{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-743548bea2e0400c88996cd6a1e0177c","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"881889b210d7affe599a5f5446ec1521d3369d8e3bace2fd9f27b7a4266a96b9","doi":"10.1021/ja500712z","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-f8bddb7db1a1b53f","route_slugs":["ord-743548bea2e0400c88996cd6a1e0177c-a9be17481a80"],"reactant_slugs":["ord-compound-64855d935b8d0924f0d4"],"product_slugs":["ord-compound-d53c8eb776fa1b319830"],"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_82"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"catalyst_1":{"components":[{"identifiers":[{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1578190-27-8"}],"amount":{"moles":{"value":0.01653,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"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":0.551,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=CC1C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-06-8"}],"amount":{"moles":{"value":0.551,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC(=CC1C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"660867-80-1"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_GC","type":"YIELD","percentage":{"value":92}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (chloroform-d, 23°C): δ 8.51 (d, Δν1/2 = 4.99 Hz, 1H), 7.52 (s, 1H), 7.44 (d, Δν1/2 = 5.00 Hz, 1H), 2.56 (s, 3H), 1.34 (s, 12H) (4-isomer); δ 8.83 (s, 1H), 7.97 (dd, Δν1/2 = 7.74 Hz, 1.66 Hz, 1H), 7.15 (d, Δν1/2 = 7.71 Hz, 1H), 2.58 (s, 3H), 1.34 (s, 12H) (5-isomer); δ 7.36 (dd, Δν1/2 = 9.15 Hz, 6.86 Hz, 1H), 6.41 (d, Δν1/2 = 9.14 Hz, 1H), 6.04 (d, Δν1/2 = 6.79 Hz, 1H), 2.32 (s, 3H), 1.34 (s, 12H) (6-isomer). {1H}13C NMR (chloroform-d, 23°C): δ 157.53, 148.19, 128.80, 125.89, 84.64, 24.97, 24.00 (4-isomer); δ 160.81, 154.63, 143.10, 123.09, 84.64, 24.97, 24.23 (5-isomer); δ 145.08, 142.13, 117.09, 106.29, 84.64, 24.97, 19.47 (6-isomer)."}}},"product_1_GC":{"type":"GC","details":"GC"}}}],"provenance":{"doi":"10.1021/ja500712z"}}},"entities":[{"slug":"ord-compound-64855d935b8d0924f0d4","name":"C6H7N · ORD BSKHPKMHTQYZBB-UHFFFAOYSA-N","smiles":"Cc1ccccn1","inchi":"InChI=1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3","formula":"C6H7N"},{"slug":"ord-compound-d53c8eb776fa1b319830","name":"C12H18BNO2 · ORD MBTULFIFECUURA-UHFFFAOYSA-N","smiles":"Cc1cc(B2OC(C)(C)C(C)(C)O2)ccn1","inchi":"InChI=1S/C12H18BNO2/c1-9-8-10(6-7-14-9)13-15-11(2,3)12(4,5)16-13/h6-8H,1-5H3","formula":"C12H18BNO2"}],"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-f8bddb7db1a1b53f","title":"Literature experiment — 10.1021/ja500712z","source_type":"paper","doi":"10.1021/ja500712z","url":"https://doi.org/10.1021/ja500712z","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"]}