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32846-66-5

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32846-66-5 Usage

Description

1,4-Cubanedicarboxylic acid is an organic compound characterized by its dicarboxylic acid structure, which consists of a Cubane core with two carboxylic acid functional groups attached at the 1 and 4 positions. This unique structure endows it with specific chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
1,4-Cubanedicarboxylic acid is used as a chemical intermediate for the synthesis of various ester and fluorinated derivatives. Its ability to undergo esterification with alkylsulfuric acids and fluorination with elemental fluorine makes it a versatile building block for creating novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
1,4-Cubanedicarboxylic acid and its derivatives may be employed as active pharmaceutical ingredients or as components in the development of new drugs. The unique chemical properties of the Cubane core and the functional groups attached to it can be exploited to design molecules with specific biological activities, targeting various diseases and medical conditions.
Used in Material Science:
The unique structure and properties of 1,4-Cubanedicarboxylic acid can be utilized in the development of new materials with specific characteristics, such as improved mechanical strength, thermal stability, or chemical resistance. These materials can find applications in various industries, including aerospace, automotive, and electronics.
Used in Research and Development:
1,4-Cubanedicarboxylic acid serves as an important compound for research purposes, particularly in the fields of organic chemistry, medicinal chemistry, and materials science. Its unique structure and properties make it an interesting subject for studying various chemical reactions, mechanisms, and the development of new synthetic methods and strategies.

Check Digit Verification of cas no

The CAS Registry Mumber 32846-66-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,8,4 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 32846-66:
(7*3)+(6*2)+(5*8)+(4*4)+(3*6)+(2*6)+(1*6)=125
125 % 10 = 5
So 32846-66-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H8O4/c11-7(12)9-1-2-4(9)6-5(9)3(1)10(2,6)8(13)14/h1-6H,(H,11,12)(H,13,14)

32846-66-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name cubane-1,4-dicarboxylic acid

1.2 Other means of identification

Product number -
Other names pentacyclo[4.2.0.0(2,5).0(3,8).0(4,7)]octane-1,4-dicarboxylic acid methyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:32846-66-5 SDS

32846-66-5Synthetic route

cubane-1,4-dicarboxylic acid dimethyl ester
29412-62-2

cubane-1,4-dicarboxylic acid dimethyl ester

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 4h; Heating;99%
Stage #1: cubane-1,4-dicarboxylic acid dimethyl ester With water; sodium hydroxide In methanol for 4.5h; Reflux;
Stage #2: With hydrogenchloride In water pH=Ca. 1;
99%
With sodium hydroxide In methanol; water for 8h; Heating;96.16%
cubane-1,4-dicarboxylic acid dimethyl ester
29412-62-2

cubane-1,4-dicarboxylic acid dimethyl ester

A

4-(methoxycarbonyl)-1-cubanecarboxylic acid
24539-28-4

4-(methoxycarbonyl)-1-cubanecarboxylic acid

B

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol Ambient temperature;A 95%
B 3%
With barium dihydroxide In methanol; water for 18h; Ambient temperature;
4-(methoxycarbonyl)-1-cubanecarboxylic acid
24539-28-4

4-(methoxycarbonyl)-1-cubanecarboxylic acid

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol for 4.5h; Reflux;91%
4-methoxycarbonylcubane-1-carbonyl chloride
60462-18-2

4-methoxycarbonylcubane-1-carbonyl chloride

A

cubane-1-carboxylic acid
53578-15-7

cubane-1-carboxylic acid

B

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With dmap; 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol In benzene Heating; Irradiation;A 57%
B 10.8%
5,9-dibromopentacyclo<5.3.0.02,5.03,9.04,8>decane-6,10-dione
25867-85-0

5,9-dibromopentacyclo<5.3.0.02,5.03,9.04,8>decane-6,10-dione

A

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

B

C10H8O4

C10H8O4

Conditions
ConditionsYield
With potassium hydroxide for 3.5h; Heating; Yields of byproduct given. Title compound not separated from byproducts;
1-bromo-9-oxopentacyclo<4.3.0.02,5.03,8.04,7>nonane-4-carboxylic acid
25867-88-3

1-bromo-9-oxopentacyclo<4.3.0.02,5.03,8.04,7>nonane-4-carboxylic acid

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide Heating;
5,9-dibromopentacyclo<5.3.0.02,5.03,9.04,8>decane-6,10-dione
25867-85-0

5,9-dibromopentacyclo<5.3.0.02,5.03,9.04,8>decane-6,10-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) reflux, 4 h, H2O; Yield given. Multistep reaction;
(4R,7R)-2,4-Dibromo-3a,4,7,7a-tetrahydro-4,7-methano-indene-1,8-dione

(4R,7R)-2,4-Dibromo-3a,4,7,7a-tetrahydro-4,7-methano-indene-1,8-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) conc. HCl / 1.) methanol, RT, irradiation, 2.) reflux, water
2: 1.) NaOH, 2.) aq. HCl / 1.) reflux, 4 h, H2O
View Scheme
endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal

endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / 98percent H2SO4 / 30 h / 20 - 25 °C
2: 1.) conc. HCl / 1.) methanol, RT, irradiation, 2.) reflux, water
3: 1.) NaOH, 2.) aq. HCl / 1.) reflux, 4 h, H2O
View Scheme
endo-2,4-dibromodicyclopentadiene-1,8-dione

endo-2,4-dibromodicyclopentadiene-1,8-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: endo-2,4-dibromodicyclopentadiene-1,8-dione With sulfuric acid; water In methanol UV-irradiation; Large scale reaction;
Stage #2: With water; sodium hydroxide for 3h; Reflux;
Stage #1: endo-2,4-dibromodicyclopentadiene-1,8-dione With hydrogenchloride In methanol; water Irradiation;
Stage #2: With sodium hydroxide In water Heating;
endo-2,4-dibromodicyclopentadiene-1,8-dione

endo-2,4-dibromodicyclopentadiene-1,8-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: endo-2,4-dibromodicyclopentadiene-1,8-dione With sulfuric acid In methanol; water at 25℃; UV-irradiation; Large scale reaction;
Stage #2: With sodium hydroxide In water for 3h; Favorskii rearrangement; Reflux;
C10H8Br2O

C10H8Br2O

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: C10H8Br2O With sodium hydroxide In water at 20℃; for 3h; Inert atmosphere; Reflux; Large scale;
Stage #2: With hydrogenchloride In water at 0 - 20℃; pH=1 - 2; Large scale;
1,4-dioxaspiro[4.4]nonane
176-32-9

1,4-dioxaspiro[4.4]nonane

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: bromine / 1,4-dioxane / 60 h / 10 - 20 °C / Inert atmosphere
2.1: sodium hydroxide / methanol / 3 h / Reflux
3.1: sulfuric acid / 25 h / 20 - 25 °C
4.1: hydrogenchloride / methanol; water / 40 h / Inert atmosphere; Irradiation
4.2: 1.5 h / Reflux; Inert atmosphere
4.3: 4.5 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: bromine / 1,4-dioxane
2.1: sulfuric acid / 20 °C
3.1: hydrogenchloride / methanol; water / Irradiation
3.2: Heating
View Scheme
Multi-step reaction with 4 steps
1.1: bromine / 1,4-dioxane / 22 h / 5 - 20 °C / Inert atmosphere
2.1: sodium hydroxide / methanol / 24 h / 5 - 110 °C
3.1: sulfuric acid / 30 h / 20 °C
4.1: sulfuric acid; methanol / water / Inert atmosphere; UV-irradiation; Flow reactor
4.2: 3.5 h / Reflux
4.3: 15 h / Reflux
View Scheme
2,2,5-tribromocyclopentanone ethylene acetal
25834-49-5

2,2,5-tribromocyclopentanone ethylene acetal

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol / 3 h / Reflux
2.1: sulfuric acid / 25 h / 20 - 25 °C
3.1: hydrogenchloride / methanol; water / 40 h / Inert atmosphere; Irradiation
3.2: 1.5 h / Reflux; Inert atmosphere
3.3: 4.5 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol / 24 h / 5 - 110 °C
2.1: sulfuric acid / 30 h / 20 °C
3.1: sulfuric acid; methanol / water / Inert atmosphere; UV-irradiation; Flow reactor
3.2: 3.5 h / Reflux
3.3: 15 h / Reflux
View Scheme
(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / 25 h / 20 - 25 °C
2.1: hydrogenchloride / methanol; water / 40 h / Inert atmosphere; Irradiation
2.2: 1.5 h / Reflux; Inert atmosphere
2.3: 4.5 h / Reflux; Inert atmosphere
View Scheme
(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione
32846-64-3, 65656-68-0

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione With hydrogenchloride In methanol; water for 40h; Inert atmosphere; Irradiation;
Stage #2: In water for 1.5h; Reflux; Inert atmosphere;
Stage #3: With sodium hydroxide In water for 4.5h; Reflux; Inert atmosphere;
cyclopentanone
120-92-3

cyclopentanone

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Dowex 50W-X8 resin / toluene / 30 h / Dean-Stark; Heating
2.1: bromine / 1,4-dioxane / 60 h / 10 - 20 °C / Inert atmosphere
3.1: sodium hydroxide / methanol / 3 h / Reflux
4.1: sulfuric acid / 25 h / 20 - 25 °C
5.1: hydrogenchloride / methanol; water / 40 h / Inert atmosphere; Irradiation
5.2: 1.5 h / Reflux; Inert atmosphere
5.3: 4.5 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: Dowex / benzene
2.1: bromine / 1,4-dioxane
3.1: sulfuric acid / 20 °C
4.1: hydrogenchloride / methanol; water / Irradiation
4.2: Heating
View Scheme
Multi-step reaction with 5 steps
1.1: Dowex 50WX8 (H) / benzene / 30 h / Dean-Stark; Reflux
2.1: bromine / 1,4-dioxane / 22 h / 5 - 20 °C / Inert atmosphere
3.1: sodium hydroxide / methanol / 24 h / 5 - 110 °C
4.1: sulfuric acid / 30 h / 20 °C
5.1: sulfuric acid; methanol / water / Inert atmosphere; UV-irradiation; Flow reactor
5.2: 3.5 h / Reflux
5.3: 15 h / Reflux
View Scheme
endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal

endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / 20 °C
2.1: hydrogenchloride / methanol; water / Irradiation
2.2: Heating
View Scheme
endo-2,4-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal)

endo-2,4-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal)

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / 30 h / 20 °C
2.1: sulfuric acid; methanol / water / Inert atmosphere; UV-irradiation; Flow reactor
2.2: 3.5 h / Reflux
2.3: 15 h / Reflux
View Scheme
endo-2,4-dibromocyclopentadiene-1,8-dione

endo-2,4-dibromocyclopentadiene-1,8-dione

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: endo-2,4-dibromocyclopentadiene-1,8-dione With methanol; sulfuric acid In water Inert atmosphere; UV-irradiation; Flow reactor;
Stage #2: With water for 3.5h; Reflux;
Stage #3: With sodium hydroxide In water for 15h; Favorskii Rearrangement; Reflux;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

1,4-Bis<(tert-butoxycarbonyl)amino>cubane
87830-27-1

1,4-Bis<(tert-butoxycarbonyl)amino>cubane

Conditions
ConditionsYield
With diphenylphosphoranyl azide; triethylamine for 12h; Heating;94%
With diphenyl phosphoryl azide; triethylamine for 12h; Heating;75.11%
With diphenyl phosphoryl azide; triethylamine for 16h; Reflux;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

1,4-diiodocubane
97229-08-8

1,4-diiodocubane

Conditions
ConditionsYield
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In 1,2-dichloro-ethane for 2h; Product distribution / selectivity; Reflux; Irradiation;93%
With [bis(acetoxy)iodo]benzene; iodine In benzene for 6h; Heating;85%
With [bis(acetoxy)iodo]benzene; iodine In benzene for 6h; Moriarty reaction; Inert atmosphere; Reflux;84%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

1,4-bis(hydroxymethyl)cubane
60462-27-3

1,4-bis(hydroxymethyl)cubane

Conditions
ConditionsYield
With aluminium hydride In tetrahydrofuran at 16 - 18℃; for 6h; further reagent: LiAlH4;84%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h; Reflux;74%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
Multi-step reaction with 2 steps
1: Dowex / Heating
2: lithium aluminium tetrahydride / tetrahydrofuran
View Scheme
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N1,N4-dimethoxy-N1,N4-dimethylcubane-1,4-dicarboxamide

N1,N4-dimethoxy-N1,N4-dimethylcubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With thionyl chloride for 3h; Inert atmosphere; Reflux;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 17h;
76%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

1,4-Dibromocubane
59346-70-2

1,4-Dibromocubane

Conditions
ConditionsYield
With bromine; mercury(II) oxide In various solvent(s) Heating;72%
(i) HgO, (ii) Br2; Multistep reaction;
With bromine; mercury(II) oxide In various solvent(s) at 80 - 90℃; for 2.5h; Yield given;
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

[Zn4O(cubane-1,4-dicarboxylate)3]

[Zn4O(cubane-1,4-dicarboxylate)3]

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 24h;72%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

cubane-1,4-dicarboxylic acid dimethyl ester
29412-62-2

cubane-1,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With Dowex 50W-X8 resin In methanol for 24h; Reflux;71%
2-fluoro-2,2-dinitroethylsulfuric acid
53510-13-7

2-fluoro-2,2-dinitroethylsulfuric acid

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

bis(2-fluoro-2,2-dinitroethyl) pentacyclo<4.2.0.02,5.03,8.04,7>octane-1,4-dicarboxylate

bis(2-fluoro-2,2-dinitroethyl) pentacyclo<4.2.0.02,5.03,8.04,7>octane-1,4-dicarboxylate

Conditions
ConditionsYield
at 30℃; for 0.5h;68.5%
4-Ethynylaniline
14235-81-5

4-Ethynylaniline

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

N1,N4-bis(4’-ethynylphenyl)cubane-1,4-dicarboxamide

N1,N4-bis(4’-ethynylphenyl)cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-Ethynylaniline In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
67%
4-nitro-phenol
100-02-7

4-nitro-phenol

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

1,4-Bis(4-nitrophenoxycarbonyl)cubane

1,4-Bis(4-nitrophenoxycarbonyl)cubane

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h; Esterification;60%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

5-(4-aminophenyl)-10,15,20-triphenylporphyrin
67605-64-5

5-(4-aminophenyl)-10,15,20-triphenylporphyrin

N1,N4-bis[4’-{(10’’,15’’,20’’-triphenylporphyrin)-5’’-yl}phenyl]cubane-1,4-dicarboxamide

N1,N4-bis[4’-{(10’’,15’’,20’’-triphenylporphyrin)-5’’-yl}phenyl]cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: 5-(4-aminophenyl)-10,15,20-triphenylporphyrin In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
56%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

[5-(2'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II)

[5-(2'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II)

N1,N4-bis[2’-{(10’’,20’’-bis(4’-methylphenyl)-15’’-phenylporphyrinato)zinc(II)-5’’-yl}phenylacetylene]cubane-1,4-dicarboxamide

N1,N4-bis[2’-{(10’’,20’’-bis(4’-methylphenyl)-15’’-phenylporphyrinato)zinc(II)-5’’-yl}phenylacetylene]cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: [5-(2'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II) In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
50%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

N1,N4-bis(3’-ethynylphenyl)cubane-1,4-dicarboxamide

N1,N4-bis(3’-ethynylphenyl)cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: 3-acetylenephenylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
50%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

A

1,3,4-Triiodo-cubane
129380-05-8

1,3,4-Triiodo-cubane

B

1,4-diiodocubane
97229-08-8

1,4-diiodocubane

Conditions
ConditionsYield
With tert-Butyl hypoiodite In 1,1,2-Trichloro-1,2,2-trifluoroethane for 24h; Irradiation;A 45%
B 35%
With tert-Butyl hypoiodite In 1,1,2-Trichloro-1,2,2-trifluoroethane for 24h; Irradiation;A 45%
B 35%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

N1,N4-bis(4’-iodophenyl)cubane-1,4-dicarboxamide

N1,N4-bis(4’-iodophenyl)cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: p-aminoiodobenzene In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
39%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

[5-(3'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II)

[5-(3'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II)

N1,N4-bis[3’-{(10’’,20’’-bis(4’-methylphenyl)-15’’-phenylporphyrinato)zinc(II)-5’’-yl}phenylacetylene]cubane-1,4-dicarboxamide

N1,N4-bis[3’-{(10’’,20’’-bis(4’-methylphenyl)-15’’-phenylporphyrinato)zinc(II)-5’’-yl}phenylacetylene]cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: [5-(3'-aminophenylacetylene)-10,20-bis(4'-methylphenyl)-15-phenylporphyrinato]zinc(II) In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
36%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

3-Iodoaniline
626-01-7

3-Iodoaniline

N1,N4-bis(3’-iodophenyl)cubane-1,4-dicarboxamide

N1,N4-bis(3’-iodophenyl)cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 40℃; for 2h; Inert atmosphere;
Stage #2: 3-Iodoaniline With triethylamine In dichloromethane at 0 - 40℃; for 2h; Inert atmosphere;
31%
methanol
67-56-1

methanol

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

cubane-1,4-dicarboxylic acid dimethyl ester
29412-62-2

cubane-1,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid for 18h; Inert atmosphere; Reflux;30%
With ion-exchange resin + form> Heating;
With chlorosulfonic acid 1.) 30 deg C, 30 min, 2.) 1 h; Yield given. Multistep reaction;
[5-(4′-aminophenyl)-10,15,20-triphenylporphyrinato]zinc(II)
131956-11-1

[5-(4′-aminophenyl)-10,15,20-triphenylporphyrinato]zinc(II)

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

N1,N4-bis[4’-{(10’’,15’’,20’’-triphenylporphyrinato)zinc(II)-5’’-yl}phenyl]cubane-1,4-dicarboxamide

N1,N4-bis[4’-{(10’’,15’’,20’’-triphenylporphyrinato)zinc(II)-5’’-yl}phenyl]cubane-1,4-dicarboxamide

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With 1-hydroxy-7-aza-benzotriazole; 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 20℃; for 0.5h; Inert atmosphere;
Stage #2: [5-(4′-aminophenyl)-10,15,20-triphenylporphyrinato]zinc(II) In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
28%
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

cubane-1,4-diamine dihydrochloride
87830-28-2

cubane-1,4-diamine dihydrochloride

Conditions
ConditionsYield
Stage #1: cubane-1,4-dicarboxylic acid With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol for 16h; Curtius Rearrangement; Reflux;
Stage #2: With hydrogenchloride In 1,4-dioxane; methanol; water at 20℃; for 4h;
14.5%
2,2,2-trinitroethanol
918-54-7

2,2,2-trinitroethanol

cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

bis(2,2,2-trinitroethyl) pentacyclo<4.2.0.02,5.03,8.04,7>-octane-1,4-dicarboxylate

bis(2,2,2-trinitroethyl) pentacyclo<4.2.0.02,5.03,8.04,7>-octane-1,4-dicarboxylate

Conditions
ConditionsYield
With chlorosulfonic acid 1.) 30 deg C, 30 min, 2.) 1 h; Yield given. Multistep reaction;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

1,4-cubanedicarboxylic acid dichloride
60462-24-0

1,4-cubanedicarboxylic acid dichloride

Conditions
ConditionsYield
With thionyl chloride Heating;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h; Ambient temperature;
With phosphorus pentachloride In chlorobenzene for 2h; Ambient temperature;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

A

1,3,4-Triiodo-cubane
129380-05-8

1,3,4-Triiodo-cubane

B

1,2,4,7-Tetraiodo-cubane
129380-06-9

1,2,4,7-Tetraiodo-cubane

C

1,4-diiodocubane
97229-08-8

1,4-diiodocubane

Conditions
ConditionsYield
With tert-Butyl hypoiodite In tetrachloromethane; 1,1,2-Trichloro-1,2,2-trifluoroethane Irradiation; Further byproducts given;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

C10H9BrO4

C10H9BrO4

Conditions
ConditionsYield
With hydrogen bromide In acetic acid at 70℃; for 0.25h; Yield given;
cubane-1,4-dicarboxylic acid
32846-66-5

cubane-1,4-dicarboxylic acid

(4S,5S)-4,5-Dibromo-tricyclo[4.2.0.03,8]octane-2,7-dicarboxylic acid
125848-35-3

(4S,5S)-4,5-Dibromo-tricyclo[4.2.0.03,8]octane-2,7-dicarboxylic acid

Conditions
ConditionsYield
With hydrogen bromide In acetic acid at 70℃; overnight;

32846-66-5Relevant articles and documents

Molecular Reorientation and Self-Diffusion in Solid Cubane by Deuterium and Proton NMR

Detken, A.,Zimmermann, H.,Haeberlen, U.,Poupko, R.,Luz, Z.

, p. 9598 - 9604 (1996)

Deuterium and proton NMR line shape and relaxation measurements are reported for the sym-cubane-d2 isotopomer (D3d symmetry) in the temperature range from 200 K to the melting point of the solid.The results confirm the polymorphic phase sequence: solid II solid I liquid, reported earlier by White et al.The deuterium spectrum below 215 K exhibits a Pake doublet corresponding to an axially symmetric quadrupole coupling tensor with a coupling comstant of Qc = 178 kHz.Above this temperature the spectrum develops features characteristic of the onset of dynamic processes leading to a single line at about room temperature.Longitudinal relaxation time measurements show a T1 minimum at 344 K.On transition to solid I there is a discontinuous narrowing of the line and a concomitant increase in T1.These results are quantitatively interpreted in terms of reorientational jumps of the cubane molecules between their various equivalent orientations.The jump rate k in solid II follows an Arrhenius behavior over the range of almost seven decades with an activation energy E = 62 kJ mol-1.Transition to solid I results in a discontinuous increase of k.Proton line width measurements in solid II show two motional narrowing steps.The first, at around 240 K, is due to the cubic jumps while the second, at around 375 K, corresponds to molecular self-diffusion between the lattice sites.The activation energy for this process is Ed = 83 kJ mol-1.On transition to solid I there is also a discontinuous increase in the rate of this process.The proton T1 values are predominantly affected by the reorientation process and are consistent with the deuteron data.At temperatures above 340 K, where the deuterium NMR spectrum is expected to be a single Lorentzian with a width of less than 400 Hz, it actually exhibits, in both phases II and I, a Pake doublet corresponding to an axially symmetric quadrupole coupling tensor with a very small coupling constant Q'c = 0.48 kHz.This indicates that the reaorientation process is not perfectly cubic.Possible reasons for this surprising effect are discussed.

Enantioselective synthesis of (: R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane

Houston, Sevan D.,Chalmers, Benjamin A.,Savage, G. Paul,Williams, Craig M.

supporting information, p. 1067 - 1070 (2019/02/07)

The first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed. The key step was a telescoped Strecker reaction using (S)-2-amino-2-phenylethanol as a chiral auxiliary. Exploration of an alternative synthetic approach resulted in unprecedented cubane C-H insertion.

Cubane Arrives on the Cucurbituril Scene

Jelínková, Kristyna,Surmová, Heda,Matelová, Alena,Rouchal, Michal,Prucková, Zdeňka,Dastychová, Lenka,Ne?as, Marek,Vícha, Robert

, p. 2698 - 2701 (2017/05/24)

Cubane, an intriguing chemical curiosity first studied in the early 1960s, has become a valuable structural motif and has recently been involved in the structures of a great number of prospective compounds. The first dicationic supramolecular guest 5 is prepared and derived from a 1,4-disubstituted cubane moiety, and its binding behavior toward cucurbit[n]urils (CBn) and cyclodextrins (CD) is studied. The bisimidazolium salt 5 forms 1:1 inclusion complexes with CB7, CB8, and β-CD with the respective association constants (6.7 ± 0.5) × 1011 M-1, (1.5 ± 0.2) × 109 M-1, and 2 M-1 in water. The solid-state structures of the 5@CB7 and 5@CB8 complexes are also reported.

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