• Name

  9,9'-Spirobi[9H-fluorene]-2,2'-diamine

• EINECS
• CAS No. 67665-45-6
• Article Data4
• CAS DataBase
• Density 1.36
• Solubility
• Melting Point
• Formula C₂₅H₁₈N₂
• Boiling Point
• Molecular Weight 346.431
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2.2'-Diamino-9.9'-spirobifluoren;(rac)-2,2'-diamino-9,9'-spirobifluorene;9,9'-Spirobi[9H-fluorene]-2,2'-diamine;QC-1273;[9,9']spirobifluorene-2,2'-diyldiamine;[9,9']Spirobifluoren-2,2'-diyldiamin;2,2'-diamino-9,9'-spirobifluorene;2,2'-diamine-9,9'-spirobifluorene;
• PSA 52.04000
• LogP 6.35690

Synthetic route

67665-46-7

(rac)-2,2'-dinitro-9,9'-spirobifluorene

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

Conditions

Conditions	Yield
With sodium tetrahydroborate; palladium on activated charcoal In methanol at 20℃; for 12h;	76%
With hydrogenchloride; iron

67665-47-8

2,2′-dibromo-9,9′-spirobi[9H-fluorene]

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

Conditions

Conditions	Yield
With lithium hexamethyldisilazane; CyJohnPhos; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 65℃; for 15h;	45%

1336-21-6

ammonium hydroxide

dinitrospirobifluorene

159-66-0

9,9'-spirobifluorene

7439-89-6

iron

304-59-6

Rochelle's salt

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

Conditions

Conditions	Yield
With concentrated aqueous HNO3 In ethanol; water; pyrographite; acetic acid

...Expand

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

3,3'-dibromo-9,9'-spirobifluorene-2,2'-diamine

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane for 1.5h;	89.2%

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

790674-48-5

(rac)-2,2'-diiodo-9,9'-spirobifluorene

Conditions

Conditions	Yield
Stage #1: 2,2′-diamino-9,9′-spirobifluorene With hydrogenchloride; sodium nitrite In water at 0℃; for 0.75h; Stage #2: With potassium iodide In water for 16h; Sandmeyer reaction;	72%

624-31-7

4-tolyl iodide

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

2,2'-bis(ditolylamino)-9,9'-spirobifluorene

Conditions

Conditions	Yield
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In toluene Heating / reflux;	72%

591-50-4

iodobenzene

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

2,2’-bis(N,N-diphenylamine)-9,9'-spirobifluorene

Conditions

Conditions	Yield
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In toluene Heating / reflux;	70%

3972-65-4

1-bromo-4-tert-butylbenzene

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

2,2'-bis[di-(4-t-butylphenyl)amino]-9,9'-spirobifluorene

Conditions

Conditions	Yield
With sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine In toluene for 48h; Heating / reflux;	60%

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

67665-47-8

2,2′-dibromo-9,9′-spirobi[9H-fluorene]

Conditions

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 60℃; for 0.5h;	58%

1055917-19-5

N-butyl-1,7-di(4-tert-butyl)phenoxylperylene-3,4-dicarboxylic imide-9,10-dicarboxylic anhydride

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

1380497-15-3

C73H57N3O6

Conditions

Conditions	Yield
With 1H-imidazole In toluene for 5h; Reflux; Inert atmosphere;	37%

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

5-[1-hydroxy-meth-(E)-ylidene]-2,2,4,4-tetramethyl cyclopentanone

C45H42N2

Conditions

Conditions	Yield
Stage #1: 2,2′-diamino-9,9′-spirobifluorene; 5-[1-hydroxy-meth-(E)-ylidene]-2,2,4,4-tetramethyl cyclopentanone In toluene at 160℃; for 10h; Stage #2: With polyphosphoric acid In toluene at 160℃; for 16h; Inert atmosphere;	29%

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

79-44-7

N,N-Dimethylcarbamoyl chloride

N',N',N''',N'''-tetramethyl-N,N''-[9,9']spirobifluorene-2,2'-diyl-di-urea

Conditions

Conditions	Yield
With pyridine; diethyl ether; benzene

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

6-tert-butyl-8-(5,7-di-tert-butyl-benzooxazol-2-ylamino)-4-oxo-4H-chromene-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

C83H82N6O8

Conditions

Conditions	Yield
In tetrahydrofuran Yield given;

159652-30-9

(R)-2,3-bis-tert-butoxycarbonylaminopropionic acid

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

A

C51H62N6O10

B

C38H40N4O5

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 48h; Inert atmosphere;	A 67.8 mg B 25.8 mg

...Expand

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

C63H54N6O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 48 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / 20 °C / Inert atmosphere 3: dimethyl sulfoxide / 50 °C View Scheme

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

C31H30N6O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 48 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / 20 °C / Inert atmosphere View Scheme

5032-08-6

2,2-di-(4-methoxyphenyl)acetaldehyde

67665-45-6

2,2′-diamino-9,9′-spirobifluorene

C89H74N2O8

Conditions

Conditions	Yield
Dean-Stark; Reflux;

9,9'-Spirobi[9H-fluorene]-2,2'-diamine Chemical Properties