Cyclopentylboronic acid

Base Information

• Chemical Name: Cyclopentylboronic acid
• CAS No.: 63076-51-7
• Molecular Formula: C₅H₁₁BO₂
• Molecular Weight: 113.952
• Hs Code.: 2931900090
• European Community (EC) Number: 672-296-5
• DSSTox Substance ID: DTXSID80370218
• Nikkaji Number: J1.331.473J
• Wikidata: Q72460414
• Mol file: 63076-51-7.mol

Synonyms:Cyclopentylboronic acid;63076-51-7;Cyclopentylboronicacid;Boronic acid, cyclopentyl-;MFCD01074541;cyclopentaneboronic acid;Boronic acid, B-cyclopentyl-;SCHEMBL257594;Cyclopentylboronic acid, >=95%;DTXSID80370218;VTTDFSNKIMAQTB-UHFFFAOYSA-N;AKOS009157823;AB08034;AC-9536;AM80875;CS-W000955;GS-6308;NCGC00249448-01;SY023521;A8709;C2442;FT-0624271;EN300-115787;J-520183;F0001-1713;Z1147227731

Chemical Property of Cyclopentylboronic acid

Chemical Property:

• Vapor Pressure: 0.00935mmHg at 25°C
• Melting Point: 126 °C (dec.)(lit.)
• Refractive Index: 1.449
• Boiling Point: 235.027 °C at 760 mmHg
• PKA: 10.47±0.20(Predicted)
• Flash Point: 95.941 °C
• PSA: 40.46000
• Density: 1.032 g/cm³
• LogP: 0.40340
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 114.0852098
• Heavy Atom Count: 8
• Complexity: 68.8

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclopentylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1CCCC1)(O)O
• Uses: Reactant involved in:Cross coupling reactions with quinones or aromatic aminesArylation and alkylation of diphenylisoxazoleRuphos-mediated Suzuki cross coupling reactions

Technology Process of Cyclopentylboronic acid

There total 7 articles about Cyclopentylboronic 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: 96.0%

cyclopentyldibromoborane dimethyl sulfide complex (64770-10-1) → cyclopentane boronic acid (63076-51-7)

Guidance literature:

With water; In diethyl ether; dichloromethane; under N2; to excess of H2O in Et2O added cooled (0 °C) soln. of B complex in CH2Cl2 with stirring, stirred for 10 min; water layer sepd., org. layer washed with cold H2O and brine, dried with MgSO4, evapd. in vac., recrystd. from C6H6;

DOI:10.1021/om50004a008

Reference yield: 62.0%

cyclopentene (142-29-0) → cyclopentane boronic acid (63076-51-7)

Guidance literature:

cyclopentene; With dichloroborane dioxane complex; In dichloromethane; for 4h; Heating;

With water; cooling;

DOI:10.1016/j.tetlet.2003.08.086

Reference yield: 32.0%

borane-THF (14044-65-6) + cyclopentene (142-29-0) → cyclopentane boronic acid (63076-51-7)

Guidance literature:

borane-THF; cyclopentene; In tetrahydrofuran; at 0 - 25 ℃; for 2h; Inert atmosphere;

With water; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cjoc.201800461

upstream raw materials:

cyclopentene

cyclopentyldibromoborane dimethyl sulfide complex

(CH₂S)2B-cyclo-C₅H₉

borane-THF

Downstream raw materials:

1-cyclopentyl-3-phenylpropan-1-one

4-(methoxy)phenylaminocyclopentane

2-cyclopentyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C₁₉H₂₂N₆

Refernces

• 1、 Liu, Mingshang,Huang, Hanchu,Chen, Yiyun. "Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis". supporting information. p. 1209 - 1212. Retrieved 2018/11/06.
• 2、 Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian. "Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides". . p. 2059 - 2066. Retrieved 2017/02/26.