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828-51-3

Basic Information
CAS No.: 828-51-3
Name: 1-Adamantanecarboxylic acid
Article Data: 104
Molecular Structure:
Molecular Structure of 828-51-3 (1-Adamantanecarboxylic acid)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
PSA: 37.30000
LogP: 2.28740
Synthetic route
170952-87-1

N-hydroxyiminomethyl 1-adamantanecarboxylate

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Heating;100%
768-90-1

1-Adamantyl bromide

124-38-9

carbon dioxide

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
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;
768-90-1

1-Adamantyl bromide

64-18-6

formic acid

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
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%
73532-35-1

5α-cholestan-3β-yl adamantane-1-carboxylate

A

770-71-8

1-adamantanemethanol

B

828-51-3

1-Adamantanecarboxylic acid

C

481-21-0

cholestane

D

80-97-7

Cholestanol

Conditions
ConditionsYield
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%
711-01-3

methyl adamantane-1-carboxylate

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
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;
2094-73-7

ethyl 1-adamantanecarboxylate

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With 18-crown-6 ether; tert-butylamine In diethyl ether95%
23074-42-2

1-adamantanecarbonitrile

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With potassium phosphate buffer at 30℃; for 72h; Rhodococcus sp. AJ270 cells;94.4%
64-18-6

formic acid

32314-61-7

1-nitroxyadamantane

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With sulfuric acid at 20 - 22℃; for 1h;94%
With sulfuric acid for 1h;93%
201230-82-2

carbon monoxide

2094-74-8

1-Adamantanecarbaldehyde

77418-99-6

1-adamantyl trifluoromethanesulfonate

A

828-51-3

1-Adamantanecarboxylic acid

B

97382-21-3

3-hydroxy-4-homoadamantyl 1-adamantanecarboxylate

Conditions
ConditionsYield
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%

methyl (2Z)-4-(1-adamanthyl)-2-hydroxy-4-oxo-2-butenoate

828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With Oxone; sodium hydrogencarbonate In water; acetone93%
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Specification

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.