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28920-43-6

Basic Information
CAS No.: 28920-43-6
Name: 9-Fluorenylmethyl chloroformate
Article Data: 14
Molecular Structure:
Molecular Structure of 28920-43-6 (9-Fluorenylmethyl chloroformate)
Formula: C15H11ClO2
Molecular Weight: 258.704
Synonyms: Formicacid, chloro-, fluoren-9-ylmethyl ester (8CI);Fluorene-9-methanol,chloroformate (8CI);(9H-Fluoren-9-ylmethoxy)carbonyl chloride;9H-Fluoren-9-ylmethyl chloroformate;AminoTag;FMOC chloride;FmocCl;Fmoc-Cl;Carbonochloridic acid,9H-fluoren-9-ylmethyl ester;
EINECS: 249-313-6
Density: 1.288 g/cm3
Melting Point: 62-64 °C(lit.)
Boiling Point: 393.9 °C at 760 mmHg
Flash Point: 143.6 °C
Solubility: dioxane: 0.1 g/mL, clear, colorless
Appearance: white to off-white powder
Hazard Symbols: CorrosiveC,ToxicT
Risk Codes: 34-20/21/22
Safety: 26-36/37/39-45-27
Transport Information: UN 3261 8/PG 2
PSA: 26.30000
LogP: 4.17430
Synthetic route
32315-10-9

bis(trichloromethyl) carbonate

24324-17-2

9-Fluorenylmethanol

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
With tributyl-amine In toluene at 0℃; Reagent/catalyst; Solvent; Temperature;98%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With tributyl-amine In toluene at 0℃; for 0.0666667h; Temperature; Flow reactor;98 %Chromat.
With pyridine In toluene at 0 - 20℃;
75-44-5

phosgene

24324-17-2

9-Fluorenylmethanol

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
In dichloromethane74%
In dichloromethane
With pyridine In diethyl ether 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;
With pyridine In tetrahydrofuran at 0 - 6℃; for 13.5h; Temperature; Large scale;
86-73-7

9H-fluorene

nickel-aluminium oxide

nickel-aluminium oxide

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 25 percent
2: 74 percent / CH2Cl2
View Scheme
75-44-5

phosgene

F-ether

F-ether

24324-17-2

9-Fluorenylmethanol

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
In tetrahydrofuran; water37.9 g (95.8%)
24324-17-2

9-Fluorenylmethanol

503-38-8

trichloromethyl chloroformate

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
With dmap In toluene at 20℃; for 24h;
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 83℃; for 2h;
67-66-3

chloroform

24324-17-2

9-Fluorenylmethanol

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Conditions
ConditionsYield
With oxygen In acetonitrile at 20℃; for 3h; Irradiation;
632-20-2

D-Threonine

28920-43-6

(fluorenylmethoxy)carbonyl chloride

157355-81-2

(((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane100%
1197-55-3

4-aminophenylacetic acid

28920-43-6

(fluorenylmethoxy)carbonyl chloride

Sodium; [4-(9H-fluoren-9-ylmethoxycarbonylamino)-phenyl]-acetate

Conditions
ConditionsYield
With sodium carbonate for 16h;100%
28920-43-6

(fluorenylmethoxy)carbonyl chloride

65577-07-3, 65577-08-4, 67896-52-0

(RS)-1-amino-2-methylpropylphosphinic acid

146406-32-8

(1RS)-1-(N-(9-fluorenylmethoxycarbonyl)amino)-2-methylpropylphosphinic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 4℃; for 6h;100%
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    Fmoc-Cl

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Chemistry


IUPAC Name: 9H-Fluoren-9-ylmethyl carbonochloridate
Molecular Formula: C15H11ClO2
Molecular Weight: 258.70 g/mol
SMILES: C1(c2c(cccc2)c2c1cccc2)COC(=O)Cl
InChI: InChI=1/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
EINECS: 249-313-6
Classification Code: Indicators and reagents; Mutation data
Product Categories: Aromatic Esters; N-Protecting Reagents; Biochemistry; Fluorenes; Fluorenes & Fluorenones; Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry; Fmoc-Amino acid series
Index of Refraction: 1.611 
Molar Refractivity: 69.74 cm
Molar Volume: 200.7 cm
Polarizability: 27.64×10-24 cm3 
Surface Tension: 50 dyne/cm 
Density: 1.288 g/cm
Flash Point: 143.6 °C 
Enthalpy of Vaporization: 64.38 kJ/mol 
Boiling Point: 393.9 °C at 760 mmHg 
Melting Point: 62-64 °C(lit.)
Storage temperature: 2-8 °C
Solubility: dioxane: 0.1 g/mL, clear, colorless
Sensitive  Moisture Sensitive
Vapour Pressure of 9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6): 2.06E-06 mmHg at 25 °C

Uses

 9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6) is used for tagging silica-based derivatization reagents in HPLC. It is also used to introduce FMOC group as the FMOC carbamate.

Production

As can be expected, this compound may be prepared by reacting 9-fluorenylmethanol with phosgene:

Toxicity Data With Reference

1.    

mma-sat 100 µg/plate

    MUREAV    Mutation Research. 170 (1986),23.

Safety Profile

Hazard Codes: CorrosiveC,ToxicT
Risk Statements: 34-20/21/22 
R34:Causes burns. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-45-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
RTECS: LQ6250000
F: 10-21
HazardClass: 6.1
PackingGroup of 9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6): II

Standards and Recommendations

DOT Classification:  6.1; Label: Poison, Corrosive

Specification

  9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6), its Synonyms are 1-(9-Fluorenyl)methyl chloroformate ; Carbonochloridic acid, 9H-fluoren-9-ylmethyl ester ; 9H-Fluoren-9-ylmethyl chloroformate ; Fluoren-9-ylmethyl chloroformate ; Formic acid, chloro-, fluoren-9-ylmethyl ester . It is white to off white crystalline powder.

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