| Identification | More | [Name]
6-NITROQUINOLINE | [CAS]
613-50-3 | [Synonyms]
6-NITROQUINOLINE
6-nitro-quinolin
Quinoline,6-nitro-
6-Nitroquinoline98%
6-Nitrochinolin
6-Nitro Quinoline-50g | [EINECS(EC#)]
210-346-6 | [Molecular Formula]
C9H6N2O2 | [MDL Number]
MFCD00006799 | [Molecular Weight]
174.16 | [MOL File]
613-50-3.mol |
| Chemical Properties | Back Directory | [Appearance]
beige to light brown powder | [Melting point ]
151-153 °C(lit.)
| [Boiling point ]
305.12°C (rough estimate) | [density ]
1.2190 (estimate) | [refractive index ]
1.6820 (rough estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [Water Solubility ]
Slightly soluble in water | [form ]
powder to crystal | [pka]
3.24±0.10(Predicted) | [color ]
Needles from water or alc | [BRN ]
136138 | [InChI]
InChI=1S/C9H6N2O2/c12-11(13)8-3-4-9-7(6-8)2-1-5-10-9/h1-6H | [InChIKey]
SMHPLBXIVNQFBA-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC([N+]([O-])=O)=CC=2)C=CC=1 | [CAS DataBase Reference]
613-50-3(CAS DataBase Reference) | [EPA Substance Registry System]
6-Nitroquinoline (613-50-3) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS08 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332-H351 | [Precautionary statements ]
P201-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S7:Keep container tightly closed .
S22:Do not breathe dust .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [RTECS ]
VC1900000
| [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Carc. 2 | [Toxicity]
mma-sat 100 mmol/plate MUREAV 58,11,78 |
| Hazard Information | Back Directory | [Chemical Properties]
beige to light brown powder | [Safety Profile]
Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. Seealso other nitroquinoline entries. | [Synthesis]
GENERAL STEPS: 6-bromoquinoline (0.5 mmol), copper(II) trifluoromethanesulfonate (45 mg, 0.125 mmol), potassium nitrite (KNO2, 128 mg, 1.5 mmol), and anhydrous dimethylsulfoxide (DMSO, 0.6 mL) were sequentially added to a pre-dried oven-dried pressure tube under nitrogen protection. The pressure tube was sealed with a PTFE screw cap with a micro-valve and purged by nitrogen for 5 min to remove air. Subsequently, the reaction mixture was stirred at room temperature for 10 minutes and then gradually warmed up to 130°C and the reaction was continued at this temperature for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, washed with excess ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography on silica gel (for entries 1-18 in Table 2) or basic alumina (for entries 19-23 in Table 2), using a solvent mixture of ethyl acetate and hexane as eluent, and the target product, 6-nitroquinoline, was finally obtained in good yield. | [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 12, p. 1511 - 1513
[2] Tetrahedron, 2013, vol. 69, # 31, p. 6409 - 6414 |
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