2,2-dimethoxypropane

• ChemBase ID: 78097
• Molecular Formular: C5H12O2
• Molecular Mass: 104.14758
• Monoisotopic Mass: 104.08372962
• SMILES: O(C(OC)(C)C)C
• Canonical SMILES: COC(OC)(C)C
• InChI: InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
• InChIKey: HEWZVZIVELJPQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethoxypropane
• IUPAC Traditional name: 2,2-dimethoxypropane
• Synonyms: acetone dimethyl acetal; 2,2-Dimethoxypropane; 2,2-Dimethoxypropane; Acetone dimethyl acetal 98%; 2,2-Dimethoxypropane; DMP; ACETONE DIMETHYL ACETAL; 丙酮缩二甲醇; 2,2-二甲氧基丙烷

Database IDs

• CAS Number: 77-76-9
• EC Number: 201-056-0
• MDL Number: MFCD00008479
• Beilstein Number: 635678
• PubChem SID: 24886512; 24859870; 24893272; 162042919
• PubChem CID: 6495
• Chemspider ID: 6250
• Wikipedia Title: 2,2-Dimethoxypropane

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6652705
• LogD (pH = 7.4): 0.6652705
• Log P: 0.6652705
• Molar Refractivity: 28.7296 cm^3
• Polarizability: 11.331112 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 15 g/L (20 °C) in water
• Apperance: Colorless liquid
• Melting Point: -47°C; -47°C
• Boiling Point: 79-81 °C; 79-81°C; 79-81°C; 83 °C(lit.); 83°C
• Flash Point: -10 °C; -11°C; -11°C(12°F); 14 °F
• Density: 0.847 g/mL at 25 °C(lit.); 0.848; 0.85 g/cm3
• Refractive Index: 0.848; 1.3780; n20/D 1.378; n20/D 1.378(lit.)
• Vapor Pressure: 60 mmHg ( 15.8 °C)
• Vapor Density: 3.59 (vs air)

Safety Information

• Storage Warning: Highly Flammable/Irritant/Moisture Sensitive
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN3271
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36
• Safety Statements: 26; 9-16-23-26-33-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• Explode Limits: 31 %, 58 °F; 6 %, 27 °F
• GHS Hazard statements: H225-H319
• GHS Precautionary statements: P210-P305 + P351 + P338; P210-P305+P351+P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2

Product Information

• Purity: ≥96.0% (GC); ≥99.4% (GC); 98%
• Grade: analytical standard; for GC derivatization; purum; reagent grade
• Packaging: bottle of 25 g
• Description: Alkylation reagent
• Shelf Life: (limited shelf life, expiry date on the label)
• Derivatization reagent for: Esterifications
• Linear Formula: (CH3)2C(OCH3)2

DETAILS

Sigma Aldrich - D136808

Application
Reagent for the preparation of 1,2-diols as acetonides.1
Packaging
18 L in steel drum
25, 500 mL in glass bottle
2, 2.5 L in glass bottle

REFERENCES

• Widely used for the isopropylidenation of diols; see, e.g.: Org. Synth. Coll., 9, 450, 717 (1998). Isopropylidenation of acid-sensitive carbohydrates in the presence of 2,3-Dichloro-5,6-dicyanobenzoquinone, A11879: Acta Chem. Scand., 47, 843 (1993); preparation of acyclic mixed acetals of carbohydrates: Acta Chem. Scand., 48, 80 (1994). For use in the cyclization of N-Boc serine methyl ester to the oxazolidine, see: Org. Synth. Coll., 9, 300 (1998).
• Methyl ester hydrochlorides of amino acids can be conveniently prepared with excess reagent in combination with conc. HCl. Water is removed in situ, thus displacing the equilibrium in favor of the ester: J. Org. Chem., 28, 3898 (1963). Methyl esters of non-aromatic acids can also be prepared with the reagent in MeOH with a catalytic amount of HCl or TMS chloride: Tetrahedron Lett., 38, 2685 (1997).
• Methoxylating agent for preparation of acetals by acid-catalyzed exchange: J. Org. Chem., 25, 521 (1960). Also used as a water-scavenger in the preparation of acetals from higher-boiling alcohols and ketones: Org. Synth. Coll., 5, 292 (1973).