[ CAS No. 84-83-3 ] {[proInfo.proName]}

Name: 84-83-3|1,3,3-Trimethyl-2-(formylmethylene)indoline|95%
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Quality Control of [ 84-83-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 84-83-3 ]

Product Details of [ 84-83-3 ]

CAS No. :	84-83-3	MDL No. :	MFCD00071813
Formula :	C₁₃H₁₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	201.26	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 84-83-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.31
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.27
TPSA :	20.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.33
Log Po/w (XLOGP3) :	2.53
Log Po/w (WLOGP) :	2.12
Log Po/w (MLOGP) :	2.11
Log Po/w (SILICOS-IT) :	2.75
Consensus Log Po/w :	2.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.247 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-2.6
Solubility :	0.502 mg/ml ; 0.00249 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.42
Solubility :	0.0767 mg/ml ; 0.000381 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 84-83-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 84-83-3 ]

* 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.

Upstream synthesis route of [ 84-83-3 ]
Downstream synthetic route of [ 84-83-3 ]

[ 84-83-3 ] Synthesis Path-Upstream 1~12

1
[ 118-12-7 ]
[ 68-12-2 ]
[ 84-83-3 ]

Reference： [1] Journal of Materials Chemistry C, 2017, vol. 5, # 21, p. 5111 - 5118
[2] Journal of the American Chemical Society, 2017, vol. 139, # 48, p. 17301 - 17304
[3] Chemische Berichte, 1959, vol. 92, p. 1809,1810
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8091 - 8101

2
[ 118-12-7 ]
[ 3724-43-4 ]
[ 84-83-3 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 48, p. 17301 - 17304
[2] Patent: KR2016/22280, 2016, A, . Location in patent: Paragraph 0166; 0174-0176

3
[ 1640-39-7 ]
[ 84-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1228 - 1243
[2] Patent: KR2016/22280, 2016, A,
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8091 - 8101

4
[ 19764-96-6 ]
[ 20200-86-6 ]
[ 84-83-3 ]

Reference： [1] Chemical Science, 2015, vol. 6, # 11, p. 6556 - 6563

5
[ 100-63-0 ]
[ 84-83-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8091 - 8101

6
[ 563-80-4 ]
[ 84-83-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8091 - 8101

7
[ 46149-03-5 ]
[ 84-83-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8091 - 8101

8
[ 19764-96-6 ]
[ 20200-86-6 ]
[ 84-83-3 ]

Reference： [1] Chemical Science, 2015, vol. 6, # 11, p. 6556 - 6563

9
[ 5418-63-3 ]
[ 84-83-3 ]

Reference： [1] Patent: KR2016/22280, 2016, A,

10
[ 118-12-7 ]
[ 93-61-8 ]
[ 84-83-3 ]

Reference： [1] Patent: US2126852, 1934, ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 22, p. 336
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 171
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 171

11
[ 5418-63-3 ]
[ 68-12-2 ]
[ 84-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1228 - 1243

12
[ 1592-43-4 ]
[ 20200-86-6 ]
[ 84-83-3 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 29, p. 5127 - 5130

[ 84-83-3 ] Synthesis Path-Downstream 1~86

1
[ 118-12-7 ]
[ 68-12-2 ]
[ 84-83-3 ]

Reference： [1]Journal of Materials Chemistry C,2017,vol. 5,p. 5111 - 5118
[2]Journal of the American Chemical Society,2017,vol. 139,p. 17301 - 17304
[3]Chemische Berichte,1959,vol. 92,p. 1809,1810
[4]Organic and Biomolecular Chemistry,2017,vol. 15,p. 8091 - 8101

2
[ 84-83-3 ]
[ 109-77-3 ]
[ 92968-17-7 ]

Reference： [1]Zeitschrift fur Elektrochemie und angewandte physikalische Chemie,1953,vol. 57,p. 785,786

3
[ 84-83-3 ]
[ 13399-12-7 ]
[ 108-24-7 ]
1,3-bis-{3,7-diethyl-6-[3-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-propenyl]-benzo[1,2-d;4,5-d']bisthiazolium-2-yl}-trimethinium; triperchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethoxymethyl acetate; ethyl ester of p-toluenesulfonic acid

Reference： [1]Mikhailenko,F.A. et al. [Chemistry of Heterocyclic Compounds, 1975, vol. 11, p. 324 - 329][Khimiya Geterotsiklicheskikh Soedinenii, 1975, vol. 11, p. 370 - 376]

4
[ 84-83-3 ]
[ 16105-44-5 ]
[ 3595-53-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 1328 - 1335
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1314 - 1321

5
[ 84-83-3 ]
[ 29182-42-1 ]
[ 3595-52-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 1328 - 1335
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 1314 - 1321

6
[ 84-83-3 ]
[ 52535-51-0 ]
2,2'-di<3-(1,3,3-trimethyl-2(3H)-indolylidene)-1-propenyl>-3,3,3',3'-tetramethyl-1,1'-tetramethylenedi(3H-indolium) diiodide [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 1956 - 1959
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 2212 - 2216

7
[ 84-83-3 ]
2-methyl-4,6-diphenylpyrilium tetrafluoroborate [ No CAS ]
BA⁽¹²⁷⁾S₀₀₅₃₈ [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 1295 - 1300
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 1607 - 1613

8
[ 84-83-3 ]
[ 55181-01-6 ]
1,3,3-Trimethyl-2-<3-(4-phenylbenzothiopyran-2-ylidene)propen-1-yl>-3H-indolium Perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 891 - 896
Khimiya Geterotsiklicheskikh Soedinenii,1982,p. 1173 - 1177

9
[ 84-83-3 ]
[ 77544-32-2 ]
[ 77544-26-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 172 - 175
Khimiya Geterotsiklicheskikh Soedinenii,1981,vol. 17,p. 236 - 239

10
[ 84-83-3 ]
C₂₅H₂₃N₂OS⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]
5-(1,3,3-trimethyl-3H-indolinylidene-2-propenyl)-2-(1,3,3-trimethyl-3H-indolio-2-vinyl)thiazolo<3,2-a>quinolinium 1-oxide perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,p. 343 - 346
Khimiya Geterotsiklicheskikh Soedinenii,1981,vol. 17,p. 481 - 484

11
[ 84-83-3 ]
2,4-bis(4-bromophenyl)-6-methylpyrylium boron tetrafluoride salt [ No CAS ]
C₃₁H₂₆Br₂NO⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 1295 - 1300
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 1607 - 1613

12
[ 84-83-3 ]
2,4-bis-(4-methoxy-phenyl)-6-methyl-pyrylium; perchlorate [ No CAS ]
1,3,3-Trimethyl-2-<3-<4,6-di(4-methoxyphenyl)pyranylidene-2>-1-propenyl>-3H-indoline Perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 34 - 38
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 44 - 48

13
[ 84-83-3 ]
[ 81903-37-9 ]
[ 81903-19-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,p. 183 - 189
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 206 - 213

14
[ 84-83-3 ]
3-methylpyrido<3,2,1-j,k>carbazolium perchlorate [ No CAS ]
3-<3-(1,3,3-trimethylindolinylidene-2)propenyl>pyrido<3,2,1-j,k>carbazolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 846 - 849
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 1059 - 1062

15
[ 84-83-3 ]
[ 174362-43-7 ]
2-bromo-4,6-bis<3-(1,3,3-trimethyl-2,3-dihydro-2-indolylidene)-1-propenyl>-m-xylene [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 2352 - 2358

16
[ 84-83-3 ]
2-tert-butyl-4-methylbenzopyrylium perchlorate [ No CAS ]
1,1,3-trimethyl-2-<3-(2-tert-butylbenzopyran-4-ylidene)-1-propen-1-yl>-3H-indolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 283 - 287
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 339 - 344

17
[ 84-83-3 ]
2-methyl-4-tert-butylbenzopyrylium [ No CAS ]
1,1,3-trimethyl-2-<3-(4-tert-butylbenzopyran-2-ylidene)-1-propen-1-yl>-3H-indolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 283 - 287
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 339 - 344

18
[ 84-83-3 ]
2-methyl-4-tert-butylbenzothiopyrylium perchlorate [ No CAS ]
1,1,3-trimethyl-2-<3-(4-tert-butylbenzothiopyran-2-ylidene)-1-propen-1-yl>-3H-indolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 283 - 287
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 339 - 344

19
[ 84-83-3 ]
[ 35085-89-3 ]
[ 81903-30-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,p. 183 - 189
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 206 - 213

20
[ 84-83-3 ]
1,3,6-Trimethyl-2-phenyl-cyclohepta[c]pyrrolium; perchlorate [ No CAS ]
1,3-Dimethyl-2-phenyl-6-{(E)-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-propenyl}-cyclohepta[c]pyrrolium; perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1994,vol. 30,p. 173 - 177
Khimiya Geterotsiklicheskikh Soedinenii,1994,p. 193 - 198

21
[ 84-83-3 ]
5-(1-methyl-1-(2-methylaminophenyl)ethyl)pyrazoline [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1994,vol. 30,p. 789 - 792
Khimiya Geterotsiklicheskikh Soedinenii,1994,p. 915 - 918

22
[ 84-83-3 ]
4-Methyl-1-(1-naphthylmethyl)quinolinium perchlorate [ No CAS ]
1-(1-Naphthylmethyl)-4-<3-(1,3,3-trimethyl-2-indolinylidene)-1-propenyl>quinolinium perchlorate [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1997,vol. 67,p. 1482 - 1485
[2]Russian Journal of Organic Chemistry,1998,vol. 34,p. 137 - 138

23
[ 84-83-3 ]
[ 76659-39-7 ]
2-<2-(1,3,3-trimethyl-2-methyleneindolyl)ethenyl>thiazolo<4,5-b>quinoxaline [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 1353 - 1356

24
[ 84-83-3 ]
[ 94785-83-8 ]
2-<2-(1,3,3-trimethyl-2-methyleneindolyl)-1-methylethenyl>thiazolo<4,5-b>quinoxaline [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 1353 - 1356

25
[ 84-83-3 ]
2-pentafluorophenyl-4-phenyl-5,6,7,8-tetrahydro-benzopyrylium perchlorate [ No CAS ]
1,3,3-trimethyl-2-[2-(2-pentafluorophenyl-4-phenyl-6,7-dihydro-5H-1-benzopyran-8-yl)vinyl]-3H-indolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1998,vol. 34,p. 444 - 451

26
[ 84-83-3 ]
2,6-di(2-thienyl)-4-methylpyrilium perchlorate [ No CAS ]
1,3,3-trimethyl-2-{3-[2,6-di(α-thienyl)pyran-4-ylidene]prop-1-en-1-yl}indolium perchlorate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1998,vol. 34,p. 438 - 443

27
[ 84-83-3 ]
[ 443795-60-6 ]
2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-6,7-dichlorothiazolo[4,5-b]quinoxaline [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 303 - 308

28
[ 84-83-3 ]
[ 1495-54-1 ]
N-[2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-yl-idene)ethylidene]phosphorodifluoridamide [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2006,vol. 55,p. 585 - 587

29
2-amino-3-methyl-5-diisopropylamino-1,3,4-thiadiazolium methosulphate [ No CAS ]
[ 75-75-2 ]
[ 84-83-3 ]
CH₃O₃S^(1-)*C₂₂H₃₂N₅S⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	In toluene; for 12h;Heating / reflux;	Example 1; 8.1 g of 2-amino-3-methyl-5-diisopropylamino-1,3,4-thiadiazolium methosulphate, prepared from 2-amino-5-diisopropylamino-1,3,4-thiadiazole and dimethyl sulphate, and 5 g of 1,3,3-trimethyl-2-methylene-3H-indol-omega-aldehyde were boiled in a mixture of 25 ml of toluene and 2,3 g of methanesulphonic acid for 12 hours using a water separator. After cooling, 50 ml of hexane were added and the oil which separated out was separated off. This was taken up in 200 ml of water. The aqueous phase was extracted three times with 200 ml each time of chloroform. The chloroform phase was evaporated on a rotary evaporator. This gave 2.3 g (19% of theory) of a red powder of the formula [C00019] [00241] m.p.=115 C. [00242] lambdamax(methanol)=544 nm [00243] epsilon=96235 l/mol cm [00244] lambda1/2-lambda1/10(short wavelength flank)=36 nm [00245] lambda1/2-lambda1/10(long wavelength flank)=13 nm [00246] Solubility: >2% in TFP (2,2,3,3-tetrafluoropropanol) [00247] Glass-like film

Reference： [1]Patent: US6835725,2004,B2 .Location in patent: Page column 19-20

30
[ 84-83-3 ]
[ 613-94-5 ]
[ 389610-87-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol; for 1h;Heating / reflux;	[Example 1]; <Synthesis of hydrazide ligand (L-1)>; [Show Image] 2-(1,3,3-Trimethylindoline-2-ylidene)acetaldehyde (1.0 g) and benzhydrazide (0.70 g) in ethanol (20 ml) were stirred under heating for one hour. The reaction mixture was cooled to room temperature, and water (20 ml) was added thereto. The generated solid was filtered out, washed with water (10 ml) and ethyl acetate (10 ml), followed by drying, to give the light yellow target compound (L-1) (1.3 g, yield 82%). The resulting compound was identified by 1H NMR. NMR(CDC13) delta: 8.57 (d, J = 10.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 2H), 7.5-7.4 (m, 3H), 7.25-7.1 (m, 2H), 6.90 (t, J = 8.0 Hz, 1H), 6.68 (d, J = 8.0 Hz, 1H), 5.60 (d, J = 10.0 Hz, 1H), 3.22 (s, 3H), 1.57 (s, 6H)

Reference： [1]Patent: EP2050794,2009,A1 .Location in patent: Page/Page column 70-71

31
[ 84-83-3 ]
[ 30866-24-1 ]
[ 1006589-41-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	In methanol; for 1h;Heating / reflux;	{Example 3]; <Synthesis of hydrazide ligand (L-2)>; [Show Image] 2-(1,3,3-Trimethylindoline-2-ylidene)acetaldehyde (1.0 g) and ethyl 3-hydrazino-3-oxopropionate (1.0 g) in methanol (30 ml) were stirred under heating for one hour. The solvent was removed from the reaction mixture by distillation under reduced pressure conditions. Extraction was performed with ethyl acetate, and after washing with a saline solution, the organic layer was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure conditions. Recrystallization from chloroform and hexane gave the light yellow target compound (L-2) (0.62 g, yield 38%). The resulting compound was identified by DEI-MS. DEI-MS (measured value): 329 (M+), calculated value: 329

Reference： [1]Patent: EP2050794,2009,A1 .Location in patent: Page/Page column 72-73

32
[ 865876-82-0 ]
[ 84-83-3 ]
6-methyl-2-oxo-3-[(2E,4E)-4-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-2-enoyl]-2H-pyran-4-yl difluoridoborate [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1054 - 1060

33
[ 84-83-3 ]
[ 108-45-2 ]
(3-[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate) [ No CAS ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1981 - 1991

34
[ 84-83-3 ]
[ 106-50-3 ]
(4-[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate) [ No CAS ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1981 - 1991

35
[ 84-83-3 ]
[ 2243-62-1 ]
(5-[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}-1-naphthyl)-(E)-2-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolyl)-1-ethen-1-amine bis(hydrogen sulfate) [ No CAS ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1981 - 1991

36
[ 84-83-3 ]
[ 5873-51-8 ]
C₃₈H₄₀N₄S⁽²⁺⁾*2HO₄S^(1-) [ No CAS ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1981 - 1991

37
1,2,3,3,5,6,7,7-octamethyl-3,7-dihydropyrrolo[2,3-f]indolediium di(4-methyl-1-benzenesulfonate) [ No CAS ]
[ 84-83-3 ]
2-[3-[1,3,3,5,7,7-hexamethyl-6-[3-(1,3,3-trimethyl-3H-indolium-2-yl)-2-propenylidene]-1,2,3,5,6,7-hexahydropyrrolo[2,3-f]indol-2-yliden]-1-propenyl]-1,3,3-trimethyl-3H-indolium di(4-toluenesulfonate) [ No CAS ]

Reference： [1]Dyes and Pigments,2010,vol. 85,p. 7 - 15

38
[ 84-83-3 ]
[ 1309374-44-4 ]
[ 108-24-7 ]
[ 1309374-46-6 ]

Yield	Reaction Conditions	Operation in experiment
5.6%	at 105℃; for 1h;	2-(5-(5-(4-carboxyphenylazo)-1,3,3-trimethyl-2-yliden)prop-1-enyl)-1,3,3-trimethyl-3H-indolium acetate (4). 5 g (15.6 mmol) of 5-(4-carboxyphenyl-azo)-1,3,3-trimethyl-2-methyleneindoline (2) and 3.1 g (15.4 mmol) of <strong>[84-83-3]2-(1,3,3-trimethylindolin-2-ylidene)acetaldehyde</strong> were heated in 50 mL of acetic anhydride at 105 C. for 1 h. After cooling to room temperature, acetic anhydride was removed under reduced pressure and the residue was applied to a silica gel column; elution with a gradient of 0:1-1:19 MeOH-DCM provided cyanine (4) as dark blue solid. Yield: 500 mg (5.6%); TLC Rf 0.48 (1:9 MeOH-DCM). UV/Vis (methanol) lambdamax (nm) 630 (epsilon=116,300 ESIMS 567.9 [C34H36N4O4 (M+H)+ requires 565.7].
5.6%	at 105℃; for 1h;	2-(5-(5-(4-carboxyphenylazo)-1,3,3-trimethyl-2-yliden)prop-1-enyl)-1,3,3-trimethyl-3H-indolium acetate (4). 5 g (15.6 mmol) of 5-(4-carboxyphenyl-azo)-1,3,3-trimethyl-2-methyleneindoline (2) and 3.1 g (15.4 mmol) of <strong>[84-83-3]2-(1,3,3-trimethylindolin-2-ylidene)acetaldehyde</strong> were heated in 50 mL of acetic anhydride at 105 C for 1 h. After cooling to room temperature, acetic anhydride was removed under reduced pressure and the residue was applied to a silica gel co lumn; elution with a gradient of 0:1 - 1:19 MeOH-DCM provided cyanine (4) as dark blue solid. Yield: 500 mg (5.6 %); TLC Rf 0.48 (1:9 MeOH-DCM). UV/Vis (methanol) lambdamax (nm) 630 (epsilon =116,300 M-1cm-1). ESIMS 567.9 [C34H36N4O4 (M+H)+ requires 565.7].

Reference： [1]Patent: US7956169,2011,B1 .Location in patent: Page/Page column 9-10; 15
[2]Patent: EP2397464,2011,A1 .Location in patent: Page/Page column 14

39
[ 84-83-3 ]
[ 1217552-67-4 ]
[ 1217552-77-6 ]

Reference： [1]Russian Chemical Bulletin,2008,vol. 57,p. 1734 - 1739

40
[ 84-83-3 ]
[ 1262110-39-3 ]
[ 1262110-48-4 ]

Reference： [1]Dyes and Pigments,2011,vol. 89,p. 76 - 85

41
[ 84-83-3 ]
C₁₁H₉BF₂O₂ [ No CAS ]
[ 1262110-50-8 ]

Reference： [1]Dyes and Pigments,2011,vol. 89,p. 76 - 85

42
[ 84-83-3 ]
[ 55923-05-2 ]
[ 1262110-51-9 ]

Reference： [1]Dyes and Pigments,2011,vol. 89,p. 76 - 85

43
[ 84-83-3 ]
[ 1332702-67-6 ]
[ 1332702-68-7 ]

Reference： [1]Dyes and Pigments,2012,vol. 92,p. 749 - 757

44
[ 673-22-3 ]
[ 84-83-3 ]
[ 108-94-1 ]
[ 1392488-00-4 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 13510 - 13523

45
4,4-difluoro-1,3,5,7-tetramethyl-8-(4-hydroxyphenyl)-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
[ 84-83-3 ]
[ 1403241-74-6 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 10529 - 10531,3

46
[ 84-83-3 ]
[ 2510-00-1 ]
[ 1612140-22-3 ]

Yield	Reaction Conditions	Operation in experiment
85.7%	With acetic anhydride; for 0.5h;Reflux;	2-(1H-inden-2(3H)-ylidene)malononitrile (2) (500 mg, 2.80 mmol) and MIA (1) (1.30 g, 6.10 mmol) were added to acetic anhydride (10 mL) in a two-necked round bottom flask and heated to reflux for 30 min. The solution was cooled to room temperature and 10 mL of isopropanol was added. The solution was further cooled to 0-5 C and stirred for 15 min. Solid separated was filtered off and washed with pre-cooled isopropanol to afford R1 (1.30 g, 85.7%) as dark olive green crystals. M. Pt.: 277-280 C; IR (thin film, cm-1) 3048, 2965, 2184, 1611, 1591, 1532, 1488, 1457, 1362, 1323, 1196, 1114, 1074, 1019, 792, 737; 1H NMR (400 MHz, CD3COCD3, 25 C, ppm) d 8.90 (d, J 13.5 Hz, 2H), 7.99-7.92 (m, 2H), 7.49-7.47(m, 2H), 7.36-7.32 (m, 2H), 7.27-7.25 (m, 2H), 7.18-7.11 (m, 4H), 6.62 (d, J 13.5 Hz, 2H), 3.61 (s, 6H), 1.82 (s, 12H); 13C NMR(50.3 MHz, CD2Cl2, 25 C, ppm) d 169.4, 165.1, 143.6, 140.8, 138.5,134.2, 127.8, 125.4, 124.9, 122.5, 122.2, 121.8, 120.9, 108.1, 95.0, 50.9,47.6, 29.9, 27.6; HRMS (EI): calcd for C38H34N4 (m/z) 546.2778; found 546.2774.

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 15 - 23

47
[ 84-83-3 ]
[ 1612140-23-4 ]
[ 1612140-24-5 ]

Yield	Reaction Conditions	Operation in experiment
73.6%	With acetic anhydride; at 100℃; for 1h;	Compound 3 (900 mg, 2.80 mmol) and compound 1 (1.30 g, 6.10 mmol) were added to acetic anhydride (10 mL) in a two neckedround bottom flask and heated at 100 C for one hour. The solution was cooled to room temperature and 10 mL of isopropanol was added. The solution was further cooled to 0 C and stirred for 15 min. Solid separated was filtered off and washed with ethanol until the red filtrate became clear. Finally the solid wasrefluxed with 20 mL of chloroform for 15 min and filtered to get thetitle compound R2 (1.40 g, 73.6%) as a sparkly green crystalline powder. M. Pt.: 306-309 C; IR (thin film, cm-1) 3057, 2971, 2928, 1606, 1586, 1511, 1487, 1353, 1321, 1281, 1160, 1153, 1106, 1053, 1032,1015, 916, 806, 790; 1H NMR (400 MHz, CD2Cl2, 25 C, ppm) d 8.35(d, J 14.8 Hz, 2H), 7.96-7.89 (M, 2H), 7.45-7.42 (m, 4H), 7.38-7.36(m, 2H); 7.31-7.27 (m, 2H); 7.18-7.16 (m, 2H), 6.92 (d, J 14.7 Hz,2H), 4.72e4.67 (q, 4H), 3.67 (s, 6H); 1.73 (s, 12H); 1.40 (t, 6H); 13CNMR (50.3 MHz, CD2Cl2, 25 C, ppm) d 175.1, 173.0, 172.8, 160.3,147.9, 146.3, 142.7, 141.3, 129.6, 128.3, 124.6, 121.0, 118.1, 116.4, 110.1,49.3, 42.6, 31.3, 28.4, 12.9; HRMS (EI): calculated for C43H44N4O2S(m/z) 680.3180; found 680.3178.

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 15 - 23

48
[ 84-83-3 ]
[ 1612140-25-6 ]
[ 1612140-26-7 ]

Yield	Reaction Conditions	Operation in experiment
55.3%	With acetic anhydride; at 100℃; for 1h;	Compound 6 (1.00 g, 2.46 mmol) and compound 1 (0.54 g, 2.71 mmol) were added to acetic anhydride (20 mL) in a round bottom flask and heated at 100 C for one hour. Solvent was removed under reduced pressure and water (100 mL) was added to the crude residue. The product was extracted in chloroform and the organic layer was separated, washed with water twice and removed to get crude product, which was subjected to column chromatography on silica (hexane:ethyl acetate 8:2) to afford 0.80 g (55.3%) of R3 as black powder. M. Pt.:221-224 C; IR (thin film,cm1): 3055, 2968, 2924, 2195, 1596, 1551, 1454, 1368, 1323, 1297,1208, 1116, 1092, 807, 744; 1H NMR (400 MHz, CDCl3, 25 C, ppm)d 8.78-8.71 (m, 1H), 8.33 (s, 1H), 8.23-8.19 (m, 1H), 7.87-7.77 (m,3H), 7.55-7.51 (m, 2H), 7.44-7.32 (m, 6H), 7.22-7.10 (m, 2H), 7.02-6.98 (m, 1H), 6.51-6.44 (m, 1H), 3.49 (s, 3H), 1.82 (s, 6H); 13C NMR(50.3 MHz, CD2Cl2, 25 C, ppm) d 171.0, 166.7, 156.7, 148.6, 145.7,140.7, 140.2, 139.4, 138.4, 137.8, 136.2, 135.1, 134.4, 133.4, 129.3,128.0, 125.6, 125.5, 125.0, 124.9, 123.7, 123.5, 123.1, 122.2, 122.1,121.9, 120.9, 108.5, 97.1, 95.2, 27.5; HRMS (EI): calculated forC38H27N3S2 (m/z) 589.1641; found 589.1634.

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 15 - 23

49
[ 84-83-3 ]
[ 1612140-27-8 ]
[ 1612140-28-9 ]

Yield	Reaction Conditions	Operation in experiment
49.4%	With acetic anhydride; at 100℃; for 1h;	Compound 8 (0.90 g, 1.72 mmol) and compound 1 (0.41 g, 2.06 mmol) were added to acetic anhydride (20 mL) in a round bottom flask and heated at 100 C for one hour. Reaction work-up and column purification was carried out, like previously reported for R3, to afford 0.60 g (49.4%) of R4 as blackish-brown powder. M. Pt.:166-169 C; IR (thin film, cm-1):3063, 2927, 2853, 2194, 1596, 1551, 1454, 1369, 1324, 1297, 1208,1117, 1094, 807, 794; 1H NMR (400 MHz, CDCl3, 25 C, ppm) delta 8.75-8.68 (m, 1H), 8.32 (s, 1H), 8.24-8.20 (m, 1H), 7.74-7.70 (m, 1H), 7.47-7.44 (m, 1H), 7.39-7.28 (m, 3H), 7.20-7.11 (m, 4H), 7.07-6.90 (m, 3H), 6.72-6.70 (m, 1H), 6.46-6.39 (m, 1H), 3.46 (s, 3H), 2.85-2.77 (m, 2H), 1.82 (s, 6H), 1.47-1.20 (m, 8H), 0.99-0.80 (m, 3H); 13CNMR (50.3 MHz, CDCl3, 25 C, ppm) delta 170.1, 167.4, 146.3, 143.3, 141.5, 140.7, 140.5, 138.4, 136.4, 135.5, 135.3, 134.5, 134.2, 134.1, 133.9, 129.0, 128.1, 125.8, 125.5, 125.4, 124.9, 123.9, 123.9, 123.8, 123.7, 123.5, 123.1, 122.3, 122.1, 108.3, 94.9, 59.4, 47.9, 31.5, 30.2, 30.0, 28.7, 27.8, 22.5, 14.0; HRMS (EI): calculated for C44H39N3S3 (m/z)705.2301; found 705.2290.

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 15 - 23

50
[ 1640-39-7 ]
[ 84-83-3 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1228 - 1243
[2]Patent: KR2016/22280,2016,A
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 8091 - 8101

51
[ 84-83-3 ]
9-(2-carboxy-phenyl)-6-diethylamino-1,2,3,4-tetrahydro-xanthenylium [ No CAS ]
3H-indolium-2-[2-[9-(2-carboxyphenyl)-6-(diethylamino)-2,3-dihydro-1H-xanthen-4-yl]ethenyl]-1,3,3-trimethylperchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	In acetic anhydride; at 50℃; for 1.5h;	Compound 1 (4.2 mmol, 1.58 g) and Fisheraldehyde (4.4 mmol, 0.88 g) were dissolved in acetic anhydride(25.0 mL), and the reaction mixture was stirred at 50 C for 1.5 h.Then, water (25.0 mL) was added to the reaction mixture to quenchthe reaction. After the solvent was evaporated under reduced pressure, the crude product was purified by silica gel columnchromatography using CH2Cl2/CH3CH2OH (20:1, v/v) as eluent toafford compound 2 as a green solid product. Yield: 0.59 g (25%). 1HNMR (400 MHz, CDCl3): delta 8.50 (d, J 12.0 Hz, 1H), 8.19 (d, J 8.0 Hz,1H), 7.93 (d, J 7.6 Hz, 1H), 7.55-7.62 (m, 3H),7.16 (s, 1H), 7.06 (q,2H), 6.48-6.60 (m, 3H), 5.92 (d, J 8.0 Hz, 1H), 3.57 (s, 3H), 3.48 (q,4H), 2.59 (t, J 8.0 Hz, 2H), 2.45 (t, J 8.0 Hz, 2H), 1.76 (8H), 1.13 (t,J 8.0 Hz, 6H). MS (TOF) m/z 559.4.
	With acetic anhydride; at 50℃; for 0.5h;	The product was not further purified.Used directly in the next step.Compound 2 (99.8 mg, 0.21 mmol)And Fisher's aldehyde (44.2 mg, 0.22 mmol) dissolved in 8 ml of acetic anhydride,Heat to 50 C.After the mixture was kept at the temperature for 30 minutes,The reaction mixture was quenched by adding 8 ml of water.The solvent was distilled off under reduced pressure to give a crude product.The green solid compound 3 was isolated by column chromatography gradient.

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 13495 - 13503
[2]Dyes and Pigments,2017,vol. 136,p. 817 - 824
[3]Analytical Chemistry,2016,vol. 88,p. 9746 - 9752
[4]Patent: CN104860957,2018,B .Location in patent: Paragraph 0023; 0028; 0031
[5]ChemBioChem,2019,vol. 20,p. 614 - 620

52
[ 84-83-3 ]
6-(diethylamino)-9-(4-(diethylamino)phenyl)-1,2,3,4-tetrahydroxanthylium perchlorate [ No CAS ]
6-(diethylamino)-9-(4-(diethylamino)phenyl)-4-(2-(1,3,3-trimethylindolin-2-ylidene)ethylidene)-1,2,3,4-tetrahydroxanthylium perchlorate [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 98985 - 98993

53
[ 84-83-3 ]
5-hydroxycarbonyl-1,2,3,3-tetramethylindoleninium iodide [ No CAS ]
C₂₆H₂₉N₂O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With acetic anhydride; at 145℃; for 24h;Inert atmosphere;	Under N2, 10.23 g (50.830 mmol, 1.01 eq) of the compound 1e, and 17.37 g (50.322 mmol, 1 eq) of the compound 2d were placed in 200 g of acetic anhydride and reacted at 145C for 24 hours. Cooled to room temperature,and precipitated in 2000 ml of diethyl ether. Filtered and dried under reduced pressure.The residue was purified by column (MC / MeOH = 18/1) to obtain 21.292 g (40.30 mmol) of the compound 3a. Yield 80%

Reference： [1]Patent: KR2016/22280,2016,A .Location in patent: Paragraph 0166; 0189-0191
[2]Journal of the American Chemical Society,2017,vol. 139,p. 17301 - 17304

54
[ 118-12-7 ]
[ 3724-43-4 ]
[ 84-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane; water; for 1.75h;Cooling with ice;	4 g (13.28 mol) of the compound 1c was dissolved in 320 ml of diethyl ether: 2M NaOH = 1: 3 and stirred for 30 minutes. The organic layer was passed through MgSO4,solvent was removed under reduced pressure. 3 g (17.32 mmol, 1 eq) of the compound 1d,was dissolved in 30 ml of MC and the solution dissolved in 35 ml of MC ((Chloroethylene) dimethyliminium chloride) 2.5 g (1.953 mol, 1.13 eq) was slowly added. After stirring for 15 minutes, 75 ml of 10% aqueous NaOH solution in an ice bath was slowly added. The mixture was stirred for 1 hour and 30 minutes, and the organic layer was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and used in the next reaction without further separation.

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 17301 - 17304
[2]Patent: KR2016/22280,2016,A .Location in patent: Paragraph 0166; 0174-0176

55
[ 84-83-3 ]
C₂₂H₂₂N⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]
1-Methyl-2,4-diphenyl-8-<2-(1,3,3-trimethylindolin-2-ylidene)vinyl>-5,6,7,8-tetrahydroquinolinium Perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In isopropyl alcohol; acetonitrile;Heating;	Under stirring conditions,In a mixed solution of isopropanol and acetonitrile (1: 1 by volume)2,4-phenyl-5,6,7,8-tetrahydro-1-benzopyran perchlorate 4c (wherein X is a nitrogen methyl, n is 1, R2 is hydrogen) (2.5 Mmol),And then heated to dissolve to form a reaction mixture,(1,3,3-trimethylindoline-2-ylidene) -formaldehyde (2.5 mmol)After stirring for 15-30 minutes,The filter product precipitates.The filter cake was washed with ice-free ethanol and ice-free ether,Dried and recrystallized from absolute ethanol, the yield was 95%

Reference： [1]Patent: CN104164230,2017,B .Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040

56
[ 84-83-3 ]
[ 21016-30-8 ]
1,3,3-Trimethyl-2-<2-(2,4-diphenyl-5,6-dihydrocyclopentapyran-7-yl)-vinyl>-3H-indolium Perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In isopropyl alcohol; acetonitrile;Heating;	Under stirring conditions,In a mixed solution of isopropanol and acetonitrile (1: 1 by volume)The addition of 6,7-dihydro-2,4-diphenyl-5H-cyclopenta [b] pyrylium perchlorate for 4d (wherein X is oxygen, n is 0 and R2 is hydrogen) (2.5 Mmol),And then heated to dissolve to form a reaction mixture,(1,3,3-trimethylindoline-2-ylidene) -formaldehyde (2.5 mmol)After stirring for 15-30 minutes, the product was filtered.The filter cake was washed with ice-free ethanol and ice-free ether,Dried and recrystallized from absolute ethanol to obtain product 6k,Yield 95%

Reference： [1]Patent: CN104164230,2017,B .Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052

57
[ 84-83-3 ]
2-methyl-4,6-diphenylpyrilium tetrafluoroborate [ No CAS ]
(1-methyl-2,4-diphenyl-6-((1E,3E)-3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)pyryl-1-ium) tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69 mg	With acetic anhydride; for 1h;Reflux;	Pyrylium salt 6jc26 (50 mg, 0.14 mmol) and 2-(i,3,3-Trimethylindolin-2-ylidene)acetaldehyde (28 mg, 0.14 mmol) in acetic anhydride (2 mL) were stirred at reflux for 1 hour. The reaction was cooled and co-evaporated with toluene (x 3), washed with ether and decanted (x 2). The residue was purified by column chromatography DCM/MeOH and transferred to a vial to give a blue solid 69 mg.[0176] oeH(DMSO-d6, 400 MHz) 8.47 (t, 1 H, J = 13.2, HC=), 8.26-8.10 (m, 4 H, Ar), 7.95 (s, 1 H, Ar), 7.90-7.59 (m, 8 H, Ar), 7.53-7.44 (m, 2 H, Ar), 7.35 (t, 1 H, J = 7.6, Ar), 6.58 (d, 1 H, J = 13.2, HC=), 6.39 (br s, 1 H, HC=), 3.73 (s, 3 H, NMe), 1.74 (s, 6 H, 2 x CH3).

Reference： [1]Patent: WO2017/112668,2017,A1 .Location in patent: Paragraph 0098; 0175; 0176

58
[ 84-83-3 ]
2-methyl-4,6-di-p-tolylpyrylium boron tetrafluoride salt [ No CAS ]
2,4-di-p-tolyl-6-((1E,3E)-3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)pyrylium boron tetrafluoride salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71 mg	With acetic anhydride; for 0.5h;Reflux;	Pyrylium salt 6jc50-2 (50 mg, 0.14 mmol) and 2-(l,3,3-Trimethylindolin-2- ylidene)acetaldehyde (28 mg, 0.14 mmol) in acetic anhydride (2 mL) were stirred at reflux for 30 minutes. The reaction was cooled and co-evaporated with toluene (x 3), washed with ether and decanted (x 2). The blue solid was transferred to a vial to give 71 mg.[0178] oeH(DMSO-d6, 400 MHz) 8.41 (t, 1 H, J = 14.0, HC=), 8.09 (d, 1 H, J = 8.0, Ar), 8.05 (d, 1 H, J = 8.0, Ar), 7.91 (s, 1 H, Ar), 7.88-7.72 (m, 1 H, Ar), 7.62 (d, 1 H, J = 8.0, Ar), 7.5 1- 7.37 (m, 6 H, Ar), 7.30-7.24 (m, 1 H, Ar), 6.45 (d, 1 H, J = 14.0, HC=), 6.35 (br s, 1 H, HC=), 3.65 (s, 3 H, NMe), 2.43 (s, 3 H, ArCH3), 2.40 (s, 3 H, ArCH3), 1.69 (s, 6 H, 2 x CH3).

Reference： [1]Patent: WO2017/112668,2017,A1 .Location in patent: Paragraph 0177; 0178

59
[ 84-83-3 ]
C₂₄H₂₆NO₄⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]
C₃₇H₃₉N₂O₄⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With acetic anhydride; at 50℃; for 0.5h;	The mixture of compound 5 (1.0 g, 2.65 mmol) and fisher aldehyde (6) (0.53 g, 2.65 mmol) in acetic anhydride (20 mL) was stirred at 50C for 30 min. After quenching the reaction with water, acetic anhydride was removed under vacuum. The crude was dissolved in dichloromethane (40 mL) and washed sequentially with aqueous sodium bicarbonate (2×60 mL), water (2×60 mL), and brine (1×60 mL). The organic layer was collected, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and the resulting crude product was purified by column chromatography with DCM/EtOH (100:1 to 20:1, v/v) as an eluent to yield a green solid (1.2 g, 81%). 1H NMR (400 MHz, CDCl3): delta 8.55-8.51 (d, J = 16.0 Hz, 1H), 8.20-8.18 (d, J = 8.0 Hz, 1H), 7.69-7.65 (t, J = 8.0 Hz, 1H), 7.56-7.52 (t, J = 8.0 Hz, 1H), 7.40-7.33 (m, 2H), 7.21-7.17 (t, J = 8.0 Hz 1H), 7.12-7.10 (d, J = 8.0 Hz, 2H) 6.68-6.66 (d, J = 8.0 Hz, 1H), 6.58-6.54 (d, J = 16.0 Hz, 2H), 6.03-5.99 (d, J = 16.0 Hz, 1H), 3.62 (s, 3H), 3.50-3.45 (q, J = 6.0 Hz 4H), 2.64-2.60 (m, 2H), 2.28-2.19 (m, 2H), 1.79-1.62 (m, 8H), 1.24-1.21 (t, J = 6.0 Hz 6H). 13C NMR (100 MHz, CDCl3): delta 173.16, 163.49, 156.14, 152.21, 143.12, 140.77, 136.24, 128.91, 125.20, 121.30, 113.77, 112.47, 110.63, 99.42, 96.00, 49.28, 45.39, 31.74, 28.69, 26.79, 20.66, 12.71. IR (cm-1): 2929.48, 1721.13, 1623.12, 1549.74, 1437.80, 1364.98, 1287.25, 1247.29, 1222.42, 1039.37, 1015.63, 922.64, 796.06, 747.76, 710.27. HRMS (FAB) calcd for C37H40N2O3 [M+H]+, 560.3040; found, 560.3000.

Reference： [1]Inorganica Chimica Acta,2017,vol. 468,p. 140 - 145

60
[ 86-90-8 ]
[ 84-83-3 ]
[ 108-94-1 ]
[ 99-07-0 ]
C₃₅H₃₄BrN₂O₃⁽¹⁺⁾ [ No CAS ]
C₃₅H₃₄BrN₂O₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 8091 - 8101

61
[ 84-83-3 ]
7-(diethylamino)-2-methylchromenylium perchlorate [ No CAS ]
C₄₀H₄₅N₃O⁽²⁺⁾*2ClO₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	In acetic anhydride; at 50℃; for 0.666667h;	A solution of 14 3 (200.0mg, 0.60mmol) and Fisher aldehyde (241.4mg, 1.2mmol) in 17 acetic anhydride (8.0mL) was heated to 50C for 40min. Then, 18 water (8.0mL) was slowly added to the mixture to quench the reaction. The solvent was removed under reduced pressure to give the crude product. The crude product was purified by column chromatograph on silica gel eluting with dichloromethane and methanol (20:1, v/v) to afford product as dark brown solid (63.0mg, 16%). Mp>250.0C. IR nu (KBr, cm-1): 2975, 1632, 1549, 1498, 1444, 1227, 1090. 1H NMR (400MHz, DMSO-d6) delta 8.50 (d, J=8.5Hz, 1H, Ar-H), 8.35 (d, J=15.3Hz, 2H, 2×CH), 7.96 (d, J=9.2Hz, 1H, Ar-H), 7.81 (d, J=7.3Hz, 2H, 2×Ar-H), 7.73 (d, J=7.9Hz, 2H, 2×Ar-H), 7.66 (d, J=8.5Hz, 1H, Ar-H), 7.57 (t, J=7.6Hz, 2H, 2×Ar-H), 7.48 (t, J=7.4Hz, 2H, 2×Ar-H), 7.36 (d, J=9.0Hz, 1H, Ar-H), 7.06 (d, J=15.3Hz, 2H, 2×CH), 7.01 (s, 1H, Ar-H), 3.92 (s, 6H, 2×CH3), 3.68 (q, J=5.6Hz, 4H, 2×CH2), 1.82 (s, 12H, 4×CH3), 1.24 (t, J=6.6Hz, 6H, 2×CH3). 13C NMR (151MHz, DMSO-d6) delta 178.7, 167.5, 158.5, 154.8, 147.4, 146.0, 142.7, 142.6, 131.9, 129.2, 127.6, 123.1, 116.3, 116.1, 114.0, 113.6, 112.5, 106.8, 96.1, 50.9, 45.6, 33.2, 27.0, 12.9. HRMS (ESI+): m/z=291.6763 (calcd for [M- 2ClO4-]2+, 291.6781).

Reference： [1]Dyes and Pigments,2018,vol. 149,p. 505 - 511

62
[ 84-83-3 ]
C₃₅H₄₂ClNOP⁽¹⁺⁾*Br^(1-) [ No CAS ]
C₃₀H₄₁ClN₂O [ No CAS ]