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Merck
CN

M1903

Malononitrile

~98%, crystalline

Synonym(s):

Dicyanomethane

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About This Item

Linear Formula:
CH2(CN)2
CAS Number:
109-77-3
Molecular Weight:
66.06
EC Number:
203-703-2
UNSPSC Code:
12352200
MDL number:
MFCD00001883
Beilstein/REAXYS Number:
773697

Key Documents

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InChI

1S/C3H2N2/c4-2-1-3-5/h1H2

InChI key

CUONGYYJJVDODC-UHFFFAOYSA-N

SMILES string

N#CCC#N

assay

~98%

form

crystalline

color

off-white to brown

bp

220 °C (lit.)

mp

30-32 °C (lit.)

density

1.049 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
114H3457
112H0682
083H3432
038H3402
014H3445

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Xin Feng et al.
Journal of the American Chemical Society, 134(48), 19942-19947 (2012-11-16)
Switchable reaction patterns of β-substituted cyclic enones via amine-based dienamine activation are reported. While γ-regioselective vinylogous Michael addition was observed with alkylidenemalononitriles, a completely different [4 + 2] cycloaddition was obtained with allylidene- or alkynylidenemalononitrile substrates, affording densely substituted bicyclo[2.2.2]octanes
Xianxing Jiang et al.
Chemical communications (Cambridge, England), 47(29), 8289-8291 (2011-06-23)
We present here the synthesis of dicyano-2-methylenebut-3-enoates as novel Diels-Alder dienes through an efficient PPh(3)-catalyzed strategy, and an unprecedented PPh(3)-catalyzed addition/all-carbon-based asymmetric inverse-electron-demand Diels-Alder sequence reaction is disclosed for the first time.
Dayong Tian et al.
Chemosphere, 88(8), 994-1000 (2012-04-17)
Organic chemicals usually coexist as a mixture in the environment, and the mixture toxicity of organic chemicals has received increased attention. However, research regarding the joint effects of reactive chemicals is lacking. In this study, we examined two kinds of
Xiao-Gang Yin et al.
Organic & biomolecular chemistry, 10(8), 1506-1509 (2012-01-11)
A cascade Michael/Michael/oxa-Michael reaction between curcumins and isatylidene malononitriles has been developed. Multicyclic spirooxindoles were prepared in excellent yields and diastereoselectivities. DMAP was found to catalyze this transformation efficiently under mild reaction conditions.
Jonghan Shin et al.
Journal of Alzheimer's disease : JAD, 26 Suppl 3, 135-145 (2011-10-06)
2-(1-{6-[(2-[fluorine-18]fluoroethyl)(methyl)amino]-2-naphthyl}-ethylidene)malononitrile (FDDNP) is the first positron emission tomography (PET) molecular imaging probe to visualize Alzheimer's disease (AD) pathology in living humans. The most unique features of FDDNP are that (1) it is the only currently available radiotracer to image neurofibrillary
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