FMOC-Glycine supplier | CasNO.29022-11-5

Name
Fmoc-Glycine
EINECS 249-373-3
CAS No. 29022-11-5
Article Data54
CAS DataBase
Density 1.316 g/cm³
Solubility
Melting Point 174-178 °C
Formula C₁₇H₁₅NO₄
Boiling Point 545.7 °C at 760 mmHg
Molecular Weight 297.31
Flash Point 283.8 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms N-(9-Fluorenylmethoxycarbonyl)glycine;Fmoc-Gly;Npc 14692;Fmoc-L-Glycine;N-α-Fmoc-glycine;N-((9H-Fluoren-9-ylmethoxy)carbonyl)glycine;Fmoc-Gly-OH;2-(9H-fluoren-9-ylmethoxycarbonylamino)acetate;Glycine, N-((9H-fluoren-9-ylmethoxy)carbonyl)-;
PSA 75.63000
LogP 3.00060

Synthetic route

: 4-((tert-butyldimethylsilyl)oxy)benzyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate

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

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.0833333h; Reagent/catalyst;	97%

: 56-40-6
glycine

polymer-bound Fmoc-O-succinimide: polymer-bound Fmoc-O-succinimide

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

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 24h;	96%

: 909114-66-5
9-fluorenylmethyl 4,6-dimethoxy-1,3,5-triazinyl carbonate

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 0.333333h;	96%

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

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone Ambient temperature;	95%
Stage #1: glycine 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;	86%
With pyridine In methanol
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;

: 56-40-6
glycine

: 4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

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

Conditions

Conditions	Yield
With triethylamine In water Ambient temperature;	94%

: 1131148-55-4
1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 2h;	94%

: 1370440-40-6
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-morpholino-2-oxoacetimidoyl cyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	93.5%

: 1370440-28-0
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-amino-2-oxoacetimidoyl cyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium carbonate In water; acetone at 20℃; for 4h; pH=9 - 10;	93%
With sodium hydrogencarbonate In water; acetone	90.8%

: 1235983-29-5
(9H-fluoren-9-yl)methyl 2-oxopyridin-1(2H)-yl carbonate

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	92.8%

: 1235983-26-2
diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}-2-cyanoacetate

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	92.1%

: 1370440-36-0
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	92.1%

: 1370440-32-6
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-(ethylamino)-2-oxoacetimidoyl cyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	91.8%

: 1235983-28-4
N-{[(9H-fluoren-9-yl)methoxy]carbonyloxy}picolinimidoyl cyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	91.6%

: 329308-95-4
Fmoc-Gly-N3

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

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; water cooling;	90%

: 100803-86-9
3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;	88%

: 56-40-6
glycine

: Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 2h;	88%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 56-40-6
glycine

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

Conditions

Conditions	Yield
In ethanol; water at 60℃; for 4h; chemoselective reaction;	85%
Stage #1: (fluorenylmethoxy)carbonyl chloride; glycine With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 4h; Stage #2: With hydrogenchloride In water pH=2;	85%
With sodium carbonate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide 1.) 0 deg C, 30 min; 2.) up to RT, 1 h;	62%

: 88744-04-1
(9-fluorenyl)methyl pentafluorophenyl carbonate

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone Ambient temperature;	84%

: 121616-32-8
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate

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

Conditions

Conditions	Yield
With water; sodium hydroxide In isopropyl alcohol at 20℃; for 1h; chemoselective reaction;	84%

: 1235983-25-1
diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}malonate

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	82.9%

: 99503-04-5
Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With tertiary amine In 1,4-dioxane; water for 3h;	81%

: 618068-91-0
N-Fmoc-glycine 2-(2-acetylphenyl)-1-methylethyl ester

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

Conditions

Conditions	Yield
In acetonitrile for 4h; Photolysis;	56%

: 1235983-27-3
{[(9H-fluoren-9-yl)methoxy]carbonyloxy}carbonimidoyl dicyanide

: 56-40-6
glycine

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone	48.5%

: C20H23NO4Si

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

Conditions

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

PEGA1900-resin-NH-(CO(CH2)7)-OCOCH2NHFmoc: PEGA1900-resin-NH-(CO(CH2)7)-OCOCH2NHFmoc

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

Conditions

Conditions	Yield
With chymotrypsin In phosphate buffer for 16h; pH=8;

PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-OCOCH2NHFmoc: PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-OCOCH2NHFmoc

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

Conditions

Conditions	Yield
With chymotrypsin In phosphate buffer for 16h; pH=8;

: Fmoc-Gly-MFE

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

B: 70672-05-8
3-O-methylfluorescein

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; cathepsin B In phosphate buffer at 37℃; pH=6.7; Enzyme kinetics;

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

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

B N-(9-fluorenylmethoxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine pentafluorophenyl ester: N-(9-fluorenylmethoxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine pentafluorophenyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / Et3N / CH2Cl2 / 1 h / 20 °C 2: 96 percent / aq. Na2CO3 / acetonitrile / 0.33 h / 20 °C View Scheme

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

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 156939-65-0
(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	98%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	89%

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

: 97-51-8
5-Nitrosalicylaldehyde

Val-Ala-Gly-Phe-Wang resin: Val-Ala-Gly-Phe-Wang resin

A: (S)-2-(2-{(S)-2-[(S)-2-(2-Hydroxy-5-nitro-benzylamino)-3-methyl-butyrylamino]-propionylamino}-acetylamino)-3-phenyl-propionic acid

B: (S)-2-[2-((S)-2-{(S)-2-[(2-Amino-acetyl)-(2-hydroxy-5-nitro-benzyl)-amino]-3-methyl-butyrylamino}-propionylamino)-acetylamino]-3-phenyl-propionic acid

Conditions

Conditions	Yield
Multistep reaction;	A n/a B 100%

...Expand

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

Fmoc-Lys(Dde)-Rink-PS-resin: Fmoc-Lys(Dde)-Rink-PS-resin

: {1-carbamoyl-5-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetylamino]-pentyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
Stage #1: Fmoc-Lys(Dde)-Rink-PS-resin With 1H-imidazole; 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride In dichloromethane for 3h; Stage #2: N-(fluoren-9-ylmethoxycarbonyl)glycine With benzotriazol-1-ol; dacarbazine In N,N-dimethyl-formamide Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane	100%

Pro-Val-Leu-Cys(Trt)-Ala-Wang resin: Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

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

Gly-Pro-Val-Leu-Cys(Trt)-Ala-Wang resin: Gly-Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

Conditions

Conditions	Yield
Stage #1: Pro-Val-Leu-Cys(Trt)-Ala-Wang resin; N-(fluoren-9-ylmethoxycarbonyl)glycine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h;	100%

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

: 115057-37-9
Fmoc-Gly-NH2

Conditions

Conditions	Yield
With N-hydroxybenzotriazole ammonium salt; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	100%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With Rink amide resin after treatment with piperidine in DMF; benzotriazol-1-ol; dacarbazine In N,N-dimethyl-formamide at 120℃; for 0.0833333h; microwave irradiation; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	93%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling; Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling;	86%

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

monomethoxy-polyethylene glycol: monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)glycine terminated monomethoxy-polyethylene glycol: N-(9-fluorenylmethoxycarbonyl)glycine terminated monomethoxy-polyethylene glycol

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	100%

: 1075176-19-0
C16H17N

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

: 1075176-20-3
C33H30N2O3

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran	100%

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

: 35661-40-6
N-Fmoc L-Phe

: 71989-14-5
Fmoc-(tBu)Asp-OH

: 119831-72-0
Fmoc-Arg(Pbf)-OH

: 146982-27-6
(S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid

: H-Asp(OtBu)-Phe-Lys(Aloc)-Arg(Pmc)-Gly-OH

Conditions

Conditions	Yield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane for 0.25h; solid phase reaction; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; Automated synthesizer; solid phase reaction; Stage #3: N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Arg(Pbf)-OH; (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid Further stages;	100%

Yield

Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane for 0.25h; solid phase reaction;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; Automated synthesizer; solid phase reaction;
Stage #3: N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Arg(Pbf)-OH; (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid Further stages;

100%

...Expand

: 1258442-42-0
C96H146N8O8S

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

: C112H157N9O11S

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	100%

FMOC-Glycine Specification

The FMOC-Glycine, with the CAS registry number 29022-11-5, is also known as N-((9H-Fluoren-9-ylmethoxy)carbonyl)glycine. It belongs to the product categories of Protected Amino Acids; Fluorenes, Flurenones; Aminoacids Derivatives; Amino Acid Derivatives; Amino Acids; Glycine [Gly, G]; Fmoc-Amino Acids and Derivatives; Amino Acids (N-Protected); Biochemistry; Fmoc-Amino Acids; Fmoc-Amino Acid Series. Its EINECS registry number is 249-373-3. This chemical's molecular formula is C₁₇H₁₅NO₄ and molecular weight is 297.3053. Its IUPAC name is called 2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid. This chemical is white to light yellow crystal powder. The product should be sealed at temperature of 2-8 °C.

Physical properties of FMOC-Glycine: (1)ACD/LogP: 3.20; (2)ACD/LogD (pH 5.5): 1.43; (3)ACD/LogD (pH 7.4): -0.21; (4)ACD/BCF (pH 5.5): 2.72; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 22.49; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.619; (12)Molar Refractivity: 79.32 cm³; (13)Molar Volume: 225.8 cm³; (14)Surface Tension: 58.6 dyne/cm; (15)Density: 1.316 g/cm³; (16)Flash Point: 283.8 °C; (17)Enthalpy of Vaporization: 86.78 kJ/mol; (18)Boiling Point: 545.7 °C at 760 mmHg; (19)Vapour Pressure: 9.69E-13 mmHg at 25°C.

Preparation: this chemical can be prepared by glycine and 9H-fluoren-9-ylmethyl chloroformate. This reaction will need reagent aq. Na₂CO₃.

Uses of FMOC-Glycine: it can be used to produce Fmoc-Gly-ONp at temperature of 0 °C. This reaction will need reagent DCC and solvent ethyl acetate. The yield is about 77%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCC(=O)O
(2)InChI: InChI=1S/C17H15NO4/c19-16(20)9-18-17(21)22-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15H,9-10H2,(H,18,21)(H,19,20)
(3)InChIKey: NDKDFTQNXLHCGO-UHFFFAOYSA-N

Product Name

Fmoc-Glycine

Synthetic route

FMOC-Glycine Specification

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