Neopentyl alcohol

Base Information

• Chemical Name: Neopentyl alcohol
• CAS No.: 75-84-3
• Molecular Formula: C5H12O
• Molecular Weight: 88.1497
• European Community (EC) Number: 200-907-3
• UN Number: 1325
• UNII: 5I067PJD7S
• DSSTox Substance ID: DTXSID9052501
• Nikkaji Number: J4.163G
• Wikipedia: Neopentyl_alcohol
• Wikidata: Q3270847
• Metabolomics Workbench ID: 135738
• ChEMBL ID: CHEMBL458630
• Mol file: 75-84-3.mol

Synonyms:2,2-dimethylpropanol;neopentyl alcohol

Chemical Property of Neopentyl alcohol

Chemical Property:

• Appearance/Colour: colorless waxy crystalline solid
• Vapor Pressure: 10.8mmHg at 25°C
• Melting Point: 52-56 °C(lit.)
• Refractive Index: 1.406
• Boiling Point: 113.1 °C at 760 mmHg
• PKA: 15.24±0.10(Predicted)
• Flash Point: 36.7 °C
• PSA: 20.23000
• Density: 0.811 g/cm³
• LogP: 1.02480
• Water Solubility.: 3.5 g/100 mL at 25℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 88.088815002
• Heavy Atom Count: 6
• Complexity: 33.7

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: F:Flammable
• Statements: R11:
• Safety Statements: S16:; S33:; S7/9:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Alcohols (
• Canonical SMILES: CC(C)(C)CO

Technology Process of Neopentyl alcohol

There total 137 articles about Neopentyl alcohol 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: 39.0%

pivaloyl chloride (3282-30-2) → 2,2-dimethyl-propanol-1 (75-84-3) + pivalaldehyde (630-19-3)

Guidance literature:

With tri-n-butyl-tin hydride; triphenylphosphine; indium(III) chloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(99)02016-X

Reference yield:

Benzoic acid 3-methanesulfonyloxy-2,2-dimethyl-propyl ester (90839-64-8) → 2,2-dimethyl-propanol-1 (75-84-3) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/ja00329a046

Reference yield:

2,2,4-trimethylpentane (540-84-1) → 2,2-dimethyl-propanol-1 (75-84-3) + 2,4,4-trimethyl-2-pentanol (690-37-9) + acetone (67-64-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; manganese (II) acetate tetrahydrate; ozone; at 95 ℃; for 4h;

upstream raw materials:

2,4,4-trimethyl-1-pentene

formaldehyd

tert-butylmagnesium bromide

tert-butylmagnesium chloride

Downstream raw materials:

neopentyl chloroformate

phthalic acid mononeopentyl ester

sulfurous acid bis-(2,2-dimethyl-propyl) ester

methacrylic acid neopentyl ester

Refernces

10.1021/jo01375a001

The study focuses on the synthesis and characterization of neopentyl esters of acrylic and methacrylic acids. Neopentyl alcohol, a key reactant, was prepared using two methods: the Whitmore method involving tert-butylmagnesium chloride and pivalyl chloride, and the more practical lithium aluminum hydride reduction of pivalic acid. Neopentyl acrylate was synthesized from neopentyl alcohol and either acryloyl chloride or acrylic acid, while neopentyl methacrylate was prepared from neopentyl alcohol and either methacryloyl chloride or methacrylic acid. The esters' physical properties were measured and reported. The study also highlighted the partly hindered character of neopentyl methacrylate, which affected its saponification process.

1,4-Diazabicyclo[2.2.2]octane (DABCO)- an efficient reagent in the synthesis of alkyl tosylates or sulfenates

10.1055/s-1997-1372

The study investigates the use of 1,4-diazabicyclo[2.2.2]octane (DABCO) as an efficient reagent in the synthesis of alkyl tosylates and sulfenates. DABCO is found to be a promising substitute for pyridine and triethylamine in these reactions. The substrates, which are various alcohols, are converted into the desired tosylates and sulfenates using DABCO and the respective acid chlorides as reagents. The study provides examples of successful conversions, such as the synthesis of tosylates from neopentyl alcohol and trans-4-tert-butylcyclohexanol, and sulfenates from 2-methylcyclohexanol and other alcohols. The study also explores the use of different solvents, finding that tert-butyl methyl ether (t-BuOMe) and ethyl acetate (EtOAc) are good alternatives to chlorinated solvents like chloroform and dichloromethane. The study concludes that DABCO is a convenient, colorless, crystalline base that can be easily purified and dried by sublimation, making it a practical choice for these types of organic synthesis reactions.