Basic information
- CAS
1498-88-0- Standard SMILES
CN1c2ccccc2C(C)(C)C12C=Cc1cc([N+](=O)[O-])ccc1O2- InChIKey
PSXPTGAEJZYNFI-UHFFFAOYSA-N- Molecular formula
- C19H18N2O3
- Average molar mass
- 322.4 g/mol
- Monoisotopic mass
- 322.13174244
Overview
photochromic dye
Names & identifiers
- Preferred name
- 1',3'-dihydro-1',3',3'-trimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-(2H)indole)
- IUPAC
- 1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]
- English name
- 1,3,3-Trimethylindolino-6'-nitrobenzopyrylospiran
- Molecular formula
- C19H18N2O3
- Molecular weight
- 322.36
Names & synonyms
1498-88-0Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-1',3',3'-Trimethyl-6-nitroindolene-2-spiro-2-benzopyranDTXSID70871845Spiro(2H-1-benzopyran-2,2'-(2H)indole), 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-1',3'-Dihydro-1',3',3'-trimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-(2H)indole)1,3,3-trimetylindolino-6-nitro benzopyrylospiranTMINBPSTNSBRefChem:8888046-NO2-BIPSDTXCID70819464
Show more names
NSC 206176SP 1 (dye)AKOS 904251' 3'-DIHYDRO-1' 3' 3'-TRIMETHYL-6-NITR&Spiro[1,3,3-trimethylindole-(6'-nitrochroman)]1,3,3-Trimethylindolino-6-nitrobenzopyrylospirane1',3'-dihydro-1',3',3'-trimethyl-6-nitro-spiro(2H1,3,3-trimethyl-6'-nitroindole-2-spiro-2'-benzopyran
216-102-51',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indoline]1,3,3-Trimethylindolino-6'-nitrobenzopyrylospiranMFCD000591751',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]6'-Nitro-1,3,3-trimethylindolinobenzopyrylspiranSpiro[2H-1-benzopyran-2,2'-indoline], 1',3',3'-trimethyl-6-nitro-1,3,3-Trimethyl-6'-nitroindoline-2-spiro-2'-benzopyran
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 58.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 555
Physicochemical properties
- Melting point
- 32 °C · 32°C
- Boiling point
- 460.98 °C · 460.98°C (rough estimate)
- Density
- 1.2336 · 1.2336 (rough estimate)
- refractive index
- 1.614 · 1.6140 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 2.41 · 2.41±0.40(Predicted)
- color
- Light yellow to Yellow to Green
- λmax
- 242 nm · 242 nm in ethanol
- InChI
- InChI=1S/C19H18N2O3/c1-18(2)15-6-4-5-7-16(15)20(3)19(18)11-10-13-12-14(21(22)23)8-9-17(13)24-19/h4-12H,1-3H3
- InChIKey
- PSXPTGAEJZYNFI-UHFFFAOYSA-N
- SMILES
- C12(C(C)(C)C3=C(N1C)C=CC=C3)OC1=CC=C([N+]([O-])=O)C=C1C=C2
- EWG's Food Scores
- 1 · 1
- EPA Substance Registry System
- 2 H-1-benzopyran-2,2'-[2H]indole], · Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro- (1498-88-0)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- WG9810000
- hs_code
- 29349990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationSpiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-: INACTIVE
Applications
UsesNitroBIPS is used as a photochromic dye which can be incorporated in poly(vinylalcohol)(PVA) by electro-spinning to form PVA-spiropyran nanofibres. It has photo-responsive behaviour that may be useful in optical data storage applications. It can be used to dope liquid crystal to develop a coloured scattering device that is dual responsive and allows the initiation of electrohydrodynamic instabilities(EHDI). Addition of NitroBIPS can modify the transparency from 100% to 16%, providing a shielding effect which can be used for smart window applications. It may also be used to enhance the adhesion property of polystyrene(PS) on the glass substrate by improving the shear strength by a factor of 7.
General Description1′,3′-Dihydro-1′,3′,3′-trimethyl-6-nitrospiro(2H-1-benzopyran-2,2′-(2H)-indole)(NitroBIPS) is a photochromic biocompatible spiropyran molecule that has six nitro groups positioned at the benzopyran section. It has a colourless leuco spiropyran form(SP) and coloured trans-merocyanine form(MC) that exhibits absorption peaks in the ultraviolet and visible regions respectively. NitroBIPS possesses a higher quantum yield in comparison to other spiropyran molecules and dissolves in a variety of solvents.
Suppliers68 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]
Related reactions
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Compound notes
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