isoquinoline

• ChemBase ID: 3931
• Molecular Formular: C9H7N
• Molecular Mass: 129.15858
• Monoisotopic Mass: 129.05784923
• SMILES: c1ccc2cnccc2c1
• Canonical SMILES: c1ccc2c(c1)cncc2
• InChI: InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
• InChIKey: AWJUIBRHMBBTKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: isoquinoline
• IUPAC Traditional name: isoquinoline
• Synonyms: Isoquinoline; Isoquinoline; 2-Azanaphthalene; benzo[c]pyridine; 2-benzanine; 异喹啉

Database IDs

• CAS Number: 119-65-3
• EC Number: 204-341-8
• MDL Number: MFCD00006898
• Beilstein Number: 107549
• Merck Index: 145222
• PubChem SID: 24857022; 46507258; 24896011; 160967366
• PubChem CID: 8405
• CHEBI ID: 16092
• CHEMBL: 12315
• Chemspider ID: 8098
• DrugBank ID: DB04329
• Unique Ingredient Identifier: JGX76Y85M6
• Wikipedia Title: Isoquinoline

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5720623
• LogD (pH = 7.4): 1.7422261
• Log P: 1.7450502
• Molar Refractivity: 40.3513 cm^3
• Polarizability: 17.07871 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.14
• LOG S: -1.66
• Solubility (Water): 2.81e+00 g/l

PROPERTIES

Physical Property

• Apperance: yellowish oily liquid, hygroscopic platelets when solid
• Melting Point: 24-27°C; 26 - 28 °C; 26-28 °C(lit.); 26-28°C
• Boiling Point: 241-243°C; 242°C; 242-243 °C(lit.); 242-243°C
• Flash Point: 102 °C; 102°C; 107°C(225°F); 215.6 °F
• Density: 1.090; 1.099; 1.099 g/cm3; 1.099 g/mL at 25 °C(lit.)
• Refractive Index: 1.6245; n20/D 1.623(lit.)
• pKa: pK_BH^+=5.14

Safety Information

• Storage Warning: Toxic/Harmful/Irritant/Air Sensitive/Store under Argon
• RTECS: NW6825000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3; II
• Risk Statements: 22-24-36/38; 22-24-38; R:22-27
• Safety Statements: 20-26-27-36/37-45; 36/37-45; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H310-H315; H311-H302-H315-H319
• GHS Precautionary statements: P280-P302 + P350-P310; P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥85% (GC); ≥97.0% (GC); 90-92%; 95+%; 97%; 97+%
• Grade: purum; technical; technical grade
• Empirical Formula (Hill Notation): C9H7N

DETAILS

MP Biomedicals - 05206087

MP Biomedicals Rare Chemical collection

DrugBank - DB04329

Drug information: experimental

Sigma Aldrich - I28208

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 282162

Packaging
100, 500 mL in glass bottle

REFERENCES

• Reacts with various acid halides in the presence of CN^- to give "Reissert compounds" (1-cyano-2-acyl 1,2-dihydro derivatives). For reviews, see: Chem. Rev., 55, 511 (1955); Adv. Het. Chem., 9, 1 (1968); 24, 187 (1979). 1-Alkylisoquinolines can be prepared by alkylation of the Li or Na derivatives of Reissert compounds: Org. Synth. Coll., 4, 641 (1963); 6, 115 (1988). For formation of Reissert compounds from a variety of carbonyl, sulfonyl and phosphoryl halides under milder, phase-transfer conditions, see: Synthesis, 497 (1977). For 'direct' cyanation by a modified Reissert procedure in the presence of tosyl chloride followed by DBU, see: J. Org. Chem., 49, 4056 (1984).
• A one-step synthesis of 1-nitroisoquinoline has been reported in which isoquinoline reacts with KNO₂ in the presence of acetic anhydride and DMSO. The reaction is considered to be analogous to the Pfitzner-Moffatt oxidation (see Dimethyl sulfoxide, A13280): J. Chem. Soc., Perkin 1, 1777 (1996).