• Name

  1-ADAMANTANE CARBOXALDEHYDE

• EINECS
• CAS No. 2094-74-8
• Article Data146
• CAS DataBase
• Density 1.167 g/cm³
• Solubility
• Melting Point 189-198 °C
• Formula C₁₁H₁₆O
• Boiling Point 239.244 °C at 760 mmHg
• Molecular Weight 164.247
• Flash Point 82.129 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Tricyclo[3.3.1.1^3,7]decane-1-carboxaldehyde;1-Formyladamantane;Adamantane-1-carbaldehyde;
• PSA 17.07000
• LogP 2.40170

Synthetic route

770-71-8

1-adamantanemethanol

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 1.75h; Ambient temperature;	100%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; for 1h; Swern oxidation;	98%
Stage #1: 1-adamantanemethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;	98%

828-51-3

1-Adamantanecarboxylic acid

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	64%
Stage #1: 1-Adamantanecarboxylic acid With lithium aluminium tetrahydride Stage #2: Swern Oxidation;	62%

C4H5ClO3S

770-71-8

1-adamantanemethanol

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
In dichloromethane for 1h;	98%

23074-42-2

1-adamantanecarbonitrile

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
Stage #1: 1-adamantanecarbonitrile With hydrogenchloride; tin(ll) chloride In diethyl ether at 0 - 25℃; for 22h; Stephen reduction; Stage #2: With water In diethyl ether at 20 - 60℃;	95%
With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 40℃; for 1h; Inert atmosphere; Sealed tube;	77%
Multi-step reaction with 2 steps 1: CH2Cl2 / 120 h / Heating 2: 1) Et3SiH, 2) H2O / 1) CH2Cl2, 1 h room temperature; 4 h reflux, 2) heating View Scheme

1502-00-7

N,N-dimethyltricyclo<3.3.1.13,7>decane-1-carboxamide

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction;	87%

73296-58-9

α-Azido-1-adamantylmethyl phenyl sulfide

A

2094-74-8

1-Adamantanecarbaldehyde

B

882-33-7

diphenyldisulfane

Conditions

Conditions	Yield
In chlorobenzene at 120℃; for 8h;	A 82% B 80.5 mg

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

770-71-8

1-adamantanemethanol

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
Stage #1: 1-adamantanemethanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at 0℃; Stage #2: 1,1,1,3',3',3'-hexafluoro-propanol With pyridine In dichloromethane at 0 - 20℃; for 24h;	81%

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

768-90-1

1-Adamantyl bromide

68-12-2, 33513-42-7

N,N-dimethyl-formamide

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With lithium sodium In tetrahydrofuran at 20℃; for 0.0833333h; Substitution; Bouveault reaction; ultrasonic irradiation;	75%
With sodium; lithium In tetrahydrofuran at 20℃; for 0.0833333h; Bouveault reaction;	75%
With lithium In diethyl ether for 5h;	36%

201230-82-2

carbon monoxide

281-23-2

adamantane

A

2094-74-8

1-Adamantanecarbaldehyde

B

ethyl 1-adamantanecarboxylate

ethyl 1-adamantanecarboxylate

Conditions

Conditions	Yield
With aluminum tri-bromide; carbon tetrabromide; methyl-cyclopentane In various solvent(s) at 20℃; for 1h;	A 72% B n/a

...Expand

81311-58-2

N-cyclohexyl-1-adamantanecarboxamide

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
Stage #1: N-cyclohexyladamantane-1-carboxamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere; Stage #2: With triethylsilane In dichloromethane at 0 - 25℃; Inert atmosphere; Stage #3: With citric acid In tetrahydrofuran; dichloromethane; water at 45℃; for 2h; chemoselective reaction;	70%

828-51-3

1-Adamantanecarboxylic acid

A

770-71-8

1-adamantanemethanol

B

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With lithium; ethylamine at 17℃; for 6h;	A 9% B 51%

768-90-1

1-Adamantyl bromide

201230-82-2

carbon monoxide

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 100℃; under 60800 Torr; for 3h;	46%
With 2,2'-azobis-(2,4-dimethylvaleronitrile); tri-n-butyl-tin hydride In decane; toluene at 80℃; under 64604.3 Torr; for 0.2h; Continuous microflow reactor;	86 %Chromat.

770-71-8

1-adamantanemethanol

A

2094-74-8

1-Adamantanecarbaldehyde

B

78679-70-6

(1-adamantanyl)methyl 1-adamantanecarboxylate

Conditions

Conditions	Yield
With iodine; potassium carbonate In tert-butyl alcohol at 20℃; for 26h;	A 41% B 32%

108-36-1

1,3-dibromobenzene

17768-41-1

adamantylmethylamine

A

2094-74-8

1-Adamantanecarbaldehyde

B

N-[(adamantan-1-yl)methyl]aniline

C

1283234-35-4

N-(1-adamantylmethyl)-3-bromoaniline

D

1283234-38-7

N,N'-bis(1-adamantylmethyl)benzene-1,3-diamine

Conditions

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 7h; Inert atmosphere; Reflux;	A 12% B 7% C 39% D 4%

...Expand

23074-42-2

1-adamantanecarbonitrile

A

2094-74-8

1-Adamantanecarbaldehyde

B

17768-41-1

adamantylmethylamine

Conditions

Conditions	Yield
With sodium hydride; sodium iodide In tetrahydrofuran; mineral oil at 85℃; for 20h; Inert atmosphere;	A 29% B 7%

α-azido-1-adamantylmethyl phenyl sulfoxide

A

1212-08-4

S-Phenyl benzenethiosulfonate

B

2094-74-8

1-Adamantanecarbaldehyde

C

23074-42-2

1-adamantanecarbonitrile

D

882-33-7

diphenyldisulfane

Conditions

Conditions	Yield
In chlorobenzene at 120℃; for 1h;	A 45 mg B 4.1% C 28.5% D 20 mg

...Expand

201230-82-2

carbon monoxide

281-23-2

adamantane

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 10h; Ambient temperature;	21%
With gallium(III) trichloride In 1,2-dichloro-ethane at 20℃; under 760 Torr; for 0.666667h; Product distribution; Further Variations:; Pressures; Temperatures; Solvents; Reagents;	84 % Chromat.

770-71-8

1-adamantanemethanol

A

828-51-3

1-Adamantanecarboxylic acid

B

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane	A 5% B n/a

17774-98-0

Adamantan-1-carbonsaeure-N2-p-tosylhydrazid

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With sodium carbonate at 160 - 165℃;

2094-73-7

ethyl 1-adamantanecarboxylate

A

2094-74-8

1-Adamantanecarbaldehyde

B

75-07-0

acetaldehyde

Conditions

Conditions	Yield
With dimethylsulfide borane complex; pyridinium chlorochromate 1) THF, reflux, 1 h, 2.) CH2Cl2, reflux, 1 h; Yield given. Multistep reaction;

2094-72-6

1-Adamantanecarbonyl chloride

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
trifluorormethanesulfonic acid; antimony pentafluoride In various solvent(s) for 6h; Ambient temperature;

C13H20N(1+)*BF4(1-)

A

1501-94-6

N-ethyl-1-adamantanecarboxamide

B

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With triethylsilane; water 1) CH2Cl2, 1 h room temperature; 4 h reflux, 2) heating; Yield given. Multistep reaction;	A 4 % Spectr. B n/a

6-(tricyclo[3.3.1.13,7]dec-1-yl)spiro[tricyclo[3.3.1.13,7]decane-2,3'-1',2',3'-trioxan]-5'-one

A

700-58-3

2-Adamantanone

B

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
In various solvent(s) at 170 - 220℃; Thermodynamic data; Quantum yield; activation energy at unimolecular thermolysis, solvent effects, effect of oxygen;

711-01-3

methyl adamantane-1-carboxylate

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride
Multi-step reaction with 2 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.25 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C View Scheme

16664-32-7

3-adamantan-1-yl-1-tert-butyl-aziridin-2-one

2094-74-8

1-Adamantanecarbaldehyde

Conditions

Conditions	Yield
With methanesulfonic acid

1-Adamantylcarboxaldehyde Specification