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| CAS No.: | 28920-43-6 |
|---|---|
| Name: | 9-Fluorenylmethyl chloroformate |
| Molecular Structure: | |
|
|
|
| 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: |
 C, T
|
| 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 |
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bis(trichloromethyl) carbonate
- 24324-17-2
9-Fluorenylmethanol
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
| Conditions | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| In dichloromethane | 74% |
| 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
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 25 percent 2: 74 percent / CH2Cl2 View Scheme |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; water | 37.9 g (95.8%) |
- 24324-17-2
9-Fluorenylmethanol
- 503-38-8
trichloromethyl chloroformate
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
| Conditions | Yield |
|---|---|
| With dmap In toluene at 20℃; for 24h; |
- 115134-37-7
Fmoc-OH
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
| Conditions | Yield |
|---|---|
| With thionyl chloride In N,N-dimethyl-formamide at 83℃; for 2h; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium carbonate In 1,4-dioxane | 100% |
- 1197-55-3
4-aminophenylacetic acid
- 28920-43-6
(fluorenylmethoxy)carbonyl chloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium hydroxide In 1,4-dioxane; water at 4℃; for 6h; | 100% |
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Chemistry
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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 cm3
Molar Volume: 200.7 cm3
Polarizability: 27.64×10-24 cm3
Surface Tension: 50 dyne/cm
Density: 1.288 g/cm3
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: 
C,
T
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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