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Sigma-Aldrich

Dimethyl malonate

purum, ≥96.0% (GC)

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Linear Formula:
CH2(COOCH3)2
CAS Number:
108-59-8
Molecular Weight:
132.11
Beilstein:
774261
EC Number:
203-597-8
MDL number:
MFCD00008460
PubChem Substance ID:
329759847
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

100

grade

purum

Assay

≥96.0% (GC)

refractive index

n20/D 1.413 (lit.)
n20/D 1.413

bp

180-181 °C (lit.)

mp

−62 °C (lit.)

density

1.156 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC(=O)OC

InChI

1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3

InChI key

BEPAFCGSDWSTEL-UHFFFAOYSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Ingalill Andersson et al.
The clinical respiratory journal, 1(1), 23-29 (2007-07-01)
Eating problems are common in patients with chronic obstructive pulmonary disease (COPD), and intake of micronutrients might be lower than recommended. To study dietary intake, serum and urinary concentration of trace elements and vitamins in elderly underweight patients with established
Paul R Blakemore et al.
Organic letters, 7(21), 4721-4724 (2005-10-08)
[reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate.
F D Ledley et al.
Biochemical and biophysical research communications, 177(3), 1076-1081 (1991-06-28)
In most animal species and many prokaryotes, methylmalonyl CoA mutase catalyzes isomerization between methylmalonyl CoA and succinyl CoA using adenosylcobalamin as a cofactor. We describe the absence of this enzyme in Aspergillus nidulans based on the absence of enzyme activity
Luiz Fernando Freire Royes et al.
Pharmacology, biochemistry, and behavior, 83(1), 136-144 (2006-02-14)
Methylmalonic acidemias are metabolic disorders caused by a severe deficiency of methylmalonyl CoA mutase activity, which are characterized by neurological dysfunction, including convulsions. It has been reported that methylmalonic acid (MMA) accumulation inhibits succinate dehydrogenase (SDH) and beta-hydroxybutyrate dehydrogenase activity
K Hiroi et al.
Chemical & pharmaceutical bulletin, 48(3), 405-409 (2000-03-22)
The Lewis acid-mediated reactions of allene-ene compounds, derived from 3-methylcitronellal or dimethyl malonate, were carried out using various Lewis acids such as ethylaluminum dichloride, diethylaluminum chloride, titanium chloride, zinc chloride etherate, or boron trifluoride etherate, affording unexpectedly intramolecular [2+2]cycloaddition products
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