Benzenepropanoic acid, b-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]- supplier

Name
3-N-FMOC-3-PHENYLPROPIONIC ACID
EINECS
CAS No. 180181-93-5
Article Data6
CAS DataBase
Density 1.275 g/cm³
Solubility
Melting Point
Formula C₂₄H₂₁NO₄
Boiling Point 617 °C at 760 mmHg
Molecular Weight 387.435
Flash Point 326.9 °C
Transport Information
Appearance
Safety 61
Risk Codes 50
Molecular Structure
Hazard Symbols N
Synonyms 3-(9 h-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid;Fmoc-3-amino-3-phenylpropionic acid;
PSA 75.63000
LogP 5.13200

Synthetic route

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 3646-50-2
3-Amino-3-phenylpropionic acid

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 25h;	100%
With sodium hydroxide In 1,4-dioxane at 20℃; for 4h;	77%
With N-ethyl-N,N-diisopropylamine

: (±)-(9H-fluoren-9-yl)methyl 5-oxo-3-phenylisoxazolidine-2-carboxylate

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

Conditions

Conditions	Yield
With acetic acid; zinc In tetrahydrofuran; water at 40℃; for 4h; Inert atmosphere; chemoselective reaction;	95%

: 3646-50-2
3-Amino-3-phenylpropionic acid

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 0℃; for 3h;

: 100-52-7
benzaldehyde

: 190656-01-0
N-(9-fluorenylmethoxycarbonyloxy)hydroxylamine

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium 2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-olate / ethyl acetate / 4 h / 40 °C / Inert atmosphere 2: acetic acid; zinc / tetrahydrofuran; water / 4 h / 40 °C / Inert atmosphere View Scheme

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: 18856-63-8
(4-ethylphenyl)isothiocyanate

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 2-{2-[(Z)-4-Ethyl-phenylimino]-6-oxo-4-phenyl-tetrahydro-pyrimidin-1-yl}-acetamide

Conditions

Conditions	Yield
Multistep reaction;	95%

...Expand

: 76-05-1
trifluoroacetic acid

: 207908-96-1
4-[5-(4-aminobutyl)thien-2-yl]butylamine

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

trityl chloride resin: trityl chloride resin

: [3-(4-[5-(4-ammoniobutyl)-2-thienyl]butylamino)-3-oxo-1-phenylpropyl]ammonium ditrifluoroacetate

Conditions

Conditions	Yield
Multistep reaction.;	73%

...Expand

: 31575-35-6
2-fluoropyrimidine

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 852632-28-1
C13H14N4O

Conditions

Conditions	Yield
Stage #1: (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine solid phase reaction; Stage #2: With piperidine In N,N-dimethyl-formamide solid phase reaction; Stage #3: 2-fluoropyrimidine Further stages;	23%

: 123622-48-0
5-(9H-fluoren-9-ylmethoxycarbonyl)aminopentanoic acid

: 250280-31-0
5-(9H-fluoren-9-ylmethoxy)-1,3,4-oxadiazol-2(3H)-one

: N,N'-bis-Boc-1-guanylpyrazole

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C16H24N6O4

Conditions

Conditions	Yield
Multistep reaction.;	22 mg

...Expand

: 185116-42-1
3-(9-fluorenylmethyloxycarbonyl)aminobenzoic acid

: 250280-31-0
5-(9H-fluoren-9-ylmethoxy)-1,3,4-oxadiazol-2(3H)-one

: N,N'-bis-Boc-1-guanylpyrazole

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C18H20N6O4

Conditions

Conditions	Yield
Multistep reaction.;	6 mg

...Expand

: 250280-31-0
5-(9H-fluoren-9-ylmethoxy)-1,3,4-oxadiazol-2(3H)-one

: 287959-61-9
5-[N-(4-methylpyridin-2-yl)amino]pentanoic acid

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 3-{N-[N'-(5-(4-methylpyridin-2-ylamino)pentanoyl)hydrazino]carbonyl}amino-3-phenylpropionic acid

Conditions

Conditions	Yield
Multistep reaction.;	17 mg

...Expand

: 77128-70-2
N-(9-fluorenylmethoxycarbonyl)sarcosine

: 175452-89-8
α-methyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate ester

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 368443-82-7
α-methyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)aspartate

Fmoc-(2S)-Phe: Fmoc-(2S)-Phe

: 1053615-12-5
(2S)-phenylalanyl-[(3R/S)-3-amino-3-phenylpropanoyl]-[α-methyl (2R)-glutamyl]-sarcosyl-[α-methyl (2R)-aspartate] diester

Conditions

Conditions	Yield
Multistep reaction.;	150 mg

...Expand

: 71989-33-8
Fmoc-Ser(tBu)-OH

: 1074-59-5
3-(imidazol-4-yl)propionic acid

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: (S)-2-amino-3-(8-hydroxy-5-(N,N-dimethyl)sulfonamidoquinoline-2-yl)propionic acid hydrochloride

Fmoc-Pro: Fmoc-Pro

: [3-(imidazol-4-yl)propionic acid]-Pro-β-dimethylcysteine-[(S)-2-amino-3-(8-hydroxy-5-(N,N-dimethyl)sulfonamidoquinoline-2-yl)propionic acid]-Ser-Ser-NH2

Conditions

Conditions	Yield
Multistep reaction;

...Expand

trityl chloride polystyrene resin: trityl chloride polystyrene resin

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C24H20NO4Pol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;

: 2-chlorotrityl chloride polystyrene resin

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C43H33ClNO4Pol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; not specified;

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 200642-62-2
[3-[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]-3-oxo-1-phenylpropyl]carbamic acid 9H-fluoren-9-yl methyl ester

Conditions

Conditions	Yield

: 4548-45-2
2-chloro-5-nitropyridine

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: 1235447-27-4
C14H14N4O3

Conditions

Conditions	Yield
Stage #1: (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine solid phase reaction; Stage #2: With piperidine In N,N-dimethyl-formamide solid phase reaction; Stage #3: 2-chloro-5-nitropyridine Further stages;

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C24H20ClNO3

Conditions

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C39H45NO6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: magnesium chloride; pyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl 4,16-dioxo-2-phenyl-1-azacyclohexadecane-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: magnesium chloride; pyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl-4,9-dioxo-2-phenylazonane-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C38H35NO6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C33H33NO7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl 4, 10-dioxo-2-phenylazecane-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl 1,5-dioxo-3-phenyl-1,2,3,4,5,6,7,8-octahydrobenzo[c]azecine-6-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl-4,11-dioxo-2-phenyl-1-azacycloundecane-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl 1,5-dioxo-3-phenyl-2,3,4,5,6,7,8,9-octahydro-1H-benzo[c][1]azacycloundecine-6-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: ethyl 4,8-dioxo-6-phenyl-1-oxa-5-azacycloundecane-9-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: piperidine / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C32H31NO6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C33H33NO6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere View Scheme

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

: C37H33NO6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.1: pyridine; magnesium chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

Benzenepropanoic acid, b-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]- Specification

The CAS register number of Benzenepropanoic acid, b-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]- is 180181-93-5. It also can be called as Fmoc-3-amino-3-phenylpropionic acid and the systematic name about this chemical is 3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-phenylpropanoic acid. The molecular formula about this chemical is C₂₄H₂₁NO₄and the molecular weight is 387.43.

Physical properties about Benzenepropanoic acid, b-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]- are: (1)ACD/LogP: 5.16; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.75; (4)ACD/LogD (pH 7.4): 1.99; (5)ACD/BCF (pH 5.5): 189.73; (6)ACD/BCF (pH 7.4): 3.34; (7)ACD/KOC (pH 5.5): 590.14; (8)ACD/KOC (pH 7.4): 10.4; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 55.84 Å²; (13)Index of Refraction: 1.632; (14)Molar Refractivity: 108.44 cm³; (15)Molar Volume: 303.7 cm³; (16)Polarizability: 42.99x10^-24cm³; (17)Surface Tension: 57.2 dyne/cm; (18)Density: 1.275 g/cm³; (19)Flash Point: 326.9 °C; (20)Enthalpy of Vaporization: 96.2 kJ/mol; (21)Boiling Point: 617 °C at 760 mmHg; (22)Vapour Pressure: 4.43E-16 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CC(c1ccccc1)NC(=O)OCC4c2ccccc2c3c4cccc3
(2)InChI: InChI=1/C24H21NO4/c26-23(27)14-22(16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)
(3)InChIKey: PTSLRPMRTOVHAB-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C24H21NO4/c26-23(27)14-22(16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)
(5)Std. InChIKey: PTSLRPMRTOVHAB-UHFFFAOYSA-N

Product Name

3-N-FMOC-3-PHENYLPROPIONIC ACID

Synthetic route

Benzenepropanoic acid, b-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]- Specification

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