55%| A353427|Formula:C17H19ClN2O|Molecular Weight:302.798650000+ products instock " />
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CAS No. : | 92-32-0 | MDL No. : | MFCD00011725 |
Formula : | C17H19ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | INCIMLINXXICKS-UHFFFAOYSA-M |
M.W : | 302.80 | Pubchem ID : | 7085 |
Synonyms : |
Pyronin G; Pyronin J
|
Chemical Name : | 3,6-Bis(dimethylamino)xanthylium chloride |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P202-P201-P264-P280-P302+P352-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301-H315-H319-H341 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; at 60℃; for 0.5h;Inert atmosphere; | In a screw-cap test tube to a suspension of Pyronin Y (50 mg; 0.165 mmol) in MeCN (1 mL) <strong>[122194-07-4]dimethyl N,N-diisopropylphosphoramidite</strong> (32 mg; 0.165 mmol) was added at r.t. under Ar. The reaction mixture was warmed up to 60 C. and stirred for 30 min at this temperature. After cooling down to 0 C., DDQ (37 mg; 0.165 mmol) was added, and the reaction mixture was stirred for additional 10 min at 0 C. After warming up to r.t., the reaction mixture was directly subjected to column chromatography on SiO2 (30 g; MeCN?MeCN/H2O 20:1+0.1 v/v % of TFA). Fractions containing the title compound were evaporated to dryness, dissolved in water and extracted with CH2Cl2 (3*). The combined extracts were dried with Na2SO4 and evaporated to yield 32 mg (40%) of a dark violet solid. 1H NMR (400 MHz, CD3CN): delta=1.23 (d, JH-H=6.8 Hz, 6H, NiPr2), 1.26 (d, JH-H=6.8 Hz, 6H, NiPr2), 3.29 (s, 12H, 2*NMe2), 3.44-3.60 (m, 2H, NiPr2), 3.72 (d, JH-P=11.5 Hz, 3H, OMe), 6.74-6.77 (m, 2Har), 7.15 (dd, JH-H=9.9 and 2.7 Hz, 2Har), 8.89 (d, JH-H=9.9 Hz, 2Har) ppm. 13C NMR (100 MHz, CD3CN, APT): delta=18.1 (+), 21.8 (+, d, JC-P=2.7 Hz), 21.9 (+, d, JC-P=2.7 Hz), 47.0 (+, m), 52.0 (+, d, JC-P=5.8 Hz), 96.2 (+), 114.7 (+), 116.0 (-, d, JC-P=9.2 Hz), 132.2 (+, d, JC-P=3.3 Hz), 156.9 (-), 157.4 (-, d, JC-P=11.7 Hz) ppm. 31P NMR (162 MHz, CD3CN): delta=20.1 ppm. MS (ESI): m/z (positive mode, rel. int., %)=444.4 (100) [M-Cl]+. HPLC: tR=13.1 min (91%), B/A=30/70-100/0 in 25 min, column 4*250 mm, 1.2 mL/min, detection at 254 nm. UV/Vis (MeCN): lambdamax (epsilon)=616 nm (52455 M-1cm-1); fluorescence (MeCN): lambdaexcit=590 nm, lambdaem=649 nm, phifl=0.39. Standard: Oxazine 4, phifl=0.63 (MeOH). UV/Vis (PBS 7.4): lambdamax (epsilon)=628 nm (46051 M-1cm-1); fluorescence (PBS 7.4): lambdaexcit=590 nm, lambdaem=664 nm, phifl=0.11. Standard: Oxazine 4, phifl=0.63 (MeOH). |