122-87-2

Basic information

• Product Name: N-(4-HYDROXYPHENYL)GLYCINE
• Synonyms: HYDROXY-N-PHENYLGLYCINE;LABOTEST-BB LT00452650;GLYCIN;GLYCIN, PHOTO;n-(4-hydroxyphenyl)-glycin;p-hydroxyphenylglycine;TIMTEC-BB SBB003884;N-(4-HYDROXYPHENYL)GLYCINE
• CAS NO: 122-87-2
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 204-580-8
• Product Categories: Glycine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 122-87-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 244 °C (dec.)(lit.)
• Boiling Point: 295.73°C (rough estimate)
• Flash Point: 223.7 °C
• Appearance: White to beige-brown or brown-gray/Powder
• Density: 1.2917 (rough estimate)
• Vapor Pressure: 9.49E-09mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: -20°C
• Solubility: almost transparency in HCl1+1
• PKA: 2.17±0.10(Predicted)
• Merck: 14,4837
• CAS DataBase Reference: N-(4-HYDROXYPHENYL)GLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-HYDROXYPHENYL)GLYCINE(122-87-2)
• EPA Substance Registry System: N-(4-HYDROXYPHENYL)GLYCINE(122-87-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-R36/37/38
• Safety Statements: 26-36-S36-S26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 122-87-2(Hazardous Substances Data)

Usage

Chemical Properties

white to beige-brown or brown-grey powder

Uses

Photographic developer. In determination of iron; detection and determination of phosphorus and silicon. Acid indicator in bacteriology.

Definition

ChEBI: A phenol that is the N-(4-hydroxyphenyl) derivative of glycine. Synthesised by reaction of p-aminophenol with chloracetic acid, it is used as a photographic developing agent.

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)/p-1

Synthetic route

5-(P-benzyloxyphenyl) hydantoin (69489-38-9) + (D)-p-benzyloxyphenylglycine (901188-62-3) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With acetic acid; Pd-C In conc. NaOH; hydrogen	92%

2N-hydrochloric acid + 2.22N-sodium hydroxide + DL-p-hydroxyphenylglycine methyl ester (56405-21-1) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
	76%

2N-sodium hydroxide + 4-hydroxyphenyl-glycine ethyl ester (26850-28-2) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With hydrogenchloride	66.5%

sodium glyoxylate (2706-75-4) + phenol (108-95-2) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With ammonium acetate In water	50.4%

potassium glyoxylate (58645-34-4) + phenol (108-95-2) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With ammonium acetate In water	33.6%

Glyoxilic acid (298-12-4) + phenol (108-95-2) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With ammonium acetate In water	28.9%

2-((4-hydroxyphenyl)amino)acetonitrile (28363-27-1) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With sodium hydroxide

sodium monochloroacetic acid (3926-62-3) + 4-amino-phenol (123-30-8) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With water at 85 - 90℃;

4-amino-phenol (123-30-8) + chloroacetic acid (79-11-8) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With water
With water; sodium acetate

4-amino-phenol (123-30-8) + chloroacetic acid (79-11-8) → N-(hydroxyphenyl)glycine (122-87-2) + (4-hydroxy-phenylimino)-di-acetic acid (3987-54-0)

Conditions	Yield
With sodium hydroxide

water (7732-18-5) + 4-amino-phenol (123-30-8) + chloroacetic acid (79-11-8) → N-(hydroxyphenyl)glycine (122-87-2)

ethanol (64-17-5) + 4-amino-phenol (123-30-8) + glyoxal sodium disulfide → N-(hydroxyphenyl)glycine (122-87-2) + N-(4-hydroxy-phenyl)-glycine-(4-hydroxy-anilide) (83051-82-5)

4-amino-phenol (123-30-8) + 4-amino-phenol chloroacetate → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With water

4-amino-phenol (123-30-8) + sodium disulfite-compound of glyoxal → N-(hydroxyphenyl)glycine (122-87-2) + N-(4-hydroxy-phenyl)-glycine-(4-hydroxy-anilide) (83051-82-5)

Conditions	Yield
With ethanol

p-aminophenol hydrochloride (51-78-5) → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHSO3 / 20 °C 2: diluted NaOH-solution View Scheme

aqueous sodium nitrite + 5-(4'-hydroxyphenyl)hydantoic acid → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
In water

d-(-)-alpha-phenylglycinol + d-bromocamphor sulfonic acid monohydrate → D-p-hydroxyphenylglycine*d-bromocamphor sulfonic acid + N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
In water

salt of l-N-methyl ephedrine + N-salicyliden-d-p-hydroxyphenyl glycine → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
With ammonia In hydrogenchloride; dichloromethane; water

N-acetyl-D-4-hydroxyphenylglycine methyl ester → N-(hydroxyphenyl)glycine (122-87-2)

Conditions	Yield
In hydrogenchloride

N-(hydroxyphenyl)glycine (122-87-2) → DL-p-hydroxyphenylglycine methyl ester (56405-21-1)

Conditions	Yield
In methanol; HCl (gas)	99%
With thionyl chloride In methanol

methanol (67-56-1) + N-(hydroxyphenyl)glycine (122-87-2) → DL-p-hydroxyphenylglycine methyl ester (56405-21-1)

Conditions	Yield
With 732 strong acid resin at 65 - 70℃; Reagent/catalyst;	96.1%
With hydrogenchloride

sulfuric acid (7664-93-9) + N-(hydroxyphenyl)glycine (122-87-2) → DL-p-hydroxyphenylglycine methyl ester (56405-21-1)

Conditions	Yield
With ammonium hydroxide In methanol	89.5%

di-tert-butyl dicarbonate (24424-99-5) + N-(hydroxyphenyl)glycine (122-87-2) + sodium hydrogencarbonate (144-55-8) → (R)-N-(tert-butoxycarbonyl)-4-hydroxyphenylglycine methyl ester (1101105-15-0)

Conditions	Yield
With thionyl chloride In methanol; ethyl acetate	87%

di-tert-butyl dicarbonate (24424-99-5) + N-(hydroxyphenyl)glycine (122-87-2) → N-t-butoxycarbonyl-p-hydroxyphenylglycine (53249-34-6)

Conditions	Yield
With triethylamine In methanol; water; ethyl acetate; benzene	86%

N-(hydroxyphenyl)glycine (122-87-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide	80%

Isatin-5-sulfonic acid sodium salt dihydrate + N-(hydroxyphenyl)glycine (122-87-2) + isatin-5-monosulphonic acid (7313-70-4) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
With acetic acid In water	79.4%

N-(hydroxyphenyl)glycine (122-87-2) + benzyl chloroformate (501-53-1) → DL-N-benzyloxycarbonyl-p-hydroxyphenylglycine

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; water	75%

N-(hydroxyphenyl)glycine (122-87-2) + indole-2,3-dione (91-56-5) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
In water; acetic acid	68%

N-(hydroxyphenyl)glycine (122-87-2) + water (7732-18-5) + iron(III) chloride (7705-08-0) + salicylaldehyde (90-02-8) + sodium hydroxide (1310-73-2) → [FeNa((Z)-2-(2-hydroxybenzylideneamino)acetate(2-))2(H2O)4]2*2H2O

Conditions	Yield
In methanol; ethanol; water 2-(4-hydroxyphenyl)aminoacetic acid, NaOH and salicylaldehyde dissolved in MeOH; heated with stirring for 2 h; cooled to room temp.; EtOH soln. of FeCl3 added with stirring; stirred for 0.5 h; NaOH in distd. H2O added; stirred for 0.5 h; filtered; crystd. from filtrate by slow evapn. at room temp. for 1 wk; elem. anal.;	63%

N-(hydroxyphenyl)glycine (122-87-2) + 2-oxo-propionic acid (127-17-3) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
In water	62%

N-(hydroxyphenyl)glycine (122-87-2) + water (7732-18-5) + iron(III) chloride (7705-08-0) + salicylaldehyde (90-02-8) + sodium hydroxide (1310-73-2) → [Fe((E)-2-(2-hydroxybenzylideneamino)-3-hydroxy-3-(2-hydroxyphenyl)propanoate(3-))]2*7.5H2O

Conditions	Yield
In methanol; ethanol; water HOC6H4NH2CH2COOH, NaOH and HOC6H4CHO in MeOH heated with stirring (2 h);cooled to room temp.; EtOH soln. of FeCl3 added with stirring; stirred (0.5 h); aq. NaOH added; stirred (0.5 h); filtered; crystd. from filtrat e; more NaOH and HOC6H4CHO added; crystd. for 1 wk; elem. anal.;	45%

N-(hydroxyphenyl)glycine (122-87-2) + Glyoxilic acid (298-12-4) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
In water	37.2%

tridecanal (10486-19-8) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C80H33NO

Conditions	Yield
In chlorobenzene for 3h; Reflux;	35.1%

thiophene-2-carbaldehyde (98-03-3) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C72H11NOS

Conditions	Yield
In chlorobenzene for 3h; Reflux;	34.8%

caprinaldehyde (112-31-2) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C77H27NO

Conditions	Yield
In chlorobenzene for 3h; Reflux;	33.6%

N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) + isobutyraldehyde (78-84-2) → C71H15NO

Conditions	Yield
In chlorobenzene for 3h; Reflux;	33.4%

formaldehyd (50-00-0) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → N-(4-hydroxyphenyl)-3,4-fulleropyrrolidine

Conditions	Yield
In toluene Heating;	33%

N-(hydroxyphenyl)glycine (122-87-2) + butyraldehyde (123-72-8) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C71H15NO

Conditions	Yield
In chlorobenzene for 3h; Reflux;	32.3%

N-(hydroxyphenyl)glycine (122-87-2) + 3,4-dimethoxy-benzaldehyde (120-14-9) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C76H17NO3

Conditions	Yield
In chlorobenzene for 3h; Reflux;	32%

2,2'-bithiophene-5-carboxaldehyde (3779-27-9) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C76H13NOS2

Conditions	Yield
In chlorobenzene for 3h; Reflux;	31.6%

heptanal (111-71-7) + N-(hydroxyphenyl)glycine (122-87-2) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C74H21NO

Conditions	Yield
In chlorobenzene for 3h; Reflux;	30.9%

Upstream product

• 28363-27-1 2-((4-hydroxyphenyl)amino)acetonitrile 
• 123-30-8 4-amino-phenol 
• 56405-21-1 DL-p-hydroxyphenylglycine methyl ester 
• 26850-28-2 4-hydroxyphenyl-glycine ethyl ester 
• 58645-34-4 potassium glyoxylate 
• 108-95-2 phenol 
• 2706-75-4 sodium glyoxylate 
• 298-12-4 Glyoxilic acid 
• 69489-38-9 5-(P-benzyloxyphenyl)-hydantoin 
• 901188-62-3 (D)-p-benzyloxyphenylglycine 
• 51-78-5 p-aminophenol hydrochloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 79-11-8 chloroacetic acid 

Downstream Products

• 56405-21-1 DL-p-hydroxyphenylglycine methyl ester 
• 68490-25-5 C₁₇H₃₃NO₃Si₃ 
• 150-75-4 N-methyl-p-aminophenol 
• 124-38-9 carbon dioxide 
• 145005-86-3 (2E,4E)-4-(Carboxymethyl-amino)-6-[(E)-4-hydroxy-phenylimino]-hexa-2,4-dienoic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 73547-50-9 (R)-2-<3-(3,4-diacetoxybenzoyl)-3-methylureido>-2-(4-hydroxyphenyl)acetic acid 

Relevant articles and documents

Process for preparing 5-arylhydantoins using 5-hydantoin, a halogenating agent and p-phenol

The present invention provides a novel process for the preparation of 5-arylhydantoins as an important intermediate of (D)-arylglycines (e.g., (D)-p-hydroxyphenyl-glycine) useful for the synthesis of semisynthetic penicillines and cephalosporins, the process comprising (i) reacting a 5-unsubstituted hydantoin compound with a halogenating agent and (ii) reacting the resulting product with a p-unsubstituted phenol compound, the hydroxy group of which may be protected, to substitute the 5-position of the hydantoin compound with the phenol compound at the para position.

Polyunsaturated fatty acid derivatives, pharmaceutical compositions containing the same, method for the preparation thereof, and their use as medicament

The compounds of the Formula (I) STR1 wherein R1 is a C18-24 alkenyl containing at least two double bonds, or --(CH2)n --CH(NH2)m --COOH X is 0, NH or C1-4 alkyl-N, Y is CONH2, COOH or COOMe, wherein Me is hydrogen metal, and R2 is a side chain of a any amino acid except L-GLU or L-ASP at α-position or a group of Formula wherein k is zero or an integer of 1, n is zero or an integer of 1 to 3, m is zero or an integer of 1 to 4, A is hydroxyl or one A is hydroxyl and the other A is hydrogen. M is H or R1 --CO and X and R1 are as defined above and their salts having tyrosine kinase inhibitor activity can be used as antitumor agents.

Novel spergualin-related compounds and compositions

The present invention relates to novel spergualin-related compounds represented by the general formula [I]: STR1 wherein X is --(CH2)1?5 or STR2 Y is a hydrogen atom or a residue obtained by removing a hydroxyl group from the carboxyl group of an amino acid or a peptide; m is 0, 1 or 2 and n is 1 or 2, with the proviso that Y is not a hydrogen atom when n is 2 and m is 0. This compounds are stable and exhibit a high immunosuppressive activity.