[ CAS No. 29150-63-8 ] {[proInfo.proName]}

Name: 29150-63-8|Benzo[1,2-b:3,4-b':5,6-b'']trithiophene|96%
Brand: Ambeed
SKU: A126098
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Quality Control of [ 29150-63-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 29150-63-8 ]

Product Details of [ 29150-63-8 ]

CAS No. :	29150-63-8	MDL No. :	MFCD22381057
Formula :	C₁₂H₆S₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DKSAJSCNXULKER-UHFFFAOYSA-N
M.W :	246.37	Pubchem ID :	44225674
Synonyms :

Calculated chemistry of [ 29150-63-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.59
TPSA :	84.72 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	4.98
Log Po/w (WLOGP) :	5.33
Log Po/w (MLOGP) :	4.06
Log Po/w (SILICOS-IT) :	7.04
Consensus Log Po/w :	4.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.24
Solubility :	0.0014 mg/ml ; 0.00000569 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.5
Solubility :	0.0000783 mg/ml ; 0.000000318 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.24
Solubility :	0.00142 mg/ml ; 0.00000578 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.36

Safety of [ 29150-63-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 29150-63-8 ]

* 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 [ 29150-63-8 ]

[ 29150-63-8 ] Synthesis Path-Downstream 1~67

1
[ 106032-17-1 ]
[ 29150-63-8 ]
[ 122357-57-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205
[2]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205

2
[ 113201-28-8 ]
[ 29150-63-8 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 273 - 276
[2]Journal of Organic Chemistry,1989,vol. 54,p. 4203 - 4205

4
[ 29150-63-8 ]
[ 211737-28-9 ]
2,5,8-tris(5-hexyl-2-thienyl)benzo[1,2-b:3,4-b':5,6-b'']trithiophene [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 273 - 276

5
[ 29150-63-8 ]
[ 655249-04-0 ]
2,5,8-tris[5-(5-hexyl-2-thienyl)-2-thienyl]benzo[1,2-b:3,4-b':5,6-b'']trithiophene [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 273 - 276

6
[ 351014-15-8 ]
[ 29150-63-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium sulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 190℃; for 12h;Inert atmosphere;	50mL round bottom flask was added compound 2 (0.94g, 2mmol), sodium sulfide nonahydrate (2.67g, 12mmol) and N- methylpyrrolidinone (20mL), 190 under nitrogen for 12 hours.After the reaction was cooled to room temperature, poured into aqueous ammonium chloride solution, filtered, the cake washed with petroleum ether and subjected to silica gel column chromatography eluent, to give a white solid 3 (0.33g, 67% yield).
62%	With sodiumsulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 180 - 190℃; for 38h;	Synthesis Example 3 Synthesis of benzo[1,2-b:3,4-b':5,6-b"]trithiophene (Scheme 1-(2)) [Show Image] In a 30 mL round-bottom flask, sodium sulfide nonahydrate (7.74 g, 32.2 mmol) and NMP (138 mL) were placed and stirred for 15 minutes. Subsequently, 1,3,5-trichloro-2,4,6-tris(trimethylsilylethynyl)benzene (3.0 g, 6.38 mmol) obtained in Synthesis Example 2 was added and heated at 180-190C for 38 hours. After completion of the reaction, the reaction mixture was poured into a saturated aqueous ammonium chloride solution (700 mL) and a precipitated solid substance was obtained by filtration. The resultant solid substance was extracted with chloroform (210 mL), washed with saturated saline solution and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure and purification was performed by column chromatography (hexane, butch, Rf = 0.5) to obtain a white solid substance (814 mg, 62%). 1H-NMR(270MHz,CDCl3)δ7.64(d,J=5.4Hz,3H)7.54(d,J=5.4Hz,3H); 13C-NMR(99.5MHz,CDCl3)δ131.94, 131.55, 125.11, 122.44; M.S.(70eV,EI)m/z=246(M+); m.p.156.7-157.7C
60%	With sodiumsulfide nonahydrate; In 1-methyl-pyrrolidin-2-one; at 185 - 195℃; for 12h;	Under nitrogen atmosphere, sodium sulfide nonahydrate (1.54 g, 6.42 mmol) was added to anhydrous NMP (40 ml) and the mixture was stirred for ten minutes. To this mixture, 1,3,5-trichloro-2,4,6-tris[(trimethylsilyl)ethinyl]benzene (Compound 100)(500 mg, 1.07 mmol) was added, followed by heating at 185C to 195C for 12 hours. Upon completion of the reaction, the mixture was poured into water (400 ml) and precipitated solid was collected by filtration. The solid thus obtained was dissolved in chloroform (200 ml), and the resulting solution was washed with saturated saline. The solution was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. Solid thus obtained was purified by a column chromatography (silica gel and hexane), thereby white crystalline Compound 104 was obtained (156 mg, yield: 60%). 1H-NMR (270 MHz, CDCl3) δ7.64 (d, J=5.4 Hz, 3H) 7.54 (d, J=5.4 Hz, 3H), M.S. (70eV, EI) m/z=246 (M+)

Reference： [1]Patent: CN103288848,2016,B .Location in patent: Paragraph 0126-0127
[2]Organic Letters,2009,vol. 11,p. 2473 - 2475
[3]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 36
[4]Patent: EP2147923,2010,A1 .Location in patent: Page/Page column 18
[5]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5
[6]Patent: WO2017/98455,2017,A1 .Location in patent: Page/Page column 6; 7
[7]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340
[8]European Journal of Organic Chemistry,2017,vol. 2017,p. 5966 - 5974

7
[ 1174223-25-6 ]
[ 29150-63-8 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3230 - 3233
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 13594 - 13598
Angew. Chem.,2015,vol. 127,p. 13798 - 13802,5

8
[ 29150-63-8 ]
[ 1174223-26-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-Bromosuccinimide; In dichloromethane; acetic acid; at 20℃; for 48h;Inert atmosphere; Darkness;	Example 4 Synthesis of 2,5,8-Tribromobenzo[1,2-b:3,4-b':5,6-b"]trithiophene (33) [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flask, benzo[1,2-b:4,5-b':5.6-b"]trithiophene (800 mg, 3.25 mmol) obtained in Synthesis Example 3, methylene chloride (22.7 mL) and acetic acid (5.7 mL) were added. Under light exclusion conditions, NBS (1.73 g, 9.74 mmol) was added little by little and stirred at room temperature 48 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration and washed with ethanol (50 mL) and THF (20 mL) to obtain a light purple solid substance (1.2 g, 76%). 1H-NMR(270MHz,CDCl3)δ7.51(s,3H);M.S.(70eV,EI)m/z=484(M+)
52%	With N-Bromosuccinimide; In chloroform; for 12h;Inert atmosphere; Reflux;	General procedure: Under a nitrogen gas stream to IC-7-3 (14.5 g, 60.33 mmol) obtained in Step 2 and NBS (11.81 g, 66.36 mmol) in 200 ml of chloroform was refluxed for 12 hours. After the reaction was terminated by using MgSO4 and the organic layer was separated with methylene chloride to remove the water from the organic layer. After removing the solvent in water is removed, the organic layer was purified by column chromatography (Hexane: MC = 15: 1 (v / v)) to obtain the IC-7-2 (11.75 g, yield 61%). Instead of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) the IC-12-3 (20 g, 81.18 mmol) and NBS (47.68To g, 267.89 mmol), and performs the same procedure of the Preparation Example 7 step 3 to obtain a IC-15-2 (20.39 g, yield 52%).

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5
[2]Patent: WO2017/98455,2017,A1 .Location in patent: Page/Page column 7
[3]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340
[4]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070
[5]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 39
[6]Organic Letters,2009,vol. 11,p. 3230 - 3233
[7]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016
[8]Patent: KR101609027,2016,B1 .Location in patent: Paragraph 0205; 0206; 0316-0318

9
[ 29150-63-8 ]
[ 1260140-90-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

10
[ 29150-63-8 ]
[ 1260140-91-7 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070
[2]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

11
[ 29150-63-8 ]
[ 1260140-86-0 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

12
[ 29150-63-8 ]
[ 1260140-87-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

13
[ 29150-63-8 ]
[ 1260140-92-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

14
[ 29150-63-8 ]
[ 1260140-93-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070
[2]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

15
[ 29150-63-8 ]
[ 111-83-1 ]
[ 1227939-54-9 ]
[ 1227939-55-0 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070

16
[ 29150-63-8 ]
[ 1066-45-1 ]
[ 1289556-30-4 ]

Yield	Reaction Conditions	Operation in experiment
94%		Under nitrogen, a 100 mL Schlenk flask was charged with compound 3 (1.14 g, 4.6 mmol) and anhydrous tetrahydrofuran(50 mL) was added and the solution was cooled to -78 C. A solution of n-butyllithium in hexane (11.6 mL, 2.4M) was slowly added dropwise to the solution, After stirring, the reaction was continued for 1 hour at -78 C. Then, trimethyltin chloride (12 mL, 1.0 M) was added. The reaction was continued for 1 hour while maintaining the temperature and the system was stirred overnight at room temperature. The organic phase was extracted with dichloromethane, and the combined organic phases were washed successively with saturated brine and water, dried over anhydrous sodium sulfate, filtered, and the organic solvent was removed by rotary evaporation, and recrystallized from ethanol to obtain white solid 4 (3.18g, 94 %).

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4061 - 4070
[2]Patent: CN103288848,2016,B .Location in patent: Paragraph 0129-0131
[3]Journal of Materials Chemistry A,2013,vol. 1,p. 8270 - 8279
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 14188 - 14192
Angew. Chem.,2018,vol. 130,p. 14384 - 14388,5

17
[ 29150-63-8 ]
[ 33513-42-7 ]
[ 1227938-51-3 ]

Yield	Reaction Conditions	Operation in experiment
83%		Example 3 Synthesis of 2-Benzo[1,2-b:4,5-b':5,6-b"]trithiophenealdehyde (80) [Show Image] Under a nitrogen atmosphere, in a test tube, benzo[1,2-b:4,5-b':5,6-b"]trithiophene (100 mg, 0.405 mmol) obtained in Synthesis Example 3, DMF (0.10 mL, 1.34 mmol) and 1,2-dichloroethane (1.3 mL) were placed. In an ice bath, phosphorus oxychloride (0.13 mL, 1.34 mmol) was added and refluxed for 17 hours. Subsequently, DMF (0.10 mL, 13.4 mmol) and phosphorus oxychloride (0.13 mL, 1.34 mmol) were added, and refluxed for further 17 hours. After a 10% aqueous potassium hydroxide solution was added, the reaction mixture was extracted with chloroform (10 mL x 2), washed with saturated saline solution (40 mL x 3) and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, the residue was purified by column chromatography (silica gel, chloroform, Rf= 0.4) to obtain a yellow solid substance (92.7 mg, 83%). 1H-NMR(400MHz,CDCl3)δ10.07(s,1H),8.12(s,1H), 7.56-7.5 (m,4H); 13C-NMR(99.5MHz,CDCl3)δ183.9, 141.9, 136.5, 135.4, 132.5, 132.2, 131.9, 131.1, 130.7, 126.0, 125.8, 122.6, 122.41; M.S.(70eVEI)m/z=274(M+)

Reference： [1]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 38-39

18
[ 108-70-3 ]
[ 29150-63-8 ]

Reference： [1]Patent: EP2361915,2011,A1
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5
[3]Patent: CN103288848,2016,B
[4]Patent: WO2017/98455,2017,A1
[5]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340

19
[ 29150-63-8 ]
[ 111-83-1 ]
[ 1227939-54-9 ]
[ 1227939-55-0 ]
[ 1227939-53-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 14 Alkylation reaction of <strong>[29150-63-8]BTT</strong> via lithiation [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flask, benzo[1,2-b:4,5-b':5,6-b"]trithiophene (Scheme -(2)) (800 mg, 3.25 mmol) obtained in Synthesis Example 3 and tetrahydrofuran (22.7 mL) were placed and cooled to 0C. To this, a 1.59 mol/l n-butyllithium hexane solution (4. 5mL, 7.15 mmol) was added and stirred for 2 hours. Thereafter, temperature was increased to 60C. To the mixture, n-octyl bromide (2.5 g, 13.0 mmol) was added and reacted for 12 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (20 mL) to obtain a light yellow substance. The resultant solid substance was separated and analyzed by HPLC. As a result, it was found that a production ratio of raw materials (Scheme 1-(2)):1030:1031:1032 is 3:29:39:21.

Reference： [1]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 44

20
[ 29150-63-8 ]
[ 111-64-8 ]
[ 1227939-56-1 ]
[ 1227939-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; In dichloromethane; at -78℃; for 2h;Inert atmosphere;	Example 15 Acylation reaction of <strong>[29150-63-8]BTT</strong> via the Friedel-Crafts reaction [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flask benzo[1,2-b:4,5-b': 5,6-b"]trithiophene (Scheme 1-(2)) (800 mg, 3.25 mmol), obtained in Synthesis Example 3 and methylene chloride (22.7 mL) were placed and cooled to -78C. To this, aluminum chloride (2.11 g, 13.0 mmol) and octanoyl chloride (1.16 g, 13.0 mmol) were added and stirred for 2 hours and then temperature was increased to room temperature. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration, washed with water (20 mL) to obtain a light yellow solid substance. The resultant solid substance was separated and analyzed by HPLC. As a result, it was found that a production ratio of 1033:1034 is 21:32.

Reference： [1]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 44-45

21
[ 29150-63-8 ]
[ 1227939-36-7 ]

Reference： [1]Patent: EP2361915,2011,A1
[2]Patent: EP2361915,2011,A1

22
[ 29150-63-8 ]
[ 1227939-33-4 ]

Reference： [1]Patent: EP2361915,2011,A1
[2]Patent: EP2361915,2011,A1

23
[ 29150-63-8 ]
2,5,8-tris(4-(N-(1-naphthyl)-N-phenyl-amino)phenyl)benzo[1,2-b:3,4-b':5,6-b"]trithiophene [ No CAS ]

Reference： [1]Patent: EP2361915,2011,A1
[2]Patent: EP2361915,2011,A1

24
[ 29150-63-8 ]
[ 1227939-58-3 ]

Reference： [1]Patent: EP2361915,2011,A1

25
[ 29150-63-8 ]
[ 1174223-26-7 ]
[ 1227938-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In dichloromethane; acetic acid; at 20℃; for 24h;Inert atmosphere; Darkness;	Example 16 Dibromination reaction of <strong>[29150-63-8]BTT</strong> by NBS bromination reaction [Show Image] Under a nitrogen atmosphere, in a 50 mL three-neck flash, benzo[1,2-b:4,5-b':5,6-b"]trithiophene (Scheme 1-(2)) (800 mg, 3.25 mmol) obtained in Synthesis Example 3, methylene chloride (22.7 mL) and acetic acid (5.7 mL) were added. Under light exclusion conditions, NBS (1.16 g, 6.5 mmol) was added little by little and stirred at room temperature for 24 hours. After completion of the reaction, water (20 mL) was added. A precipitated solid substance was obtained by filtration and washed with ethanol (50 mL) and water (20 mL) to obtain a light purple solid substance. The resultant solid substance was analyzed by HPLC. As a result, it was found that a production ratio of 34:35:33 is 0.01:1:0.17.

Reference： [1]Patent: EP2361915,2011,A1 .Location in patent: Page/Page column 45

26
[ 108-73-6 ]
[ 29150-63-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1816 - 1818
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016
[3]Patent: KR101609027,2016,B1
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 14188 - 14192
Angew. Chem.,2018,vol. 130,p. 14384 - 14388,5

27
[ 35991-61-8 ]
[ 29150-63-8 ]

Yield	Reaction Conditions	Operation in experiment
51%	With chloranil; In toluene; for 48h;Reflux;	General procedure: Chloranil and dihydrothiophene derivative were refluxed in toluene. After completion of the reaction (monitored by TLC), the excess of chloranil was removed by mean of vacuum filtration. Then the filtrate was concentrated under reduced pressure to provide the crude product which was subsequently purified by column chromatography (silica gel; hexane as eluent) to afford the desired product.
49%	With chloranil; In toluene; at 100℃; for 48h;Inert atmosphere;	General procedure: IC-7-4 (20 g, 81.84 mmol) obtained in Step 1 and chloranil (72.25 g, 327.36 mmol) and toluene (400 ml) was stirred in a nitrogen stream for 2 days at 100 C . After the end of reaction vacuum filter to remove the chloranil method, removing the solvent from the filtrate was filtered by column chromatography (Hexane: MC = 5: 1 (v / v)) to give IC-7-3 (14.95 g, yield: 76 %). Instead of IC-7-4 (20 g, 81.84 mmol) the use of IC-12-4 (10 g, 39.62 mmol) the performs the same procedure as Step 2 Preparation Example 7 to obtain a IC-12-3 (9.68 g, yield 49%).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1816 - 1818
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14188 - 14192
Angew. Chem.,2018,vol. 130,p. 14384 - 14388,5
[3]Patent: KR101609027,2016,B1 .Location in patent: Paragraph 0200; 0201; 0277-0279
[4]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016

28
[ 29150-63-8 ]
C₃₃H₂₄O₃S₆ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016

29
[ 29150-63-8 ]
benzo[1,2-b:3,4-b':5,6-b'']-tri(benzo[4',5']thieno[2',3'-d']thiophene) [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016

30
[ 29150-63-8 ]
2,5,8-tris(2-methylthiophenyl)benzo[1,2-b:3,4-b’:5,6-b”]trithiophene [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 10011 - 10016

31
[ 151721-79-8 ]
[ 29150-63-8 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 6270 - 6274
Angew. Chem.,2016,vol. 128,p. 6378 - 6382,5
[2]Patent: CN103288848,2016,B
[3]Patent: WO2017/98455,2017,A1
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 5966 - 5974
[5]Journal of Materials Chemistry A,2021,vol. 9,p. 3333 - 3340

32
[ 29150-63-8 ]
C₆₈H₄₁N₅S₃ [ No CAS ]