N-(hydroxymethyl)acetamide

• ChemBase ID: 53568
• Molecular Formular: C3H7NO2
• Molecular Mass: 89.09318
• Monoisotopic Mass: 89.04767847
• SMILES: C(=O)(NCO)C
• Canonical SMILES: CC(=O)NCO
• InChI: InChI=1S/C3H7NO2/c1-3(6)4-2-5/h5H,2H2,1H3,(H,4,6)
• InChIKey: HWJHZLJIIWOTGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(hydroxymethyl)acetamide
• IUPAC Traditional name: formicin
• Synonyms: N-(Hydroxymethyl)acetamide; (Acetamido)methanol; (Acetylamino)methanol; Acetamidomethanol; Acetamidomethanol; N-(Hydroxymethyl)acetamide; Formicin; 乙酰氨基甲醇; N-(羟甲基)乙酰胺

Database IDs

• CAS Number: 625-51-4
• EC Number: 210-897-2
• MDL Number: MFCD00014417
• Beilstein Number: 506226
• Merck Index: 144242
• PubChem SID: 162058331; 24845007
• PubChem CID: 69365

CALCULATED PROPERTIES

• Acid pKa: 12.411318
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3866134
• LogD (pH = 7.4): -1.3866171
• Log P: -1.3866134
• Molar Refractivity: 20.4644 cm^3
• Polarizability: 8.1675 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 47-52°C; 48-52 °C; 48-52°C
• Density: 1.14

Safety Information

• Storage Warning: Hygroscopic; IRRITANT; Irritant/Hygroscopic/Store under Argon
• RTECS: AC3610000
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (CHN); 98%
• Linear Formula: CH3CONHCH2OH

DETAILS

Sigma Aldrich - 00315

Other Notes
Reagent used for chloromethylations of aromatics [avoiding the carcinogenic bis(chloromethyl) ether] and for amidomethylation reactions1,2

REFERENCES

• Thiol blocking group for cysteine residues in peptide synthesis: Tetrahedron Lett., 3057 (1968); J. Am. Chem. Soc., 91, 502 (1969); 94, 5456 (1972); Helv. Chim. Acta, 54, 927 (1971); Org. Synth. Coll., 6, 5 (1988). Cleavage can be effected with Hg(OAc)₂ under mild conditions, or by treatment with iodine with concomitant oxidation to the cystine derivative. For peptide reagents, see Appendix 6.
• Used for the introduction of the acetamidomethyl group into the aromatic nucleus by electrophilic substitution. For reviews of amidomethylation, see: Org. React., 14, 52 (1965); Synthesis, 49, (1970); 85, 181 (1984).