(3,3,3-Trifluoroprop-1-en-2-yl)boronic acid

Base Information

• Chemical Name: (3,3,3-Trifluoroprop-1-en-2-yl)boronic acid
• CAS No.: 357274-85-2
• Molecular Formula: C3H4 B F3 O2
• Molecular Weight: 139.87
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID10382208
• Nikkaji Number: J1.520.551B
• Wikidata: Q82173520
• Mol file: 357274-85-2.mol

Synonyms:357274-85-2;(3,3,3-Trifluoroprop-1-en-2-yl)boronic acid;3,3,3-trifluoroprop-1-en-2-ylboronic Acid;ALPHA-(TRIFLUOROMETHYL)ETHENYL BORONIC ACID;[1-(trifluoromethyl)vinyl]boronic acid;Boronic acid, [1-(trifluoromethyl)ethenyl]-;3,3,3-trifluoroprop-1-en-2-yl boronic acid;SCHEMBL539841;DTXSID10382208;1-(Trifluoromethyl)ethenylboronic Acid;AKOS006229294;AB15473;[1-(trifluoromethyl) vinyl]boronic acid;[1-(Trifluoromethyl)ethenyl]boronic acid;1-(TRIFLUOROMETHYL)VINYLBORONIC ACID;CS-0451654;FT-0739757;EN300-209634;(3,3,3-trifluoroprop-1-en-2-yl)-boronic acid;[1-(TRIFLUOROMETHYL)ETHENYL]-BORONIC ACID;F1913-0313

Chemical Property of (3,3,3-Trifluoroprop-1-en-2-yl)boronic acid

Chemical Property:

• Boiling Point: 183.8°Cat760mmHg
• PKA: 7.31±0.43(Predicted)
• Flash Point: 64.9°C
• PSA: 40.46000
• Density: 1.42g/cm³
• LogP: 0.11690
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 140.0256440
• Heavy Atom Count: 9
• Complexity: 119

Purity/Quality:

98%min ^*data from raw suppliers

3,3,3-trifluoroprop-1-en-2-ylboronicacid 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C(=C)C(F)(F)F)(O)O
• Uses: (3,3,3-Trifluoroprop-1-en-2-yl)boronic Acid is used in catalytic enantioselective synthesis of Heterocyclic vicinal Fluoroamines using asymmetric protonation.

Technology Process of (3,3,3-Trifluoroprop-1-en-2-yl)boronic acid

There total 5 articles about (3,3,3-Trifluoroprop-1-en-2-yl)boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-bromo-3,3,3-trifluoropropene (1514-82-5) → α-(trifluoromethyl)ethenyl boronic acid (357274-85-2)

Guidance literature:

With Trimethyl borate; magnesium; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(01)00636-0

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + 2-bromo-3,3,3-trifluoropropene (1514-82-5) → α-(trifluoromethyl)ethenyl boronic acid (357274-85-2)

Guidance literature:

With magnesium; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1246/cl.2004.1206

Reference yield:

4,4,6-trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane (1011460-68-6) → α-(trifluoromethyl)ethenyl boronic acid (357274-85-2)

Guidance literature:

With hydrogenchloride; In water; acetone; at 90 ℃; for 6h;

DOI:10.1016/j.tetlet.2021.153147

upstream raw materials:

2-bromo-3,3,3-trifluoropropene

Trimethyl borate

4,4,6-trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane

Downstream raw materials:

4-chloro-1-nitro-2-(3,3,3-trifluoroprop-1-en-2-yl)benzene

2-(3,3,3-trifluoroprop-1-en-2-yl)benzaldehyde

1-methoxy-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene

ethyl 4-(3,3,3-trifluoroprop-1-en-2-yl)benzoate

Refernces

• 1、 Lai, Samson,Lin, Wen Xuan,Perrin, David M.,Takaesu, Noah. "Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations". supporting information. . Retrieved 2021/05/31.
• 2、 Fujita, Takeshi,Konno, Naruki,Watabe, Yota,Ichitsuka, Tomohiro,Nagaki, Aiichiro,Yoshida, Jun-ichi,Ichikawa, Junji. "Flash generation and borylation of 1-(trifluoromethyl)vinyllithium toward synthesis of α-(trifluoromethyl)styrenes". . p. 72 - 76. Retrieved 2018/02/09.