D(-)-4-Hydroxyphenylglycine supplier

Name
D(-)-4-Hydroxyphenylglycine
EINECS 245-247-7
CAS No. 22818-40-2
Article Data32
CAS DataBase
Density 1.396 g/cm³
Solubility 5 g/L (20 °C) in water
Melting Point 240 °C (dec.)(lit.)
Formula C₈H₉NO₃
Boiling Point 365.8 °C at 760 mmHg
Molecular Weight 167.164
Flash Point 175 °C
Transport Information
Appearance off-white powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzeneaceticacid, a-amino-4-hydroxy-, (R)-;(R)-2-(4-Hydroxyphenyl)glycine;(aR)-a-Amino-4-hydroxybenzeneacetic acid;D-(-)-2-(p-Hydroxyphenyl)glycine;D-(-)-Amino(4-hydroxyphenyl)acetic acid;D-(-)-a-(4-Hydroxyphenyl)glycine;D-(-)-a-Amino-p-hydroxyphenylaceticacid;D-p-Hydroxyphenylglycine;D-a-p-Hydroxyphenylglycine;p-Hydroxy-D-phenylglycine;
PSA 83.55000
LogP 1.17690

Synthetic route

: potassium cyanide

: 123-08-0
4-hydroxy-benzaldehyde

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With nitrilase AY487533 In aq. acetate buffer at 20℃; for 1h; pH=8; Enzymatic reaction; enantioselective reaction;	97.8%

: 2420-17-9
5-(4-hydroxy-phenyl)-imidazolidine-2,4-dione

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 48h; 0.1 M potassium phosphate buffer (pH = 8.0); cells of Pseudomonas sp. AJ-11220 (bacterioal strain H-231); ivestigate steric configuration of the product; other time;	94%
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; Product distribution; pH 8.0; enzymatic reaction, other solvents, temperatures, reagents, times;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;
Multistep reaction;

: D-5-(p-hydroxyphenyl)hydantoin

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 48h; 0.1 M potassium phosphate buffer (pH = 8.0); cells of Pseudomonas sp. AJ-11220 (bacterioal strain H-231); investigate steric configuration of the product; other time;	94%

: L-5-(p-hydroxyphenyl)hydantoin

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 48h; 0.1 M potassium phosphate buffer (pH = 8.0); cells of Pseudomonas sp. AJ-11220 (bacterioal strain H-231); ivestigate steric configuration of the product; other time;	94%

: 104-15-4
toluene-4-sulfonic acid

: D-2-(4-hydroxyphenyl)-2-(4-methoxybenzyloxycarbonylamino)acetic acid

: 75-05-8
acetonitrile

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 35103-34-5
N-(p-methoxybenzyl)acetamide

Conditions

Conditions	Yield
for 3.5h; Mechanism; Ambient temperature;	A 93% B 36%

...Expand

: 54582-01-3
(R)-N-phenylacetyl-D-(4-hydroxyphenyl)-glycine

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With hydrogenchloride; water at 50℃; for 10h;	93%

/PBLFF019-1440/: /PBLFF019-1440/

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With ammonium hydroxide In water at 5℃; for 2h;	91.6%

: 67-56-1
methanol

: 1327278-14-7
4-((3R,5S)-2-oxo-5-phenyl-morpholin-3-yl)phenyl acetate

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester

Conditions

Conditions	Yield
With 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid In water at 20℃; under 3040.2 Torr; for 24h;	A 65% B n/a

...Expand

: 27460-85-1
N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

: 104-15-4
toluene-4-sulfonic acid

: 75-05-8
acetonitrile

A: 762-84-5
N-tert-butylacetamide

B: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; acetonitrile Mechanism; Ambient temperature;	A 51% B n/a

...Expand

: 60114-00-3
(S)-2-Amino-3-{[(R)-carboxy-(4-hydroxy-phenyl)-methyl]-amino}-propionic acid

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With hydrogenchloride

: 43189-38-4
(R)-ethyl 2-amino-2-(4-hydroxyphenyl)acetate

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With sodium hydroxide

: 13253-44-6
5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 24h; Product distribution; 0.1 M potassium phosphate buffer (pH = 8.0); bacterioal strain H-319; also H-968;

: 72500-37-9
α-(aminocarbonyl)amino-4-hydroxybenzeneacetic acid

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 7.5; enzymatic reaction;

: 1007-06-3
DL-5-cyanoethylhydantoin

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 24h; Product distribution; 0.1 M potassium phosphate buffer (pH = 8.0); bacterioal strain H-231; also H-618;

: 69598-75-0
complestatin

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 25698-18-4
(R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

C: 2-(3,5-dichloro-4-hydroxyphenyl)-2,2-dihydroxyacetic acid

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid at 105℃; for 22h;

...Expand

: 6324-01-2
p-hydroxyphenylglycine

: 22818-40-2
D-4-hydroxyphenylglycine

: 68780-35-8
N-carbamyl-D-p-hydroxyphenylglycine

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite at 0℃;

: 43189-12-4
(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 32462-30-9
(S)-hydroxyphenylglycine

Conditions

Conditions	Yield
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; for 5h; pH=6.5; Title compound not separated from byproducts;

: 43189-12-4
(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 32462-30-9
(S)-hydroxyphenylglycine

C: 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester

D: 26531-82-8
(S)-methyl 2-amino-2-(4-hydroxyphenyl)acetate

Conditions

Conditions	Yield
With Bacillus licheniformis; sodium hydrogencarbonate; 1-ethyl-3-methylimidazolium acetate In water; water-d2 at 30℃; for 3h;

...Expand

: 39391-39-4
(-)-nocardicin A

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl 2: aq. HCl View Scheme

: 6324-01-2
p-hydroxyphenylglycine

A: 22818-40-2
D-4-hydroxyphenylglycine

B: 32462-30-9
(S)-hydroxyphenylglycine

Conditions

Conditions	Yield
With hydrogenchloride; C15H13O4S(1-)K(1+); C15H12ClO4S(1-)K(1+) In water; isopropyl alcohol Resolution of racemate;
With sodium alginate chiral column In water Concentration; Reagent/catalyst; Resolution of racemate;
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate;
With ChirosilRCA(+) at 50℃; Temperature; Resolution of racemate; Sonication;
With perchloric acid at 25℃; pH=1; Reagent/catalyst; Resolution of racemate;

: 54713-12-1
N-phenylacetyl-(4-hydroxyphenyl)-glycine

A: 103-82-2
phenylacetic acid

B: 54582-01-3
(R)-N-phenylacetyl-D-(4-hydroxyphenyl)-glycine

C: 22818-40-2
D-4-hydroxyphenylglycine

D: 32462-30-9
(S)-hydroxyphenylglycine

Conditions

Conditions	Yield
With penicillin G acylase; water; sodium carbonate for 0.333333h; pH=8.0; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;

...Expand

: 1327278-02-3
4-(((S)-4,5-dihydro-4-phenyloxazol-2-yl)methyl)phenyl acetate

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C 2: platinum(IV) oxide; hydrogen / 3040.2 Torr 3: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 4: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

: 1327278-09-0
4-((S)-5,6-dihydro-2-oxo-5-phenyl-2H-1,4-oxazin-3-yl)phenyl acetate

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: platinum(IV) oxide; hydrogen / 3040.2 Torr 2: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 3: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

: 1327278-14-7
4-((3R,5S)-2-oxo-5-phenyl-morpholin-3-yl)phenyl acetate

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 2: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

: 1327277-97-3
4-(((S)-2-hydroxy-1-phenylethylcarbamoyl)methyl)phenyl acetate

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C 1.2: 4 h / -78 - 20 °C 2.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C 3.1: platinum(IV) oxide; hydrogen / 3040.2 Torr 4.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 5.1: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C
1.2: 4 h / -78 - 20 °C
2.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C
3.1: platinum(IV) oxide; hydrogen / 3040.2 Torr
4.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr
5.1: hydrogenchloride; water / 24 h / 90 - 100 °C
View Scheme

: 65448-20-6
4-acetoxyphenylacetyl chloride

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: dichloromethane / 0 - 20 °C 2.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C 2.2: 4 h / -78 - 20 °C 3.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C 4.1: platinum(IV) oxide; hydrogen / 3040.2 Torr 5.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 6.1: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: dichloromethane / 0 - 20 °C
2.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C
2.2: 4 h / -78 - 20 °C
3.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C
4.1: platinum(IV) oxide; hydrogen / 3040.2 Torr
5.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr
6.1: hydrogenchloride; water / 24 h / 90 - 100 °C
View Scheme

: 38177-33-2
(4-acetoxyphenyl)acetic acid

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: thionyl chloride / 3 h / Reflux 2.1: dichloromethane / 0 - 20 °C 3.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C 3.2: 4 h / -78 - 20 °C 4.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C 5.1: platinum(IV) oxide; hydrogen / 3040.2 Torr 6.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr 7.1: hydrogenchloride; water / 24 h / 90 - 100 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: thionyl chloride / 3 h / Reflux
2.1: dichloromethane / 0 - 20 °C
3.1: diethylamino-sulfur trifluoride / dichloromethane / 1.25 h / -78 °C
3.2: 4 h / -78 - 20 °C
4.1: selenium(IV) oxide / ethyl acetate / 1 h / 75 °C
5.1: platinum(IV) oxide; hydrogen / 3040.2 Torr
6.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid / water / 24 h / 20 °C / 3040.2 Torr
7.1: hydrogenchloride; water / 24 h / 90 - 100 °C
View Scheme

: 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester

: 22818-40-2
D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With hydrogenchloride; water at 90 - 100℃; for 24h;
With sulfuric acid In water at 2℃; for 0.0833333h; pH=8.7; Enzymatic reaction;
With water Enzymatic reaction;

: 67-56-1
methanol

: 22818-40-2
D-4-hydroxyphenylglycine

: 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 10h;	100%
With thionyl chloride at 20℃; for 10h;	100%
With thionyl chloride at 20℃; for 15h;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 22818-40-2
D-4-hydroxyphenylglycine

: 27460-85-1
N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 0 - 20℃;	100%
With sodium carbonate In water; acetone at 20℃;	100%
With sodium hydroxide In 1,3-dioxane; water at 20℃; for 4h;	99%

: 67-56-1
methanol

: 22818-40-2
D-4-hydroxyphenylglycine

: 57591-61-4, 68697-60-9, 127369-30-6, 134694-94-3
methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at -15℃; Inert atmosphere; Reflux;	100%
With thionyl chloride at 0 - 75℃; for 2h;	100%
With acetyl chloride at 0 - 55℃; for 19.5h; Inert atmosphere; Large scale reaction;	99%

: 22818-40-2
D-4-hydroxyphenylglycine

: 79-22-1
methyl chloroformate

: 77568-43-5
(R)-2-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino]acetic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	99%

: 67-56-1
methanol

: 22818-40-2
D-4-hydroxyphenylglycine

: 86963-42-0
α-phenylethanesulfonic acid

: C9H11NO3*C8H10O3S

Conditions

Conditions	Yield
With thionyl chloride at 25℃; for 4h; Time; Reflux; Large scale;	98.72%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 22818-40-2
D-4-hydroxyphenylglycine

: 69651-48-5
N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water for 16h; Ambient temperature; pH=8;	98%

: 22818-40-2
D-4-hydroxyphenylglycine

: 135544-68-2
N-(allyloxycarbonyloxy)succinimide

: 84792-41-6
(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 5h;	98%

: 22818-40-2
D-4-hydroxyphenylglycine

: 57591-61-4, 68697-60-9, 127369-30-6, 134694-94-3
methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride In methanol at 20℃; for 10h;	98%
With thionyl chloride In methanol at 0 - 20℃;

: 22818-40-2
D-4-hydroxyphenylglycine

: D-3,5- 2H2-4-hydroxyphenylglycine

Conditions

Conditions	Yield
With potassium tetrachloroplatinate; water-d2; hydrogen chloride for 24h; Schlenk technique; Reflux; Inert atmosphere;	98%

: 22818-40-2
D-4-hydroxyphenylglycine

: 108-24-7
acetic anhydride

: 37784-23-9
N-acetyl-(R)-2-(4-hydroxyphenyl)glycine

Conditions

Conditions	Yield
In acetic acid for 30h; Ambient temperature;	96.6%
With sodium hydrogencarbonate In water for 0.166667h; Ambient temperature; Yield given;
With sodium hydroxide In water at 0 - 5℃; for 2.5h;

: 22818-40-2
D-4-hydroxyphenylglycine

: 209460-85-5
(2R)-2-Amino-2-(4-hydroxycyclohexyl)acetic Acid

Conditions

Conditions	Yield
With hydrogen; nickel In water at 85℃; under 112509 Torr; for 4h;	96%
With hydrogen; Ni-Raney
With sodium hydroxide; hydrogen; nickel In water at 80℃; under 5171.48 Torr; for 72h;

: 22818-40-2
D-4-hydroxyphenylglycine

: 87462-12-2
N,N-diisopropyl-3-phenyl-2-propen-1-amine

: 1333234-68-6
2-amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With methanesulfonic acid at 120℃; for 20h;	96%

: 22818-40-2
D-4-hydroxyphenylglycine

: 173948-30-6
(E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine

: 1333234-68-6
2-amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
Stage #1: D-4-hydroxyphenylglycine; (E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine With methanesulfonic acid at 120℃; for 20h; Stage #2: With sodium hydroxide In water pH=7;	96%

: 22818-40-2
D-4-hydroxyphenylglycine

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 178119-93-2
Nα-Fmoc-(4-hydroxy)-D-phenylglycine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water for 8.41667h;	95%
With sodium carbonate In 1,4-dioxane at 0 - 20℃; for 2h;

: 22818-40-2
D-4-hydroxyphenylglycine

: 1493-27-2
ortho-nitrofluorobenzene

: C14H12N2O5

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 100℃; for 16h; sealed tube;	95%

: benzyloxycarbonyl succinimide

: 22818-40-2
D-4-hydroxyphenylglycine

: 26787-75-7
(R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With potassium carbonate In water; acetone at 15 - 35℃; pH=8-9;	95%

: 22818-40-2
D-4-hydroxyphenylglycine

: 501-53-1
benzyl chloroformate

: 26787-75-7
(R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water; toluene at 0 - 20℃; for 1.5h;	93%
With sodium carbonate In dichloromethane; water at 0 - 25℃;	88%
With sodium hydrogencarbonate In water at 18 - 25℃; for 2.33333h; Inert atmosphere;	53%
With sodium hydrogencarbonate In water for 1h;
With potassium hydroxide In water at 0 - 20℃; for 0.0833333h;

: 64-17-5
ethanol

: 22818-40-2
D-4-hydroxyphenylglycine

: 43189-38-4
(R)-ethyl 2-amino-2-(4-hydroxyphenyl)acetate

Conditions

Conditions	Yield
Stage #1: ethanol; D-4-hydroxyphenylglycine With methanesulfonic acid at 10 - 78℃; for 2h; Stage #2: With sodium hydroxide; water In water at 5 - 40℃; for 3h; pH=7 - 7.5;	92%
Stage #1: ethanol; D-4-hydroxyphenylglycine With methanesulfonic acid at 10 - 78℃; for 2h; Stage #2: With sodium hydroxide In water at 5 - 40℃; for 3h; pH=7.0 - 7.5;	92%
Stage #1: ethanol; D-4-hydroxyphenylglycine With methanesulfonic acid at 10 - 78℃; Large scale reaction; Stage #2: With sodium hydroxide In water at 5℃; for 3h; Large scale reaction;	90%
With thionyl chloride at 20℃; for 10h;

: 22818-40-2
D-4-hydroxyphenylglycine

: (R),6(S)-bis(4-hydroxyphenyl)piperazine-2,5-dione

Conditions

Conditions	Yield
In ethylene glycol for 24h; Reflux;	92%

: 22818-40-2
D-4-hydroxyphenylglycine

: 98-88-4
benzoyl chloride

: 37784-33-1
(R)-2-benzamido-2-(4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 3h;	88%
With sodium carbonate In dichloromethane; water at 0 - 25℃;	66%
With sodium hydrogencarbonate

: 22818-40-2
D-4-hydroxyphenylglycine

: 792892-61-6
(R)-4'-hydroxy-3',5'-diiodophenylglycine

Conditions

Conditions	Yield
With Iodine monochloride; acetic acid at 20℃; for 72h;	87%
With Iodine monochloride In acetic acid	78%
With Iodine monochloride; acetic acid at 20℃; for 72h; Inert atmosphere;	65%
With Iodine monochloride; acetic acid at 20℃; for 72h; Inert atmosphere;

: 186581-53-3, 908094-01-9
diazomethane

: 22818-40-2
D-4-hydroxyphenylglycine

: 78307-39-8
methyl 4-methoxyphenyl-D-phenylglycinate

Conditions

Conditions	Yield
In methanol; diethyl ether for 24h; Ambient temperature;	86%

: 67-56-1
methanol

: 24424-99-5
di-tert-butyl dicarbonate

: 22818-40-2
D-4-hydroxyphenylglycine

: 143323-49-3, 141518-55-0
(R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

Conditions

Conditions	Yield
Stage #1: methanol; D-4-hydroxyphenylglycine With thionyl chloride at 0℃; for 18h; Heating / reflux; Stage #2: di-tert-butyl dicarbonate With N-ethyl-N,N-diisopropylamine In methanol for 4h; pH=4 - 10;	85%
Stage #1: methanol; D-4-hydroxyphenylglycine With thionyl chloride Heating / reflux; Stage #2: di-tert-butyl dicarbonate With triethylamine In 1,4-dioxane; water at 25℃;	83%

...Expand

D(-)-4-Hydroxyphenylglycine Specification

The CAS register number of D-4-Hydroxyphenylglycine is 22818-40-2. It also can be called as (R)-alpha-Amino-4-hydroxybenzeneacetic acid and the IUPAC name about this chemical is (2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetate. The molecular formula about this chemical is C₈H₉NO₃and the molecular weight is 167.16. It belongs to the following product categories, such as Pharmaceutical Intermediates; Amino Acids Series; Miscellaneous Biochemicals; Cephalosporins; Peptide Synthesis; Phenylglycine Derivatives; Unnatural Amino Acid Derivatives and so on. This chemical is mainly used to produce semi-synthetic antibiotic amoxicillin.

Physical properties about D-4-Hydroxyphenylglycine are: (1)ACD/LogP: -0.13; (2)ACD/LogD (pH 5.5): -1.37; (3)ACD/LogD (pH 7.4): -3.12; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.16; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 38.77Å²; (12)Index of Refraction: 1.664; (13)Molar Refractivity: 43.94 cm³; (14)Molar Volume: 118.4 cm³; (15)Polarizability: 17.41x10^-24cm³; (16)Surface Tension: 70.1 dyne/cm; (17)Enthalpy of Vaporization: 74.24 kJ/mol; (18)Boiling Point: 446.3 °C at 760 mmHg; (19)Vapour Pressure: 9.49E-09 mmHg at 25°C.

DL-hydroxyphenylglycine can be prepared by the reaction of Anise aldehyde cyclization and hydrolysis, and also use the Methanol esterification and tartaric acid resolution, can produce the D-4-Hydroxyphenylglycine.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CNc1ccc(O)cc1
(2)InChI: InChI=1/C8H9NO3/c10-7-3-1-6(2-4-7)9-5-8(11)12/h1-4,9-10H,5H2,(H,11,12)
(3)InChIKey: WRUZLCLJULHLEY-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C8H9NO3/c10-7-3-1-6(2-4-7)9-5-8(11)12/h1-4,9-10H,5H2,(H,11,12)
(5)Std. InChIKey: WRUZLCLJULHLEY-UHFFFAOYSA-N

Product Name

D(-)-4-Hydroxyphenylglycine

Synthetic route

D(-)-4-Hydroxyphenylglycine Specification

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