3-hydroxypropanenitrile

• ChemBase ID: 87198
• Molecular Formular: C3H5NO
• Molecular Mass: 71.0779
• Monoisotopic Mass: 71.03711379
• SMILES: OCCC#N
• Canonical SMILES: OCCC#N
• InChI: InChI=1S/C3H5NO/c4-2-1-3-5/h5H,1,3H2
• InChIKey: WSGYTJNNHPZFKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxypropanenitrile
• IUPAC Traditional name: ethylene cyanohydrin
• Synonyms: 3-Hydroxypropionitrile; 2-Cyanoethan-1-ol; 3-Hydroxypropanenitrile; 2-Cyanoethanol; Ethylene cyanohydrin; Hydracrylonitrile; 2-Cyanoethyl Alcohol; 2-Hydroxycyanoethane; 2-Hydroxyethyl Cyanide; Glycol Canohydrin; NSC 2598; 3-Hydroxypropionitrile; ETHYLENECYANOHYDRIN; 2-CYANOETHANOL; 3-Hydroxypropionitrile; 2-氰乙醇; 3-羟丙腈; 氰化乙醇; 3-羟基丙腈

Database IDs

• CAS Number: 109-78-4
• EC Number: 203-704-8
• MDL Number: MFCD00002826
• Beilstein Number: 635773
• Merck Index: 143794
• PubChem SID: 24854166; 24846946; 162074314
• PubChem CID: 8011

CALCULATED PROPERTIES

• Acid pKa: 15.1908455
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.7456322
• LogD (pH = 7.4): -0.7456322
• Log P: -0.7456322
• Molar Refractivity: 18.0246 cm^3
• Polarizability: 6.7570677 Å^3
• Polar Surface Area: 44.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -46 °C(lit.); -46°C; -46°C
• Boiling Point: 227-228°C; 227-228°C; 228 °C(lit.)
• Flash Point: 113 °C; 113°C; 128°C(262°F); 235.4 °F
• Auto Ignition Point: 922 °F
• Density: 1.04 g/ml; 1.04 g/mL at 25 °C(lit.); 1.041
• Refractive Index: 1.425; 1.4250; n20/D 1.425(lit.); n20/D 1.426
• Vapor Pressure: <0.1 mmHg ( 20 °C)
• Vapor Density: 2.5 (vs air)

Safety Information

• Storage Warning: Irritant/Light Sensitive/Store under Argon
• RTECS: MU5250000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38; R:36
• Safety Statements: 26; 26-37; S:26
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Explode Limits: 12.1 %
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >99%; ≥98.0% (GC); ≥99%; ≥99.0% (GC); 97%; 98%; 99%
• Grade: puriss.; purum; ReagentPlus®
• Impurities: ≤0.1% water; ≤3% ethylene glycol
• Linear Formula: HOCH2CH2CN

DETAILS

MP Biomedicals - 05215859

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02154998

(Hydracrylonitrile; 3-Hydroxypropionitrile) Purity: >99% 1 ml = approx. 1.04 g

Sigma Aldrich - 109924

Packaging
1 kg in glass bottle
5, 250 g in glass bottle

Sigma Aldrich - 236357

Packaging
50 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Protection of carboxylic acids as 2-cyanoethyl esters can be accomplished by DCC-DMAP coupling. The esters can be cleaved with TBAF in DMF-THF: Chem. Pharm. Bull., 42, 147 (1994), or Na₂S in methanol: Chem. Pharm. Bull., 42, 1579 (1994).
• Can also be used to protect the phosphate group, by condensation with 2,4,6-Triisopropylbenzenesulfonyl chloride, A11458: Chem. Pharm. Bull.,25, 2844 (1977), or DCC: J. Am. Chem. Soc., 83, 159 (1961). Cleavage can be effected with an amine: Tetrahedron Lett., 23, 5119 (1982), ammonia: J. Org. Chem., 59, 2482 (1994); Tetrahedron Lett., 35, 4311 (1994), or TBAF: Tetrahedron Lett., 1255 (1976).
• Precursor of 2-cyanoethyl 2,2,2-trichloroethyl phosphorochloridate, a reagent for the phosphorylation of nucleosides: Synthesis, 831 (1980); see 2,2,2-Trichloroethanol, L08163.