2523-44-6

Basic information

• Product Name: 2-Chlorofluorene
• Synonyms: 2-Chloro-9H-fluorene;9H-Fluorene, 2-chloro-;Fluorene, 2-chloro-;2-CHLOROFLUORENE
• CAS NO: 2523-44-6
• Molecular Formula: C₁₃H₉Cl
• Molecular Weight: 200.66
• Product Categories: Electronic Chemicals
• Mol File: 2523-44-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 96-97°C
• Boiling Point: 258.08°C (rough estimate)
• Flash Point: 157.5 °C
• Appearance: white crystal
• Density: 1.1740 (rough estimate)
• Vapor Pressure: 0.000265mmHg at 25°C
• Refractive Index: 1.6012 (estimate)
• CAS DataBase Reference: 2-Chlorofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorofluorene(2523-44-6)
• EPA Substance Registry System: 2-Chlorofluorene(2523-44-6)

Safety Data

• Hazardous Substances Data: 2523-44-6(Hazardous Substances Data)

Usage

Uses

2-Chloro-9H-fluorene acts as a reagent for the synthesis and the antibacterial functions of N-alkyl and N-amylamidinohydrazones of acetophanones, benzophenones and 2-acylfluorenes.

InChI:InChI=1/C13H9Cl/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7H2

Synthetic route

5-chloro-2-phenyl-benzyl chloride → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; Trimethylacetic acid In tetrahydrofuran at 25℃; for 18h; Glovebox; Schlenk technique; Inert atmosphere;	99%

[2-(3-chlorobenzyl)phenyl]trimethylsilane → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; (R)-10-camphorsulfonic acid; tetrahydrothiophene gold(III) bromide In methanol; chloroform at 27℃; for 3h; Schlenk technique; Inert atmosphere;	90%

2-bromo-4,4’-dichloro-1,1’-biphenyl (179526-95-5) + diazomethyl-trimethyl-silane (18107-18-1) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate; potassium carbonate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	90%

2-iodo-4’-chlorobiphenyl (343945-64-2) + 1,1-dibromomethane (74-95-3) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With potassium acetate; palladium diacetate; potassium hydrogencarbonate; isopropyl alcohol In N,N-dimethyl acetamide; water; N,N-dimethyl-formamide at 75℃; for 10h; Schlenk technique; Inert atmosphere;	84%

(E)-1-((4′-chloro-2′-methyl-[1,1′-biphenyl]-2-yl)diazenyl)-pyrrolidine → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With trifluoroacetic acid In toluene at 100℃; for 1h;	75%

2-iodo-4-chlorobiphenyl + 1,1-dibromomethane (74-95-3) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With potassium acetate; palladium diacetate; potassium hydrogencarbonate; isopropyl alcohol In N,N-dimethyl acetamide; water; N,N-dimethyl-formamide at 75℃; for 10h; Schlenk technique; Inert atmosphere;	64%

thionyl chloride (7719-09-7) + 9H-fluorene (86-73-7) → 2-chloro-9H-fluorene (2523-44-6)

sulfuryl dichloride (7791-25-5) + 9H-fluorene (86-73-7) + diethyl ether (60-29-7) → 2-chloro-9H-fluorene (2523-44-6)

9H-fluorene (86-73-7) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6)

9H-fluorene (86-73-7) + chloroform (67-66-3) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
at 0 - 5℃;

9H-fluorene (86-73-7) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6) + 2,7-dichloro-9H-fluorene (7012-16-0)

9H-fluorene (86-73-7) + chloroform (67-66-3) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6) + 2,7-dichloro-9H-fluorene (7012-16-0)

Conditions	Yield
at 0 - 5℃;

9H-fluorene (86-73-7) + antimonypentachloride (7647-18-9) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6) + 2,7-dichloro-9H-fluorene (7012-16-0)

Conditions	Yield
verschiedene Loesungsmittel, bei verschiedenen Temperaturen;

9H-fluorene (86-73-7) + iodine (7553-56-2) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6) + 2,7-dichloro-9H-fluorene (7012-16-0)

Conditions	Yield
verschiedene Loesungsmittel, bei verschiedenen Temperaturen;

9H-fluorene (86-73-7) + chloroform (67-66-3) + chlorine (7782-50-5) → 2-chloro-9H-fluorene (2523-44-6) + 2,7-dichloro-9H-fluorene (7012-16-0) + 2,4,7-trichlorofluorene (7061-81-6)

Conditions	Yield
at 0 - 5℃;

fluorenediazonium chloride-(2) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With hydrogenchloride; copper(l) chloride

2-phenylbenzyl chloride (38580-83-5) + 1-chloro-4-[2-(chloromethyl)phenyl]benzene (854234-88-1) → 9H-fluorene (86-73-7) + 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dimethoxyethane at 100℃; for 3h; Inert atmosphere;

2-bromo-4,4’-dichloro-1,1’-biphenyl (179526-95-5) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / 23 °C / Inert atmosphere 2.1: Echavarren's catalyst / 1,2-dichloro-ethane / 3 h / 120 °C / Sealed tube; Inert atmosphere View Scheme

(E)-(2-(pyrrolidin-1-yldiazenyl)phenyl)boronic acid + 4-chloro-1-iodo-2-methylbenzene (23399-70-4) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,4-dioxane; water / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: trifluoroacetic acid / toluene / 1 h / 100 °C View Scheme

1-Bromo-2-iodobenzene (583-55-1) → 2-chloro-9H-fluorene (2523-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 5 h / 110 °C / Inert atmosphere 2: bis(tri-t-butylphosphine)palladium(0); sodium hydroxide / water; 1,4-dioxane / 56 h / 25 °C / Inert atmosphere View Scheme

benzophenone (119-61-9) + 2-chloro-9H-fluorene (2523-44-6) → C26H19ClO

Conditions	Yield
Stage #1: 2-chloro-9H-fluorene With n-butyllithium In tetrahydrofuran at -90 - -78℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran at -90 - 20℃; for 3.5h; Inert atmosphere;	80%

2,2'-dibromobiphenyl (13029-09-9) + 2-chloro-9H-fluorene (2523-44-6) → 2-chloro-9,9'-spirobi[fluorene]

Conditions	Yield
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In o-xylene at 135℃; for 11h; Reagent/catalyst; Temperature; Inert atmosphere;	71%

2-chloro-9H-fluorene (2523-44-6) + tropylium tetrafluoroborate (27081-10-3) → 2-chloro-9-(2,4,6-cycloheptatrienyl)fluorene (360565-24-8)

Conditions	Yield
Stage #1: 2-chloro-9H-fluorene With n-butyllithium In diethyl ether; hexane Stage #2: tropylium tetrafluoroborate In hexane; benzene Heating;	64%

2-chloro-9H-fluorene (2523-44-6) + 3,5-dimethylphenyl boronic acid (172975-69-8) → 2-(3,5-dimethylphenyl)-9H-fluorene

Conditions	Yield
With C32H39Br2N3O10Pd; potassium carbonate In ethanol; water at 90℃; for 0.5h; Suzuki Coupling; Inert atmosphere;	33%

2-chloro-9H-fluorene (2523-44-6) → 2-chloro-9H-fluoren-9-one (3096-47-7)

Conditions	Yield
With sodium dichromate; acetic acid
With chromic acid; acetic acid
With potassium hydroxide

2-chloro-9H-fluorene (2523-44-6) → 7-chloro-2-nitrofluorene (6939-05-5)

Conditions	Yield
With nitric acid; acetic acid at 70 - 80℃;
With nitric acid

2-chloro-9H-fluorene (2523-44-6) → 2-bromo-7-chloro-9H-fluorene (99586-26-2)

Conditions	Yield
With chloroform; bromine; iron

2-chloro-9H-fluorene (2523-44-6) → 2-chloro-7-iodo-fluorene

Conditions	Yield
With sulfuric acid; iodine; nitric acid; acetic acid zuletzt Behandeln bei Siedetemperatur;

2-chloro-9H-fluorene (2523-44-6) + chloroacetic acid (79-11-8) → (7-chloro-fluoren-2-yl)-acetic acid (41146-72-9)

Conditions	Yield
With iron(III) oxide; potassium bromide

9-fluorenone (486-25-9) + 2-chloro-9H-fluorene (2523-44-6) → 2-Chlor-9'-hydroxy-9,9'-bifluorenyl (56485-95-1)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 1636531/; Multistep reaction;

ethanol (64-17-5) + 2-chloro-9H-fluorene (2523-44-6) → Bis-(4-chlor-2,2'-biphenylylen)-1,3-butadien (56486-04-5)

Conditions	Yield
With potassium hydroxide

tetrabenzo[5.5]fulvalene (746-47-4) + 2-chloro-9H-fluorene (2523-44-6) → 2-Chlor-9,9':9',9''-terfluorenyl (56486-11-4)

Conditions	Yield
With pyridine; potassium hydroxide

2-chloro-9H-fluoren-9-one (3096-47-7) + 2-chloro-9H-fluorene (2523-44-6) → 2,2'-Dichlor-9-hydroxy-9,9'-bifluorenyl (56486-06-7)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 1951643/; Multistep reaction;

9-Brom-9,9'-bifluorenyl (13295-92-6) + 2-chloro-9H-fluorene (2523-44-6) → 2-Chlor-9,9':9',9''-terfluorenyl (56486-11-4)

Conditions	Yield
(i) nBuBr, Li, (ii) /BRN= 2006319/; Multistep reaction;

2-(9H-fluoren-9-ylidene)acetaldehyde (4425-71-2) + 2-chloro-9H-fluorene (2523-44-6) → 2-Chloro-9-[2-fluoren-9-ylidene-eth-(Z)-ylidene]-9H-fluorene

Conditions	Yield
With potassium hydroxide

2-chloro-9H-fluorene (2523-44-6) + 2-Chlor-9,9'-bifluorenyliden (56485-92-8) → 2,2''-Dichlor-9,9':9',9''-terfluorenyl (56486-14-7)

Conditions	Yield
With pyridine; potassium hydroxide

2-chloro-9H-fluorene (2523-44-6) + 2-Chlor-9-brom-9,9'-bifluorenyl (56485-93-9) → 2,2'-Dichlor-9,9':9',9''-terfluorenyl (56486-13-6)

Conditions	Yield
(i) nBuBr, Li, (ii) /BRN= 2482126/; Multistep reaction;

Upstream product

• 20893-81-6 fluorene-2-diazonium ; chloride 
• 64-19-7 acetic acid 
• 7719-09-7 thionyl chloride 
• 86-73-7 9H-fluorene 
• 7791-25-5 sulfuryl dichloride 
• 60-29-7 diethyl ether 
• 7782-50-5 chlorine 
• 67-66-3 chloroform 
• 7647-18-9 antimonypentachloride 
• 7553-56-2 iodine 
• 179526-95-5 2-bromo-4,4’-dichloro-1,1’-biphenyl 
• 1679-18-1 4-Chlorophenylboronic acid 
• 98-80-6 phenylboronic acid 
• 105901-07-3 1-bromo-2-(3-chlorobenzyl)benzene 

Downstream Products

• 7012-23-9 2-chlorofluoren-9-ol 
• 63242-18-2 (7-Chloro-9H-fluoren-2-yl)-phenyl-methanol 
• 63242-29-5 2-Chloro-7-(chloro-phenyl-methyl)-9H-fluorene 
• 5096-17-3 N-(7-chloro-fluoren-2-yl)-acetamide 
• 6957-60-4 2-chloro-7-nitro-fluoren-9-one 
• 7356-53-8 2-amino-7-chloro-fluoren-9-ol 
• 6957-61-5 2-amino-7-chloro-fluoren-9-one 
• 6957-62-6 7-chloro-fluoren-2-ylamine 
• 6939-05-5 7-chloro-2-nitrofluorene 
• 63242-08-0 (7-Chloro-9H-fluoren-2-yl)-phenyl-methanone 

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