| Identification | More | [Name]
2,6-Dimethoxyphenylboronic acid | [CAS]
23112-96-1 | [Synonyms]
2,6-DIMETHOXYBENZENEBORONIC ACID
2,6-DIMETHOXYPHENYLBORONIC ACID
AKOS BRN-0146
CHEMBRDG-BB 3200972
RARECHEM AH PB 0108
TIMTEC-BB SBB003736
2,6-Dimethoxyphenylboronic acid ,98%
2,6-Dimethoxyphenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
679-862-0 | [Molecular Formula]
C8H11BO4 | [MDL Number]
MFCD01318987 | [Molecular Weight]
181.98 | [MOL File]
23112-96-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige powder | [Melting point ]
110-112 °C (lit.) | [Boiling point ]
372.8±52.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [form ]
Powder | [pka]
8.58±0.58(Predicted) | [color ]
White to beige | [Detection Methods]
HPLC,NMR | [BRN ]
3032352 | [InChI]
InChI=1S/C8H11BO4/c1-12-6-4-3-5-7(13-2)8(6)9(10)11/h3-5,10-11H,1-2H3 | [InChIKey]
BKWVXPCYDRURMK-UHFFFAOYSA-N | [SMILES]
B(C1=C(OC)C=CC=C1OC)(O)O | [CAS DataBase Reference]
23112-96-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
29319090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige powder | [Uses]
Reactant for:• ;Suzuki-Miyaura reactions1,2,3,4,5 | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 2,6-dimethoxyphenylboronic acid from trimethyl borate and m-phenylene dimethyl ether was as follows: 41.5 g (0.3 mol) of 1,3-dimethoxybenzene and 170 g of THF were added to a dry 1L three-neck flask. The reaction system was cooled to -30~-40°C under nitrogen protection and stirred. 240 ml (0.6 mol) of n-butyllithium in hexane solution was added slowly dropwise. After the dropwise addition, the reaction system was slowly warmed to 10~30°C and maintained at this temperature for 1 hour. Subsequently, the system was again cooled to -30~-40 °C and 62.4 g (0.6 mol) of trimethyl borate was slowly added dropwise. After the dropwise addition was completed, the reaction was maintained at this temperature for 1 hour. After the reaction was completed, 148 g of concentrated hydrochloric acid and 150 g of water were added to the system and stirred at 20-30 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure until no solvent evaporated. The residue was dissolved in 200 g of water and stirred for 20 min, followed by filtration using a Brinell funnel to give 45 g of white solid product in 90.0% yield. The product was analyzed by gas chromatography and the purity was 99.0%. | [References]
[1] Patent: WO2004/24738, 2004, A1. Location in patent: Page/Page column 13-14
[2] Patent: CN105348240, 2016, A. Location in patent: Paragraph 0059; 0060
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4664 - 4668
[4] Organic Letters, 2012, vol. 14, # 16, p. 4250 - 4253
[5] Patent: KR2016/90242, 2016, A. Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166; 0167; 0168 |
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