5-Chloro-1,3-dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine is a chemical compound with a spiro-structured indole and naphthoxazine ring system, as well as a chlorine substituent at position 5 of the indole ring. 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] is a heterocyclic organic molecule that is used in research and development, particularly in the pharmaceutical and agrochemical industries. It has potential biological activities and can be used as a building block for the synthesis of various pharmaceutical products. The specific properties and uses of this compound can vary depending on the context in which it is employed, making it a versatile and potentially valuable chemical in various scientific and industrial applications.

Upstream product

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Downstream Products

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Relevant articles and documents

Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: Synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation

The novel racemic indolinospirobenzopyrans (5-7), indolinospironaphthopyrans (11-14) and indolinospironaphtho-1,4-oxazine (17) were synthesized by an aldol type of condensation of 1′,3′,3′- trimethyl-2 ′-methyleneindoline and its 5-substituted derivatives with an appropriately substituted hydroxybenzaldehyde, hydroxynaphthaldehyde or nitrosonaphthol. An unequivocal proof of the stereostructures of 9 and 17 was obtained by the single-crystal X-ray diffraction method. A substituted indoline ring and the benzopyran ring in 9 and the naphtho-1,4-oxazine moiety in 17 are interconnected via the common chiral atom and positioned almost perpendicularly to each other. The five-membered 2,3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Of all the compounds of this series, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 μM) cells but not the growth of normal fibroblasts (WI38). Indolinospirobenzopyrans (8-10) showed significant cytostatic activities against all tumor cell lines. However, these compounds also exhibited a cytotoxic effect on normal human fibroblasts. The indolinospirobenzopyrans 4, 6-8, 10 and the indolinospironaphtho-1,4-oxazine 16 showed, albeit modest, selectivity as antiviral agents against varicella-zoster virus (VZV) and/or cytomegalovirus (CMV) (EC50 within the concentration range of 1.0-12.6 μM).

NMR studies of the structure of the photoinduced forms of photochromic spironaphthoxazines

Irradiation at 355 nm with a pulsed laser of the colourless 1,3-dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]-naphth[2,1-b][1,4] oxazine] results in formation of photomerocyanines (coloured forms of photochromic compounds); this and its chloro derivative were studied by NMR spectroscopy. This has allowed us to confirm the structure of the stereoisomers. The colourless and coloured forms exist in thermal equilibrium. Integration of certain photomerocyanine signals allowed us to calculate the thermal kinetics of bleaching k, the half-life τ and the activation enthalpy ΔH? at different low temperatures and from these temperature dependence studies of the thermal decay rate, the thermal energy barrier for the decay of the coloured metastable state to the colourless form was determined.

SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE

Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.