2,2-dimethylpropanal

• ChemBase ID: 85611
• Molecular Formular: C5H10O
• Molecular Mass: 86.1323
• Monoisotopic Mass: 86.07316494
• SMILES: O=CC(C)(C)C
• Canonical SMILES: O=CC(C)(C)C
• InChI: InChI=1S/C5H10O/c1-5(2,3)4-6/h4H,1-3H3
• InChIKey: FJJYHTVHBVXEEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethylpropanal
• IUPAC Traditional name: pivalaldehyde
• Synonyms: Trimethylacetaldehyde; Pivalaldehyde; 2,2-Dimethylpropanal; 2,2-Dimethylpropanone; 2,2-Dimethylpropionaldehyde; NSC 22043; Neopentaldehyde; Neopentanal; Pivalic Aldehyde; Pivaldehyde; Trimethylacetaldehyde; 2,2-Dimethylpropanal; pivalaldehyde; Pivalaldehyde; TRIMETHYLACETALDEHYDE; 三甲基乙醛; 特戊醛; 三甲基乙醛; 特戊醛

Database IDs

• CAS Number: 630-19-3
• EC Number: 211-134-6
• MDL Number: MFCD00006962
• Beilstein Number: 506060
• PubChem SID: 162072727; 24887363; 24900418
• PubChem CID: 12417

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.4175744
• LogD (pH = 7.4): 1.4175744
• Log P: 1.4175744
• Molar Refractivity: 25.4207 cm^3
• Polarizability: 10.010134 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Colourless Liquid
• Melting Point: 6 °C(lit.); 6°C; 6°C
• Boiling Point: 71-74°C; 74 °C/730 mmHg(lit.); 74°C; 74°C; 74-76°C; ca 75°C
• Flash Point: -15.5°C; -15°C(5°F); -16 °C; -16°C; -2°C(28°F); 3.2 °F; 4 °F
• Density: 0.775; 0.783; 0.785; 0.793 g/ml; 0.793 g/mL at 25 °C(lit.)
• Refractive Index: 1.3794; n20/D 1.378(lit.); n20/D 1.379

Safety Information

• Storage Condition: 2-8°C, Desiccate; Refrigerator
• Storage Warning: Air Sensitive; Highly Flammable/Irritant/Light Sensitive/Air Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1989; UN1989; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II; III
• Australian Hazchem: 3YE
• Risk Statements: 11; 11-36/37; 11-37/38; R:11
• Safety Statements: 16-23; 9-16-26-46; 9-16-33; S:9-16-29
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 129
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H315-H335; H225-H319-H335
• GHS Precautionary statements: P210-P243-P403; P210-P261; P210-P301+P310-P305+P351+P338-P403+P233
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1989 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 96%; ca 75% in tert-butanol; TECH
• Grade: purum
• Impurities: ~1% pivalic acid
• Linear Formula: (CH3)3CCHO

DETAILS

MP Biomedicals - 02157067

Light yellow
1 ml = approx. 0.78 g

Sigma Aldrich - T71501

Application
Commonly used building block in aldol condensation reactions.
Employed in a study of the asymmetric cyanation of aldehydes with TMS-CN and a chiral vandium (V)-salen complex.
Packaging
5, 25, 100 mL in glass bottle

REFERENCES

• Promotes the epoxidation of alkenes with molecular oxygen: Tetrahedron Lett., 33, 6827 (1992).
• Derivatizing agent for amino acids, forming oxazolidinones as volatile derivatives for GC: Anal. Biochem., 49, 442 (1972); Aust. J. Biol. Sci., 26, 831 (1973).
• For formation of the fused pyrrolidino-oxazolidinone from L-proline, catalyzed by trifluoroacetic acid, and use of the product in a synthesis of ɑ-branched amino acids, see: Org. Synth.Coll., 9, 626 (1998):
  
• For use in the protection of asparagine as a tetrahydropyrimidinone derivative, see: Org. Synth.Coll., 9, 17 (1998). For use of this system in ɑ-alkylation of (S)-asparagine with self-regeneration of the stereogenic center, see: J. Org. Chem., 63, 4706 (1998).
• The imine formed with ethylamine has been used to convert aryl chlorides to the hindered tertiary amides: N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)benzamides, which can be ortho metallated cleanly at higher temperatures than other amide systems: J. Org. Chem., 60, 8417 (1995).