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Sigma-Aldrich

Benzaldehyde dimethyl acetal

99%

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Synonym(s):
α,α-Dimethoxytoluene
Linear Formula:
C6H5CH(OCH3)2
CAS Number:
1125-88-8
Molecular Weight:
152.19
Beilstein:
2044501
EC Number:
214-413-0
MDL number:
MFCD00008491
PubChem Substance ID:
24853541
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.493 (lit.)

bp

87-89 °C/18 mmHg (lit.)

density

1.014 g/mL at 25 °C (lit.)

SMILES string

COC(OC)c1ccccc1

InChI

1S/C9H12O2/c1-10-9(11-2)8-6-4-3-5-7-8/h3-7,9H,1-2H3

InChI key

HEVMDQBCAHEHDY-UHFFFAOYSA-N

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General description

The abstraction of α-hydrogen atoms from benzaldehyde dimethyl acetal by active bromine at 80°C has been investigated.

Benzaldehyde dimethyl acetal is derived from the condensation reaction between benzaldehyde and methanol. It is used as a protecting group.

Application

Benzaldehyde dimethyl acetal used as an effective reagent for the construction of selenocarbonyl compounds.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

156.2 °F - closed cup

Flash Point(C)

69 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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1151. Polar influences in radical reactions. Part IV. The abstraction of benzylic hydrogen atoms from substituted benzyl methyl ethers and benzaldehyde dimethyl acetals by atomic bromine.
Huang RL and Lee KH.
Journal of the Chemical Society, 5963-5969 (1964)
Tetrahedron Letters, 33, 7865-7865 (1992)
One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species
Traboni S, et al.
Tetrahedron Letters, 60, 1777-1780 (2019)
N Sakairi et al.
Carbohydrate research, 246, 61-73 (1993-08-17)
Treatment of phenyl alpha-maltoside with an excess of alpha, alpha-dimethoxytoluene in the presence of (+)-10-camphorsulfonic acid, followed by partial hydrolysis to remove unstable acyclic acetal substituents, gave phenyl 3,2':4',6'-di-O-benzylidene-alpha-maltoside. Thus, one of the benzylidene groups formed an eight-membered cyclic acetal
Simona Matrella et al.
Macromolecular bioscience, 15(7), 927-940 (2015-03-18)
Intrinsic antimicrobial thermoplastic A(BC)n copolymers (n = 1, 2, 4), where A was poly(ethylene glycol) (PEG), BC was a random chain of methylmethacrylate (MMA), and alkyl-aminoethyl methacrylate (AAEMA), were synthesized and the antimicrobial activity and hemolyticity were evaluated on plaques obtained by

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