3-Hydroxyadamantane-1-carboxylic acid supplier

Name
3-Hydroxyadamantane-1-carboxylic acid
EINECS
CAS No. 42711-75-1
Article Data34
CAS DataBase
Density 1.419 g/cm³
Solubility
Melting Point 203 °C
Formula C₁₁H₁₆O₃
Boiling Point 357.2 °C at 760 mmHg
Molecular Weight 196.246
Flash Point 184 °C
Transport Information
Appearance
Safety 26-36/37/39-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Adamantanecarboxylicacid, 3-hydroxy- (7CI);1-Carboxy-3-adamantanol;3-Carboxy-1-hydroxyadamantane;Tricyclo[3.3.1.13,7]decane-1-carboxylicacid, 3-hydroxy-;
PSA 57.53000
LogP 1.40230

Synthetic route

: 828-51-3
1-Adamantanecarboxylic acid

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0℃;	98%
Stage #1: 1-Adamantanecarboxylic acid With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; tert-butyl alcohol at 40℃; for 0.5h; Green chemistry; Stage #2: With potassium permanganate In water; tert-butyl alcohol at 60℃; for 8.5h; Green chemistry;	94.12%
With nitric acid at 10 - 35℃; for 3.5h; Time;	92.6%

acetylacetonatocobalt(Co(AA)2): acetylacetonatocobalt(Co(AA)2)

: 828-51-3
1-Adamantanecarboxylic acid

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With acetic acid	80%

: 770-71-8
1-adamantanemethanol

A: 38584-37-1
1-hydroxy-3-hydroxymethyladamantane

B: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1-adamantanemethanol With nitric acid at 20℃; for 1h; Stage #2: With hydrazine hydrate In butan-1-ol for 3h; Reflux;	A 75% B 8%

: 64-18-6
formic acid

: 5001-18-3
1,3-adamantandiol

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1,3-adamantandiol With sulfuric acid at 35℃; for 0.5h; Stage #2: formic acid at 20 - 40℃; for 3h;	38%

: 828-51-3
1-Adamantanecarboxylic acid

A: 56674-87-4
4-oxoadamantane-1-carboxylic acid

B: 81968-77-6
4-hydroxyadamantane-1-carboxylic acid

C: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide; phosphate buffer; oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; investigation of the oxy-functionalization of adamantane-1-carboxylic acid;	A 12% B 5% C 34%

...Expand

: 21816-08-0
3-bromoadamantane-1-carboxylic acid

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With silver nitrate In 1,4-dioxane

: 828-51-3
1-Adamantanecarboxylic acid

A: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

B: 880-50-2
3-fluoro-1-adamantane-carboxylic acid

Conditions

Conditions	Yield
With difluoroether

: 68435-07-4
1-methoxycarbonyl-3-hydroxyadamantane

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol

: 3-(p-Toluolsulfonyloxy)adamantan-1-carbonsaeure

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With 1,4-dioxane; water; triethylamine solvolysis;

: 768-90-1
1-Adamantyl bromide

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 20 °C 1.2: 4.5 h / 10 - 35 °C 2.1: nitric acid / 5.5 h / 10 - 35 °C View Scheme

: 828-51-3
1-Adamantanecarboxylic acid

A: 56674-87-4
4-oxoadamantane-1-carboxylic acid

B: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; C60H66N183Fe(2+)3O4S(2-) In water at 60℃; for 24h;	A 6 %Chromat. B 26 %Chromat.

: 64-18-6
formic acid

: 5001-18-3
1,3-adamantandiol

A: 828-51-3
1-Adamantanecarboxylic acid

B: 39269-10-8
adamantane-1,3-dicarboxylic acid

C: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1,3-adamantandiol With sulfuric acid at 35℃; for 0.5h; Stage #2: formic acid at 20 - 40℃; for 3h;

...Expand

: 768-95-6
1-adamanthanol

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 3.25 h / 10 - 35 °C 2: nitric acid / 3.5 h / 10 - 35 °C View Scheme

: 50795-82-9
3-nitroxyadamantane-1-carboxylic acid

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With acetic acid; urea In water at 25 - 90℃; for 5h;

: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: C19H24O5

Conditions

Conditions	Yield
With methanesulfonic acid at 50℃; Friedel-Crafts Alkylation;	100%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 42711-77-3
3-iodoadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With hydrogen iodide at 60℃; for 16h;	99.8%
With phosphorus pentoxide; phosphoric acid; potassium iodide at 120℃; for 3h; Inert atmosphere;	95%
With phosphoric acid; phosphorus pentoxide; potassium iodide

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 21816-08-0
3-bromoadamantane-1-carboxylic acid

Conditions

Conditions	Yield
With hydrogen bromide at 90℃; for 3.5h;	99.8%
With hydrogen bromide In water at 90℃; for 4.5h;	92%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 74-88-4
methyl iodide

: 68435-07-4
1-methoxycarbonyl-3-hydroxyadamantane

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In acetone at 20℃; for 48h;	99%

: 1221151-98-9
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: C45H42O12

Conditions

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	97%

: 67-56-1
methanol

: 828-51-3
1-Adamantanecarboxylic acid

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

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

B: 68435-07-4
1-methoxycarbonyl-3-hydroxyadamantane

Conditions

Conditions	Yield
With sulfuric acid Reflux;	A 97% B n/a

...Expand

: 67-56-1
methanol

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 68435-07-4
1-methoxycarbonyl-3-hydroxyadamantane

Conditions

Conditions	Yield
With sulfuric acid In 1,2-dichloro-ethane for 20h; Heating;	96%
With sulfuric acid for 12h; Inert atmosphere; Reflux;

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 182496-69-1
25,26,27,28-tetrahydroxy-2,8,14,20-tetrathiacalix[4]arene

: p-(3-carboxy-1-adamantyl)thiacalix[4]arene

Conditions

Conditions	Yield
trifluorormethanesulfonic acid In trifluoroacetic acid for 24h; Heating;	96%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 248590-47-8
25,26,27,28-tetrakis(hydroxy)calix[4]arene

: 765943-01-9
p-(3-carboxy-1-adamantyl)calix[4]arene

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In 1,2-dichloro-ethane at 85 - 90℃; for 12h;	96%
With trifluorormethanesulfonic acid; trifluoroacetic acid In 1,2-dichloro-ethane at 60 - 65℃; for 10h;

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 38584-37-1
1-hydroxy-3-hydroxymethyladamantane

Conditions

Conditions	Yield
	95%
Stage #1: 3-hydroxyadamantane-1-carboxylic acid With sodium tetrahydroborate In tetrahydrofuran at 0 - 31℃; for 2.5h; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 30℃; for 14.5h; Stage #3: With water In tetrahydrofuran at 0 - 10℃; for 1h;	29.5 g

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 40556-45-4
1-fluoro-3-(trifluoromethyl)adamantane

Conditions

Conditions	Yield
With sulfur tetrafluoride; water at -178 - 40℃; for 24h; Autoclave;	95%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 71-36-3
butan-1-ol

: 247029-06-7
n-butyl 3-hydroxy-1-adamantanecarboxylate

Conditions

Conditions	Yield
With sulfuric acid In toluene for 5h; Heating / reflux;	94.1%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 67-68-5
dimethyl sulfoxide

: (methylthio)methyl 3-hydroxyadamantane-1-carboxylate

Conditions

Conditions	Yield
With triethylamine at 160℃; under 760.051 Torr; for 20h; Pummerer Sulfoxide Rearrangement; Schlenk technique; Inert atmosphere; Green chemistry;	94%

: 868-77-9
2-methyl-2-propenoic acid 2-hydroxyethyl ester

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 2-methacryloyloxyethyl 3-hydroxy-1-adamantanecarboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 12 - 20℃; for 22h; Temperature; Reagent/catalyst; Concentration;	93.9%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 71-43-2
benzene

: 113392-33-9
1,4-di(3-carboxy-1-adamantyl)benzene

Conditions

Conditions	Yield
With sulfuric acid at 15 - 20℃; for 4h;	93%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 100-39-0
benzyl bromide

: C25H28O3

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 100-46-9
benzylamine

: N-benzyl-3-hydroxyadamantane-1-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;	91%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 814-68-6
acryloyl chloride

: 3-carboxy-1-adamantyl acrylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	90.6%

sodium boron hydride (NaBH4): sodium boron hydride (NaBH4)

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 38584-37-1
1-hydroxy-3-hydroxymethyladamantane

Conditions

Conditions	Yield
In tetrahydrofuran	90%

: 923-26-2
2-hydroxypropyl methacrylate

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 1-methacryloyloxypropane-2-yl 3-hydroxy-1-adamantanecarboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 12 - 20℃; for 22h; Temperature; Reagent/catalyst; Solvent; Concentration;	89.8%

: 95-16-9
1,3-Benzothiazole

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: (1s,3r,5R,7S)-3-(benzo[d]thiazol-2-yl)adamantan-1-ol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h;	89%

: 95-16-9
1,3-Benzothiazole

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: C17H19NOS

Conditions

Conditions	Yield
With [Co(dyimethylglyoximate(1-))2(pyridine)2]PF6; tetrabutylammonium acetate In ethyl acetate at 40 - 44℃; for 30h; Irradiation; Schlenk technique; Inert atmosphere;	88%

: 1230076-22-8
2,3,4-tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: C23H32O10

Conditions

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	87%

: 1584705-82-7
(((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane)

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 1624333-35-2
(1r,3s,5R,7S)-3-((trifluoromethyl)thio)adamantan-1-ol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; sodium dodecyl sulfate; silver nitrate In water at 50℃; for 12h; Inert atmosphere;	86%

: 106-42-3
para-xylene

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 120383-96-2
1,4-di(3-carboxy-1-adamantyl)-2,5-dimethylbenzene

Conditions

Conditions	Yield
With sulfuric acid at 15 - 20℃; for 4h;	85%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 637-44-5
phenylpropyolic acid

: C18H20O

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 110℃; for 12h;	85%

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 107-30-2
chloromethyl methyl ether

: methoxymethyl-3-hydroxyadamantane-1-carboxylate

Conditions

Conditions	Yield
With triethylamine at 10℃; for 1h; Temperature; Inert atmosphere;	85%

3-Hydroxyadamantane-1-carboxylic acid Chemical Properties

Molecule structure of 3-Hydroxyadamantane-1-carboxylic acid (CAS NO.42711-75-1):

IUPAC Name: (5S,7R)-3-Hydroxyadamantane-1-carboxylate
Molecular Weight: 196.24 g/mol
Molecular Formula: C₁₁H₁₆O₃
Melting Point: 203 °C
Index of Refraction: 1.638
Molar Refractivity: 49.72 cm³
Molar Volume: 138.2 cm³
Surface Tension: 77.2 dyne/cm
Density: 1.419 g/cm3
Flash Point: 184 °C
Enthalpy of Vaporization: 69.75 kJ/mol
Boiling Point: 357.2 °C at 760 mmHg
Vapour Pressure: 1.55E-06 mmHg at 25 °C
SMILES: O=C(O)C13CC2CC(CC(O)(C1)C2)C3
InChI: InChI=1/C11H16O3/c12-9(13)10-2-7-1-8(3-10)5-11(14,4-7)6-10/h7-8,14H,1-6H2,(H,12,13)
InChIKey: CJJMAWPEZKYJAP-UHFFFAOYAF
Product Categories of 3-Hydroxyadamantane-1-carboxylic acid (CAS NO.42711-75-1: Adamantane derivatives;Carboxylic Acids;Carboxylic Acids;Ring Systems

3-Hydroxyadamantane-1-carboxylic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S37/39:Wear suitable gloves and eye/face protection.
Hazard Note: Irritant
HazardClass: IRRITANT

3-Hydroxyadamantane-1-carboxylic acid Specification

3-Hydroxyadamantane-1-carboxylic acid (CAS NO.42711-75-1) is also named as 1-carboxy-3-hydroxyadamantane ; 3-hydroxytricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid ; tricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid, 3-hydroxy- ; 1-Carboxy-3-adamantanol ; 3-Carboxy-1-hydroxyadamantane ; 3-hydroxy-1-adamantanecarboxylic acid ; 3-Hydroxy-adamantane-1-carboxylic acid ; 3-hydroxyadamantanecarboxylic acid ; 3-Hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid .

Product Name

3-Hydroxyadamantane-1-carboxylic acid

Synthetic route

3-Hydroxyadamantane-1-carboxylic acid Chemical Properties

3-Hydroxyadamantane-1-carboxylic acid Safety Profile

3-Hydroxyadamantane-1-carboxylic acid Specification

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