{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-34826959d1bc4c97898ab86dc41580e6","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"087df913920cc63c451089a4080c9c97ab3ecbb883274cbd31089c2be3b089e9","doi":"10.1021/jacs.5b07154","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-05a85ade6785422e","route_slugs":["ord-34826959d1bc4c97898ab86dc41580e6-a9dad3fdb02f","ord-34826959d1bc4c97898ab86dc41580e6-7ae5a1887189"],"reactant_slugs":["ord-compound-a0dac1a6b55c416b7f51"],"product_slugs":["ord-compound-7192c545f502e6d4d284","ord-compound-704b710996b071728756"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_1222"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-54-3"}],"amount":{"volume":{"value":0.5999988,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC2=C(C1)C3=CC(=CC=C3N2[Si](C(C)C)(C(C)C)C(C)C)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1803309-95-6"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.005,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OCCCC)C=1C=CN=C(C1)C=2N=CC=C(C2)C(=O)OCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"69641-93-6"}],"amount":{"moles":{"value":0.01,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.4,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":0.025,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C=2C=CC=3C4=CC(=CC=C4N(C3C2)[Si](C(C)C)(C(C)C)C(C)C)CC"},{"type":"CAS_NUMBER","value":"1803310-03-3"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":53}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC=C3C(=C2)C=4C=C(C=CC4N3[Si](C(C)C)(C(C)C)C(C)C)CC"},{"type":"CAS_NUMBER","value":"1803310-10-2"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":27}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (600 MHz, CDCl3) δ 8.16 (t, J = 2.3 Hz, 1H), 8.06 – 8.03 (m, 1H), 7.91 (d, J = 2.9 Hz, 1H), 7.65 (dt, J = 8.3, 4.6 Hz, 1H), 7.63 – 7.58 (m, 1H), 7.25 – 7.21 (m, 1H), 2.82 (q, J = 8.1 Hz, 2H), 2.00 (dtt, J = 15.7, 7.9, 3.4 Hz, 3H), 1.40 – 1.35 (m, 15H), 1.20 (q, J = 7.0 Hz, 18H); 13C NMR (151 MHz, CDCl3) δ 145.2, 144.2, 135.6, 131.8, 129.1, 126. 8, 126.5, 125.55, 121.20, 119.19, 119.13, 114.22, 28.92, 25.30, 18.99, 16.43, 14.08;"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1021/jacs.5b07154"}}},"entities":[{"slug":"ord-compound-a0dac1a6b55c416b7f51","name":"C23H33NSi · ORD BGSQHMSMBCFURC-UHFFFAOYSA-N","smiles":"CCc1ccc2c(c1)c1ccccc1n2[Si](C(C)C)(C(C)C)C(C)C","inchi":"InChI=1S/C23H33NSi/c1-8-19-13-14-23-21(15-19)20-11-9-10-12-22(20)24(23)25(16(2)3,17(4)5)18(6)7/h9-18H,8H2,1-7H3","formula":"C23H33NSi"},{"slug":"ord-compound-7192c545f502e6d4d284","name":"C29H44BNO2Si · ORD IVUCTLXQIKOKRL-UHFFFAOYSA-N","smiles":"CCc1ccc2c(c1)c1ccc(B3OC(C)(C)C(C)(C)O3)cc1n2[Si](C(C)C)(C(C)C)C(C)C","inchi":"InChI=1S/C29H44BNO2Si/c1-12-22-13-16-26-25(17-22)24-15-14-23(30-32-28(8,9)29(10,11)33-30)18-27(24)31(26)34(19(2)3,20(4)5)21(6)7/h13-21H,12H2,1-11H3","formula":"C29H44BNO2Si"},{"slug":"ord-compound-704b710996b071728756","name":"C29H44BNO2Si · ORD NEHYVXORCLZNEC-UHFFFAOYSA-N","smiles":"CCc1ccc2c(c1)c1cc(B3OC(C)(C)C(C)(C)O3)ccc1n2[Si](C(C)C)(C(C)C)C(C)C","inchi":"InChI=1S/C29H44BNO2Si/c1-12-22-13-15-26-24(17-22)25-18-23(30-32-28(8,9)29(10,11)33-30)14-16-27(25)31(26)34(19(2)3,20(4)5)21(6)7/h13-21H,12H2,1-11H3","formula":"C29H44BNO2Si"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-05a85ade6785422e","title":"Literature experiment — 10.1021/jacs.5b07154","source_type":"paper","doi":"10.1021/jacs.5b07154","url":"https://doi.org/10.1021/jacs.5b07154","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}