Salicyluric acid supplier | CasNO.487-54-7

Name
2-HYDROXYHIPPURIC ACID
EINECS 207-661-6
CAS No. 487-54-7
Article Data10
CAS DataBase
Density 1.401 g/cm³
Solubility soluble in water
Melting Point 164-169 °C
Formula C₉H₉NO₄
Boiling Point 489.79 °C at 760 mmHg
Molecular Weight 195.175
Flash Point 250.016 °C
Transport Information
Appearance light gray crystalline powder
Safety 24/25-36/37/39-27-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Hippuricacid, o-hydroxy- (8CI);Salicyluric acid (6CI);(2-Hydroxybenzoyl)glycine;2-Hydroxyhippuric acid;N-(o-Hydroxybenzoyl)glycine;N-Salicyloylglycine;NSC524135;Salicyloylglycine;o-Hydroxyhippuric acid;
PSA 86.63000
LogP 0.59750

Synthetic route

: 178633-73-3
(2-Hydroxy-benzoylamino)-acetic acid benzyl ester

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol 0 deg C, then 0oom temp., overnight;	92%

: 56-40-6
glycine

: 1441-87-8
salicyloyl chloride

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide at 20℃;	90%
With sodium hydroxide; water Erwaermen des nach dem Ansaeuern erhaltenen Reaktionsprodukts mit wss. Natronlauge;

: 27796-49-2
(2-methoxyphenyl)(methoxycarbonylmethylamino)-methanone

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
	40%

: 64-17-5
ethanol

: 2-glycyloxy-benzoic acid ; perchlorate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
at 20℃; Kinetics;

: 56145-98-3
N-salicyloyl-glycine amide

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide

: 856119-90-9
2-azidoacetoxy-benzoic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With acetic acid methyl ester; platinum Hydrogenation;
With palladium on activated charcoal; acetic acid Hydrogenation;

: 2-(N-benzyloxycarbonyl-glycyloxy)-benzoic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With palladium on activated charcoal; 2-methoxy-ethanol Hydrogenolyse;

: 116601-30-0
2-(N-benzyloxycarbonyl-glycyloxy)-benzoic acid benzyl ester

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With palladium on activated charcoal; 2-methoxy-ethanol Hydrogenolyse;

: 92505-60-7
2-methoxycarbonyloxy-benzoyl chloride

: 56-40-6
glycine

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide Behandeln des Reaktionsgemischs mit konz. Natronlauge;

: 54539-61-6
2-hydroxybenzoyl azide

: 56-40-6
glycine

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide

: C12H17NO4Si

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide for 2h;

: 61141-14-8
anionic phenyl salicylate

: 56-40-6
glycine

A: 487-54-7
Salicyluric acid

B: 69-72-7
salicylic acid

C: 108-95-2
phenol

Conditions

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 35℃; Rate constant; different contents of CH3CN;

...Expand

: 50331-25-4
(2,4-dioxo-4H-benzo[e][1,3]oxazin-3-yl)-acetic acid

: ammonium hydroxide

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
at 100℃; im Rohr;

2-glycyloxy-benzoic acid amide perchlorate: 2-glycyloxy-benzoic acid amide perchlorate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With sodium hydroxide

2-glycyloxy-benzoic acid-perchlorate: 2-glycyloxy-benzoic acid-perchlorate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With water

carbonylsalicylic acid: carbonylsalicylic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With ammonium hydroxide at 100℃; im Bombenrohr;

: 92505-60-7
2-methoxycarbonyloxy-benzoyl chloride

glycocoll ester: glycocoll ester

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With diethyl ether Verseifen des Reaktionsproduktes mit Natronlauge;

: 119-36-8
methyl salicylate

sodium-salt of glycine: sodium-salt of glycine

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
With ethanol

: 54539-61-6
2-hydroxybenzoyl azide

: furan-2,3,5(4H)-trione pyridine (1:1)

: 56-40-6
glycine

A: 487-54-7
Salicyluric acid

B compound (mp: 230-231 degree ): compound (mp: 230-231 degree )

...Expand

: 7601-90-3
perchloric acid

: 2-glycyloxy-benzoic acid ; perchlorate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
at 20℃; Kinetics;

: 7732-18-5
water

: 2-glycyloxy-benzoic acid ; perchlorate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
at 20℃; Kinetics;

: 109-86-4
2-methoxy-ethanol

: 116601-30-0
2-(N-benzyloxycarbonyl-glycyloxy)-benzoic acid benzyl ester

palladium/charcoal: palladium/charcoal

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Hydrogenolyse;

...Expand

: 856119-90-9
2-azidoacetoxy-benzoic acid

: 64-19-7
acetic acid

palladium/charcoal: palladium/charcoal

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 79-20-9
acetic acid methyl ester

: 856119-90-9
2-azidoacetoxy-benzoic acid

platinum: platinum

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 69-72-7
salicylic acid

diazotized 4.4'-diamino-stilbene-disulfonic acid-(2.2'): diazotized 4.4'-diamino-stilbene-disulfonic acid-(2.2')

A: 487-54-7
Salicyluric acid

B compound (mp: 230-231 degree ): compound (mp: 230-231 degree )

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / 1.) N-cyclohexyl-N'-<2-(4-methylmorpholin-4-ylium)ethyl>carboximide toluene-4-sulfonate; 2.) Et3N / acetonitrile / 1.) 30 min.; 2.) 0 deg C --> room temp., overnight 2: 92 percent / H2 / Pd/C / methanol / 0 deg C, then 0oom temp., overnight View Scheme

...Expand

: 579-75-9
2-Methoxybenzoic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 31 percent / chloroethylcarbonate / tetrahydrofuran 2: 40 percent View Scheme

: 14216-34-3
2-methoxycarbonyloxy-benzoic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5 2: diethyl ether / Verseifen des Reaktionsproduktes mit Natronlauge View Scheme
Multi-step reaction with 2 steps 1: PCl5 2: NaOH-solution / Behandeln des Reaktionsgemischs mit konz. Natronlauge View Scheme

: 118-58-1
benzyl salicylate

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: palladium/charcoal; 2-methoxy-ethanol / Hydrogenolyse View Scheme

: 69-72-7
salicylic acid

: 487-54-7
Salicyluric acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethylaniline; benzene 2: PCl5 3: diethyl ether / Verseifen des Reaktionsproduktes mit Natronlauge View Scheme
Multi-step reaction with 2 steps 1: PCl5; diethyl ether; pyridine 2: palladium/charcoal; 2-methoxy-ethanol / Hydrogenolyse View Scheme
Multi-step reaction with 3 steps 1: dimethylaniline; benzene 2: PCl5 3: NaOH-solution / Behandeln des Reaktionsgemischs mit konz. Natronlauge View Scheme
Multi-step reaction with 2 steps 1: chloroform; pyridine 2: platinum; methyl acetate / Hydrogenation View Scheme

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 99-61-6
3-nitro-benzaldehyde

: 16352-91-3
2-{4-[3-(nitrobenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl]}phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	88%

...Expand

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 123-08-0
4-hydroxy-benzaldehyde

: 2-{4-[4-(acetoxybenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl]}phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	88%

...Expand

: 487-54-7
Salicyluric acid

: 75755-40-7
2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine

: 192046-51-8
2-Hydroxy-N-{[1-methyl-1-(methyl-phenyl-carbamoyl)-ethylcarbamoyl]-methyl}-benzamide

Conditions

Conditions	Yield
In acetonitrile 0 deg C --> room temp., overnight;	86%

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 100-10-7
4-dimethylamino-benzaldehyde

: 16352-93-5
2-{4-[4-(dimethylamino)benzylidene]-5-oxo-4,5-dihydrooxazol-2-yl}phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	85%

...Expand

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 104-88-1
4-chlorobenzaldehyde

: 2-{4-[4-(chlorobenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl]}phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	85%

...Expand

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 1122-91-4
4-bromo-benzaldehyde

: 2-{4-[4-(bromobenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl]}phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	85%

...Expand

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 16352-92-4
2-[4-(3,4-dimethoxybenzylidene)-5-oxo-4,5-dihydrooxazol-2-yl]phenyl acetate

Conditions

Conditions	Yield
With sodium acetate Erlenmeyer-Plochl-Bergmann; Reflux;	80%

...Expand

: 487-54-7
Salicyluric acid

: 6038-19-3
3-aminodihydrothiophen-2(3H)-one hydrochloride

: 1258323-53-3
2-hydroxy-N-(2-oxo-2-(2-oxotetrahydrothiophen-3-ylamino)ethyl)benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 60℃; for 1h;	80%

: 504-64-3
carbon suboxide

: 487-54-7
Salicyluric acid

: [(2-Hydroxy-4,5-dioxo-4H,5H-pyrano[3,2-c]chromene-3-carbonyl)-amino]-acetic acid

Conditions

Conditions	Yield
In acetone 0 deg C, 5 h then r.t., 48 h;	70%

: copper(II) perchlorate hexahydrate

: 487-54-7
Salicyluric acid

: Cu(2+)*2C6H4(OH)CONHCH2COO(1-)*3H2O=Cu(C6H4(OH)CONHCH2COO)2*3H2O

Conditions

Conditions	Yield
With triethylamine In methanol addn. of Et3N (1 equiv.) to ligand, addn. of Cu(ClO4)2 (0.5 equiv.), standing for 2-3 days (pptn.); collection (filtration), recrystn. (50% Me2CO);	70%

: 504-64-3
carbon suboxide

: 487-54-7
Salicyluric acid

: [(2,4-Dioxo-chroman-3-carbonyl)-amino]-acetic acid

Conditions

Conditions	Yield
In acetone C3O2:acetone=1:500; 0 deg C, 4 h then r.t., 48 h;	68%

: 487-54-7
Salicyluric acid

: 56-17-7
cystamine dihydrochioride

: 1429128-83-5
N,N'-(2,2'-(2,2'-disulfanediylbis(ethane-2,1-diyl)bis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(2-hydroxybenzamide)

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 60℃; for 1h;	65%

: 487-54-7
Salicyluric acid

: 7646-85-7
zinc(II) chloride

: Zn(2+)*2C6H4(OH)CONHCH2COO(1-)*5H2O=Zn(C6H4(OH)CONHCH2COO)2*5H2O

Conditions

Conditions	Yield
With triethylamine In methanol addn. of Et3N (1 equiv.) to ligand, addn. to ZnCl2 (0.5 equiv.), stirring for 2 days (pptn); collection (filtration), drying (vac., over P2O5); elem. anal.;	56%

: cobalt(II) chloride hexahydrate

: 487-54-7
Salicyluric acid

: Co(2+)*2C6H4(OH)CONHCH2COO(1-)*H2O*CH3OH=Co(C6H4(OH)CONHCH2COO)2*H2O*CH3OH

Conditions

Conditions	Yield
With triethylamine In methanol addn. of Et3N (1 equiv.) to ligand, addn. to CoCl2 (0.5 equiv.), stirring for 24 h (pptn.); collection (filtration), drying (vac. over P2O5); elem. anal.;	53%

: oxovanadium(IV) sulfate

: 487-54-7
Salicyluric acid

: VO(2+)*H(1+)*OC6H4C(O)NCH2COO(3-)*2H2O=VO(OC6H4C(O)NCH2COO)H(H2O)2

Conditions

Conditions	Yield
With AcONa*3H2O; NaOH In ethanol; water N2-atmosphere; dropwise addn. of 1 equiv. VOSO4 to mixt. of ligand and AcONa (in 50% aq. EtOH), pH-adjustment to 4.5 (NaOH); standing for 1 week (pptn.), collection (filtration), washing (aq. EtOH), drying (vac.); elem. anal.;	40%

: copper(II) perchlorate hexahydrate

: 487-54-7
Salicyluric acid

: Cu(3+)*C6H4(O)CONCH2COO(3-)*2H2O*CH3OH=CuC9H6NO4*2H2O*CH3OH

Conditions

Conditions	Yield
With triethylamine In methanol addn. of Et3N (2 equiv.) into soln. of ligand, addn. to soln. of Cu(ClO4)2 (1 equiv.), stirring 6 h; collection (filtration), drying (60°C); elem. anal.;	35%

: 67-56-1
methanol

: 487-54-7
Salicyluric acid

: 55493-89-5
salicyluric acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride

: 487-54-7
Salicyluric acid

: furan-2,3,5(4H)-trione pyridine (1:1)

A: 56-40-6
glycine

B: 69-72-7
salicylic acid

...Expand

: 487-54-7
Salicyluric acid

: 108-24-7
acetic anhydride

: 100-52-7
benzaldehyde

: 16352-89-9
2-(2-acetoxy-phenyl)-4-((Z)-benzyliden)-4H-oxazol-5-one

Conditions

Conditions	Yield
With sodium acetate

...Expand

Salicyluric acid Specification

The Salicyluric acid with CAS registry number of 487-54-7 is also known as 2-Hydroxyhippuric acid. The IUPAC name is 2-[(2-Hydroxybenzoyl)amino]acetic acid. It belongs to product categories of Aromatics Compounds; Aromatics. Its EINECS registry number is 207-661-6. In addition, the formula is C₉H₉NO₄ and the molecular weight is 195.17. This chemical is stable at normal temperature and pressure, and it should be sealed in a ventilated and dry place. What's more, it is a light gray crystalline powder.

Physical properties about Salicyluric acid are: (1)ACD/LogP: 0.81; (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; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 5; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.604; (11)Molar Refractivity: 47.955 cm³; (12)Molar Volume: 139.342 cm³; (13)Surface Tension: 65.897 dyne/cm; (14)Density: 1.401 g/cm³; (15)Flash Point: 250.016 °C; (16)Enthalpy of Vaporization: 79.642 kJ/mol; (17)Boiling Point: 489.79 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Salicyluric acid: it is prepared by reaction of (2-hydroxy-benzoylamino)-acetic acid benzyl ester. The reaction needs reagent H₂, catalyst Pd/C and solvent methanol at the temperature of 0 °C over night. The yield is about 92%.

Salicyluric acid is prepared by reaction of (2-hydroxy-benzoylamino)-acetic acid benzyl ester.

Uses of Salicyluric acid: it is used to produce [(2-hydroxy-4,5-dioxo-4H,5H-pyrano[3,2-c]chromene-3-carbonyl)-amino]-acetic acid by reaction with propadienedione. The reaction occurs with solvent acetone at 0 °C for 5 hours and r.t. for 48 hours. The yield is about 70%.

Salicyluric acid is used to produce [(2-hydroxy-4,5-dioxo-4H,5H-pyrano[3,2-c]chromene-3-carbonyl)-amino]-acetic acid by reaction with propadienedione.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. After using it, take off immediately all contaminated clothing. 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. Canonical SMILES: C1=CC=C(C(=C1)C(=O)NCC(=O)O)O
2. InChI: InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
3. InChIKey: ONJSZLXSECQROL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	oral	> 1gm/kg (1000mg/kg)		Farmaco, Edizione Scientifica. Vol. 30, Pg. 399, 1975.
mouse	LDLo	intravenous	600mg/kg (600mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES CARDIAC: CHANGE IN RATE	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
pigeon	LDLo	intravenous	2080mg/kg (2080mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CHANGE IN RATE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
pigeon	LDLo	subcutaneous	5730mg/kg (5730mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES CARDIAC: CHANGE IN RATE	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
rat	LD50	subcutaneous	3gm/kg (3000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CHANGE IN RATE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.

Product Name

2-HYDROXYHIPPURIC ACID

Synthetic route

Salicyluric acid Specification

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