1-ADAMANTANECARBOXAMIDE Chemical Properties

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

BRN 

2047887

CAS DataBase Reference

5511-18-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

AU4452000

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-ADAMANTANECARBOXAMIDE Usage And Synthesis

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

1-ADAMANTANECARBOXAMIDE(5511-18-2)Related Product Information

• 1-ADAMANTANECARBOXAMIDE
• ADAMANTANE-1-CARBOHYDRAZIDE
• Adamantane
• (1-ADAMANTANECARBONYL-D-ARG0,HYP3,BETA-(2-THIENYL)-ALA5,8,D-PHE7)-BRADYKININ
• N-Antipyrinyl-1-adamantanecarboxamide
• AURORA 401
• N-(5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-1-adamantanecarboxamide
• N-[4-(1-pyrrolidinylsulfonyl)phenyl]-3-(1H-1,2,4-triazol-1-yl)-1-adamantanecarboxamide
• N-(5-bromo-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-1-adamantanecarboxamide
• TOSLAB 865133
• 4-[(1-ADAMANTYLCARBONYL)AMINO]BENZOIC ACID
• TIMTEC-BB SBB007551
• AURORA 402
• 2-[(ADAMANTANE-1-CARBONYL)-AMINO]-3-(1H-INDOL-3-YL)-PROPIONIC ACID
• N-(2-HYDROXYETHYL)-1-ADAMANTANECARBOXAMIDE
• N-HYDROXYADAMANTANE-1-CARBOXAMIDE
• TIMTEC-BB SBB006373
• TIMTEC-BB SBB001230