1,3-Difluoro-2-propanol

Base Information

• Chemical Name: 1,3-Difluoro-2-propanol
• CAS No.: 453-13-4
• Molecular Formula: C3H6 F2 O
• Molecular Weight: 96.0768
• Hs Code.: 29055998
• European Community (EC) Number: 207-216-6
• NSC Number: 76034,21305
• UNII: R8ZM2LQG7K
• DSSTox Substance ID: DTXSID1060009
• Nikkaji Number: J79.621B
• Wikipedia: 1,3-Difluoro-2-propanol
• Wikidata: Q3494631
• Mol file: 453-13-4.mol

Synonyms:1,3-difluoro-2-propanol;difluoro-2-propanol

Chemical Property of 1,3-Difluoro-2-propanol

Chemical Property:

• Appearance/Colour: CLEAR COLOURLESS LIQUID
• Vapor Pressure: 68.5mmHg at 25°C
• Refractive Index: n20/D 1.373(lit.)
• Boiling Point: 131.3°Cat760mmHg
• PKA: 12.67±0.20(Predicted)
• Flash Point: 42.2°C
• PSA: 20.23000
• Density: 1.106g/cm³
• LogP: 0.28630
• Storage Temp.: Flammables area
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 96.03867113
• Heavy Atom Count: 6
• Complexity: 28

Purity/Quality:

98%min ^*data from raw suppliers

1,3-Difluoro-2-propanol(StabilizedwithNaF) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(CF)O)F
• General Description: 1,3-Difluoro-2-propanol is a fluorinated alcohol that serves as a substrate for C–F bond activation by nucleophilic attack, particularly involving the {Pt₂S₂} core. The hydroxyl group in 1,3-difluoro-2-propanol plays a critical role in facilitating the reaction through hydrogen bonding, which aids in fluoride anion departure and stabilizes the transition state. This reactivity highlights its utility in studying C–F bond cleavage mechanisms and the influence of non-covalent interactions in such transformations.

Technology Process of 1,3-Difluoro-2-propanol

There total 6 articles about 1,3-Difluoro-2-propanol 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:

1,3-Dichloro-2-propanol (96-23-1) → epifluorohydrine (503-09-3) + 1,3-difluoro-2-propanol (453-13-4) + 1-chloro-3-fluoroisopropanol (146580-24-7,453-11-2) + 3-monochloro-1,2-propanediol (96-24-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

With potassium fluoride; at 80 ℃; for 0.5h; under 750.075 Torr; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

1,2-Dichloropropane (26198-63-0,78-87-5) → epifluorohydrine (503-09-3) + 1,3-difluoro-2-propanol (453-13-4) + 1-chloro-3-fluoroisopropanol (146580-24-7,453-11-2) + 3-monochloro-1,2-propanediol (96-24-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

With potassium fluoride; at 95 ℃; for 24.7h; under 750.075 Torr; Time; Inert atmosphere;

Reference yield:

epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 1,3-difluoro-2-propanol (453-13-4)

Guidance literature:

With potassium hydrogen bifluoride; In diethylene glycol; at 160 - 170 ℃; for 2.5h;

DOI:10.1002/hlca.19600430425

upstream raw materials:

epichlorohydrin

1,3-Dichloro-2-propanol

1,2-Dichloropropane

Downstream raw materials:

methylene chloride

methyl 3-{[2-fluoro-1-(fluoromethyl)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoate

[Pt2(dppp)2(μ-S)(μ-SCH2CH(OH)CH2F)]F

N-tert-butyl-2-[(1,3-difluoropropan-2-yl)oxy]benzenesulfonamide

Refernces

C_sp3-F bond activation by nucleophilic attack of the {Pt ₂S₂} core assisted by non-covalent interactions

10.1039/b801889h

The study focuses on the activation of the carbon-fluorine (C–F) bond in 1,3-difluoro-2-propanol by the nucleophilic attack of the {Pt2S2} core, a complex with significant nucleophilic properties. The reaction proceeds via an SN2 mechanism, where the sulfur atoms in the [Pt2(dppp)2(μ-S)2] complex act as nucleophiles, facilitated by the hydrogen bond from the alcohol group of the organic substrate, which is crucial for the departure of the fluoride anion. The study demonstrates that the presence of an OH group in the substrate plays a key role in the C–F bond activation, and the reaction leads to the formation of a new complex, [Pt2(dppp)2(μ-S)(μ-SCH2CH(OH)CH2F]F. The research also includes theoretical calculations using DFT methods to support the proposed mechanism and to understand the role of the OH group in the reaction. This work not only contributes to the understanding of C–F bond activation but also provides insights into the role of non-covalent interactions, such as hydrogen bonding, in facilitating chemical transformations.