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Fmoc-L-Methionine

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Name

Fmoc-L-Methionine

EINECS 276-258-5
CAS No. 71989-28-1 Density 1.282 g/cm3
PSA 100.93000 LogP 4.12230
Solubility N/A Melting Point 121-123 °C(lit.)
Formula C20H21NO4S Boiling Point 614.6 °C at 760 mmHg
Molecular Weight 371.457 Flash Point 325.5 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 22-24/25-36/37/39-27-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 71989-28-1 (Fmoc-L-Methionine) Hazard Symbols IrritantXi
Synonyms

L-Methionine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(S)-2-[[[(9H-Fluoren-9-yl)methoxy]carbonyl]amino]-4-methylsulfanylbutanoicacid;(S)-N-Fmoc-methionine;L-Fmoc-Methionine;N-(9-Fluorenylmethoxycarbonyl)-L-methionine;N-Fluorenylmethoxycarbonyl-L-methionine;NSC 334292;

Article Data 18

Fmoc-L-Methionine Synthetic route

500872-34-4

2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid methyl ester

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With aluminium trichloride; N,N-dimethyl-aniline In dichloromethane98%
63-68-3

L-methionine

88744-04-1

(9-fluorenyl)methyl pentafluorophenyl carbonate

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;84%
63-68-3

L-methionine

1131148-55-4

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;84%
63-68-3

L-methionine

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;80%
63-68-3

L-methionine

28920-43-6

(fluorenylmethoxy)carbonyl chloride

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
Stage #1: L-methionine With chloro-trimethyl-silane In dichloromethane for 1h; Inert atmosphere; Reflux;
Stage #2: (fluorenylmethoxy)carbonyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 1.5h;
80%
In acetonitrile at 20℃; for 0.25h; pH=9.2; aq. borate buffer;
Stage #1: L-methionine With sodium carbonate In 1,4-dioxane; water Cooling with ice;
Stage #2: (fluorenylmethoxy)carbonyl chloride In 1,4-dioxane; water at 20℃; for 5h;
63-68-3

L-methionine

82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃;78%
Stage #1: L-methionine With N-cyclohexyl-cyclohexanamine In acetone at 20℃;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In water; acetonitrile at 0 - 20℃; pH=8;
Stage #3: With potassium hydrogensulfate In water; acetonitrile pH=2 - 3;
61%
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 - 20℃; for 2h;

C23H29NO4SSi

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With methanol In dichloromethane for 0.5h; Ambient temperature; Yield given;

N-Fmoc-L-methionine phenacyl ester

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;
63-68-3

L-methionine

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2Cl2 / 1 h / Heating
2: CH2Cl2 / 72 h / Ambient temperature
3: MeOH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
5269-64-7

O-(Trimethylsilyl)methionine

71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 72 h / Ambient temperature
2: MeOH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme

Fmoc-L-Methionine Chemical Properties

IUPAC Name: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoic acid
Molecular Formula: C20H21NO4S
Formula Weight of Fmoc-Met-OH (CAS NO.71989-28-1): 371.45 g/mol
Melting point: 121-123 °C
alpha: -29 °(c=1,DMF 24 °C)
refractive index: -29.5 °(C=1, DMF) 
Surface Tension: 55.9 dyne/cm
Index of Refraction: 1.615
storage temp.: 2-8 °C
Form: Solid
Density: 1.282 g/cm3
Flash Point: 325.5 °C
Enthalpy of Vaporization: 95.88 kJ/mol
Boiling Point: 614.6 °C at 760 mmHg
Appearance: White to yellowish. (Light.)
Vapour Pressure: 5.8E-16 mmHg at 25 °C
Solubility of Fmoc-Met-OH (CAS NO.71989-28-1): Insoluble in cold water 
Product Categories: Protected Amino Acids;Fluorenes, Flurenones;Amino Acids;Methionine [Met, M];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Nutritional Supplements;Fmoc-Amino acid series
Following is the structure of  Fmoc-Met-OH (CAS NO.71989-28-1):
          

Fmoc-L-Methionine Toxicity Data With Reference

Chronic toxicity of Fmoc-Met-OH (CAS NO.71989-28-1), repeated or prolonged exposure is not known to aggravate medical condition. And it hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

Fmoc-L-Methionine Safety Profile

Hazard Codes :Irritant Xi
Risk Statements : 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements : 22-24/25-36/37/39-27-26 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany : 3

Fmoc-L-Methionine Specification

 Fmoc-Met-OH (CAS NO.71989-28-1) is stable under normal temperatures and pressures. It should avoid the condition of strong oxidants. And it is also incompatible with other materials strong oxidizing agents. Its hazardous decomposition products are carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide, sodium oxide. Its hazardous polymerization has not been reported. Handling of  Fmoc-Met-OH (CAS NO.71989-28-1), keep away from heat, and sources of ignition. Empty containers pose a fire risk, evaporate the residue under a fume hood. Ground all equipment containing material. And do not breathe dust.

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