2094-74-8

Basic information

• Product Name: 1-ADAMANTANE CARBOXALDEHYDE
• Synonyms: 1-ADAMANTANE CARBOXALDEHYDE;1-Adamantylcarboxaldehyde;Tricyclo[3.3.1.13,7]decane-1-carboxaldehyde;1-AdaMantanecarboxaldehyde (7CI,8CI);1-AdaMantane;Adamantane-1-carbaldehyde;ADAMANTANE-1-ALDEHYDE
• CAS NO: 2094-74-8
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.246
• Mol File: 2094-74-8.mol

Chemical Properties

• Melting Point: 189-198 °C
• Boiling Point: 239℃
• Flash Point: 82℃
• Appearance: /
• Density: 1.166
• CAS DataBase Reference: 1-ADAMANTANE CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTANE CARBOXALDEHYDE(2094-74-8)
• EPA Substance Registry System: 1-ADAMANTANE CARBOXALDEHYDE(2094-74-8)

Safety Data

• Hazardous Substances Data: 2094-74-8(Hazardous Substances Data)

Usage

Description

1-Adamantane Carboxaldehyde is an organic compound characterized by its adamantane core, which is a rigid and symmetrical carbon cage structure. 1-ADAMANTANE CARBOXALDEHYDE features a carboxaldehyde functional group attached to the adamantane framework, making it a versatile intermediate in the synthesis of various pharmaceuticals and bioactive molecules.

Uses

Used in Pharmaceutical Industry:
1-Adamantane Carboxaldehyde is used as an intermediate for the synthesis of 2-adamantyl-substituted thiazolidin-4-ones, which possess anti-HIV activities. These compounds have the potential to inhibit the replication of the HIV virus, providing a valuable contribution to the development of antiretroviral therapies.
Additionally, 1-Adamantane Carboxaldehyde is used in the synthesis of Saxagliptin (S143500), a medication used to treat type 2 diabetes. Saxagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor that helps regulate blood sugar levels by increasing the levels of insulin and decreasing the levels of glucagon in the body.

Synthetic route

1-adamantanemethanol (770-71-8) → 1-Adamantanecarbaldehyde (2094-74-8)

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%

1-Adamantanecarboxylic acid (828-51-3) → 1-Adamantanecarbaldehyde (2094-74-8)

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 + 1-adamantanemethanol (770-71-8) → 1-Adamantanecarbaldehyde (2094-74-8)

Conditions	Yield
In dichloromethane for 1h;	98%

1-adamantanecarbonitrile (23074-42-2) → 1-Adamantanecarbaldehyde (2094-74-8)

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

N,N-dimethyltricyclo<3.3.1.13,7>decane-1-carboxamide (1502-00-7) → 1-Adamantanecarbaldehyde (2094-74-8)

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

α-Azido-1-adamantylmethyl phenyl sulfide (73296-58-9) → 1-Adamantanecarbaldehyde (2094-74-8) + diphenyldisulfane (882-33-7)

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

1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + 1-adamantanemethanol (770-71-8) → 1-Adamantanecarbaldehyde (2094-74-8)

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%

carbon monoxide (201230-82-2) + adamantane (281-23-2) → 1-adamanthanol (768-95-6) + 1-Adamantanecarboxylic acid (828-51-3) + 1-Adamantanecarbaldehyde (2094-74-8)

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%

1-Adamantyl bromide (768-90-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1-Adamantanecarbaldehyde (2094-74-8)

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%

carbon monoxide (201230-82-2) + adamantane (281-23-2) → 1-Adamantanecarbaldehyde (2094-74-8) + ethyl 1-adamantanecarboxylate

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

N-cyclohexyl-1-adamantanecarboxamide (81311-58-2) → 1-Adamantanecarbaldehyde (2094-74-8)

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%

1-Adamantanecarboxylic acid (828-51-3) → 1-adamantanemethanol (770-71-8) + 1-Adamantanecarbaldehyde (2094-74-8)

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

1-Adamantyl bromide (768-90-1) + carbon monoxide (201230-82-2) → 1-Adamantanecarbaldehyde (2094-74-8)

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.

1-adamantanemethanol (770-71-8) → 1-Adamantanecarbaldehyde (2094-74-8) + (1-adamantanyl)methyl 1-adamantanecarboxylate (78679-70-6)

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

1,3-dibromobenzene (108-36-1) + adamantylmethylamine (17768-41-1) → 1-Adamantanecarbaldehyde (2094-74-8) + N-[(adamantan-1-yl)methyl]aniline + N-(1-adamantylmethyl)-3-bromoaniline (1283234-35-4) + N,N'-bis(1-adamantylmethyl)benzene-1,3-diamine (1283234-38-7)

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%

1-adamantanecarbonitrile (23074-42-2) → 1-Adamantanecarbaldehyde (2094-74-8) + adamantylmethylamine (17768-41-1)

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 → S-Phenyl benzenethiosulfonate (1212-08-4) + 1-Adamantanecarbaldehyde (2094-74-8) + 1-adamantanecarbonitrile (23074-42-2) + diphenyldisulfane (882-33-7)

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

carbon monoxide (201230-82-2) + adamantane (281-23-2) → 1-Adamantanecarbaldehyde (2094-74-8)

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.

1-adamantanemethanol (770-71-8) → 1-Adamantanecarboxylic acid (828-51-3) + 1-Adamantanecarbaldehyde (2094-74-8)

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

Adamantan-1-carbonsaeure-N2-p-tosylhydrazid (17774-98-0) → 1-Adamantanecarbaldehyde (2094-74-8)

Conditions	Yield
With sodium carbonate at 160 - 165℃;

ethyl 1-adamantanecarboxylate (2094-73-7) → 1-Adamantanecarbaldehyde (2094-74-8) + acetaldehyde (75-07-0)

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

1-Adamantanecarbonyl chloride (2094-72-6) → 1-Adamantanecarbaldehyde (2094-74-8)

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

C13H20N(1+)*BF4(1-) → N-ethyl-1-adamantanecarboxamide (1501-94-6) + 1-Adamantanecarbaldehyde (2094-74-8)

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 → 2-Adamantanone (700-58-3) + 1-Adamantanecarbaldehyde (2094-74-8)

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

methyl adamantane-1-carboxylate (711-01-3) → 1-Adamantanecarbaldehyde (2094-74-8)

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

3-adamantan-1-yl-1-tert-butyl-aziridin-2-one (16664-32-7) → 1-Adamantanecarbaldehyde (2094-74-8)

Conditions	Yield
With methanesulfonic acid