L-Phenylglycinamide supplier

Name
H-PHG-NH2 HCL
EINECS 813-110-6
CAS No. 6485-52-5
Article Data46
CAS DataBase
Density 1.178 g/cm³
Solubility
Melting Point 131-132 °C
Formula C₈H₁₀N₂O
Boiling Point 322.8 °C at 760 mmHg
Molecular Weight 150.18
Flash Point 149 °C
Transport Information
Appearance
Safety 36/37
Risk Codes 43
Molecular Structure
Hazard Symbols Xi
Synonyms Acetamide,2-amino-2-phenyl-, L-(+)- (8CI);Benzeneacetamide, α-amino-, (S)-;(2S)-2-Amino-2-phenylethanamide;L-Phenylglycinamide;L-Phenylglycine amide;L-α-Phenylglycine amide;(2S)-2-amino-2-phenylethanamide;
PSA 69.11000
LogP 1.57230

Synthetic route

: 19883-41-1
D-phenylglycine methyl ester hydrochloride

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With ammonium hydroxide In toluene at 20℃;	94%

: 6591-61-3, 24461-61-8, 26682-99-5, 37760-98-8
(S)-Phenylglycine methyl ester

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With ammonium hydroxide In toluene for 16h; Ambient temperature;	71%
With methanol; ammonia

: 15028-39-4
L-2-phenylglycine methyl ester hydrochloride

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With ammonia In water at 20℃;	71%
With ammonium hydroxide for 96h; Ambient temperature;	68%
With ammonium hydroxide

: 2935-35-5
(S)-2-phenylglycine

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
Stage #1: (S)-2-phenylglycine With thionyl chloride In methanol at 0 - 20℃; Stage #2: (S)-2-phenylglycine In methanol at 20℃; Stage #3: With ammonia In water; toluene at 20℃;	46%
Multi-step reaction with 2 steps 1: 92 percent / thionyl chloride / 0.33 h / Heating 2: 68 percent / 28percent aq. NH3 / 96 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 2: methanol; NH3 View Scheme

: 155385-85-6
(-)-1S-<(cyano phenyl methyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With hydrogenchloride In formic acid for 18h;

: 700-63-0
Phenylglycinamid

: 6485-52-5
L-phenylglycine amide

: 700-63-0
Phenylglycinamid

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 51581-15-8
phenylglycine butyl ester hydrochloride

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With Candida antarctica lipase B-Novozym 435; ammonia In tert-butyl alcohol at 40℃; for 4h; Title compound not separated from byproducts;

: 72651-17-3
phenylglycine ethyl ester hydrochloride

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With Candida antarctica lipase B-Novozym 435; ammonia In tert-butyl alcohol at 40℃; for 4h; Title compound not separated from byproducts;

: 24461-61-8, 26682-99-5, 37760-98-8, 6591-61-3
phenylglycine methyl ester

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With Candida antarctica lipase B; Novozym 435; ammonia In tert-butyl alcohol at 40℃; for 4h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With Candida antarctica lipase B on Accurel EP 100-SP 611; ammonia In tert-butyl alcohol at -20℃; for 24h; Title compound not separated from byproducts;

: 700-63-0
Phenylglycinamid

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

C: 2935-35-5
(S)-2-phenylglycine

D: 875-74-1
(R)-phenylglycine

Conditions

Conditions	Yield
With Rhodococcus sp. AJ270 In phosphate buffer at 30℃; for 2h; pH=7.62; Title compound not separated from byproducts;
With Rhodococcus sp. AJ270 cells In phosphate buffer at 30℃; for 2h; pH=7.0; Title compound not separated from byproducts;
With potassium phosphatr buffer; Rhodococcus sp.AJ270 cells at 30℃; for 2h; pH=7.0; Enzymatic reaction;
With potassium phosphate buffer; Rhodococcus sp. AJ270 sells at 30℃; for 2h; pH=7.0; Product distribution;

...Expand

: 16750-42-8, 41804-94-8
2-amino-2-phenylacetonitrile

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

C: 2935-35-5
(S)-2-phenylglycine

Conditions

Conditions	Yield
With phosphate buffer; Pantoea endophytica 26.2.2 permeabilized cells at 28℃; for 0.5h; pH=7.4;

...Expand

: 16750-42-8, 41804-94-8
2-amino-2-phenylacetonitrile

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

C: 875-74-1
(R)-phenylglycine

D: 45789-64-8
(R)-phenylglycine nitrile

Conditions

Conditions	Yield
With phosphate buffer; Pantoea sp. 17.3.1 permeabilized cells; Triton X-100 at 4℃; for 0.333333h; pH=7.4;

...Expand

: 155385-82-3
(-)-1-benzylideneamino-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 percent / methanol / 24 h / Heating 2: hydrochloric acid / formic acid / 18 h View Scheme

: 60079-51-8
(S)-phenylglycinamide hydrochloride

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With potassium carbonate In water

: 16750-42-8, 41804-94-8
2-amino-2-phenylacetonitrile

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With Klebsiella oxytoca 38.1.2 nitrile hydratase at 30℃; Reactivity; Time; Enzymatic reaction; stereoselective reaction;

: 16750-42-8, 41804-94-8
2-amino-2-phenylacetonitrile

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With Klebsiella oxytoca 38.1.2 nitrile hydratase at 30℃; for 0.0833333h; Reactivity; Time; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;

: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With Pd/AlO(OH) In toluene at 60℃; for 48h;

: 53641-60-4
2-phenylglycinonitrile hydrochloride

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With recombinant Rhodopseudomonas palustris HaA2 nitrile hydratase; water at 5℃; pH=5; citrate buffer; enantioselective reaction;

: D-phenylglycine nitrile tartaric acid

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With hysratase/amidase Novo SP 361 In aq. phosphate buffer at 20℃; for 3h; pH=5; Catalytic behavior; Enzymatic reaction; Overall yield = 11 %;	A n/a B n/a

: (S)-methyl 2-amino-2-phenylacetate hydrochloride

: 6485-52-5
L-phenylglycine amide

Conditions

Conditions	Yield
With ammonium hydroxide In water at 20℃; under 760.051 Torr; for 120h; Inert atmosphere;	11.2 g

: potassium cyanide

: 100-52-7
benzaldehyde

A: 6485-52-5
L-phenylglycine amide

B: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

Conditions

Conditions	Yield
With nitrilase AY487533W186A mutant In aq. acetate buffer at 20℃; for 1h; pH=8; Enzymatic reaction; Overall yield = 79.5 %; enantioselective reaction;	A n/a B n/a

...Expand

: 6485-52-5
L-phenylglycine amide

: 76-83-5
trityl chloride

: 1041016-90-3
C27H24N2O

Conditions

Conditions	Yield
In dichloromethane at 20℃;	95%

: 6485-52-5
L-phenylglycine amide

: 66003-76-7
Diphenyliodonium triflate

: (S)-2-phenyl-2-(phenylamino)acetamide

Conditions

Conditions	Yield
With potassium phosphate; copper diacetate In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;	94%

: 696-62-8
para-iodoanisole

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(4-methoxyphenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	92%

: 444-29-1
2-iodo(trifluoromethyl)benzene

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(2-trifluoromethylphenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	92%

: 6485-52-5
L-phenylglycine amide

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

: 769195-19-9
(2S)-2({(1Z)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-]pyrazin-7(8H)-yl]prop-1-enyl}amino-2-phenylethanamide)

Conditions

Conditions	Yield
With acetic acid In isopropyl alcohol at 45℃; for 10h;	91.3%
In acetic acid; isopropyl alcohol at 50℃; for 18h;

: 615-37-2
ortho-methylphenyl iodide

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(2-methylphenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	91%

: 90-14-2
1-Iodonaphthalene

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(naphthalene-1-yl)-2-phenylethanamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	91%

: 6485-52-5
L-phenylglycine amide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: L-phenylalanine α-(N',N'-dimethylformamidino) nitrile

Conditions

Conditions	Yield
With pyridine-2-sulfonyl chloride at 20℃; Condensation; dehydration;	90%

: 591-50-4
iodobenzene

: 6485-52-5
L-phenylglycine amide

: 170900-66-0
(S)-2-amino-N,2-diphenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	90%
With copper(l) iodide; potassium carbonate In toluene at 90℃; for 24h; Inert atmosphere; Sealed tube;	86%

: 625-99-0
3-iodochlorobenzene

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(3-chlorophenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	89%

: 6485-52-5
L-phenylglycine amide

: 41302-34-5
2-(methoxycarbonyl)cyclohexanone

: 679789-06-1
methyl 2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohex-1-ene-1-carboxylate

Conditions

Conditions	Yield
With acetic acid In methanol at 40℃; for 1h;	87%

: 942475-04-9
C11H10F2O3

: 6485-52-5
L-phenylglycine amide

: C19H18F2N2O3

Conditions

Conditions	Yield
With acetic acid In methanol at 40℃; for 2h;	87%

: 6485-52-5
L-phenylglycine amide

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

: 769195-20-2
(2S)-2({(1R)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]propyl}amino)-2-phenylethanamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In acetonitrile at 20℃; for 5h; Reagent/catalyst; stereoselective reaction;	87%

: 1120-90-7
3-iodopyridine

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-2-phenyl-N-(pyridin-3-yl)acetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	85%

: 42558-54-3
Methyl 4-methyl-3-oxopentanoate

: 6485-52-5
L-phenylglycine amide

: 679789-04-9
methyl (2Z)-3-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}-4-methylpent-2-enoate

Conditions

Conditions	Yield
With acetic acid In isopropyl alcohol at 40℃;	84%

: 610-97-9
o-iodo-methyl-benzoic acid

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(2-methoxycarbonylphenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	83%

: 769195-26-8
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester

: 6485-52-5
L-phenylglycine amide

: (S,Z)-methyl 3-(2-amino-2-oxo-1-phenylethylamino)-4-(2,4,5-trifluorophenyl)but-2-enoate

Conditions

Conditions	Yield
With acetic acid In ethanol at 40℃; for 16h; Solvent; Schiff Reaction; Inert atmosphere;	80%

: 6485-52-5
L-phenylglycine amide

: 105-45-3
acetoacetic acid methyl ester

: 679789-03-8
methyl (2Z)-3-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}but-2-enoate

Conditions

Conditions	Yield
With acetic acid In methanol at 40℃; for 1h;	77%

: 122-84-9
4-methoxybenzyl methyl ketone

: 6485-52-5
L-phenylglycine amide

: C19H21N3O2

Conditions

Conditions	Yield
With hydrogenchloride; sodium cyanide In methanol; water at 5 - 45℃; for 34.25h;	77%

: 6485-52-5
L-phenylglycine amide

: 37779-49-0
methyl 3-oxo-4-phenylbutanoate

: 679789-05-0
methyl (2Z)-3-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}-4-phenylbut-2-enoate

Conditions

Conditions	Yield
With acetic acid In isopropyl alcohol at 50℃; for 18h;	74%

: 108-86-1
bromobenzene

: 6485-52-5
L-phenylglycine amide

: 170900-66-0
(S)-2-amino-N,2-diphenylacetamide

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;	72%
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	50%

: 6485-52-5
L-phenylglycine amide

: 110-13-4
2,5-hexanedione

: (S)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-2-phenylacetamide

Conditions

Conditions	Yield
With MgI2 etherate In dichloromethane for 8h; Reflux;	70%

: 6485-52-5
L-phenylglycine amide

: 98760-08-8
(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

: 500767-14-6
(2S,5S,6S)-3-aza-6-[(tert-butyloxycarbonyl)amino]-5-hydroxy-2,7-diphenylheptanoyl amide

Conditions

Conditions	Yield
In isopropyl alcohol Heating;	63%

: 6485-52-5
L-phenylglycine amide

: 95-92-1
oxalic acid diethyl ester

: 127479-02-1
phenyl-5 piperazinetrione-2,3,6

Conditions

Conditions	Yield
With sodium methylate In methanol; ethanol for 0.75h; Heating;	61%

: 6485-52-5
L-phenylglycine amide

: 50264-63-6
1-(4-fluoro-benzyl)-1H-indazole-3-carboxylic acid

: 1185282-02-3
N-[(1S)-2-amino-2-oxo-1-phenylethyl]-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 18 - 25℃; for 18h;	60%

: 636-98-6
p-nitrobenzene iodide

: 6485-52-5
L-phenylglycine amide

: (S)-2-amino-N-(4-nitrophenyl)-2-phenylacetamide

Conditions

Conditions	Yield
With caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine In toluene at 50℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;	60%

: 933786-13-1
4-(4-(3-chlorophenyl)-1H-pyrazol-3-yl)-1H-pyrrole-2-carboxylic acid

: 6485-52-5
L-phenylglycine amide

: N-((S)-carbamoyl(phenyl)methyl)-4-(4-(3-chlorophenyl)-1H-pyrazol-3-yl)-1H-pyrrole-2-carboxamide

Conditions

Conditions	Yield
With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 20h;	58%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;

L-Phenylglycinamide Specification

The Benzeneacetamide, α-amino-, (αS)-, with the CAS registry number 6485-52-5, has the systematic name of (2S)-2-amino-2-phenylethanamide. It belongs to the product category of Protected Amino Acids, and should be stored at 0-5°C. The molecular formula of this chemical is C₈H₁₀N₂O.

The physical properties of Benzeneacetamide, α-amino-, (αS)- are as following: (1)ACD/LogP: -0.11; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1.57; (6)ACD/KOC (pH 7.4): 17.88; (7)#H bond acceptors: 3; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 23.55 Å²; (11)Index of Refraction: 1.588; (12)Molar Refractivity: 42.9 cm³; (13)Molar Volume: 127.4 cm³; (14)Polarizability: 17×10^-24cm³; (15)Surface Tension: 54 dyne/cm; (16)Density: 1.178 g/cm³; (17)Flash Point: 149 °C; (18)Enthalpy of Vaporization: 56.47 kJ/mol; (19)Boiling Point: 322.8 °C at 760 mmHg; (20)Vapour Pressure: 0.000272 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N)[C@@H](N)c1ccccc1
(2)InChI: InChI=1/C8H10N2O/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H2,10,11)/t7-/m0/s1
(3)InChIKey: KIYRSYYOVDHSPG-ZETCQYMHBM

Product Name

H-PHG-NH2 HCL

Synthetic route

L-Phenylglycinamide Specification

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