2292-79-7

Basic information

• Product Name: CONGRESSANE
• Synonyms: PENTACYCLO[7.3.1.14,12.02,7.06,11]TETRADECANE;DIAMANTANE;DIAMANTINE;CONGRESSANE;4,4'-Methylene-1,1'-methylene-5,6'-cyclo-3,2'-bicyclohexane;Pentacyclo[5.3.1.12,6.14,11.19,14]tetradecane;Congressane Pentacyclo[7.3.1.1(4,12).0(2,7).0(6,11)]tetradecane
• CAS NO: 2292-79-7
• Molecular Formula: C₁₄H₂₀
• Molecular Weight: 188.31
• Product Categories: Adamantane derivatives
• Mol File: 2292-79-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 236-237°
• Boiling Point: 258.34°C (rough estimate)
• Flash Point: 98.1℃
• Appearance: /
• Density: 1.092
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Merck: 14,2538
• CAS DataBase Reference: CONGRESSANE(CAS DataBase Reference)
• NIST Chemistry Reference: CONGRESSANE(2292-79-7)
• EPA Substance Registry System: CONGRESSANE(2292-79-7)

Safety Data

• Hazardous Substances Data: 2292-79-7(Hazardous Substances Data)

Usage

Purification Methods

Purify diamantane by repeated crystallisation from MeOH or pentane. Alternatively purify it by dissolving it in CH2Cl2, washing with 5% aqueous NaOH and water, and drying (MgSO4). The solution is filtered, concentrated to a small volume, an equal weight of alumina is added, and the solvent evaporated. The residue is placed on an activated alumina column (ca 4 x weight of diamantane) and eluted with pet ether (b 40-60o). Eight sublimations and twenty zone refining experiments gave material m 251o of 99.99% purity by differential analysis [Gund et al. Tetrahedron Lett 3877 1970, Courtney et al. J Chem Soc Perkin Trans I 2691 1972]. [For spectra see Cupas et al. J Am Chem Soc 87 919 1965.]

InChI:InChI=1/C14H20/c1-7-2-12-10-4-8-5-11(9(1)10)13(3-7)14(12)6-8/h7-14H,1-6H2

Synthetic route

3-methyldiamantane (30545-28-9) → diamantane (2292-79-7)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 215℃; under 760 Torr; for 5.5h;	100%

binor-S → diamantane (2292-79-7)

Conditions	Yield
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h;	99%

(+/-)-D3-tritwistane (75500-94-6, 77122-04-4, 116347-56-9) → diamantane (2292-79-7)

Conditions	Yield
With aluminum tri-bromide In carbon disulfide for 5h; Ambient temperature;	94%

tetrahydrobinor-S (51966-18-8) → diamantane (2292-79-7)

Conditions	Yield
With aluminum tri-bromide; isopropyl alcohol In cyclohexane at 25 - 50℃; for 4h; Product distribution / selectivity;	81%
With aluminum tri-bromide; ethanol In cyclohexane at 25 - 50℃; for 4h; Product distribution / selectivity;	80%
With aluminum tri-bromide; sulfuric acid In cyclohexane at 25 - 40℃; for 3h; Product distribution / selectivity;	78%

1,1,2,2-tetrachloroethylene (127-18-4) + diamantane-3-spiro-3'-diazirine (105522-49-4) → diamantane (2292-79-7) + diamantane-3-one (30545-23-4)

Conditions	Yield
With sulfuric acid	A 29.7% B 64%

1,1-Dichloroethylene (75-35-4) + diamantane-3-spiro-3'-diazirine (105522-49-4) → diamantane (2292-79-7) + diamantane-3-one (30545-23-4) + diamantan-1-ol (30545-19-8) + (3-diamantyl)acetic acid (105522-50-7)

Conditions	Yield
With sulfuric acid Further byproducts given;	A 6.9% B 7.4% C 60.2% D 19.05%
With sulfuric acid Further byproducts given;	A 18.8% B 24% C 24.2% D 4.2%

4-hydroxy-12-hydroxymethyltetracyclo<7.3.1.02,7.06,11>tridecane (130504-29-9) → diamantane (2292-79-7) + diamantane-3-one (30545-23-4) + 3-hydroxydiamantane (30545-24-5) + 2-methyl-3-oxadiamantane (132658-78-7)

Conditions	Yield
With phosphoric acid at 180℃; for 2h; Further byproducts given;	A 7% B 2% C 3% D 57%

4-hydroxy-12-hydroxymethyltetracyclo<7.3.1.02,7.06,11>tridecane (130504-29-9) → diamantane (2292-79-7) + 3-hydroxydiamantane (30545-24-5) + 10-oxa-2(3)-homodiamantane (127494-76-2) + 2-methyl-3-oxadiamantane (132658-78-7)

Conditions	Yield
With phosphoric acid at 180℃; for 2h; Further byproducts given;	A 7% B 3% C 20% D 57%

1,1,2,2-tetrachloroethylene (127-18-4) + diamantane-3-spiro-3'-diazirine (105522-49-4) → diamantane (2292-79-7) + diamantane-3-one (30545-23-4) + diamantan-1-ol (30545-19-8)

Conditions	Yield
With sulfuric acid	A 49.9% B 36.6% C 5%

Trichloroethylene (79-01-6) + diamantane-3-spiro-3'-diazirine (105522-49-4) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + diamantane-3-one (30545-23-4) + 3-chlorodiamantane (30651-01-5)

Conditions	Yield
With sulfuric acid Further byproducts given;	A 24.7% B 12.7% C 37% D 17%
With sulfuric acid Further byproducts given;	A 22% B 7.6% C 37.3% D 24%
With sulfuric acid for 3h; Further byproducts given;	A 24.7% B 12.7% C 37% D 17%

4-hydroxy-12-hydroxymethyltetracyclo<7.3.1.02,7.06,11>tridecane (130504-29-9) → diamantane (2292-79-7) + 3-hydroxydiamantane (30545-24-5) + 10-oxa-2(3)-homodiamantane (127494-76-2)

Conditions	Yield
at 180℃; for 2h; Mechanism; other tetracyclic diols;	A 7% B 3% C 20%

Dispiro2,6>decan-10',1"-cyclopropan> (105883-30-5) → diamantane (2292-79-7)

Conditions	Yield
With aluminum tri-bromide In cyclohexane for 5h; Heating;	13%

6,6,10,10-tetramethylpentacyclo<5.3.0.02,5.03,9.04,8>decane (120676-59-7) → diamantane (2292-79-7)

Conditions	Yield
With aluminum tri-bromide In cyclohexane for 5h; Heating;	9%

1,1-Dichloroethylene (75-35-4) + 4-hydroxydiamantane (30651-03-7) → diamantane (2292-79-7) + 4-diamantylacetic acid (110082-20-7) + 3,9-diamantanebisacetic acid (110082-25-2) + 4,9-diamantanebisacetic acid (110082-14-9)

Conditions	Yield
With sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

Trichloroethylene (79-01-6) + 4-hydroxydiamantane (30651-03-7) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

Trichloroethylene (79-01-6) + diamantan-1-ol (30545-19-8) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

Trichloroethylene (79-01-6) + 3-hydroxydiamantane (30545-24-5) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

1-methyldiamantane (26460-76-4) → adamantane (281-23-2) + diamantane (2292-79-7)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 225℃; under 760 Torr; for 5.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

4-methyldiamantane (28375-86-2) → adamantane (281-23-2) + diamantane (2292-79-7)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 245℃; under 760 Torr; for 5.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

4-hydroxydiamantane (30651-03-7) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 3-chlorodiamantane (30651-01-5)

Conditions	Yield
With 1,1,2,2-tetrachloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Yields of byproduct given;

4-hydroxydiamantane (30651-03-7) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With Trichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

4-hydroxydiamantane (30651-03-7) → diamantane (2292-79-7) + 4-diamantylacetic acid (110082-20-7) + 3,9-diamantanebisacetic acid (110082-25-2) + 4,9-diamantanebisacetic acid (110082-14-9)

Conditions	Yield
With 1,1-Dichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

1-chlorodiamantane (32401-16-4) → diamantane (2292-79-7) + diamantan-1-ol (30545-19-8) + 1-Diamantyllithium (69261-61-6) + C18H28O + 1-(1-diamantyl)diamantane

Conditions	Yield
With Li (2percent Na) In pentane at 35℃; Product distribution; other halide: bromide; other solvent: Et2O; other temperature: -45 degC;	A 17.5 % Chromat. B 4 % Chromat. C 76 % Spectr. D n/a E 2.5 % Chromat.

diamantan-1-ol (30545-19-8) → diamantane (2292-79-7) + 4-hydroxydiamantane (30651-03-7) + 1-chlorodiamantane (32401-16-4)

Conditions	Yield
With 1,1,2,2-tetrachloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Yields of byproduct given;

diamantan-1-ol (30545-19-8) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With Trichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

diamantan-1-ol (30545-19-8) → diamantane (2292-79-7) + (3-diamantyl)acetic acid (105522-50-7) + 4-diamantylacetic acid (110082-20-7) + 4,9-diamantanebisacetic acid (110082-14-9)

Conditions	Yield
With 1,1-Dichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

3-hydroxydiamantane (30545-24-5) → diamantane (2292-79-7) + 4-hydroxydiamantane (30651-03-7) + 1-chlorodiamantane (32401-16-4) + 3-chlorodiamantane (30651-01-5)

Conditions	Yield
With 1,1,2,2-tetrachloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

3-hydroxydiamantane (30545-24-5) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 3-chlorodiamantane (30651-01-5)

Conditions	Yield
With 1,1,2,2-tetrachloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Yields of byproduct given;

3-hydroxydiamantane (30545-24-5) → diamantane (2292-79-7) + 1-chlorodiamantane (32401-16-4) + 4-diamantylchloroacetic acid (110082-26-3) + 4,9-diamantanebischloroacetic acid (110082-15-0)

Conditions	Yield
With Trichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

3-hydroxydiamantane (30545-24-5) → diamantane (2292-79-7) + (3-diamantyl)acetic acid (105522-50-7) + 4-diamantylacetic acid (110082-20-7) + 3,9-diamantanebisacetic acid (110082-25-2)

Conditions	Yield
With 1,1-Dichloroethylene; sulfuric acid at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given;

diamantane (2292-79-7) → diamantan-1-ol (30545-19-8)

Conditions	Yield
With oxygen; nitric acid; trifluoroacetic acid Reagent/catalyst;	97%
With 2,3,4,5,6-pentafluoroperoxybenzoic acid; MoO3*2H2O; sodium acetate In dichloromethane; 1,2-dichloro-ethane at 30 - 60℃; for 6h; Reagent/catalyst;	71%
Stage #1: diamantane With nitric acid; acetic acid at 15 - 20℃; for 1h; Stage #2: With acetic acid; urea In water at 100℃; for 1h;	36%
(i) AcCl, AlCl3, (ii) aq. HCl; Multistep reaction;
Multi-step reaction with 2 steps 1: nitric acid / acetic acid / 1 h / 15 - 20 °C 2: urea; acetic acid / water / 25 - 100 °C View Scheme

diamantane (2292-79-7) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-(diamantan-1-yl)formamide

Conditions	Yield
With nitric acid at 20 - 85℃; for 2h;	96%

diamantane (2292-79-7) + benzene (71-43-2) → 4,9-diphenyldiamantane

Conditions	Yield
With aluminium trichloride; t-butyl bromide at 20℃; for 1h;	94%
With aluminum (III) chloride; t-butyl bromide at 0 - 20℃; Inert atmosphere;	84%
Stage #1: diamantane; benzene With t-butyl bromide; aluminum (III) chloride at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride; water In benzene	76.6%

diamantane (2292-79-7) → 4-chlorodiamantane (32401-17-5) + 1-chlorodiamantane (32401-16-4)

Conditions	Yield
With tetrachloromethane at 150℃; for 5h; Reagent/catalyst; Temperature; Time; Sealed tube;	A 7% B 93%
With tetrachloromethane at 150℃; for 5h;	A 9% B 90%
With methanol; tetrachloromethane; bis(acetylacetonate)oxovanadium at 150℃; for 1h;	A 40% B 60%
With Wilkinson's catalyst; dichloromethane at 180℃; for 30h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

acetamide (60-35-5) + diamantane (2292-79-7) → N-(diamantan-1-yl)acetamide (30545-21-2) + N-(4-diamantyl)acetamide (63707-74-4)

Conditions	Yield
With tetrachloromethane at 150℃; for 5h; Temperature; regioselective reaction;	A 90% B 9%

diamantane (2292-79-7) → diamantane-3-one (30545-23-4)

Conditions	Yield
With sulfuric acid at 70 - 75℃; for 40h;	86%
With sulfuric acid at 75℃; for 10h;	69%
With sulfuric acid at 70 - 80℃; for 48h;	65%

diamantane (2292-79-7) → 1-nitroxydiamantane (941305-71-1)

Conditions	Yield
With nitric acid In dichloromethane at 0 - 20℃;	85%
With nitric acid In acetic acid for 4.5h;
With nitric acid In acetic acid at 15 - 20℃; for 1h;

diamantane (2292-79-7) + acetonitrile (75-05-8) → N-(diamantan-1-yl)acetamide (30545-21-2)

Conditions	Yield
With nitric acid; acetic acid at 20℃; for 2h; Ritter Amidation;	85%

diamantane (2292-79-7) → diamantane-1-amine hydrochloride (30545-22-3)

Conditions	Yield
Stage #1: diamantane With nitric acid; acetic acid at 20℃; for 4.5h; Stage #2: With urea at 90℃; for 2h; Stage #3: With hydrogenchloride	84%
Multi-step reaction with 5 steps 1: nitric acid / acetic acid / 4.5 h 2: acetic acid / 90 °C 3: nitric acid / acetic acid / 90 °C 4: sodium hydroxide / water 5: hydrogenchloride / diethyl ether View Scheme

diamantane (2292-79-7) → 1,4-dichlorodiamantane

Conditions	Yield
With methanol; tetrachloromethane; bis(acetylacetonate)oxovanadium at 150℃; for 5h;	80%

diamantane (2292-79-7) → MDT-14 (39646-84-9)

Conditions	Yield
Stage #1: diamantane With nitric acid Schlenk technique; Stage #2: With sulfuric acid Schlenk technique;	78%
Stage #1: diamantane With nitric acid Stage #2: With sulfuric acid	78%
With sulfuric acid; nitric acid	78%
With sulfuric acid
Multi-step reaction with 2 steps 1: 62 percent / Br2 / Fe / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 4 h / 20 °C 2: 70 percent / H2O; HCl / dimethylformamide / 36 h / Heating View Scheme

diamantane (2292-79-7) → 4-hydroxydiamantane (30651-03-7) + MDT-14 (39646-84-9) + diamantan-1-ol (30545-19-8)

Conditions	Yield
Stage #1: diamantane With nitric acid In dichloromethane at 0 - 20℃; for 1h; Stage #2: With sulfuric acid In chloroform at -15 - 0℃; for 1.5h; Further stages.;	A 8% B 78% C 7%
Stage #1: diamantane With nitric acid In dichloromethane at 0 - 20℃; for 1h; Stage #2: With sulfuric acid In chloroform at -15 - 0℃; for 0.0666667h; Further stages.;	A 44% B 22% C 24%

Upstream product

• 79-01-6 Trichloroethylene 
• 30651-03-7 4-hydroxydiamantane 
• 30545-19-8 diamantan-1-ol 
• 30545-24-5 3-hydroxydiamantane 
• 105522-49-4 diamantane-3-spiro-3'-diazirine 
• 13002-57-8 heptacyclo<8,4,0,0^2,12,0^3,8,0^4,6,0^5,9,0^11,13>tetradecane 
• 60526-61-6 Pentacyclo<8.3.1.0^2,8.0^4,13.0^7,12>tetradecan-5-on 
• 41171-89-5 3-Methylentetracyclo[6,3,1,0^2.6,0^5.10]dodecan 
• 13970-00-8 heptacyclo[8.4.0.0^2,12.0^3,8.0^4,6.0^5,9. 0^11,13]tetradecane 
• 77079-57-3 4-pentacyclo<8.4.0.0^2,7.0^3,12.0^6,11>tetradecanone 
• 77079-56-2 C₁₄H₂₀O 
• 51966-18-8 tetrahydrobinor-S 
• 60526-52-5 Pentacyclo<5.5.1.1^1,5.0^3,10.0^10,13>tetradecan 
• 60526-51-4 Protodiamantan 

Downstream Products

• 30545-19-8 diamantan-1-ol 
• 67-66-3 chloroform 
• 30545-17-6 1-bromodiamantane 
• 30545-21-2 N-(diamantan-1-yl)acetamide 
• 30545-30-3 4-bromo-diamantane 
• 63707-74-4 N-(4-diamantyl)acetamide 
• 1331868-28-0 4,9-bis(4-heptyloxyphenyl)diamantane 
• 1187679-86-2 4,9-bis(4-hexyloxyphenyl)diamantane 
• 1187679-85-1 4,9-bis(4-pentyloxyphenyl)diamantane 
• 1187679-84-0 4,9-bis(4-butyloxyphenyl)diamantane 
• 1187679-83-9 4,9-bis(4-propyloxyphenyl)diamantane 
• 1187679-82-8 4,9-bis(4-ethoxyphenyl)diamantane 
• 1187679-81-7 4,9-bis(4-methoxyphenyl)diamantane 
• 1187679-95-3 4,9-bis(4-hexanoyloxyphenyl)diamantane 

Relevant articles and documents

Single-Step Reductive Isomerisation of Unsaturated Polycyclics to C4n+6H4n+12 Diamondoid Cage Hydrocarbons with Sodium Borohydride/Triflic Acid

-

Hydroisomerization of hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecanes to diamantane induced by ionic liquids

Hydroisomerization of endo-endo-, exo-exo-, exo-endo-, and endo-exo-, hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecanes to diamantane was performed for the first time in 80–96% yields under the action of ionic liquids (ILs), [Et3NH]+[Al2Cl7]? and [BMIM]+[Fe2Cl7]?. Ionic liquids have multiple functions, promoting the following reactions of hexacyclotetradecanes: hydrogenation, dehydrogenation, and skeletal rearrangement; simultaneously, they serve as HCl donors.

-

-

Temperature Controls Guest Uptake and Release from Zn4L4 Tetrahedra

We report the preparation of triazatruxene-faced tetrahedral cage 1, which exhibits two diastereomeric configurations (T1 and T2) that differ in the handedness of the ligand faces relative to that of the octahedrally coordinated metal centers. At lower temperatures, T1 is favored, whereas T2 predominates at higher temperatures. Host-guest studies show that T1 binds small aliphatic guests, whereas T2 binds larger aromatic molecules, with these changes in binding preference resulting from differences in cavity size and degree of enclosure. Thus, by a change in temperature the cage system can be triggered to eject one bound guest and take up another.