1-Adamantanecarboxylic acid supplier

Name
1-Adamantanecarboxylic acid
EINECS 212-584-6
CAS No. 828-51-3
Article Data104
CAS DataBase
Density 1.231 g/cm³
Solubility insoluble in water
Melting Point 172-176 °C
Formula C₁₁H₁₆O₂
Boiling Point 304.708 °C at 760 mmHg
Molecular Weight 180.247
Flash Point 142.042 °C
Transport Information
Appearance white to off-white crystalline powder
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Adamantanecarboxylicacid (6CI,7CI,8CI);1-Adamantane-1-carboxylic acid;1-Carboxyadamantane;Adamantoic acid;1-Admantane carboxylic acid;1-Adamantanecarboxylic acid;
PSA 37.30000
LogP 2.28740

Synthetic route

: 170952-87-1
N-hydroxyiminomethyl 1-adamantanecarboxylate

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
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

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;

: 768-90-1
1-Adamantyl bromide

: 64-18-6
formic acid

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

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%

: 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

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%

...Expand

: 711-01-3
methyl adamantane-1-carboxylate

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

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;

: 2094-73-7
ethyl 1-adamantanecarboxylate

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In diethyl ether	95%

: 23074-42-2
1-adamantanecarbonitrile

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

...Expand

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

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With Oxone; sodium hydrogencarbonate In water; acetone	93%

: C20H36O2Si

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With water; N,N-dimethyl-formamide at 70℃; for 3h; Green chemistry; chemoselective reaction;	93%

: 64-18-6
formic acid

: 768-95-6
1-adamanthanol

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid at 15 - 20℃; for 0.116667h; Koch-Haaf reaction;	92%
With sulfuric acid at 0 - 10℃;	42%
With hexane; sulfuric acid
Stage #1: 1-adamanthanol With sulfuric acid at 20℃; Koch-Haaf Carboxylation; Stage #2: formic acid at 10 - 35℃; for 3.5h; Reagent/catalyst; Koch-Haaf Carboxylation;	98.9 %Chromat.
With sulfuric acid at 10 - 35℃; for 3.25h;

: 75-04-7
ethylamine

: 73532-35-1
5α-cholestan-3β-yl adamantane-1-carboxylate

A: 828-51-3
1-Adamantanecarboxylic acid

B: 1501-94-6
N-ethyl-1-adamantanecarboxamide

C: 481-21-0
cholestane

D: 80-97-7
Cholestanol

Conditions

Conditions	Yield
With lithium In tetrahydrofuran at 17℃; Further byproducts given;	A 4% B 92% C 7% D 85%

...Expand

: 73532-34-0
5α-cholestane-3β,6β-diyl bis-(adamantane-1-carboxylate)

A: 828-51-3
1-Adamantanecarboxylic acid

B: 481-21-0
cholestane

C: 80-97-7
Cholestanol

D: 35490-51-8
5α-cholestan-6β-ol

Conditions

Conditions	Yield
With 18-crown-6 ether; tert-butylamine Further byproducts given;	A 92% B 45% C 27% D 6%

...Expand

: octadecyl adamantane-1-carboxylate

A: 112-92-5
1-octadecanol

B: 593-45-3
octadecane

C: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With 18-crown-6 ether; tert-butylamine In diethyl ether	A 53% B 40% C 90%

...Expand

: C27H34O2Si

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With water; N,N-dimethyl-formamide at 70℃; for 3h; Green chemistry; chemoselective reaction;	89%

: 5511-18-2
adamantane-1-carboxamide

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With niobium(V) oxide; water In neat (no solvent) for 24h; Reflux; Inert atmosphere;	83%

: 281-23-2
adamantane

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
	81%
In acetonitrile	69%
Multi-step reaction with 2 steps 1: 83 percent / HNO3 / 0.5 h 2: 93 percent / H2SO4 / 1 h View Scheme

: 2094-74-8
1-Adamantanecarbaldehyde

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With sodium cyanide; pyridinium chlorochromate In tetrahydrofuran at 45℃;	78%
With poly[4-(diacetoxyiodo)styrene]; 2,2,6,6-tetramethyl-piperidine-N-oxyl In acetone at 20℃; for 24h;
With 9-oxyl-9-azabicyclo<3.3.1>nonan-3-one; oxygen; nitric acid; sodium nitrite In water; acetonitrile at 23℃; under 760.051 Torr; for 8h; Sealed tube;	98 mg

: 770-71-8
1-adamantanemethanol

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With C22H36IrNP(1+)*CF3O3S(1-); potassium hydroxide In toluene at 120℃; for 75h;	77%
With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;	72%
With potassium hydroxide; zinc(II) oxide In 1,3,5-trimethyl-benzene at 164℃; for 36h; Inert atmosphere; Schlenk technique;	67%

: 201230-82-2
carbon monoxide

: 281-23-2
adamantane

A: 768-95-6
1-adamanthanol

B: 828-51-3
1-Adamantanecarboxylic acid

C: 2094-74-8
1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
trifluorormethanesulfonic acid In various solvent(s) under 62057.8 Torr; for 10h; Ambient temperature;	A 6% B 75% C n/a
trifluorormethanesulfonic acid In various solvent(s) under 62057.8 Torr; for 10h; Product distribution; Ambient temperature; variation of superacid catalyst systems, in absence of solvent;	A n/a B n/a C 0.2%

...Expand

: 75-34-3
1,1-dichloroethane

: 281-23-2
adamantane

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
	75%

: 201230-82-2
carbon monoxide

: 768-95-6
1-adamanthanol

: 828-51-3
1-Adamantanecarboxylic acid

Conditions

Conditions	Yield
With Sulfate; zirconium(IV) oxide In dichloromethane at 150℃; under 37503 Torr; for 18h; Carbonylation; Koch;	72%
silver trifluoromethanesulfonate In hexane at 150℃; under 37503 Torr; for 18h; Koch carbonylation;	64%

1-Adamantanecarboxylic acid 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.

Product Name

1-Adamantanecarboxylic acid

Synthetic route

1-Adamantanecarboxylic acid Specification

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