| Identification | More | [Name]
5-Chloro-2-methoxyphenylboronic acid | [CAS]
89694-48-4 | [Synonyms]
5-CHLORO-2-METHOXY-BENZENEBORONIC ACID
5-CHLORO-2-METHOXYPHENYLBORONIC ACID
AKOS BRN-0073
CHEMBRDG-BB 3200964
RARECHEM AH PB 0263
5-Chloro-2-Methoxyphenylboroni
5-CHLORO-2-METHOXPHENYL BORONIC ACID
4-Chloroanisole-2-boronic acid
5-Chloro-2-methoxyphenylboronic Acid (contains varying amounts of Anhydride)
5-Chloro-2-methoxyphenylboronic acid ,98% | [EINECS(EC#)]
618-292-9 | [Molecular Formula]
C7H8BClO3 | [MDL Number]
MFCD01318966 | [Molecular Weight]
186.4 | [MOL File]
89694-48-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
134-141 °C(lit.) | [Boiling point ]
360.2±52.0 °C(Predicted) | [density ]
1.32±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
7.58±0.58(Predicted) | [color ]
White | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C7H8BClO3/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4,10-11H,1H3 | [InChIKey]
FMBVAOHFMSQDGT-UHFFFAOYSA-N | [SMILES]
B(C1=CC(Cl)=CC=C1OC)(O)O | [CAS DataBase Reference]
89694-48-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
Reactant for:• ;Boron-Heck arylation1• ;Suzuki-Miyaura reaction2 | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 5-chloro-2-methoxyphenylboronic acid from trimethyl borate and 2-bromo-4-chloroanisole is as follows: 5-chloro-2-methoxyphenylboronic acid (Structure 37 of Scheme XI, wherein R1 = H, R2 = Cl) was prepared in a similar manner to 5-fluoro-2-methoxyphenylboronic acid (Example 107). This was done as follows: in a dry reaction flask, 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 eq.) was added, cooled to -78°C under anhydrous and oxygen-free conditions, n-butyllithium (2.5 M hexane solution, 3.62 mL, 9.0 mmol, 1.0 eq.) was slowly added and the reaction was stirred for 30 minutes. Subsequently, trimethyl borate (3.0 mL, 26 mmol, 2.9 eq.) was added dropwise and the reaction was continued at -78°C for 2 hours. After completion of the reaction, it was slowly warmed to room temperature, the reaction was quenched with water, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 1.30 g (77% yield) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid. The compound did not require further purification and could be used directly in the next step of the reaction. Next, the crude 5-chloro-2-methoxyphenylboronic acid was used for the synthesis of methyl (5'-chloro-2'-methoxy-4-nitro-2-biphenylyl) carboxylate (Structure 39 of Scheme XI, where R1 = H, R2 = Cl). | [References]
[1] Patent: US5688808, 1997, A
[2] Patent: US5688810, 1997, A
[3] Patent: US5693646, 1997, A
[4] Patent: US5693647, 1997, A
[5] Patent: US5696127, 1997, A |
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