Home Cart 0 Sign in  
X

[ CAS No. 22304-67-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 22304-67-2
Chemical Structure| 22304-67-2
Chemical Structure| 22304-67-2
Structure of 22304-67-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 22304-67-2 ]

Related Doc. of [ 22304-67-2 ]

Alternatived Products of [ 22304-67-2 ]

Product Details of [ 22304-67-2 ]

CAS No. :22304-67-2 MDL No. :MFCD11505923
Formula : C9H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :PBDGBKWOAPXYHT-UHFFFAOYSA-N
M.W : 180.16 Pubchem ID :12533772
Synonyms :

Safety of [ 22304-67-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22304-67-2 ]

* 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.

  • Downstream synthetic route of [ 22304-67-2 ]

[ 22304-67-2 ] Synthesis Path-Downstream   1~37

YieldReaction ConditionsOperation in experiment
entspr. 4,6-Dimethoxyverb., AlCl3/Nitrobenzol;
4.6-Dimethoxy-5-methyl-isophthalaldehyd, HBr;
(yield)40percent;
  • 2
  • [ 22304-74-1 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride; nitrobenzene at 125℃;
  • 3
  • [ 5673-07-4 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Br2 / acetic acid 2: n-BuLi 3: AlCl3; PhNO2 / 125 °C
  • 4
  • [ 28006-86-2 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-BuLi 2: AlCl3; PhNO2 / 125 °C
  • 5
  • [ 22304-67-2 ]
  • [ 95-64-7 ]
  • 4,6-bis((3,4-dimethylphenylimino)methyl)-2-methylbenzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With acetic acid In ethanol at 50℃; for 6h; Inert atmosphere;
  • 6
  • [ 22304-67-2 ]
  • [ 58519-05-4 ]
  • C134H92N12O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With trifluoroacetic acid In N,N-dimethyl-formamide at 110℃; for 96h; Inert atmosphere;
  • 7
  • [ 100-97-0 ]
  • [ 608-25-3 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
58% With trifluoroacetic acid for 6h; Reflux; Inert atmosphere;
46% Stage #1: hexamethylenetetramine; 2-methylbenzene-1,3-diol With trifluoroacetic acid at 100℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride; water at 100℃; for 4h; Inert atmosphere;
45% Stage #1: hexamethylenetetramine; 2-methylbenzene-1,3-diol With trifluoroacetic acid at 80℃; Stage #2: With hydrogenchloride; water at 80℃; for 1h;
44% Stage #1: hexamethylenetetramine; 2-methylbenzene-1,3-diol In trifluoroacetic acid at 70 - 100℃; for 76h; Inert atmosphere; Stage #2: With hydrogenchloride; water In trifluoroacetic acid at 100℃; for 1h;

  • 8
  • [ 1236035-51-0 ]
  • [ 22304-67-2 ]
  • [ 1415963-97-1 ]
YieldReaction ConditionsOperation in experiment
32% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 9
  • [ 22304-67-2 ]
  • [ 20205-29-2 ]
  • [ 1415963-98-2 ]
YieldReaction ConditionsOperation in experiment
40% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 10
  • [ 22304-67-2 ]
  • 5-methoxy-2,3,3-trimethyl-1-propyl-3<i>H</i>-indolium; iodide [ No CAS ]
  • [ 1415963-99-3 ]
YieldReaction ConditionsOperation in experiment
39% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 11
  • [ 22304-67-2 ]
  • [ 5418-63-3 ]
  • [ 1415963-95-9 ]
YieldReaction ConditionsOperation in experiment
43% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 12
  • [ 22304-67-2 ]
  • [ 57019-81-5 ]
  • [ 1415964-00-9 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 13
  • [ 22304-67-2 ]
  • [ 20849-57-4 ]
  • [ 1415963-96-0 ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine In isopropyl alcohol for 6.5h; Reflux;
  • 14
  • [ 54-85-3 ]
  • [ 22304-67-2 ]
  • [ 1427388-11-1 ]
YieldReaction ConditionsOperation in experiment
90% In methanol Reflux;
  • 15
  • [ 22304-67-2 ]
  • [ 149525-64-4 ]
  • C57H66N6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In chloroform
  • 16
  • [ 4097-89-6 ]
  • [ 22304-67-2 ]
  • C39H48N8O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In chloroform at 20℃; for 24h;
  • 19
  • [ 22304-67-2 ]
  • C21H36Cl2N2O4Pt2S2 [ No CAS ]
  • C21H36Cl2N2O4Pt2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium sulfate / dichloromethane / 4 h / Reflux 2: sodium acetate / methanol / 18 h / Reflux
  • 20
  • [ 22304-67-2 ]
  • C29H39Cl2N4O2Pt2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium sulfate / dichloromethane / 4 h / Reflux 2: sodium acetate / methanol / 18 h / Reflux 3: dichloromethane / 48 h / 20 °C
  • 21
  • [ 22304-67-2 ]
  • [ 13330-41-1 ]
  • 7'-hydroxy-1,3,3,8'-tetramethylspiro[indoline-2,2'-chromene]-6'-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With piperidine In isopropyl alcohol for 0.166667h; Reflux; 6-Formyl-7-hydroxy-1',3',3',8-tetramethylspiro[[2H]chromene-2,2-indoline] (2a). Piperidine (0.1 mL) was added dropwise to a solution of 1,2,3,3-tetramethylindoleninium perchlorate (274 mg, 1 mmol) and 4,6-diformyl-2-methylresorcinol (1)-(190 mg, 1.05 mmol) in isopropyl alcohol (5 mL) with heating and the reaction mixture was refluxed for 10 min. The solvent was evaporated, the residue was purified by column chromatography on silica gel (eluent chloroform). The product was recrystallized from hexane. The yield was 68%, m.p. 82 °C.IR, /cm-1: 2965 (OH); 1634 (C=O); 1608 (C=C); 1101, 925 (Cspiro-O). 1H NMR (CDCl3), : 1.16 (s, 3 H, C(3)CH3);1.24 (s, 3 H, C(3)CH3); 1.82 (s, 3 H, C(8)CH3); 2.69 (s, 3 H,NCH3); 5.65 (d, 1 H, C(3)H, J = 10.3 Hz); 6.52 (d, 1 H,C(7)H, J = 7.7 Hz); 6.78-6.88 (m, 2 H, C(4)H and C(5)H);7.02-7.10 (m, 2 H, C(5)H and C(4)H); 7.16 (td, 1 H,C(6)H, J = 7.6 Hz, J = 1.2 Hz); 9.64 (s, 1 H, CHO); 11.64 (s, 1 H, OH). MS (EI, 70 eV), m/z (Irel(%)): 335 (72.4) [M+];320 (39.8); 159 (100.0); 158 (52.3); 144 (36.0). Found (%):C, 75.23; H, 6.25; N, 4.21. C21H21NO3. Calculated (%): C, 75.20;H, 6.31; N, 4.18.
  • 22
  • [ 22304-67-2 ]
  • ClO4(1-)*C13H16NO2(1+) [ No CAS ]
  • 6-formyl-5'-carboxy-7-hydroxy-1',3',3',8-tetramethylspiro[[2H]chromene-2,2'-indoline] [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With piperidine In isopropyl alcohol for 0.166667h; Reflux; General procedure: Piperidine (0.1 mL) was added dropwise to a solution of 1,2,3,3-tetramethylindoleninium perchlorate (274 mg, 1 mmol) and 4,6-diformyl-2-methylresorcinol (1)-(190 mg, 1.05 mmol) in isopropyl alcohol (5 mL) with heating and the reaction mixture was refluxed for 10 min. The solvent was evaporated, the residue was purified by column chromatography on silica gel (eluent chloroform).
  • 23
  • [ 608-25-3 ]
  • [ 3473-63-0 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-methylbenzene-1,3-diol; formamidine acetic acid With acetic anhydride In tetrahydrofuran at 55℃; for 24h; Sealed tube; Stage #2: With hydrogenchloride; water for 18h;
Stage #1: 2-methylbenzene-1,3-diol; formamidine acetic acid With acetic anhydride In tetrahydrofuran at 55℃; for 24h; Stage #2: With hydrogenchloride In water at 20℃; for 20h; 1.1.1 1) Synthesis of 4,6-dihydroxy-5-methyl-1,3-benzaldehyde Add to 250mL round bottom flask1 g (8.06 mmol) of 2-methyl m-diphenol and 3.35 g (32.2 mmol) of formamidine acetate,Add 150mL of dry THF as solvent,When heated to 55 ° C,Add 6.1 ml (64.5 mmol) of acetic anhydride,The reaction was continued for 24h. After the reaction was completed, the solvent was distilled off under vacuum, and 100 ml of water was added and stirred at room temperature for 2 h.Add 50 ml of 1M dilute hydrochloric acid and stir for 18 h. Suction filtered out orange-red solid,Washed twice with 100ml of water,Wash twice with 50ml petroleum ether,Get intermediate4,6-dihydroxy-5-methyl-1,3-benzaldehyde.
Stage #1: 2-methylbenzene-1,3-diol; formamidine acetic acid With acetic anhydride In tetrahydrofuran Stage #2: With water
Stage #1: 2-methylbenzene-1,3-diol; formamidine acetic acid With acetic anhydride In tetrahydrofuran at 95℃; for 24h; Stage #2: In tetrahydrofuran; water Acidic conditions;

  • 24
  • [ 22304-67-2 ]
  • [ 5418-63-3 ]
  • 7'-hydroxy-1,3,3,8'-tetramethylspiro[indoline-2,2'-chromene]-6'-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine In isopropyl alcohol for 2.5h; Reflux; 7'-hydroxy-1,3,3,8'-tetramethylspiro[indoline-2,2'-chromene]-6'-carbaldehyde (2) A mixture of triethylamine (0.14 mL, 1 mmol) and propan-2-ol (3 mL) was added dropwise to a boiling mixture of 3H-indolium salt 3 (0.3 g, 1 mmol), dihydroxyisophthalic aldehyde 2 (0.18 g, 1 mmol), and propan-2-ol (12 mL) over 30 min. The reaction mixture was refluxed for 2 h, the solvent was evaporated, the residue was purified by column chromatography on Al2O3 (eluent chloroform) and recrystallized. The yield was 54%, m.p. 110.5-112 °C (from heptane). Found (%): C, 75.35; H, 6.52; N, 4.03. C21H21NO3. Calculated (%): C, 75.20; H, 6.31; N, 4.18. 1H NMR (CDCl3), δ: 1.18 (s, 3 H, C(3)Me); 1.26 (s, 3 H, C(3)Me); 1.84 (s, 3 H, C(8')Me); 2.71 (s, 3 H, C(1)Me); 5.67 (d, 1 H, H(3'), J = 10.3 Hz); 6.54 (d, 1 H, H(7), J = 7.7 Hz); 6.84 (d, 1 H, H(4'), J = 10.3 Hz); 6.86 (dt, 1 H, H(5), J = 7.4 Hz, J = 1.0 Hz); 7.07 (dd, 1 H, H(4), J = 7.3 Hz, J = 0.9 Hz); 7.10 (s, 1 H, H(5')); 7.18 (dt, 1 H, H(6), J = 7.6 Hz, J = 1.2 Hz); 9.66 (s, 1 H, 6'-CHO); 11.67 (s, 1 H, 7'-OH).
  • 25
  • [ 22304-67-2 ]
  • C49H51N5O4Zn(2+)*2ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / isopropyl alcohol / 2.5 h / Reflux 2: isopropyl alcohol / 2 h / Reflux 3: [(2)H6]acetone / 20 °C
  • 26
  • [ 608-25-3 ]
  • [ 76-05-1 ]
  • [ 22304-67-2 ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: 2-methylbenzene-1,3-diol; trifluoroacetic acid With hexamethylenetetramine at 70℃; for 72h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 100℃; for 1h;
  • 27
  • [ 22304-67-2 ]
  • trans-1,2-Diaminocyclohexane [ No CAS ]
  • C30H44N4O4 [ No CAS ]
  • C60H72N8O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% In chloroform at 20℃; for 168h; Inert atmosphere;
  • 28
  • [ 22304-67-2 ]
  • trans-1,2-Diaminocyclohexane [ No CAS ]
  • C60H72N8O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In chloroform at 20℃; for 168h; Inert atmosphere;
  • 29
  • [ 22304-67-2 ]
  • [ 62-53-3 ]
  • 2-methyl-4,6-bis((phenylimino)methyl)benzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium sulfate In methanol; dichloromethane for 4h; Reflux;
  • 30
  • [ 22304-67-2 ]
  • [ 100-46-9 ]
  • 4,6-(bis(benzylimino)methyl)-2-methylbenzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium sulfate In methanol; dichloromethane for 4h; Reflux;
  • 31
  • [ 22304-67-2 ]
  • [ 618-36-0 ]
  • 2-methyl-4,6-bis((1-phenylethyl)imino)methylbenzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With sodium sulfate In methanol; dichloromethane for 4h; Reflux;
  • 32
  • tetrafluoroboric acid [ No CAS ]
  • [ 22304-67-2 ]
  • [ 3119-93-5 ]
  • C29H28N2O2S2(2+)*2BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.2% Stage #1: 4,6-dihydroxy-5-methyl-1,3-benzenedicarboxaldehyde; N-ethyl-2-methylbenzothiazolium iodide With piperidine In ethanol at 95℃; for 24h; Sealed tube; Stage #2: tetrafluoroboric acid In ethanol at 20 - 25℃; for 2h; 1.1.2 2) Synthesis of target product cyanine dye In a 50 mL round bottom flask, 179 mg (1 mmol) of intermediates 4,6-dihydroxy-5-methyl-1,3-benzaldehyde and 610 mg (2 mmol) of 3-ethyl-2-methylbenzothiazolium were added. IodideAdd 10 mL of absolute ethanol as a solvent,100 μl piperidine as a catalyst,Stir the reaction for 24 h at 95 ° C under closed conditions.Then the reaction was cooled to room temperature, 100 μl of fluoroboric acid was added, and the reaction was stirred at room temperature (20-25 ° C) for 2 hours.The solvent was distilled off under reduced pressure,Recrystallized from dichloro and petroleum ether.Finally, 483 mg of a black solid, that is, a near-infrared emitting cyanine fluorescent dye, was obtained with a yield of 71.2%.
  • 33
  • [ 22304-67-2 ]
  • [ 134-81-6 ]
  • C37H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; acetic acid Reflux;
  • 34
  • [ 22304-67-2 ]
  • [ 3119-93-5 ]
  • C29H28N2O2S2(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.2% Stage #1: 4,6-dihydroxy-5-methyl-1,3-benzenedicarboxaldehyde; N-ethyl-2-methylbenzothiazolium iodide With piperidine In ethanol at 95℃; for 24h; Inert atmosphere; Stage #2: With tetrafluoroboric acid In ethanol Inert atmosphere;
  • 35
  • [ 22304-67-2 ]
  • [ 72492-77-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / 6 h / 80 °C 2: water; sodium hydroxide / 1 h / 20 °C
  • 36
  • [ 22304-67-2 ]
  • 3,6,15-triamino-1,8,13-trihexyloxytriptycene [ No CAS ]
  • C206H236N12O24 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With trifluoroacetic acid In N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube; Inert atmosphere;
  • 37
  • tetrafluoroboric acid [ No CAS ]
  • [ 22304-67-2 ]
  • [ 5418-63-3 ]
  • C33H35N2O2(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 4,6-dihydroxy-5-methyl-1,3-benzenedicarboxaldehyde; 1,2,3,3-tetramethyl-3H-indolium iodide With piperidine In ethanol at 95℃; for 24h; Sealed tube; Stage #2: tetrafluoroboric acid In ethanol for 2h; Sealed tube; 2.2. Synthesis of the probe DpIn A mixture of compound 1 (45 mg, 0.25 mmol), 1,2,3,3-tetramethyl1indolium Iodide (165 mg, 0.55 mmol) and twodrops piperidine were dissolved in 10 mL EtOH. The reaction mixturewas stirred for 24 h at 95 C under sealed condition. Aftercooling to room temperature, added 150 lL HBF4 and kept stirringScheme 1. The structures of subcellular-targeting cyanines and the synthesis route of the probe DpIn and NaIn. i) a. Formamidine acetate, acetic anhydride, THF, 95 C, 24 h;bH2O, H+. ii) a. EtOH, piperidine; b. HBF4.Y. Cai, C. Liu, Z. Lei et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 265 (2022) 1204042 for 2 h. In this progress, the product precipitated as a brown powderand was isolated by filtration and recrystallized from aqueousethanol (70 mg, yield 63%). M.p. 300 C; HRMS: m/z [C33H35N2-O2 + H2O-BF4 - ]+ = 509.2799, calcd for 509.2710. 1H NMR(400 MHz, DMSO d6) d = 8.81 (s, 1H), 8.09 (d, J = 15.2 Hz, 2H),7.76 (d, J = 7.6 Hz, 2H), 7.67 (d, J = 8 Hz, 2H) 7.55-7.51 (m, 4H),7.44 (t, J = 15.2 Hz, 2H), 3.82 (s, 12H), 1.75 (d, J = 3.2 Hz, 12H),1.40 (s, 3H). 13C NMR(100 MHz, DMSO d6) d = 197.89, 179.12,142.72, 142.52, 129.15, 127.29, 123.00, 117.26, 113.44, 104.66,83.30, 50.61, 32.86, 28.43, 27.39, 27.30, 19.03.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 22304-67-2 ]

Aryls

Chemical Structure| 4396-13-8

[ 4396-13-8 ]

2,4,6-Trihydroxyisophthalaldehyde

Similarity: 1.00

Chemical Structure| 34374-88-4

[ 34374-88-4 ]

2,4,6-Trihydroxybenzene-1,3,5-tricarbaldehyde

Similarity: 1.00

Chemical Structure| 3328-71-0

[ 3328-71-0 ]

2,4-Dihydroxyisophthalaldehyde

Similarity: 1.00

Chemical Structure| 487-70-7

[ 487-70-7 ]

2,4,6-Trihydroxybenzaldehyde

Similarity: 1.00

Chemical Structure| 95-01-2

[ 95-01-2 ]

2,4-Dihydroxybenzaldehyde

Similarity: 1.00

Aldehydes

Chemical Structure| 4396-13-8

[ 4396-13-8 ]

2,4,6-Trihydroxyisophthalaldehyde

Similarity: 1.00

Chemical Structure| 34374-88-4

[ 34374-88-4 ]

2,4,6-Trihydroxybenzene-1,3,5-tricarbaldehyde

Similarity: 1.00

Chemical Structure| 3328-71-0

[ 3328-71-0 ]

2,4-Dihydroxyisophthalaldehyde

Similarity: 1.00

Chemical Structure| 487-70-7

[ 487-70-7 ]

2,4,6-Trihydroxybenzaldehyde

Similarity: 1.00

Chemical Structure| 95-01-2

[ 95-01-2 ]

2,4-Dihydroxybenzaldehyde

Similarity: 1.00