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CAS No.: | 828-51-3 |
---|---|
Name: | 1-Adamantanecarboxylic acid |
Article Data: | 104 |
Molecular Structure: | |
Formula: | C11H16O2 |
Molecular Weight: | 180.247 |
Synonyms: | 1-Adamantanecarboxylicacid (6CI,7CI,8CI);1-Adamantane-1-carboxylic acid;1-Carboxyadamantane;Adamantoic acid;1-Admantane carboxylic acid;1-Adamantanecarboxylic acid; |
EINECS: | 212-584-6 |
Density: | 1.231 g/cm3 |
Melting Point: | 172-176 °C |
Boiling Point: | 304.708 °C at 760 mmHg |
Flash Point: | 142.042 °C |
Solubility: | insoluble in water |
Appearance: | white to off-white crystalline powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-36-26 |
PSA: | 37.30000 |
LogP: | 2.28740 |
N-hydroxyiminomethyl 1-adamantanecarboxylate
1-Adamantanecarboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water for 2h; Heating; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-Adamantyl bromide With iodine; magnesium In diethyl ether for 2h; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether for 3.5h; Inert atmosphere; | 96.5% |
With magnesium; ethylene dibromide 1.) diethyl ether, 35 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid In hexane for 5h; Cooling with ice; | 96% |
With sulfuric acid In tetrahydrofuran at 5 - 10℃; for 3h; | 95% |
With sulfuric acid In tetrahydrofuran at 5 - 10℃; for 3h; Green chemistry; | 95% |
5α-cholestan-3β-yl adamantane-1-carboxylate
A
1-adamantanemethanol
B
1-Adamantanecarboxylic acid
C
cholestane
D
Cholestanol
Conditions | Yield |
---|---|
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran at 46℃; further reagent; | A 2% B 96% C 43% D 57% |
With lithium; ethylamine at 17℃; further reagent; | A 65% B 4% C 4% D 94% |
Conditions | Yield |
---|---|
With aluminum tri-bromide; ethanethiol for 24h; 0 deg C to room temp.; | 95.2% |
With iodine; aluminium In acetonitrile at 80℃; for 18h; | 94% |
With bis(tri-n-butyltin)oxide In toluene for 72h; Heating; | 10% |
Multi-step reaction with 3 steps 1: 88 percent / P4S10 / dioxane / 6 h / Heating 2: 29 percent / NH2OH*HCl, CH3ONa / methanol / 1 h 3: 100 percent / HCl / H2O / 2 h / Heating View Scheme | |
With methanol; sodium hydroxide Reflux; |
Conditions | Yield |
---|---|
With 18-crown-6 ether; tert-butylamine In diethyl ether | 95% |
1-adamantanecarbonitrile
1-Adamantanecarboxylic acid
Conditions | Yield |
---|---|
With potassium phosphate buffer at 30℃; for 72h; Rhodococcus sp. AJ270 cells; | 94.4% |
Conditions | Yield |
---|---|
With sulfuric acid at 20 - 22℃; for 1h; | 94% |
With sulfuric acid for 1h; | 93% |
carbon monoxide
1-Adamantanecarbaldehyde
1-adamantyl trifluoromethanesulfonate
A
1-Adamantanecarboxylic acid
B
3-hydroxy-4-homoadamantyl 1-adamantanecarboxylate
Conditions | Yield |
---|---|
trifluorormethanesulfonic acid In tetrachloromethane at 0℃; for 3h; | A 21% B 94% |
With 2,6-di-tert-butyl-4-methylpyridine; 5A molecular sieve; trifluorormethanesulfonic acid In tetrachloromethane at 0℃; for 3h; Yields of byproduct given; | A n/a B 94% |
1-Adamantanecarboxylic acid
Conditions | Yield |
---|---|
With Oxone; sodium hydrogencarbonate In water; acetone | 93% |
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The IUPAC name of 1-Adamantanecarboxylic acid is adamantane-1-carboxylic acid. With the CAS registry number 828-51-3, it is also named as 1-Carboxyadamantane. The product's categories are Organic Acids; Adamantanes; C11 to C12; Carbonyl Compounds; Carboxylic Acids. Besides, it is white to off-white crystalline powder, which should be stored in sealed place. In addition, its molecular formula is C11H16O2 and molecular weight is 180.25.
The other characteristics of this product can be summarized as:
(1)EINECS: 212-584-6; (2)ACD/LogP: 2.59; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.864; (5)ACD/LogD (pH 7.4): 0.078; (6)ACD/BCF (pH 5.5): 10.284; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 114.633; (9)ACD/KOC (pH 7.4): 1.877; (10)#H bond acceptors: 2; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.573; (14)Molar Refractivity: 48.23 cm3; (15)Molar Volume: 146.455 cm3; (16)Surface Tension: 52.61 dyne/cm; (17)Density: 1.231 g/cm3; (18)Flash Point: 142.042 °C; (19)Melting Point: 172-176 °C; (20)Enthalpy of Vaporization: 59.953 kJ/mol; (21)Boiling Point: 304.708 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Uses of 1-Adamantanecarboxylic acid:
1-Adamantanecarboxylic acid is an intermediate of sensitive material. It is also an intermediate used in organic synthesis and medicine synthesis. Additionally, it is used to produce Rimantadine hydrochloride. Similarly, it can be used to prepare 3-Hydroxyadamantan-1-carboxylic acid.
This reaction needs Perfluoro-cis-2-N-butyl-3-N-propyloxaziridine and CCl3F at ambient temperature for 70 hours. The yield is 82 %.
Safety information of 1-Adamantanecarboxylic acid:
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. Please do not breathe dust. And in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Moreover, you should wear suitable protective clothing to avoid contact with skin and eyes.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1C2CC3CC1CC(C2)(C3)C(=O)O
(2)InChI: InChI=1S/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)
(3)InChIKey: JIMXXGFJRDUSRO-UHFFFAOYSA-N
The toxicity data of 1-Adamantanecarboxylic acid is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | intraperitoneal | > 600mg/kg (600mg/kg) | Pharmaceutical Chemistry Journal Vol. 8, Pg. 396, 1974. | |
mouse | LD50 | unreported | 600mg/kg (600mg/kg) | BEHAVIORAL: ANTICONVULSANT | Russian Pharmacology and Toxicology Vol. 43, Pg. 73, 1980. |