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109924

Sigma-Aldrich

3-Hydroxypropionitrile

97%

Synonym(s):

2-Cyanoethanol, Ethylene cyanohydrin, Hydracrylonitrile

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About This Item

Linear Formula:
HOCH2CH2CN
CAS Number:
109-78-4
Molecular Weight:
71.08
Beilstein/REAXYS Number:
635773
MDL number:
MFCD00002826
UNSPSC Code:
12352100
PubChem Substance ID:
24846946
NACRES:
NA.22

vapor density

2.5 (vs air)

vapor pressure

<0.1 mmHg ( 20 °C)

assay

97%

autoignition temp.

922 °F

expl. lim.

12.1 %

refractive index

n20/D 1.425 (lit.)

bp

228 °C (lit.)

mp

−46 °C (lit.)

density

1.04 g/mL at 25 °C (lit.)

SMILES string

OCCC#N

InChI

1S/C3H5NO/c4-2-1-3-5/h5H,1,3H2

InChI key

WSGYTJNNHPZFKR-UHFFFAOYSA-N

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General description

3-Hydroxypropionitrile, at low 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) surface excesses, has the phospholipid oriented with the polar headgroups pointing out of the solution.

3-Hydroxypropionitrile serves as an intermediate through nucleophilic addition or hydrogenation to synthesize heterocyclic rings, mercaptopropanoic acid, or cyclophosphamide.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-Catalyzed Multicomponent Cascade Reaction of 3-Hydroxypropionitrile: Synthesis of Substituted Dihydrochalcones
Zheng J, et al.
The Journal of Organic Chemistry (2023)
Hartwig Pohl et al.
Langmuir : the ACS journal of surfaces and colloids, 26(4), 2473-2476 (2009-11-20)
Phospholipids are a main component of cell membranes. Therefore, the experimental investigation of the self-organization of phospholipids is of great interest. Here we present results concerning the orientation of the phospholipid 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) at the surface of the polar solvents
Kid Törnquist et al.
European journal of pharmacology, 453(1), 1-11 (2002-10-24)
Sphingolipid derivatives cause diverse effects towards the regulation of intracellular free Ca(2+) concentrations ([Ca(2+)](i)) in a multitude of nonexcitable cells. In the present investigation, the effect of C-8 ceramide-1-(2-cyanoethyl) phosphate (C1CP) on store-operated Ca(2+) (SOC) entry was investigated. C1CP evoked
M Duverger-Van Bogaert et al.
Toxicology letters, 7(4-5), 311-319 (1981-02-01)
The mutagenicity of acrylonitrile (ACN) was tested with Salmonella typhimurium TA1530 after a preincubation period of the chemical with a rat liver post-mitochondrial fraction in liquid medium. Several pretreatments were applied to the animals before the preparation of the liver
M Lambotte-Vandepaer et al.
Toxicology letters, 7(4-5), 321-327 (1981-02-01)
Urines collected from rats injected with acrylonitrile (ACN) were mutagenic towards Salmonella typhimurium TA1530; this activity was reduced when the animals were pretreated by pyrazole (inhibitor of alcohol dehydrogenase) and suppressed after pretreatment either by CoCl2 and SKF 525-A (inhibitors
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