Trimethylacetaldehyde

Base Information

• Chemical Name: Trimethylacetaldehyde
• CAS No.: 630-19-3
• Molecular Formula: C5H10O
• Molecular Weight: 86.1338
• Hs Code.: 29121900
• European Community (EC) Number: 211-134-6
• NSC Number: 22043
• UNII: SSC20260QW
• DSSTox Substance ID: DTXSID2060888
• Nikkaji Number: J102.084F
• Wikipedia: Pivaldehyde
• Wikidata: Q2097441
• Mol file: 630-19-3.mol

Synonyms:pivaldehyde

Chemical Property of Trimethylacetaldehyde

Chemical Property:

• Appearance/Colour: clear slightly yellow liquid
• Vapor Pressure: 96.5mmHg at 25°C
• Melting Point: 6 °C(lit.)
• Refractive Index: n20/D 1.378(lit.)
• Boiling Point: 77.5 °C at 760 mmHg
• Flash Point: 4 °F
• PSA: 17.07000
• Density: 0.794 g/cm³
• LogP: 1.23140
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Negligible
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 49.4

Purity/Quality:

98% ^*data from raw suppliers

Pivaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi,F+
• Hazard Codes: F,Xi,F+
• Statements: 11-37/38-43
• Safety Statements: 16-23-33-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC(C)(C)C=O
• Description: Trimethylacetaldehyde (also known as Pivaldehyde) is the trimethyl form of acetaldehyde. It is an aldehyde with a sterically bulky R group, the tertiary-butyl group being attached to the carbonyl, >C=O. It is a useful reagent in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It is useful in streoselective synthesis application as well as in aldol condensation reactions. As a derivative of acetaldehyde, trimethyl acetaldehyde can be used for the production of acetate. It can also be used as the precursor for manufacturing of pyridine derivatives, pentaerythritol, and crotonaldehyde.
• Uses: Commonly used building block in aldol condensation reactions. Trimethylacetaldehyde is used as a stereoselective synthesis application. It is also used as a building block used in aldol condensation reactions. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Technology Process of Trimethylacetaldehyde

There total 243 articles about Trimethylacetaldehyde 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%

2,2-dimethyl-propanol-1 (75-84-3) + diethylazodicarboxylate (1972-28-7,218603-74-8) → diethyl hydrazodicarboxylate (4114-28-7) + pivalaldehyde (630-19-3)

Guidance literature:

With zinc dibromide; In toluene; for 2.5h; Reflux;

DOI:10.1016/j.tetlet.2009.01.080

Reference yield: 8.2%

2-Methylbutyraldehyde (96-17-3,57456-98-1) + isoprene (78-79-5,9003-31-0) → 3-methyl-butan-2-one (563-80-4) + 2-methyl-but-2-ene (513-35-9) + 3-Methyl-1-butene (563-45-1) + pivalaldehyde (630-19-3)

Guidance literature:

With steam; calcium phosphate catalyst TU 103-134-72; at 380 ℃; Product distribution; Rate constant; Kinetics; other conditions - var. space velocity of adding reagent, var. dilution with steam, var. temp., var. contact time, other object - activation energy data;;

Reference yield:

2,2-dimethylpropanoic anhydride (1538-75-6) + benzoic acid anhydride (93-97-0) → benzaldehyde (100-52-7) + pivalaldehyde (630-19-3) + benzoic acid (65-85-0,8013-63-6) + Trimethylacetic acid (75-98-9)

Guidance literature:

With hydrogen; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 80 ℃; for 48h; under 22501.8 Torr; Further Variations:; Catalysts; reaction time; Product distribution;

DOI:10.1246/bcsj.74.1803

upstream raw materials:

formic acid

3-butyloxy-2-methyl-butanol-⁽²⁾

3-isopentyloxy-2-methyl-butan-2-ol

3-benzyloxy-2-methyl-butan-2-ol

Downstream raw materials:

1-(4-tert-Butyl-cyclohex-1-enyl)-2,2-dimethyl-propan-1-ol

2,3-dihydro-2-(1,1-dimethylethyl)benzothiazole

2-tert.-Butyl-4,5-dimethyl-6-phenyl-tetrahydro-2H-1,3,4-oxadiazin

N-<2,2-Dimethyl-propyliden>-cyclohexylamin-N-oxid

Refernces

• 1、 K. Bains, Amreen,Ankit, Yadav,Adhikari, Debashis. "Bioinspired Radical-Mediated Transition-Metal-Free Synthesis of N-Heterocycles under Visible Light". . p. 324 - 329. Retrieved 2020/11/30.
• 2、 Shimada, Kazuaki,Isogami, Megumi,Maeda, Kitami,Nishinomiya, Rei,Korenaga, Toshinobu. "Convenient synthesis of 2,3-dihydro-1,2,4-thiadiazoles, 4,5-dihydro-1,3-thiazoles, and 1,3-thiazoles through a [4+1]-type oxidative ring closure of 1,3-thiaza-1,3-butadienes". . p. 881 - 900. Retrieved 2020/09/09.