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Search for "nitrophenyl" in Full Text gives 158 result(s) in Beilstein Journal of Organic Chemistry.

A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis

  • Mukund G. Kulkarni,
  • Mayur P. Desai,
  • Deekshaputra R. Birhade,
  • Yunus B. Shaikh,
  • Ajit N. Dhatrak and
  • Ramesh Gannimani

Beilstein J. Org. Chem. 2012, 8, 1725–1729, doi:10.3762/bjoc.8.197

Graphical Abstract
  • method for the synthesis of 3-methylquinoline-4-carbaldehyde. It was considered that a properly substituted 2-(2-nitrophenyl)pent-4-enal [25][26][27] could be a fitting intermediate for this purpose. Such an intermediate is easily accessible through the Wittig-olefination–Claisen-rearrangement protocol
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Published 11 Oct 2012

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

  • Zhi-Cong Geng,
  • Jian Chen,
  • Ning Li,
  • Xiao-Fei Huang,
  • Yong Zhang,
  • Ya-Wen Zhang and
  • Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

Graphical Abstract
  • -butyl 3-hydroxy-5-(4-nitrophenyl)pyrazolidine-1,2-dicarboxylate (4a): 80% yield, >20/1 dr, 92% ee. The enantiomeric ratio was determined by HPLC on Chiralpak OD-H column (10% 2-propanol/hexane, 1 mL/min), tmajor = 7.219 min, tminor = 6.013 min; [α]D26 −11.8 (c 0.38, acetone); 1H NMR (400 MHz, CDCl3) δ
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Published 09 Oct 2012
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  • ): 1714 (C=O), 1638 (C=C) cm−1. 4-(2-((4-Nitrophenyl)hydroxymethyl)acryloyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl (5k): Yield (DABCO): 33 mg (22%); yield (quinuclidine): 120 mg (79%); yellow powder; mp 102–104 °C; EIMS m/z (% relative intensity): M+ 377 (15), 363 (12), 189 (8), 160 (25), 154 (51), 140
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Published 12 Sep 2012

Synthesis of diverse indole libraries on polystyrene resin – Scope and limitations of an organometallic reaction on solid supports

  • Kerstin Knepper,
  • Sylvia Vanderheiden and
  • Stefan Bräse

Beilstein J. Org. Chem. 2012, 8, 1191–1199, doi:10.3762/bjoc.8.132

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  • of substituted polymer-bound nitroarenes 1{a–k} are available (Scheme 1, Figure 1). Reaction optimization In order to optimize the reaction conditions, the temperature for the Bartoli reaction on solid supports was systematically changed. For the reaction of (4-chloro-3-nitrophenyl)carboxymethyl
  • after thin-layer chromatography. A slightly higher temperature was optimal for the reaction of (3-methyl-4-nitrophenyl)carboxymethyl-polystyrene (1{i}) with the less active vinyl magnesium bromide 2{a} (Figure 3). In addition to this, we also varied the amount of Grignard reagent for the reaction of 1{h
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Published 26 Jul 2012

Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction

  • George Iakobson and
  • Petr Beier

Beilstein J. Org. Chem. 2012, 8, 1185–1190, doi:10.3762/bjoc.8.131

Graphical Abstract
  • aromatic meta- and para-nitro-(pentafluorosufanyl)benzenes (1 and 2) are made by direct fluorination of the corresponding bis(nitrophenyl)disulfides [10][11][12]. A recent report also described a two step synthesis of SF5-benzenes from diaryl disulfides avoiding the use of elemental fluorine [13]. While
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Published 25 Jul 2012

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

  • Friederike I. Nollmann,
  • Andrea Dowling,
  • Marcel Kaiser,
  • Klaus Deckmann,
  • Sabine Grösch,
  • Richard ffrench-Constant and
  • Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

Graphical Abstract
  • hexafluorophosphate (HBTU) in dimethylformamide (DMF) and N,N-diisopropylethylamine (DIEA) in N-methylpyrrolidone (NMP), assisted by microwave irradiation. After the final Fmoc-deprotection with 20% piperidine in DMF, the N-terminus was formylated with para-nitrophenyl formate (pNPF) in the presence of N
  • , Germany) in N-methylpyrrolidone (NMP; VWR, Germany; c = 2 mol/L). Fmoc protecting groups were cleaved with 20% piperidine in DMF by using microwave irradiation as well. Formylation. The free N-terminus was formylated with 5 equiv para-nitrophenyl formate (pNPF; Sigma Aldrich, Germany) and 3 equiv N
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Published 11 Apr 2012
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  • method using molecular fluorine (F2) was reported [33]. Thus, bis(p- or m-nitrophenyl) disulfide was treated with F2 diluted with nitrogen (F2:N2 = 1:9 v/v) at low temperature in acetonitrile to give the nitrophenylsulfur pentafluoride in ca. 40% yield. However, in addition to the low yields, this method
  • has also been reported [37]. The multistep method has recently been extended to the preparation of 2-naphthylsulfur pentafluoride and heteroarylsulfur pentafluorides [22][38][39][40][41]. 5-Nitrophenyl-1,3-bis(sulfur pentafluoride) was prepared by reaction of the corresponding polymeric disulfide with
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Published 29 Mar 2012

Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

  • Karel Křenek,
  • Petr Šimon,
  • Lenka Weignerová,
  • Barbora Fliedrová,
  • Marek Kuzma and
  • Vladimír Křen

Beilstein J. Org. Chem. 2012, 8, 428–432, doi:10.3762/bjoc.8.48

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  • , Czech Republic 10.3762/bjoc.8.48 Abstract The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety
  • yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio. Keywords: α-ManNAc; glycosidase; glycosylation; nitrophenyl; oxazoline; Introduction Hexosamines are fundamental structural elements and precursors of the peptidoglycan and membrane lipopolysaccharide layer as well as of
  • synthesis of ManNAc-containing compounds, as well as the substrates for the hypothetical α-N-acetylmannopyranosidase, are required. This paper describes new robust and effective methods for the synthesis of both o-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside (7) and p-nitrophenyl 2-acetamido-2-deoxy
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Published 20 Mar 2012

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

  • Nan Sun,
  • Bin Li,
  • Jianping Shao,
  • Weimin Mo,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2012, 8, 61–70, doi:10.3762/bjoc.8.6

Graphical Abstract
  • -substituted arylamines, could be also converted into their dithiocarbamates, which could smoothly afford high yield of their corresponding isothiocyanates by further treatment with TCT (Table 4, entries 5–7). To our surprise, in the case of 4-nitroaniline as the substrate, only 13% of 4-nitrophenyl
  • (CAS No: 2719-32-6, Table 4, entry 7): Yield: 91%; white solid; mp 121–122 °C (lit. [63]: mp 119–120 °C); IR (KBr): 2138 cm−1; 1H NMR (CDCl3) δ 7.30–7.32 (m, 2H), 7.65–7.67 (m, 2H); GC–EIMS m/z: 160 [M+, 100%]. 4-Nitrophenyl isothiocyanate (CAS No: 2131-61-5, Table 4, entry 8): Yield: 13%; white solid
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Published 10 Jan 2012

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

  • Jiří Kulhánek and
  • Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

Graphical Abstract
  • -IM-(π-A)2 (16), A-π-IM-(π-D)2 (17), A-π-IM-(π-A)2 (18), and D-π-IM-(π-D)2 (19). 4,5-Bis(4-nitrophenyl)imidazole was utilized as a suitable acceptor moiety and was further modified with a thiophene π-linker as an auxiliary electron donor (20). These basic push–pull imidazoles were mainly investigated
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Published 05 Jan 2012

A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates

  • Xinghua Wu,
  • Yu Chen,
  • Herve Aloysius and
  • Longqin Hu

Beilstein J. Org. Chem. 2011, 7, 1030–1035, doi:10.3762/bjoc.7.117

Graphical Abstract
  • condense with p-nitrophenyl isocyanate to form the Nα-protected aminoacyl-pNAs [14]. However, commercially available p-nitrophenyl isocyanate often contains impurities due to degradation during storage; these impurities must be removed before use. In addition, a significant amount of hydantoin by-product
  • electron-withdrawing group [18][19][20]. We postulated that the selenocarboxylate/azide amidation could be a good solution to the problem of synthesizing aminoacyl-pNAs and aminoacyl-AMCs. Instead of p-nitroaniline and 7-amino-4-methylcoumarin, p-nitrophenyl azide and 7-azido-4-methylcoumarin would be used
  • Table 1 and Table 2, through the reaction of N-hydroxysuccinimide (HOSu)-activated esters or mixed anhydrides of Nα-protected amino acids with sodium hydrogen selenide to form their corresponding Nα-protected amino selenocarboxylate, followed by the coupling of the selenocarboxylate with p-nitrophenyl
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Published 27 Jul 2011

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

  • Lucie Brulikova and
  • Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

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  • analogue 120 using acetic anhydride in pyridine. Synthesis of arylderivatives The synthesis of 5-[alkoxy-(4-nitrophenyl)methyl]uracils 124 (Scheme 21) has recently been investigated [34]. The authors reported the synthesis of alkoxy derivatives with alkyl chain lengths C1-C12 whose preparation started with
  • the condensation reaction of uracil and p-nitrobenzaldehyde in concentrated hydrochloric acid. Subsequently, the resulting 5-[chloro-(4-nitrophenyl)methyl]uracil (123) was reacted with different alcohols to give the corresponding ethers 124a–o. The introduction of a sugar moiety to the selected
  • analogues 124f–i afforded 5-[alkoxy(4-nitrophenyl)methyl]uridines 126f–i and 127f–i (Scheme 22) [35]. In a first step, the alkoxy uracils 124 were silylated and then reacted with a protected ribose in the presence of TMSOTf to afford diastereomeric mixtures of nucleosides 125. Diasteroisomers were separated
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Published 26 May 2011

Novel carbazole–pyridine copolymers by an economical method: synthesis, spectroscopic and thermochemical studies

  • Aamer Saeed,
  • Madiha Irfan and
  • Shahid Ameen Samra

Beilstein J. Org. Chem. 2011, 7, 638–647, doi:10.3762/bjoc.7.75

Graphical Abstract
  • : 84.3%, H: 5.9%, N: 7.1%. Poly{[N-butylcarbazole-3,6-diyl][4-(3-nitrophenyl)pyridine-2,6-diyl]} (P1b) Yellow powder; yield: 49%; IR (KBr, υ/cm−1): 3035, 2930, 2890, 1656, 1585, 1523, 1345, 1145, 800; 1H NMR (CDCl3, 300 MHz): δ 8.96 (s, Ar-8), 8.58 (s, Ar-7), 8.27 (m, Ar-H), 8.0 (d, J = 7.8 Hz, Ar-5
  • , 129.0, 127.3, 126.2, 120.7, 118.1, 116.5, 110.5, 35.2, 30.1, 29.2, 28.7, 27.2, 21.9, 14.8; Elemental analysis: Calcd C: 86.5%, H: 6.9%, N: 6.5%; found C: 83.3%, H: 6.7%, N: 6.1%. Poly{[N-octylcarbazole-3,6-diyl][4-(3-nitrophenyl)pyridine-2,6-diyl]} (P2b) Yellow powder; yield: 46%; IR (KBr, υ/cm−1): 3070
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Published 19 May 2011

CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands

  • Shuxu Gao,
  • Yu Liu and
  • Shengming Ma

Beilstein J. Org. Chem. 2011, 7, 396–403, doi:10.3762/bjoc.7.51

Graphical Abstract
  • ), 0.76), 262 (M+ (35Cl), 2.08), 139 (100); IR (neat) 2927, 2857, 1931, 1654, 1590, 1460, 1397, 1274, 1091 cm−1; HRMS-EI (m/z) calcd for C16H19O35Cl+ [M+]: 262.1124; found: 262.1130. 2-Hexyl-1-(4'-nitrophenyl)buta-2,3-dien-1-one (2e) The reaction of 1,10-phenanthroline (5.5 mg, 0.03 mmol), 2,2'-bipyridine
  • (4.7 mg, 0.03 mmol), CuCl (5.9 mg, 0.06 mmol), K2CO3 (20.8 mg, 0.15 mmol), dry toluene (1.5 mL), DBAD (13.9 mg, 0.06 mmol), and 2-hexyl-1-(4-nitrophenyl)buta-2,3-dien-1-ol (82.7 mg, 0.3 mmol)/dry toluene (1.5 mL) afforded 2e (51.4 mg, 63%) (eluent: petroleum ether/diethyl ether = 20:1): liquid; 1H NMR
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Published 07 Apr 2011

Anion–π interactions influence pKa values

  • Christopher J. Cadman and
  • Anna K. Croft

Beilstein J. Org. Chem. 2011, 7, 320–328, doi:10.3762/bjoc.7.42

Graphical Abstract
  • -nitrophenyl)-1-naphthol (2): mp 135–135.5 °C; 1H NMR δ = 7.02 (d, 2H, J = 9.15 Hz), 7.17 (s, 1H), 7.50 (m, 3H), 7.79 (d, 1H, J = 8.5 Hz), 7.93 (d, 2H, J = 9.15 Hz), 8.20 (d, 2H, J = 9.45 Hz) ppm; 13C NMR δ = 116.6, 121.6, 125.8, 125.9, 126.1, 126.7, 126.9, 127.0, 128.2, 135.2, 150.4 ppm; IR (nujol mull) ν
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Published 17 Mar 2011

Surfactant catalyzed convenient and greener synthesis of tetrahydrobenzo[a]xanthene-11-ones at ambient temperature

  • Pravin V. Shinde,
  • Amol H. Kategaonkar,
  • Bapurao B. Shingate and
  • Murlidhar S. Shingare

Beilstein J. Org. Chem. 2011, 7, 53–58, doi:10.3762/bjoc.7.9

Graphical Abstract
  • (50 MHz, CDCl3): δ 27.1, 29.3, 32.5, 34.3, 41.9, 50.9, 113.1, 116.8, 117.3, 123.9, 125.0, 127.2, 128.7, 129.4, 130.2, 131.5, 131.9, 132.6, 143.3, 145.1, 150.8, 164.2, 196.9; IR (KBr, cm−1): v 2952, 1648, 1597, 1373, 1231, 1184, 823; ES-MS: 389.14 [M+], 391.13 [M+ + 2]. 12-(2-nitrophenyl)-9,9-dimethyl
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Published 13 Jan 2011

Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

  • Kumaresh Ghosh,
  • Tanmay Sarkar and
  • Asoke P. Chattopadhyay

Beilstein J. Org. Chem. 2010, 6, 1211–1218, doi:10.3762/bjoc.6.139

Graphical Abstract
  • with 4-nitrophenyl isocyanate (obtained from 4-nitroaniline by reaction with triphosgene in dry THF) in dry THF to give urea derivative 5. Subsequent reaction of 5 with 9-chloromethylanthracene under refluxing conditions in dry CH3CN gave the chloride salt 6. Anion exchange of the salt 6 with NH4PF6
  • -N-acetylvaline salt than with L-N-acetylalanine. This is attributed to the formation of a charge transfer complex between the excited state of anthracene and the electron deficient nitrophenyl urea during the interaction process. We believe that this characteristic feature with L-N-acetylvaline is
  • nitrophenyl urea as represented in Figure 4a, takes place. This component coexists with the other components contributing large preexponential factor to the total fluorescence. This finding was not observed with L-N-acetylalanine or L-N-acetylproline salts (Table 1). Neither was this observed when the
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Published 21 Dec 2010

Catalysis: transition-state molecular recognition?

  • Ian H. Williams

Beilstein J. Org. Chem. 2010, 6, 1026–1034, doi:10.3762/bjoc.6.117

Graphical Abstract
  • relative free energy difference of about 20 kJ mol−1, by means of the OYHY…Oring hydrogen bond [23]. A two-dimensional PMF computed for 4-nitrophenyl β-xylobioside (the substrate employed in the experimental kinetics studies) with BCX using the same AM1/OPLS-AA hybrid potential, as a function of
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Published 03 Nov 2010

En route to photoaffinity labeling of the bacterial lectin FimH

  • Thisbe K. Lindhorst,
  • Michaela Märten,
  • Andreas Fuchs and
  • Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

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  • the second case, a closed-gate conformation of FimH was used for the modeling [8]. This led to somewhat different predictions, as expected, however, the same trends were revealed for ligands 1–3 and 5 in comparison with the well-known standard ligands methyl α-D-mannoside (MeMan) and p-nitrophenyl α-D
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Published 26 Aug 2010

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

  • Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

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  • . Conversion to 4-nitrophenyl trifluoromethyl sulfide (60% yield) requires prolonged irradiation in a quartz ampoule at 30–45 °C [143]. The length of the perfluoroalkyl iodide chain has no influence, although lower yields were observed using CF3I in comparison with other iodoperfluoroalkanes. A branching RFI
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Published 18 Aug 2010

Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-S-phosphorylacetates

  • Milena Trmčić and
  • David R. W. Hodgson

Beilstein J. Org. Chem. 2010, 6, 732–741, doi:10.3762/bjoc.6.87

Graphical Abstract
  • shortfalls, 2-S-(5′-thiophosphoryluridine)acetic acid esters were prepared using p-nitrophenyl bromoacetate or m-nitrophenyl bromoacetate in combination with uridine-5′-monophosphorothioate. Kinetics of hydrolysis and aminolysis of the resulting p- and m-nitrophenyl 2-S-(5′-thiophosphoryluridine)acetates
  • were determined by monitoring the formation of phenolate ions spectrophotometrically as a function of pH. The p- and m-nitrophenyl 2-S-(5′-thiophosphoryluridine)acetates showed similar reactivity profiles despite the significant difference in the pKaH values of their nitrophenolate leaving groups. Both
  • were used to predict leaving group pKa values that could lead to improved selectivity towards aminolysis while retaining reasonable reaction times. Conclusions: Both p- and m-nitrophenyl 2-S-(5′-thiophosphoryluridine)acetates show some selectivity towards aminolysis over hydrolysis, with the m
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Published 16 Aug 2010
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  • coupling of 1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)diazene and phenylboronic acid as a model reaction (Scheme 2). As described for the homogeneous catalytic conditions [29], a Lewis acid was essential for the formation of the biphenyl products. Without BF3·OEt2, no diaryl product was observed whatsoever
  • improved yields (Table 2, entry 6). Table 3 shows the effect of the molar ratio of phenylboronic acid to 1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)diazene on the reaction yield. A yield of 77% was obtained when the molar ratio was 1.25 (Table 3, entry 1). The yield of the corresponding biaryl product increased
  • Suzuki–Miyaura cross-coupling reactions of 1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)diazene and phenylboronic acid was investigated (Table 4). The catalyst could be re-used eight times and still retained high activity after separation, washing and drying under vacuum, under the same reaction conditions. To
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Published 28 Jun 2010

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

  • Norio Shibata,
  • Andrej Matsnev and
  • Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

Graphical Abstract
  • ). Interestingly, the method was developed for the synthesis of heteroaromatic diarylsulfonium salts. Thus, p-nitrophenyl trifluoromethyl sulfide was reacted first with xenon difluoride in the absence of solvent and then with boron trifluoride. The addition of an electron-rich heterocycle gave products 28 and 29
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Published 16 Jun 2010
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  • p-nitrophenyl β-galactopyranoside and β-galactosidase (Bovin testes). The subsequent transsialylation was carried out with p-nitrophenyl sialoside (pNp-αNeu5Ac) and either sialidase from Salmonella typhimurium or from Newcastle disease virus [7]. Recently, a more effective higher yielding transfer
  • a down field shifted doublet for H-4′ at δ 5.37 (J3′4′ = 2.9 Hz). A similar approach was employed for the synthesis of the protected epimer of sialyllacto-N-neotetraose 14. β-Galactosylation of 2-azidothioglucoside with p-nitrophenyl β-galactopyranoside and β-galactosidase (Bacillus circulans) gave
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Published 22 Feb 2010

Synthesis of indolo[3,2-b]carbazole-based new colorimetric receptor for anions: A unique color change for fluoride ions

  • Ajit Kumar Mahapatra,
  • Giridhari Hazra and
  • Prithidipa Sahoo

Beilstein J. Org. Chem. 2010, 6, No. 12, doi:10.3762/bjoc.6.12

Graphical Abstract
  • ][24][25][26][27][28], there is a paucity of reports on selective naked-eye chemosensors for fluoride [29][30][31]. Nitrophenyl, nitronaphthalene urea [32][33][34], naphthalene triphenyl-phosphonium [35], benzimidazolyl pyridine [36][37] and oxidized bis(indolyl)methane [38] as signal units for
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Preliminary Communication
Published 08 Feb 2010
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