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Product Name:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS:61676-62-8
Purity:97% (Min,GC) Package:100g;1kg;5kg,10kg,25kg,50kg
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| | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Basic information |
| Product Name: | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | | Synonyms: | Isopropoxyboronic acid picol ester;Isopropoxyboronic a;Isopropoxyboronic aci;2-ISOPROPOXY-4,4,5,5-TETRAMETHYL-1,3,2-DIOABOROLANE;2-Isopropoxyboronic acid, pinacol cyclic ester;sopropoxyboronic acid pinacol ester;Isopropoxyboronic acid pinacol ester
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropoxy-4,4,5,5-dimethyl-1,3,2-dioxaborolane | | CAS: | 61676-62-8 | | MF: | C9H19BO3 | | MW: | 186.06 | | EINECS: | 612-189-2 | | Product Categories: | Boric Acid| Boric Acid Ester| Potassium Trifluoroborate;B (Classes of Boron Compounds);Boric Acid Esters;Boric Acid Triesters;Boronic Acids and Derivatives;Organoborates;Organometallic Reagents;Organic boronic acid;Boronic ester;Organoborons | | Mol File: | 61676-62-8.mol |  |
| | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical Properties |
| Boiling point | 73 °C15 mm Hg(lit.) | | density | 0.912 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.409(lit.) | | Fp | 109 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | Specific Gravity | 0.912 | | color | Colorless | | Water Solubility | Soluble in water. | | Sensitive | Moisture Sensitive | | BRN | 1906370 | | InChI | InChI=1S/C9H19BO3/c1-7(2)11-10-12-8(3,4)9(5,6)13-10/h7H,1-6H3 | | InChIKey | MRWWWZLJWNIEEJ-UHFFFAOYSA-N | | SMILES | O1C(C)(C)C(C)(C)OB1OC(C)C | | CAS DataBase Reference | 61676-62-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 10-36/37/38 | | Safety Statements | 16-26-36 | | RIDADR | UN 1993 3/PG 3 | | WGK Germany | 3 | | HazardClass | 3 | | PackingGroup | III | | HS Code | 29209090 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Usage And Synthesis |
| Chemical Properties | Colorless liquid | | Uses | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes and to prepare fluorenylborolane.
It can also be used in the synthesis of following intermediates for generating conjugated copolymers:
- 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.
- 3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.
- 2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.
- 2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.
| | Uses | suzuki reaction | | Synthesis | Step c) Preparation of isopropyl pinacol borate: triisopropyl borate (261.0 g, 1.388 mol) and pinacol (142.5 g, 1.207 mol) were added to a 20 L four-necked flask, and the mixture was heated to about 90 °C and maintained for 12 to 16 hours. The progress of the reaction was monitored by gas chromatography (GC), and the completion of the reaction was measured by a pinacol content of less than 4.0%. Upon completion of the reaction, a distillation operation was performed to collect fractions with boiling points between 174 and 178 °C to obtain the target product isopropanol pinacol borate as a colorless oil. Yields ranged from 80-90% in six 20 L batches of the operation.GC analysis showed a product purity of 87-96%, while 1H NMR analysis indicated an extremely high product purity. [The difference between GC purity and 1H NMR purity is attributed to the instability of the product under GC conditions]. | | References | [1] Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4617 - 4618
[2] Organic Letters, 2012, vol. 14, # 22, p. 5644 - 5647
[3] Patent: US2013/40984, 2013, A1. Location in patent: Paragraph 0482-0483
[4] Chemische Berichte, 1989, vol. 122, p. 1777 - 1782
[5] Organic Letters, 2013, vol. 15, # 18, p. 4666 - 4669 |
| | 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products And Raw materials |
| Raw materials | Pinacol-->Triisopropyl borate | | Preparation Products | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carbonitrile-->Benzo[b]thiophene-3-boronic acid pinacol ester, 95%-->3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRAZOLO[1,5-A]PYRIDINE-->4-Difluoromethoxyphenylboronic acid pinacol ester-->3-Hydroxy-2,3-diMethylbutan-2-yl hydrogen (2,6-diMethylpyridin-3-yl)boronate-->3-CHLOROPHENYLBORONIC ACID, PINACOL ESTER-->1-Ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-->1-(2-Methoxyethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-->2-(1-NAPHTHYLENE)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER-->3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER-->2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&-->9-Octyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole |
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