1000623-95-9|3,6-Bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione| Ambeed

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Quality Control of [ 1000623-95-9 ] Purity: 95% SDS Specification

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Product Details of [ 1000623-95-9 ]

CAS No. :	1000623-95-9
Formula :	C₃₀H₃₈Br₂N₂O₂S₂
M.W :	682.57
SMILES Code :	O=C1N(CC(CC)CCCC)C(C2=CC=C(Br)S2)=C3C1=C(C4=CC=C(Br)S4)N(CC(CC)CCCC)C3=O
MDL No. :	MFCD16619382
InChI Key :	JVVGLKKTAZYUQU-UHFFFAOYSA-N
Pubchem ID :	53439694

Safety of [ 1000623-95-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 1000623-95-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	38
Num. arom. heavy atoms	18
Fraction Csp3	0.53
Num. rotatable bonds	14
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	174.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	100.48 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	5.82
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	9.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	9.97
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	6.15
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	11.75
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	8.72

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-9.75
Solubility	0.00000012 mg/ml ; 0.0000000002 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-11.97
Solubility	0.0000000007 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-11.2
Solubility	0.0000000043 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.41 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	2.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	1.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.17

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<3.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	5.52

Application In Synthesis of [ 1000623-95-9 ]

* 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 [ 1000623-95-9 ]

[ 1000623-95-9 ] Synthesis Path-Downstream 1~35

1
[ 1185885-86-2 ]
[ 1000623-95-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bromine; In chloroform; at 20 - 60℃; for 1.16667h;Inert atmosphere; Schlenk technique;	General procedure: L1-T (140mg, 0.27mmol) and 20mL chloroform were added to a 50mL round bottom flask equipped with a stirring barand a condenser. Bromine (90 mg, 0.56 mmol) was added dropwiseto the flask at room temperature. After stirring at room temperaturefor 10 min, the reaction mixture was heated to 60 C andstirred for an additional hour. After cooling, the reaction mixturewas poured into water (45 mL) and extracted with CH2Cl2. Thecombined organic layer was dried over anhydrous sodium sulfate,filtered and concentrated under reduced pressure. The crudeproduct was recrystallized from the solvent mixture of CH2Cl2 andmethanol to give the product L1-Br as a purple solid (156 mg, 86%).
80%	With N-Bromosuccinimide; In chloroform; at 50℃; for 12h;	In a 250 mL round bottom flask, compound 3 (1.0 g, 1.9 mmol) was added.50 mL of chloroform was stirred at room temperature for 10 minutes in the dark.Will dissolve N-bromosuccinimide (NBS) (746 mg, 4.2 mmol)50 mL of chloroform was slowly added dropwise to the reaction system.The reaction was refluxed at 50 C for 12 hours. After the reaction is over,The solvent was evaporated to dryness under reduced pressure. The dark purple solid was purified by column chromatography.The yield was 80%. Among them, the eluent: petroleum ether (PE) / ethyl acetate (EA) (50:1).
71%	With N-Bromosuccinimide; In chloroform; at -0.16℃; for 2h;	Compound 3 (1.01 g, 2.05 mmol) was charged in a 100 mLsingle-neck round-bottom flask filled with 50 mL of CHCl3.The mixture was cooled to 273 K and stirred while Nbromosuccinimide(NBS) was added in small portions. Themixture was allowed to warm to room temperature and stirredfor 2 h following complete addition of NBS. The reactionmixture was poured in water and extracted with CHCl3.Then CHCl3 was evaporated, the resulting red solid (darkred) was purified by column chromatography using CHCl3/petroleum ether as eluent. 0.95 g of 4 [31] were isolated (71%yield). 1H NMR (500 MHz, CDCl3): (ppm) = 8.30 (d,J = 3.7 Hz, 2 H), 6.62 (d, J = 3.7 Hz, 2 H), 3.99 (add,J = 2.7 Hz, 7.4 Hz, 4 H), 1.78-1.68 (m, 2 H), 1.39-1.24 (m,16 H), 0.92 (t, J = 7.5 Hz, 6 H), 0.88 (t, J = 7.0 Hz, 6 H). 13C(75 MHz, CDCl3): (ppm) = 161.1, 146.4, 132.9, 126.4, 122.4,115.7, 106.4, 46.4, 40.2, 30.7, 28.9, 23.9, 23.3, 14.2, 10.8. FTIR(KBr) nu max = 3422, 3084, 2957, 2926, 2859, 1657, 1556,1504.9, 1450, 1406, 1308, 1261, 1233, 1165, 1100, 1072,1027, 967, 833, 810, 731, 709, 635, 466, 430 cm-

71%	With N-Bromosuccinimide; In chloroform; at 0℃; for 12h;Darkness;	Charge a 500-ml eggplant-shape flask with the above- prepared compound (b) (3.0 g, 5.7 mmol), N-bromosuccinimide (2.5 g, 13.8 mmol), and chloroform (200 ml). Agitate the flask content for 12 hours at 0 C. under light shielding condition. After distilling the solvent away under reducedpressures, add MeOR (100 ml) to the flask. Separate the precipitate by filtration. Thus, a dark green powder (4.8 g, 71.0%) is obtained. mlz=683.1 (M+H)
70%	With N-Bromosuccinimide; acetic acid; In chloroform; at 20℃; for 12h;	3.56 g of 2,5-diethylhexyl-3,6-dithiophen-2-ylpyrrolo[3,4-c]pyrrolo-1,4-dione dissolved in 150 ml chloroform (CF) was added to a 500 ml two-necked flask. 2.50 g of N-bromosuccinimide (NBS) was added, a small amount of acetic acid was added, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed by confirming thin-layer chromatography (TLC), the solvent was concentrated to about 20 ml under reduced pressure, and ethanol was added and a solid precipitate was filtered through a filter. The solid thus separated was again dissolved in chloroform, and short column was carried out using silica to obtain a black powder. (Yield: 70%).
65%	With N-Bromosuccinimide; acetic acid; In tetrahydrofuran; at 0℃; for 12h;	the formula (5) Compound 6 (2.00g, 3.81mmol) was dissolved in 50ml of tetrahydrofuran (THF), cooled to 0 C, then added in three portions N- bromosuccinimide (NBS ) (1. 42g, 8. OOmmol), while dropping a few drops of glacial acetic acid. After 12 hours under reduced pressure the reaction solvent was distilled off, boiling range 60 C -90 C petroleum ether as eluent over a silica gel column to give 1. 69g of the formula (5) Compound 7 in a yield of 65%.
	With N-Bromosuccinimide; In chloroform; at 0℃; for 1h;	Examples Example 1; <n="44"/>a) A solution of 4.5 g of DPP 1 , 6.23 g of K2CO3 and 8.68 g of 1 -broiotamo-2-ethyl-hexyl in 60 ml of N-methyl-pyrrolidone (NMP) is heated to 14O0C for 6h. The mixture is washed with water and extracted with dichloromethane. The organic phase is then dried and filtered on a double layer of silica gel and Hyflo (CAS 91053-39-3; Fluka 56678) before it is concentrated. The residue is dissolved in 100 ml of chloroform, cooled down to O0C and 2 equivalents of N-bromosuccinimide are then added portion wise over a period of 1 h. After the reaction has been completed, the mixture is washed with water. The organic phase is extracted, dried and concentrated. The compound is then purified over a silica gel column to give 1.90 g of a violet powder of DPP 2.
	With N-Bromosuccinimide; In chloroform; at 0℃; for 1h;	A solution of 4.5 g of the 1 ,4-diketopyrrolo[3,4-c]pyrrole (DPP) derivative of the formula 1 , 6.23 g of K2CO3 and 8.68 g of 1 -bromo-2-ethyl-hexyl in 60 ml of N-methyl-pyrrolidone (NMP) is heated to 14O0C for 6h. The mixture is washed with water and extracted with <n="35"/>dichloromethane. The organic phase is then dried and filtered on a double layer of silica gel and Hyflo (CAS 91053-39-3; Fluka 56678) before it is concentrated. The residue is dissolved in 100 ml of chloroform, cooled down to 0 0C and 2 equivalents of N- bromosuccinimide are then added portion wise over a period of 1 h. After the reaction has been completed, the mixture is washed with water. The organic phase is extracted, dried and concentrated. The compound is then purified over a silica gel column to give 1.90 g of a violet powder of the DPP derivative of the formula 2.
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 4.5h;Inert atmosphere; Darkness;	General procedure: A solution of NBS (0.477 g, 2.68 mmol) in 8 mL of DMFwas slowly added to a solution of 3?,4?-di(octyloxy)-2,2?:5?,2?-terthiophene(0.675 g, 1.34 mmol) in 8 mL of DMF under argon atmosphere. The mixture wasleft with stirring for 4.5 h in dark. Then, 20 mL of water was added to thereaction mixture and the product was extracted with diethyl ether. The organicphase was consecutively washed with saturated NaHCO3 and then driedover MgSO4. The crude product was purified chromatographically on asilica gel column with hexane as an eluent, affording 0.77g of pure product(87% yield). 1HNMR(CDCl3,ppm):6.96 (d, J=4.0 Hz, 2H), 6.91 (d, J=3.8 Hz, 2H), 4.07 (t, J=6.8 Hz, 4H), 1.87-1.79(m, 4H), 1.51-1.42 (m, 4H), 1.39-1.25 (m, 16H), 0.90 (t, J=6.8Hz, 6H).

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 15547 - 15549.
[2]Australian Journal of Chemistry,2014,vol. 67,p. 1330 - 1337.
[3]RSC Advances,2015,vol. 5,p. 19520 - 19527.
[4]Journal of Organometallic Chemistry,2019,vol. 894,p. 1 - 9.
[5]Journal of Materials Chemistry A,2013,vol. 1,p. 2795 - 2805.
[6]Patent: CN108794490,2018,A .Location in patent: Paragraph 0053; 0054; 0055.
[7]Journal of Fluorescence,2016,vol. 26,p. 1939 - 1949.
[8]Patent: US9590187,2017,B2 .Location in patent: Page/Page column 40.
[9]Patent: KR101676526,2016,B1 .Location in patent: Paragraph 0197-0199.
[10]European Journal of Organic Chemistry,2017,vol. 2017,p. 4896 - 4904.
[11]RSC Advances,2016,vol. 6,p. 9023 - 9036.
[12]European Journal of Organic Chemistry,2016,vol. 2016,p. 2617 - 2627.
[13]Patent: CN103360397,2016,B .Location in patent: Paragraph 0031-0033; 0038.
[14]RSC Advances,2014,vol. 4,p. 58027 - 58035.
[15]Journal of Materials Chemistry A,2015,vol. 3,p. 4229 - 4238.
[16]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 1669 - 1675.
[17]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1983 - 1994.
[18]Organic Letters,2014,vol. 16,p. 3508 - 3511.
[19]Dyes and Pigments,2012,vol. 95,p. 126 - 133.
[20]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 462 - 469.
[21]Patent: WO2008/664,2008,A1 .Location in patent: Page/Page column 43.
[22]Patent: WO2009/47104,2009,A2 .Location in patent: Page/Page column 33; 34.
[23]Chemistry of Materials,2013,vol. 25,p. 2549 - 2556.
[24]Physical Chemistry Chemical Physics,2014,vol. 16,p. 17253 - 17265.
[25]Electrochimica Acta,2014,vol. 144,p. 211 - 220.
[26]Dyes and Pigments,2016,vol. 127,p. 37 - 44.

2
tributyl(3-dodecylcyclopenta-1,3-dien-1-yl)stannane [ No CAS ]
[ 1000623-95-9 ]
C₆₂H₉₂N₂O₂S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In toluene;Heating / reflux;	b) A solution of 500 mg of the dibrominated DPP 2, 990 mg of the tin derivative and 85 mg of Pd(PPh3)4 in 30 ml of dry toluene is refluxed overnight under inert conditions. After cooling down, the mixture is filtrated on a double layer silica gel/Hyflo, concentrated and precipitated with methanol. The precipitate is filtrated and rinsed with methanol to give 530 mg of a blue solid of DPP 3.

References: [1]Patent: WO2008/664,2008,A1 .Location in patent: Page/Page column 43.

3
[ 1000623-95-9 ]
C₂₆H₅₀SSn [ No CAS ]
[ 1143584-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In toluene;Heating / reflux;	A solution of 1.28 g of the dibrominated DPP derivative of the formula 2, 2.41 g of the tin derivative depicted above, and 215 mg of Pd(PPh3)4 in 30 ml of dry toluene is refluxed overnight under inert conditions. After cooling down, the mixture is filtrated on a double layer silica gel/Hyflo, concentrated and precipitated with methanol. The precipitate is filtrated and rinsed with methanol to give 1.17 g of a blue solid of the DPP derivative of the formula 3.

References: [1]Patent: WO2009/47104,2009,A2 .Location in patent: Page/Page column 34.

4
[ 1000623-95-9 ]
copper(l) cyanide [ No CAS ]
[ 1275588-66-3 ]

Yield	Reaction Conditions	Operation in experiment
31%	In N,N-dimethyl-formamide; at 130℃; for 8h;Inert atmosphere;	A mixture of compound 2 (249 mg, 0.365 mmol) and copper(l)cyanide (1.50 g, 16.7 mmol) in dry DMF (8 mL) is heated under argon for 8 h at 130 C. The reaction mixture is allowed to cool down to room temperature and a solution of sodium cyanide (180 g) in water (20 mL) is added. The aqueous phase is extracted with dichloromethane. The solvent is removed under reduced pressure and the residue is purified by column chromatography (dichloromethane) affording a dark violet solid (48.8 mg, 31 %).1H NMR (400 MHz, CD2CI2): delta = 8.82 (d, 3J = 4.2 Hz, 2H), 7.76 (d, 3J = 4.2 Hz, 2H), 4.03- 3.91 (m, 4H), 1 .84-1.72 (m, 2H), 1 .40-1.18 (m, 16H), 0.91-0.82 (m, 12H).13C NMR (101 MHz, CD2CI2): delta = 161 .5, 139.8, 138.3, 135.7, 134.8, 1 13.9, 1 13.7, 1 10.9, 46.4, 39.7, 30.5, 28.7, 23.9, 23,4, 14.2, 10.5.HRMS (ESI, acetonitrile/CHC 1 : 1 , pos. mode): Calcd. for [M+H] C32H39N4O2S2 575.2510. Found 575.2510.Elemental Anal. Calcd. for C32H38N4O2S2: C, 66.87; H, 6.66; N, 9.75; S, 1 1.16; O, 3.94. Found: C, 66.60; H, 6.62; N, 9.77; S, 1 1.09.CV (CH2CI2, 0.1 M TBAHFP, vs. Fc/Fc+): Ei/ ed {X IX2 ) = -1.77 V, Ei/ ed {XIX ) = -1.24 V, Ey^ (X/X+) = 0.86 V.UV-vis (CH2CI2): Amax (epsilon) = 586 (28500), 546 nm (26500 NM cm 1). The redox behavior is studied by cyclic voltammetry in dichloromethane with ferrocene as internal standard showing two reversible reductions at -1.24 V and -1.77 V as well as one reversible oxidation at 0.86 V. The optical absorption in dichloromethane shows a maximum at 586 nm. The optical band gap is determined as 2.12 eV from the absorption maxi- mum.
31%	With sodium cyanide; In water; N,N-dimethyl-formamide;	Example 1 2,5-Di(2-ethylhexyl)-3,6-bis(5-cyano-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione (A-1) A mixture of compound 2 (249 mg, 0.365 mmol) and copper(I)cyanide (1.50 g, 16.7 mmol) in dry DMF (8 mL) is heated under argon for 8 h at 130 C. The reaction mixture is allowed to cool down to room temperature and a solution of sodium cyanide (180 g) in water (20 mL) is added. The aqueous phase is extracted with dichloromethane. The solvent is removed under reduced pressure and the residue is purified by column chromatography (dichloromethane) affording a dark violet solid (48.8 mg, 31%). 1H NMR (400 MHz, CD2Cl2): delta=8.82 (d, 3J=4.2 Hz, 2H), 7.76 (d, 3J=4.2 Hz, 2H), 4.03-3.91 (m, 4H), 1.84-1.72 (m, 2H), 1.40-1.18 (m, 16H), 0.91-0.82 (m, 12H). 13C NMR (101 MHz, CD2Cl2): delta=161.5, 139.8, 138.3, 135.7, 134.8, 113.9, 113.7, 110.9, 46.4, 39.7, 30.5, 28.7, 23.9, 23.4, 14.2, 10.5. HRMS (ESI, acetonitrile/CHCl3 1:1, pos. mode): Calcd. for [M+H]C32H39N4O2S2 575.2510. Found 575.2510. Elemental Anal. Calcd. for C32H38N4O2S2: C, 66.87; H, 6.66; N, 9.75; S, 11.16; O, 3.94. Found: C, 66.60; H, 6.62; N, 9.77; S, 11.09.

References: [1]Chemical Communications,2011,vol. 47,p. 1767 - 1769.
[2]Patent: WO2012/41849,2012,A1 .Location in patent: Page/Page column 41-42.
[3]Patent: US2012/74393,2012,A1 .Location in patent: Page/Page column.

5
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]
[ 1000623-95-9 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 126 - 133.
[2]Chemistry of Materials,2013,vol. 25,p. 2549 - 2556.
[3]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 462 - 469.
[4]RSC Advances,2015,vol. 5,p. 19520 - 19527.
[5]Synlett,2015,vol. 26,p. 2109 - 2116.
[6]Patent: CN103360397,2016,B .
[7]Patent: US9590187,2017,B2 .
[8]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1983 - 1994.
[9]Patent: CN108794490,2018,A .

6
[ 1003-31-2 ]
[ 1000623-95-9 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 126 - 133.
[2]RSC Advances,2014,vol. 4,p. 58027 - 58035.
[3]Electrochimica Acta,2014,vol. 144,p. 211 - 220.
[4]RSC Advances,2015,vol. 5,p. 19520 - 19527.
[5]Dyes and Pigments,2016,vol. 127,p. 37 - 44.
[6]Patent: CN103360397,2016,B .
[7]Journal of Fluorescence,2016,vol. 26,p. 1939 - 1949.
[8]Patent: US9590187,2017,B2 .
[9]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1983 - 1994.
[10]Patent: CN108794490,2018,A .

7
[ 18908-66-2 ]
[ 1000623-95-9 ]

8
[ 1000623-95-9 ]
[ 1380584-55-3 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 126 - 133.

9
[ 1000623-95-9 ]
[ 57083-15-5 ]
[ 1241836-03-2 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 126 - 133.

10
[ 1000623-95-9 ]
[ 57083-16-6 ]
[ 1380584-54-2 ]

References: [1]Dyes and Pigments,2012,vol. 95,p. 126 - 133.

11
[ 1000623-95-9 ]
[Ir(2-phenylpyridine(-H))2(5-ethynyl-2,2'-bipyridine)](hexafluorophosphate) [ No CAS ]
(Ir(C₃NO(C₈H₁₇)C₄H₂SCCC₅H₃NC₅H₄N)(C₅H₄NC₆H₄)2)2⁽²⁺⁾*2PF₆^(1-)=[(C₃NO(C₈H₁₇)C₄H₂SCCC₅H₃NC₅H₄N)Ir(C₅H₄NC₆H₄)2]2(PF₆)2 [ No CAS ]

References: [1]Inorganic Chemistry,2012,vol. 51,p. 7957 - 7959.

12
[ 7223-38-3 ]
[ 1000623-95-9 ]
[ 1418196-26-5 ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 303 - 308.

13
[ 1000623-95-9 ]
[ 1442416-72-9 ]
[ 1442416-59-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In tetrahydrofuran; at 70℃; for 20h;Inert atmosphere;	General procedure: A 100mL two-neck round-bottom flask connected to a condenser and dry argon flow was charged with a stir bar, 2e (420mg, 0.86mmol), 3,6-di(2-bromothien-5-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione (198mg, 0.29mmol), tris(dibenzylideneacetone)dipalladium(0) (13.3mg, 0.015mmol, 10mol% Pd), tri(2-furyl)phosphine (14.6mg, 0.058mmol, 20mol%), and dry THF (30mL). The temperature was progressively raised to 70C and then the reaction mixture was stirred for 20h. The reaction mixture was then concentrated under reduced pressure and the resulting crude residue was purified by flash chromatography (eluent: hexane/EtOAc=40:1) affording 4a as a dark blue tacky solid (289mg, 85% yield). 1H NMR (400MHz, CDCl3) delta 0.62-0.66 (m, 4H), 0.87 (t, J=6.8Hz, 6H), 0.91 (t, J=7.2Hz, 6H), 1.19 (d, J=6.4Hz, 36H), 1.24-1.42 (m, 16H), 1.72-1.80 (m, 4H), 1.90-2.00 (m, 2H), 2.67 (t, J=7.6Hz, 4H), 4.03-4.13 (m, 4H), 4.20 (sept, J=6.4Hz, 6H), 7.23 (d, J=8.4Hz, 4H), 7.42 (d, J=4.0Hz, 2H), 7.58 (d, J=8.4Hz, 4H), 8.96 (d, J=4.0Hz, 2H). 13C NMR (100MHz, CDCl3) delta 10.6, 11.8, 14.1, 23.1, 23.7, 25.0, 25.6, 28.6, 30.4, 39.0, 39.2, 46.0, 64.9, 108.0, 124.0, 126.0, 128.3, 129.3, 130.7, 136.8, 139.8, 143.8, 150.0, 161.7. ESI-HRMS m/z calcdfor C66H100N2NaO8S2Si2 (M+Na+): 1191.6357; found: 1191.6323. The same procedure was followed for the synthesis of DPP-bridged triallylsilane (4b) as described below.

References: [1]Tetrahedron,2013,vol. 69,p. 5312 - 5318.

14
[ 1000623-95-9 ]
[ 1442416-58-1 ]
[ 1442416-77-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In tetrahydrofuran; at 70℃; for 20h;Inert atmosphere;	General procedure: A 100mL two-neck round-bottom flask connected to a condenser and dry argon flow was charged with a stir bar, 2e (420mg, 0.86mmol), 3,6-di(2-bromothien-5-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione (198mg, 0.29mmol), tris(dibenzylideneacetone)dipalladium(0) (13.3mg, 0.015mmol, 10mol% Pd), tri(2-furyl)phosphine (14.6mg, 0.058mmol, 20mol%), and dry THF (30mL). The temperature was progressively raised to 70C and then the reaction mixture was stirred for 20h. The reaction mixture was then concentrated under reduced pressure and the resulting crude residue was purified by flash chromatography (eluent: hexane/EtOAc=40:1) affording 4a as a dark blue tacky solid (289mg, 85% yield). 1H NMR (400MHz, CDCl3) delta 0.62-0.66 (m, 4H), 0.87 (t, J=6.8Hz, 6H), 0.91 (t, J=7.2Hz, 6H), 1.19 (d, J=6.4Hz, 36H), 1.24-1.42 (m, 16H), 1.72-1.80 (m, 4H), 1.90-2.00 (m, 2H), 2.67 (t, J=7.6Hz, 4H), 4.03-4.13 (m, 4H), 4.20 (sept, J=6.4Hz, 6H), 7.23 (d, J=8.4Hz, 4H), 7.42 (d, J=4.0Hz, 2H), 7.58 (d, J=8.4Hz, 4H), 8.96 (d, J=4.0Hz, 2H). 13C NMR (100MHz, CDCl3) delta 10.6, 11.8, 14.1, 23.1, 23.7, 25.0, 25.6, 28.6, 30.4, 39.0, 39.2, 46.0, 64.9, 108.0, 124.0, 126.0, 128.3, 129.3, 130.7, 136.8, 139.8, 143.8, 150.0, 161.7. ESI-HRMS m/z calcdfor C66H100N2NaO8S2Si2 (M+Na+): 1191.6357; found: 1191.6323. The same procedure was followed for the synthesis of DPP-bridged triallylsilane (4b) as described below.

References: [1]Tetrahedron,2013,vol. 69,p. 5312 - 5318.

15
[ 98-03-3 ]
[ 1000623-95-9 ]
[ 1423186-27-9 ]