| Identification | More | [Name]
1-ADAMANTANECARBOXAMIDE | [CAS]
5511-18-2 | [Synonyms]
1-ADAMANTANECARBOXAMIDE
ADAMANTANE-1-CARBOXAMIDE
LABOTEST-BB LT00007835
OTAVA-BB BB5030040657
SALOR-INT L496057-1EA
1-Adamantyl-carboxamide
tricyclo(3.3.1.1(sup3,7))decane-1-carboxamide
Tricyclo(3.3.1.13,7)decane-1-carboxamide
1-Adamantanecarboxamide,98%
ADAMANTANE-1-CARBOXYLIC ACID AMIDE
Adamantane-1-carboxamide, 97+%
Tricyclo[3.3.1.13,7]decane-1-carboxamide | [EINECS(EC#)]
234-074-2 | [Molecular Formula]
C11H17NO | [MDL Number]
MFCD00077200 | [Molecular Weight]
179.26 | [MOL File]
5511-18-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
188-190 °C(lit.) | [Boiling point ]
311.8°C (rough estimate) | [density ]
1.0020 (rough estimate) | [refractive index ]
1.5065 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Dichloromethane, Methanol | [form ]
Solid | [pka]
16.85±0.20(Predicted) | [color ]
White | [Usage]
Reproduction of Sindbis virus strains sensitive and resistant to 1-adamantanecarboxamide | [BRN ]
2047887 | [CAS DataBase Reference]
5511-18-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
AU4452000
| [HazardClass ]
IRRITANT | [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Reproduction of Sindbis virus strains sensitive and resistant to 1-adamantanecarboxamide | [Synthesis]
GENERAL STEPS: To a stirred mixture of 1-adamantanecarboxylic acid (11, 36.05 g, 200 mmol) and DMF (5 drops) in CH2Cl2 (360 mL) was added thionyl chloride (26.17 g, 220 mmol) in batches under cooling conditions in an ice-water bath. The resulting mixture was refluxed until the release of HCl gas ceased (usually takes 2 hours). Subsequently, the solvent and excess thionyl chloride were removed using a rotary evaporator and the crude product, adamantanoyl chloride (12), was dissolved in THF (100 mL). This solution was slowly added dropwise to concentrated ammonia (400 mL) cooled and stirred in an ice water bath. After the dropwise addition was completed, the white slurry formed was continued to be stirred at room temperature for 2 hours. The white precipitate was collected by vacuum filtration, washed with cold hexane, and dried under vacuum to give 1-adamantanecarboxamide (13). The product was a white solid with a yield of 34.06 g (95% yield) and a melting point of 177-179 °C (literature value: 185.5-191.7 °C [48]).1H-NMR (DMSO-d6, 400 MHz) δ: 6.89 (brs, 1H), 6.62 (brs, 1H), 1.93 (s, 3H), 1.73-1.74 (m , 6H), 1.60-1.68 (m, 6H). | [References]
[1] Molecules, 2018, vol. 23, # 2,
[2] Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5156 - 5159
[3] Synthetic Communications, 1988, vol. 18, # 11, p. 1179 - 1186
[4] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3988 - 3991
[5] Chemische Berichte, 1960, vol. 93, p. 226 - 230 |
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