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71989-33-8

Basic Information
CAS No.: 71989-33-8
Name: Fmoc-O-tert-Butyl-L-serine
Article Data: 16
Molecular Structure:
Molecular Structure of 71989-33-8 (Fmoc-O-tert-Butyl-L-serine)
Formula: C22H25NO5
Molecular Weight: 383.444
Synonyms: L-Serine,O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2S)-3-tert-Butoxy-2-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]propanoicacid;N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserine;O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)serine;Fmoc-Ser(tBu)-OH;
EINECS: 276-260-6
Density: 1.216 g/cm3
Melting Point: 127-131 °C
Boiling Point: 578.6 °C at 760 mmHg
Flash Point: 303.7 °C
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36/37/39-27-26
PSA: 84.86000
LogP: 4.18430
Synthetic route

Fmoc-Ser(tBu)-OMe

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With magnesium iodide In tetrahydrofuran at 120℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube; chemoselective reaction;98%
With aluminum (III) chloride In ethyl acetate Reflux;86%

N-Fmoc-L-Ser(t-But)-OEt

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With aluminum (III) chloride In ethyl acetate Reflux;84.8%
129460-16-8

(S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

A

71989-33-8

Fmoc-Ser(tBu)-OH

B

73724-45-5

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Conditions
ConditionsYield
With silica gel In toluene for 1.25h; Heating;A 76%
B 8%
18822-58-7

(S)-O-tert-butylserine

102774-86-7

9-fluorenylmethyl N-succinimidyl carbonate

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 1h;75%
82911-69-1

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

132776-33-1

O-tert-Butyl-L-serine Methyl Ester p-Toluenesulfonate

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With sodium carbonate 1.) H2O, r.t., 24 h; 2.) p-dioxane, 0 deg C to r.t., 24 h; other reagent (1. step): NaOH; Yield given. Multistep reaction;
146346-72-7

Fmoc-Ser(but)-O-Pha

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With acetic acid; zinc Yield given;
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;

Fmoc-Ser(But)-OSi(CH3)3

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
With water In 1,4-dioxane; ethyl acetate Ambient temperature; Yield given;
18822-58-7

(S)-O-tert-butylserine

82911-69-1

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

71989-33-8

Fmoc-Ser(tBu)-OH

129460-16-8

(S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: i-Pr2NEt / dioxane / 1 h / Heating
2: H2O / dioxane; ethyl acetate / Ambient temperature
View Scheme
125760-26-1

N-Fmoc serine phenacyl ester

71989-33-8

Fmoc-Ser(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 240 h
2: zinc, acetic acid
View Scheme
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  • Casno:

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Chemistry

IUPAC Name: 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoic acid 
Following is the structure of Fmoc-Ser(tBu)-OH (CAS NO.71989-33-8):
                      
Molecular Formula: C22H25NO5
Formula Weight: 383.44
EINECS: 276-260-6
Index of Refraction: 1.575
Molar Refractivity: 104.15 cm3
Molar Volume: 315.1 cm3
Density: 1.216 g/cm3
Flash Point: 303.7 °C
Storage temp.: 2-8 °C
Surface Tension: 49.5 dyne/cm
Melting point: 130.5-135.5 °C(lit.)
Enthalpy of Vaporization: 91.08 kJ/mol
Boiling Point: 578.6 °C at 760 mmHg
Vapour Pressure: 3.16E-14 mmHg at 25 °C
Product Categories of Fmoc-Ser(tBu)-OH (CAS NO.71989-33-8): Fluorenes, Flurenones;Amino Acids; Serine [Ser, S]; Fmoc-Amino Acids and Derivatives; Amino Acids (N-Protected); Biochemistry; Fmoc-Amino Acids; Fmoc-Amino acid series
Appearance of Fmoc-Ser(tBu)-OH of Fmoc-Ser(tBu)-OH (CAS NO.71989-33-8): White to Off White Powder
Solubility: Insoluble in WATER; soluble in most organic solvents 
Canonical SMILES: CC(C)(C)OCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
InChI: InChI=1S/C22H25NO5/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)
InChIKey: REITVGIIZHFVGU-UHFFFAOYSA-N

Toxicity Data With Reference

RTECS Number: No RTECS number has been assigned to Fmoc-Ser(tBu)-OH. 
 Fmoc-Ser(tBu)-OH (CAS NO.71989-33-8) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37/39-27-26 
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

Standards and Recommendations

Chemical Purity: 98-100%

Specification

 Fmoc-Ser(tBu)-OH , its cas register number 71989-33-8. It also can be called N-(9-Fluorenylmethoxycarbonyl)-O-tert-butyl-L-serine ; and Fmoc-O-tert-Butyl-L-serine .
 Fmoc-Ser(tBu)-OH (CAS NO.71989-33-8) could be stable under normal temperatures and pressures. It should avoid the condition like strong oxidants. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen. However, its hazardous polymerization has not been reported.
Storage Condition: <25°C
Other precautions: Avoid contact with material. Avoid prolonged or repeated exposure. Store in a tightly closed container in a dry, cool place. Wash thoroughly after handling material. Material should only be handled by qualified, experienced professionals.