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1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine]

1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine] structure

CAS No:
27333-47-7
Formula:
C22H20N2O
Chemical Name:
1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine]
Synonyms:
Spiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine],1,3-dihydro-1,3,3-trimethyl-;Spiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine],1,3,3-trimethyl-;1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine];1,3,3-Trimethylspiro[indoline-2,3′-[3H]naphth[2,1-b][1,4]oxazine];Variacrol Blue A;Photorom I;Photorome I;1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-h][1,4]oxazine];T 1259;1,3,3-Trimethylindolinonaphthospirooxazine;1,3,3-Trimethylindolinospironaphthooxazine;1,3,3-Trimethylindolinonaphthospiroxazine;Photopia AQ Ink Blue;1′,3′,3′-Trimethylspiro[benzo[f][1,4]benzoxazine-3,2′-indole];1,3,3-Trimethyl-1,3-dihydrospiro[indole-2,3′-naphtho[2,1-b][1,4]oxazine];120026-33-7;138780-10-6;199195-44-3;960373-06-2;1225595-26-5
Categories:
Chemical Reagents > Organic Reagents

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1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine] Basic Attributes

Molecular Weight：

328.40700

Exact Mass：

328.41

EC Number：

404-480-6

DSSTox ID：

DTXSID90344142

HScode：

2934999090

Characteristics

PSA：

24.83000

XLogP3：

5.1

Appearance：

YELLOW OR TAN POWDER OR CRYSTALLINE POWDER

Density：

1.19

Melting Point：

128 °C @ Solvent: Ethyl acetate, Hexane

Boiling Point：

529.1ºC at 760 mmHg

Flash Point：

273.8ºC

Refractive Index：

1.65

Vapor Pressure：

2.8E-11mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S37/39

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine] Use and Manufacturing

General procedure: Adding a substituted salicylaldehyde, naphthaldehyde or nitros naphthol (1 equivalent) to a solution of hydrazine iodide (1 equivalent) in isopropanol (15 V, relative to indole) Triethylamine (1.5 eq.), then stirred under nitrogen and refluxedAt night, cool to room temperature and spin dry. The residue was purified by column (eluent petroleum ether / ethyl acetate) to give the desired product.As certain representative examples of such spirooxazine compounds, may be mentioned: General procedure: A mixture of indolium iodide 1 (1.0 mmol) and choline hydroxide (10 mol %) in water (3 mL) was stirred at 80 C for 20 min. Then 1-nitroso-2-naphthol 2 (1.0 mmol) was added and the resulting mixture stirred at 80C for another 40 min. Then reaction mass was cooled to rt. The solid product was then filtered and washed with water. The synthesized product was finally purified using column chromatography technique (silica gel 100-200 mesh size) with ethyl acetate:hexane (05:95) as an eluent to give the desired spironaphthoxazine (Scheme 2 & Table 1). SNO-1: 1, 1, 3-trimethyl-1, 3-dihydrospiro[benzo[e]indole-2, 3'-naphtho[2, 1-b][1, 4]oxazine] Yield: 89%; Colorless solid; mp 123-124 oC. Reported mp 125. A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2- naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to further spiroheterocyclic oxazines are possible. 1H NMR (500 MHz, DMSO-d6) delta 8.499 (1H, d, J = 8.5 Hz, C10?-H), 7.968 (1H, s, C2?-H), 7.912 (1H, d, J = 8.6 Hz, C7?-H), 7.870-7.825 (3H, m, C6?-H, C8?-H, & C9?-H), 7.590 (1H, t, J = 8.3 Hz, C6-H), 7.418 (2H, m, C4 & C5?-H), 7.243 (1H, t, J = 8.0 Hz, C5-H), 7.075 (1H, d, J = 8.5 Hz, C7-H), 2.778 (3H, s, N-CH3), 1.594 (3H, s, C1-CH3), 1.472 (3H, s, C1-CH3).General procedure: To1, 3, 3-trimethyl-2-methylenedihydroindole(I5) (1 equivalent)Isopropanol(15 V, relative to hydrazine) was added nitroso naphthol (1 equivalent) to the solution.Then, under nitrogen, the mixture was stirred at reflux overnight, and cooled to room temperature.Spin dry. The residue was purified by column (eluent was petroleum ether / ethyl acetate).The desired product is obtained.

Computed Properties

Molecular Weight:328.4
XLogP3:5.1
Hydrogen Bond Acceptor Count:3
Exact Mass:328.157563266
Monoisotopic Mass:328.157563266
Topological Polar Surface Area:24.8
Heavy Atom Count:25
Complexity:558
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of 1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine]

Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
Latest News
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1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine]

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