naphthalene

• ChemBase ID: 103417
• Molecular Formular: C10H8
• Molecular Mass: 128.17052
• Monoisotopic Mass: 128.06260026
• SMILES: c1ccc2ccccc2c1
• Canonical SMILES: c1ccc2c(c1)cccc2
• InChI: InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
• InChIKey: UFWIBTONFRDIAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: naphthalene
• IUPAC Systematic name: bicyclo[4.4.0]deca-1,3,5,7,9-pentene; bicyclo[4.4.0]deca-2,4,6,8,10-pentene
• IUPAC Traditional name: naphthalene
• Synonyms: Naphthalene; Melting point standard 79-81°C; Camphor Tar; Mighty 150; Moth Balls; Moth Flakes; Naphthalin; Naphthaline; Naphthene; RCRA Waste Number U165; Tar Camphor; White Tar; NAPHTHALENE; mothballr; naphthalir; moth flaker; naphthalinr; antimitr; albocarbon; Naphthalene solution; Naphthalene; 萘; 熔点标准品 79-81°C; 萘 溶液; 萘

Database IDs

• CAS Number: 91-20-3
• EC Number: 200-659-6; 203-806-2; 202-049-5
• MDL Number: MFCD00001742
• Beilstein Number: 7822574; 1421310
• Merck Index: 146370
• PubChem SID: 24888246; 24851121; 24872078; 24871994; 24848808; 24864927; 162090592
• PubChem CID: 931
• CHEBI ID: 16482
• CHEMBL: 16293
• Chemspider ID: 906
• KEGG ID: C00829
• Unique Ingredient Identifier: 2166IN72UN
• Wikipedia Title: Naphthalene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.9627225
• LogD (pH = 7.4): 2.9627225
• Log P: 2.9627225
• Molar Refractivity: 42.5082 cm^3
• Polarizability: 18.077257 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Approximately 30 mg/L in water; Soluble in benzene, toluene, chloroform, CS2, ether. Insoluble in water
• Apperance: Crystalline; white; White solid crystals/flakes,; strong odor of coal tar
• Melting Point: >= 78 °C with sublimation; 77-82 °C; 79.5-81 °C; 79.5-81.0 °C; 79-81 °C (±0.3°C); 79-84 °C; 80.26°C; 80-82 °C(lit.); 80-82°C
• Boiling Point: 217.9 °C at 1013 hPa; 218 °C(lit.); 218°C; 218°C
• Flash Point: -.4 °F; 176 °F; -18 °C; 78°C(172°F); 79–87 °C; 80 °C (closed cup); 80 °C
• Auto Ignition Point: 525 °C; 540 °C at 1013 hPa (DIN 51794); 978 °F
• Density: 0.9628; 0.963; 1.0253 g/cm^3 at 20 °C; 1.14 g/cm3
• Refractive Index: 1.5821
• Vapor Pressure: .04 hPa at 20 °C; 0.03 mmHg ( 25 °C)
• Vapor Density: 4.4 (vs air); 4.42 (air = 1)
• Fluorescence: λex 265; λem 336 in cyclohexane

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: QJ0525000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); X; Harmful (Xn)
• UN Number: 1145; 1230; 1334; UN1334
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 4.1
• Packing Group: 2; 3; III
• Australian Hazchem: 2Z
• Risk Statements: 11-22-40-50/53; 11-23/24/25-39/23/24/25; 11-38-50/53-65-67; 22-40-50/53; R:10-30-40/22; R22, R40, R50/53
• Safety Statements: 36/37-46-60-61; 7-16-36/37-45; 9-16-25-33-60-61-62; S:16-28-29-36/37/39-45; S2, S36/37, S46, S60, S61
• EU Classification: F1
• EU Hazard Identification Number: 4.1B
• Emergency Response Guidebook(ERG) Number: 133
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger; Warning
• Main Hazard: Flammable, sensitizer, possible carcinogen. Dust can form explosive mixtures with air
• NFPA704:
  

  2

  2

  0
• Explode Limits: 5.9 %
• GHS Hazard statements: H225-H304-H315-H336-H410; H228-H351-H400-H410-H302; H301-H311-H331-H370; H302-H351-H410
• GHS Precautionary statements: P210-P241-P280-P301+P312-P405-P501A; P210-P261-P273-P301 + P310-P331-P501; P260-P280-P301 + P310-P311; P273-P281-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1145 3/PG 2; UN 1230 4.1/PG 2; UN 1334 4.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544); human ... CYP1A2(1544), CYP2A6(1548)mouse ... Cyp2a5(13087)

Product Information

• Purity: ≥99%; ≥98.0%; ≥98.0% (GC); ≥99%; ≥99.0% (GC); ≥99.7% (GC); 95+%; 98%; 99%; 99.6%; 99+%
• Concentration: 100 ng/μL in cyclohexane; 200 μg/mL in methanol; 5000 μg/mL in methanol
• Grade: analytical standard; analytical standard, for environmental analysis; puriss.; purum; SAJ first grade; TraceCERT®
• Packaging: ampule of 1 mL; ampule of 5000 mg
• Suitability: suitable for scintillation
• Impurities: ~0.8% thionaphthene; ≤1% thionaphthene
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H8

DETAILS

MP Biomedicals - 02151726

Scintillation Grade
Purity: 99+%
NOT FOR EXPORT

Sigma Aldrich - 147141

Packaging
1 kg in poly bottle
25 g in poly bottle
3 kg in poly drum

Sigma Aldrich - 185604

Packaging
1 kg in glass bottle
250 g in glass bottle

Sigma Aldrich - 184500

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

Sigma Aldrich - 91489

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 48641

Other Notes
This product is also available as a certified reference solution. Please reference CRM48641.

REFERENCES

• Reacts with Na metal in 1,2-dimethoxyethane to give Na naphthalenide. This radical anion is a powerful-electron donor, e.g. in reductive dehalogenation of vic-dihalides: J. Chem. Soc., Chem. Commun., 78 (1969), and in reductive cleavage of tosylates to alcohols: J. Am. Chem. Soc., 88, 1581 (1966).
• Li naphthalenide is a useful, non-nucleophilic reagent for the conversion of carboxylic acids to their dianions in cases where LDA could interfere: J. Org. Chem., 45, 1106 (1980). Similarly, has been found preferable to LDA in the lithiation of allylic nitriles: Synthesis, 358 (1981).
• Carboxylic acids react with alkyl, alkenyl or aryl chlorides in the presence of Li metal and a catalytic amount of naphthalene in THF to give ketones in fair to good yields: J. Org. Chem., 61, 6058 (1996).