Name | 2,3-Diaminonaphthalene |
Synonyms | NAPHTHALENEDIAMINE TIMTEC-BB SBB000127 2,3-Diaminonapthalene 2,3-Diaminonaphthalene 2,3-Naphthalenediamine naphthalene-2,3-diamine Naphthalene-2,3-diamine 2,3-Diaminonaphthalene(ForNoDetection) |
CAS | 771-97-1 |
EINECS | 212-241-0 |
InChI | InChI=1/C10H10N2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6H,11-12H2 |
Molecular Formula | C10H10N2 |
Molar Mass | 158.2 |
Density | 1.0968 |
Melting Point | 197-203°C |
Boling Point | 273.29°C (rough estimate) |
Flash Point | 212.3°C |
Water Solubility | Slightly soluble in water. Soluble in pyridine, dimethylsulfoxide, dimethyformamide, dil.hydrochloric acid, ethanol, ether and hot methanol. |
Solubility | pyridine: soluble50mg/mL |
Vapor Presure | 1.1E-05mmHg at 25°C |
Appearance | Crystalline Powder |
Color | Green-brown to brown |
BRN | 2206394 |
pKa | 5.36±0.10(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
Sensitive | Sensitive to light, heat and air |
Refractive Index | 1.6392 (estimate) |
MDL | MFCD00004116 |
Physical and Chemical Properties | Leaf-like crystals. The melting point is 199 ℃, the relative density is 1.0968(26/4 ℃), and the refractive index is 1.6342(26 ℃). Soluble in alcohol, ether, acetone and dilute acid, difficult to dissolve in water. |
Use | Used in organic synthesis, or a reagent for the determination of selenium. |
In vitro study | Poly(2,3-diaminonaphthalene) microspheres as a novel quencher for fluorescence-enhanced nucleic acid detection. 2,3-Diaminonaphthalene (DAN) is possibly a carcinogenic reagent. |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R45 - May cause cancer |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S53 - Avoid exposure - obtain special instructions before use. |
UN IDs | 2811 |
WGK Germany | 3 |
FLUKA BRAND F CODES | 8-10-23 |
TSCA | Yes |
HS Code | 29215900 |
Reference Show more | Liang Jin-Zhong, Wang Yi-Xue, Mei Jian-Qiu. Optimization of selenium-enriched culture conditions of Lactobacillus plantarum [J]. Science and Technology of food industry, 2017, 38(003):137-142. |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Application examples | 2, 3-diaminonaphthalene is commonly used for the quantitative analysis of nitrite/nitrate in body fluids and cell extracts, as an indicator of nitric oxide (NO) activity. The assay works on the principle that under acidic conditions, DAN reacts with NO2 − to produce a fluorescent visible naphthol triazole, which is carried out at room temperature and acidic pH. After the addition of NaOH, the pH was increased, resulting in a lower background and increased sensitivity, and the fluorescence values were determined in this environment (Ex/Em: -365/415nm). It is recommended to use 450nm to measure fluorescence to avoid fluorescence background and improve sensitivity. The fluorescence background of DAN is very low, thus ensuring maximum sensitivity. 2, 3-diaminonaphthalene can also be used as a derivatization reagent for the quantitative detection of selenium (Se) in the low concentration range. The complexation of DAN with Se results in the production of 4, 5-benzo-selenite, a complex obtained by extraction with chloroform, toluene or cyclohexane. Since the selenium complex is unstable, it can be determined by gas chromatography. NO2-test application example (DAN method) detection principle: DAN and NO2-reaction at room temperature, acidic pH 2; Naphthol triazole (naphhalen triazole) the fluorescence should be measured at pH>10. |
biological activity | 2,3-Diaminonaphthalene is a highly selective colorimetric and fluorescent reagent for selenium detection, it can also be used for the fluorescence determination of nitrite. |
purpose | for organic synthesis, or reagent for the determination of selenium. it can be used for the determination of selenium content by fluorescence spectrophotometry. It can also be used for the analysis of photochromic compounds and the synthesis of immunosuppressive agents. |
production method | is obtained by reacting 2, 3-naphthalenediol with ammonia under pressure. The solution of 2, 3-naphthalenediol and ammonia was added to the autoclave and held at 250-260 °c for 5-6h. After the reaction, the reaction mixture was sufficiently cooled, and the precipitate was filtered off, washed with a small amount of water, and dried to obtain a finished product. |