2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 154820-95-8
• Molecular Formula: C11H20 B Cl O2
• Molecular Weight: 230.543
• DSSTox Substance ID: DTXSID101165262
• Mol file: 154820-95-8.mol

Synonyms:2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;DTXSID101165262;FT-0770770;FT-0772487;2-(5-Chloro-1-penten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.038mmHg at 25°C
• Refractive Index: n20/D 1.4630
• Boiling Point: 248.52°C at 760 mmHg
• Flash Point: >230 °F
• PSA: 18.46000
• Density: 1.004 g/mL at 25 °C
• LogP: 3.19300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 230.1244877
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

trans-5-Chloro-1-penten-1-ylboronic acid pinacol ester 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=CCCCCl

Technology Process of 2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-(5-Chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 85.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-chloro-4-pentyne (14267-92-6) + dimethylsulfide borane complex (13292-87-0) → 2-(5-chloropent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (154820-95-8)

Guidance literature:

In dichloromethane; byproducts: H2; dropwise addn. of BH3*(CH3)2S (20 mmol) in (CH3)2S to soln. of pinacol (20 mmol) in dry THF; stirring for 1 h (0°C), then warming (25°C); stirring (1 h); addn. of Cl(CH2)3CCH (10 mmol) at 0°C; stirring (7 h, 25°C);; addn. of ether, pouring soln. into separatory funnel contg. satd. aq. NH4Cl; washing org. phase with satd. aq. NH4Cl, drying over MgSO4; evapg. solvent under vac.; flash chromy. of residue (hexane/ether); E/Z ratio 99:1, determined by chromy. (GLC);;

DOI:10.1016/0022-328X(92)88002-Z

Reference yield: 84.0%

1-chloro-4-pentyne (14267-92-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(5-chloropent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (154820-95-8)

Guidance literature:

With bis(cyclohexanyl)borane;

DOI:10.1021/op2002497

Reference yield: 66.0%

2-(5-chloropent-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (159087-42-0) → 2-(5-chloropent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (154820-95-8)

Guidance literature:

2-(5-chloropent-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With bis(cyclohexanyl)borane; In diethyl ether; at 20 ℃; for 0.5h;

With ethanolamine; acetic acid; In diethyl ether; at 0 - 20 ℃; Further stages.;

DOI:10.1021/jo801191v

upstream raw materials:

2,3-dimethyl-2,3-butane diol

1-chloro-4-pentyne

dimethylsulfide borane complex

2-(5-chloropent-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2-[2-(3-chloropropyl)cyclopropyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

(1R,2R)-2-(pent-4-yn-1-yl)cyclopropan-1-ol

acetic acid (1S,2S)-2-pent-4-ynylcyclopropyl ester