• Name

  2-Bromo-9,9-dimethylfluorene

• EINECS 694-710-3
• CAS No. 28320-31-2
• Article Data36
• CAS DataBase
• Density 1.346 g/cm³
• Solubility Slightly soluble in water.
• Melting Point 68 °C
• Formula C₁₅H₁₃Br
• Boiling Point 352.9 °C at 760 mmHg
• Molecular Weight 273.172
• Flash Point 165.097 °C
• Transport Information
• Appearance off kind of white crystallization
• Safety 61
• Risk Codes 51/53
• Molecular Structure
• Hazard Symbols N
• Synonyms Fluorene,2-bromo-9,9-dimethyl- (8CI);2-Bromo-9,9-dimethyl-9H-fluorene;9,9-Dimethyl-2-bromofluorene;
• PSA 0.00000
• LogP 4.75540

Synthetic route

1133-80-8

2-bromo-9H-fluorene

74-88-4

methyl iodide

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
Stage #1: 2-bromo-9H-fluorene With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃;	99%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dimethyl sulfoxide at 0℃; for 0.5h;	99%
With potassium hydroxide; potassium iodide In dimethyl sulfoxide at 20℃; for 48h;	97%

4569-45-3

9,9-dimethyl-9H-fluorene

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
With sodium bromate; hydrogen bromide; trimethylbenzylammonium bromide In dichloromethane; water at 10 - 20℃; under 760.051 Torr; for 1.5h;	90%
With N-Bromosuccinimide In dichloromethane at 20℃; for 24h;	78%
With bromine; iron(III) chloride In water at 20℃; for 13h; Heating / reflux;	20%
With bromine

C15H17Br

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene	67%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

75-36-5

acetyl chloride

899444-03-2

1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 16h;	99.3%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

74-88-4

methyl iodide

69535-83-7

2,9,9-trimethyl-9H-fluorene

Conditions

Conditions	Yield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	99%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

(2R*,3aR*,8bR*)-2-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(2R*,3aR*,8bR*)-2-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; tert-butyl XPhos In toluene Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	98%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

(1R*,3aR*,8bR*)-1-methyl-1,2,3,3a,4,8b-hexahydropenta[b]- indole

(1R*,3aR*,8bR*)-1-methyl-4-(9,9-dimethyl-9H-fluorenene-2-yl)- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate; tert-butyl XPhos In toluene Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	98%

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C33H25N

Conditions

Conditions	Yield
With potassium phosphate tribasic trihydrate; C44H43B10Br2P; palladium diacetate In ethanol; toluene at 120℃; for 36h; Kinetics; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	98%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

319906-45-1

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
With potassium iodate; sulfuric acid; iodine; acetic acid In water at 80℃; for 2.5h;	96%
With sulfuric acid; iodine; acetic acid; periodic acid In water at 50℃; for 5h;	85%
With periodic acid dihydrate; sulfuric acid; iodine; acetic acid at 65 - 90℃; for 6.5h; Inert atmosphere;	76%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

62-53-3

aniline

355832-04-1

N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	95%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 3.58333h; Inert atmosphere;	93%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 90℃; for 3h;	92%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

90-41-5

2-phenylaniline

N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	95%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 20h; Reflux;	95%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 12h;	94%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

C22H18O2

Conditions

Conditions	Yield
With C24H31Br2N3O9Pd; potassium carbonate In ethanol; water at 80℃; for 1.5h; Suzuki Coupling;	95%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

5720-06-9

2-Methoxyphenylboronic acid

2-(2"-methoxyphenyl)-9,9'-dimethylfluorene

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 20℃; for 6h;	94%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C39H27NO

C54H39NO

Conditions

Conditions	Yield
With tributylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 25h; Inert atmosphere;	93%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

63503-60-6

3-chlorophenylboronic acid

C21H17Cl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;	93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;	90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran at 80℃; for 5h; Inert atmosphere;	85%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C15H9(2)H4Br

Conditions

Conditions	Yield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;	93%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

1066-54-2

trimethylsilylacetylene

950181-08-5

1-(9,9-dimethylfluorene-2-yl)-2-(trimethylsilyl)acetylene

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 48h; Inert atmosphere;	92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Sonogashira Cross-Coupling;

76-86-8

Triphenylsilyl chloride

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

1208005-82-6

triphenyl-(9,9-dimethylfluoren-2-yl)silane

Conditions

Conditions	Yield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: Triphenylsilyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	92%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

1679-18-1

4-Chlorophenylboronic acid

1221237-82-6

2-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 2h; Inert atmosphere; Sealed tube;	91%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 5h; Heating;	88%
With palladium diacetate; sodium hydrogencarbonate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane; water at 90℃; for 5h; Schlenk technique; Inert atmosphere;	75%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

92-67-1

4-Aminobiphenyl

897671-69-1

N‑(biphenyl‑4‑yl)‑9,9‑dimethyl‑9H‑fluorene‑2‑amine

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate In toluene for 24h; Reflux;	91%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene for 24h; Reflux;	91%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃;	91%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C39H27NS

C54H39NS

Conditions

Conditions	Yield
With tributylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 23h; Inert atmosphere;	91%

1592-95-6

3-bromo-9H-carbazole

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

1207672-45-4

3-bromo-9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In para-xylene Reflux;	91%

98437-23-1

benzo[b]thiophene-2-boronic acid

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

2-(9,9-dimethyl-9H-fluoren-2-yl)benzo[b]thiophene

Conditions

Conditions	Yield
Stage #1: benzo[b]thiophene-2-boronic acid; 2-bromo-9,9-dimethyl-9H-fluorene With potassium carbonate In 1,2-dimethoxyethane; water for 0.333333h; Inert atmosphere; Stage #2: With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In 1,2-dimethoxyethane; water at 80℃; for 15h; Inert atmosphere;	91%

108-77-0

1,3,5-trichloro-2,4,6-triazine

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

3,5-bis(9,9-dimethyl-9H-fluoren-2-yl)-1-chlorotriazine

Conditions

Conditions	Yield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With iodine; magnesium In tetrahydrofuran at 55℃; for 1h; Glovebox; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 55℃; Glovebox;	90%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With iodine; magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 50℃; for 12h; Cooling with ice;	75%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With magnesium In tetrahydrofuran for 2h; Reflux; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at -10 - 20℃;	48%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

959246-70-9

9,9-dimethyl-9H-fluoren-2-ol

Conditions

Conditions	Yield
With water; sodium hydroxide at 100℃; for 8h;	90%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C22H17N

C37H29N

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene at 100℃; for 16h; Inert atmosphere;	90%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

86-74-8

9H-carbazole

866100-16-5

9-(9',9'-dimethyl-9H-fluoren-2-yl)-9H-carbazole

Conditions

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 200℃; for 30h; Ullmann reaction;	89.15%
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In 5,5-dimethyl-1,3-cyclohexadiene for 15h; Reflux; Inert atmosphere;	84%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

144981-85-1

2-iodo-9,9-dimethyl-9H-fluorene

Conditions

Conditions	Yield
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 24.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	89%
Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	89%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

102113-98-4

bis(biphenyl-4-yl)amine

C39H31N

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;	88%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

C18H10N4

C48H34N4

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere;	88%

28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

N-phenyl-N-(11,11’-dimethylbenzo[a]fluoren-9-yl)amine

C40H33N

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 100℃;	88%

2-Bromo-9,9-dimethylfluorene Specification