1-[(1R)-1-isocyanatoethyl]naphthalene

• ChemBase ID: 145139
• Molecular Formular: C13H11NO
• Molecular Mass: 197.23254
• Monoisotopic Mass: 197.08406398
• SMILES: C[C@H](c1cccc2c1cccc2)N=C=O
• Canonical SMILES: O=C=N[C@@H](c1cccc2c1cccc2)C
• InChI: InChI=1S/C13H11NO/c1-10(14-9-15)12-8-4-6-11-5-2-3-7-13(11)12/h2-8,10H,1H3/t10-/m1/s1
• InChIKey: GONOHGQPZFXJOJ-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1R)-1-isocyanatoethyl]naphthalene
• IUPAC Traditional name: 1-[(1R)-1-isocyanatoethyl]naphthalene
• Synonyms: (R)-NEI; (R)-(-)-1-(1-Naphthyl)ethyl isocyanate; (R)-(-)-1-(1-萘基)乙基异氰酸酯; (R)-(-)-1-(1-萘基)乙基 异氰酸酯

Database IDs

• CAS Number: 42340-98-7
• EC Number: 255-759-2
• MDL Number: MFCD00004015
• Beilstein Number: 4181805
• PubChem SID: 162239349; 24886122; 24853172
• PubChem CID: 170633

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0879054
• LogD (pH = 7.4): 3.0879054
• Log P: 3.0879054
• Molar Refractivity: 58.8198 cm^3
• Polarizability: 23.901312 Å^3
• Polar Surface Area: 29.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 106-108 °C/0.16 mmHg(lit.); 106-108°C/0.16m
• Flash Point: 199.4 °F; 93 °C; 93°C(199°F)
• Density: 1.118; 1.118 g/mL at 25 °C(lit.)
• Refractive Index: 1.6045; n20/D 1.604; n20/D 1.604(lit.)
• Optical Rotation: [α]20/D -45°, c = 3.5 in toluene; [α]20/D -47±2°, c = 3.5% in toluene; -47 (c=3.5 in toluene)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2206; UN2206
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/22-36/37/38-42; 36/37/38-42/43
• Safety Statements: 23-26-36/37; 23-26-36/37-45
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H319-H334-H335; H315-H317-H319-H334-H335; H331-H302-H315-H319-H335-H334-H227
• GHS Precautionary statements: P260-P280H-P305+P351+P338-P309-P310; P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311; P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2206 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0%; ≥99.0% (sum of enantiomers, GC); 97%; 98%
• Grade: for chiral derivatization
• Optical Purity: ee: 95% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: C10H7CH(CH3)NCO

DETAILS

Sigma Aldrich - 220442

Packaging
1, 5 g in ampule

Sigma Aldrich - 70725

Other Notes
Chiral derivatizing agent for the indirect resolution of alcohols, thiols and amines by chromatographic separation of diastereomeric derivatives1,2

REFERENCES

• Chiral derivatizing agent for separation of alcohols, amines and thiols by chromatography: J. Org. Chem., 39, 3904 (1974).