Vinylboronic acid MIDA ester
- Product Name
- Vinylboronic acid MIDA ester
- CAS No.
- 1104636-73-8
- Chemical Name
- Vinylboronic acid MIDA ester
- Synonyms
- 6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione;Vinylboronic acid MIDA ester;Vinylboronic acid MIDA ester 97%;2-Ethenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione;4-Methyl-8-vinyldihydro-4l4,8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborole-2,6(3H,5H)-dione
- CBNumber
- CB22523086
- Molecular Formula
- C7H9BNO4
- Formula Weight
- 181.96
- MOL File
- 1104636-73-8.mol
Vinylboronic acid MIDA ester Property
- Melting point:
- 152-156°C
- storage temp.
- 2-8°C
- form
- powder
- Appearance
- White to off-white Solid
Safety
- WGK Germany
- 2
- HS Code
- 2931900090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
N-Bromosuccinimide Price
- Product number
- 704415
- Product name
- Vinylboronic acid MIDA ester
- Purity
- 97%
- Packaging
- 1g
- Price
- $102.81
- Updated
- 2025/07/31
- Product number
- 704415
- Product name
- Vinylboronic acid MIDA ester
- Purity
- 97%
- Packaging
- 5g
- Price
- $280
- Updated
- 2025/07/31
- Product number
- 704415
- Product name
- Vinylboronic acid MIDA ester
- Purity
- 97%
- Packaging
- 25g
- Price
- $952
- Updated
- 2025/07/31
- Product number
- 704415
- Product name
- Vinylboronic acid MIDA ester
- Purity
- 97%
- Packaging
- 100g
- Price
- $3360
- Updated
- 2023/06/20
- Product number
- M220845
- Product name
- 6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
Vinylboronic acid MIDA ester Chemical Properties,Usage,Production
Uses
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings
Suzuki Cross-Coupling with MIDA Boronates
General Description
Vinylboronic acid MIDA ester, like other MIDA boronates, possesses the capacity for controlled, in situ slow-release of boronic acids under aqueous basic conditions allowing the cross-coupling of classically challenging substrates.
Synthesis
4408-64-4
1826-67-1
1104636-73-8
Trimethyl borate (94 mL, 840 mmol) and tetrahydrofuran (600 mL) were added to a 3L three-necked round-bottomed flask equipped with a stir bar. The solution was cooled to -78°C. Vinyl magnesium bromide (1.0 M solution in tetrahydrofuran, 800 mL, 800 mmol) was added dropwise through a cannula over 2 hr 45 min. The resulting solution was stirred at -78°C for 15 minutes and then at 23°C for 2 hours and 30 minutes. Dry N-methyliminodiacetic acid (235.0 g, 1.6 mol) and dimethyl sulfoxide (600 mL) were added to a separate 2L three-necked round-bottomed flask fitted with a stir bar, internal thermometer, and distillation apparatus. The solution was heated to an internal temperature of 110-115°C using an oil bath. The borate suspension was added dropwise to the hot N-methyliminodiacetic acid solution through a polytetrafluoroethylene cannula over a period of 2 hours and 10 minutes, maintaining the internal temperature between 105 and 115°C. After complete addition of the borate solution, the reaction solution was cooled to 23°C. The resulting solution was transferred to a split funnel containing water (1 L), brine (1 L), ethyl acetate (1.5 L) and acetone (1 L). The mixture was shaken to remove the aqueous layer and extracted with ethyl acetate/acetone (2:1, 260mL). The combined organic layers were washed with water (2500 mL). The combined aqueous washings were back-extracted with ethyl acetate/acetone (2:1, 2300mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuum. The resulting solid was suspended in 300 mL of acetone and 4 L of ether was added to precipitate the product. The resulting solid was collected by vacuum filtration to give vinylboronic acid methyliminodiacetate as a white solid (81.2 g, 55%). The spectral data of the product were in agreement with those previously reported by our laboratory.
References
[1] Tetrahedron, 2013, vol. 69, # 36, p. 7732 - 7740
Vinylboronic acid MIDA ester Preparation Products And Raw materials
Raw materials
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View Lastest Price from Vinylboronic acid MIDA ester manufacturers
- Product
- Vinylboronic acid MIDA ester 1104636-73-8
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 97.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-05-07