CAS No.103-90-2,4-Acetamidophenol Suppliers

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Basic Information

Molecular Structure:
CAS No.:	103-90-2
Name:	4-Acetamidophenol
Article Data:	344
Cas Database

Formula:	C₈H₉NO₂
Molecular Weight:	151.165
Synonyms:	Acetamide,N-(4-hydroxyphenyl)-;Acetanilide,4'-hydroxy- (7CI,8CI);4-(Acetylamino)phenol;4-(N-Acetylamino)phenol;4-Acetamidophenol;4-Acetaminophenol;4-Hydroxyacetanilide;4'-Hydroxyacetanilide;Alpiny;Alvedon;Anhiba;Apamid;Apamide;Banesin;Ben-u-ron;Bickie-mol;Biocetamol;Cetadol;Clixodyne;Daphalgan;Datril;Dirox;Enelfa;Eu-Med;Exdol;Gattaphen T;Homoolan;Jin Gang;Korum;Lestemp;Liquagesic;Lonarid;Lyteca;Lyteca Syrup;Minoset;Minoset Plus;Momentum;Multin;N-(4-Hydroxyphenyl)acetamide;N-Acetyl-4-aminophenol;N-Acetyl-4-hydroxyaniline;Pacemo;Pacemol;Panadol;Panadol Actifast;Panadol Extend;Panaleve;Panasorb;Panets;Panodil;Paracetamol;Paracetamol DC;Paracetamole;Parageniol;Paralen;Paramol;Paraspen;Parelan;Parmol;Pasolind N;Pedric;ketamin*e ,kush available;
EINECS:	203-157-5
Density:	1.249 g/cm³
Melting Point:	168-172 °C(lit.)
Boiling Point:	387.8 °C at 760 mmHg
Flash Point:	188.4 °C
Solubility:	14 g/L (20 °C) in water
Appearance:	White crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38-52/53-36/38-40
Safety:	26-36-61-37/39-22
PSA:	49.33000
LogP:	1.42360

Synthetic route

: 99-93-4
4-Hydroxyacetophenone

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In acetonitrile at 110℃; for 1h; Solvent; Time; chemoselective reaction;	100%
With hydroxylamine hydrochloride; tetrachlorosilane at 160℃; for 0.0583333h; microwave irradiation;	92%
With mesitylenesulfonylhydroxylamine In acetonitrile at 20℃; for 6h;	92%

: 108-24-7
acetic anhydride

: 123-30-8
4-amino-phenol

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With sodium dodecyl-sulfate In water	99%
With silica gel for 0.5h; Time; Milling;	99%
With sulfuric acid supported on poly(4-vinylpyridine) (P4VP) In dichloromethane at 20℃; for 1.25h;	98%

: 2623-33-8
4-acetoxyacetanilide

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With ammonium acetate In methanol at 20℃; for 4.5h;	99%
With ytterbium(III) triflate In isopropyl alcohol for 15h; Deacetylation; Heating;	96%
With sodium perborate In methanol at 25℃; for 0.5h;	90%

: 34523-34-7
4-hydroxyacetophenone oxime

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; perfluoropinacol; 2-methoxycarbonylphenylboronic acid In nitromethane at 20℃; for 24h; Beckmann Rearrangement; chemoselective reaction;	99%
With 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione In acetonitrile at 80℃; for 0.333333h; Inert atmosphere; Schlenk technique; Green chemistry;	98%
With carbon tetrabromide; Eosin Y; N,N-dimethyl-formamide In acetonitrile at 20℃; for 14h; Beckmann Rearrangement; Irradiation; Inert atmosphere; Green chemistry;	96%

: 100-02-7
4-nitro-phenol

: 64-19-7
acetic acid

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
at 80 - 130℃; Temperature;	98%
With sodium sulfite for 16h; Reflux;	83%
With Methyl formate; dodecacarbonyl-triangulo-triruthenium at 180℃; for 8h;	92 % Chromat.
With hydrogen at 100℃; under 760.051 Torr; for 24h; Sealed tube;	82 %Chromat.
With platinum; hydrogen at 100℃; for 24h;

: 104-91-6
p-nitrosophenol

: 64-19-7
acetic acid

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
at 80 - 130℃;	98%

: 108-24-7
acetic anhydride

: 150-13-0
4-amino-benzoic acid

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With acetic acid at 80℃; for 1h; Temperature;	97.13%

: 123-30-8
4-amino-phenol

: 123-54-6
acetylacetone

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 25℃; for 8h; Green chemistry;	97%

: 101251-09-6
(4-acetylaminophenyl)boronic acid

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With water; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry;	97%
With Oxone; potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 70℃; for 1h; chemoselective reaction;

: 60-35-5
acetamide

: 123-30-8
4-amino-phenol

: 103-90-2
4-acetaminophenol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;	96%
at 150℃; for 72h; Inert atmosphere; Sealed tube; Green chemistry;	96%
With air at 150℃; for 72h; Sealed tube;	96%

Downstream Products

573-56-8

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History

Harmon Northrop Morse had already synthesized paracetamol at Johns Hopkins University via the reduction of p-nitrophenol with tin in glacial acetic acid in 1877, but it wasn't until 1887 that clinical pharmacologist Joseph von Mering tried paracetamol on patients.
In 1893, von Mering published a paper reporting on the clinical results of paracetamol with phenacetin, another aniline derivative. Von Mering claimed that, unlike phenacetin, paracetamol had a slight tendency to produce methemoglobinemia.
Paracetamol was then quickly discarded in favor of phenacetin. The sales of phenacetin established Bayer as a leading pharmaceutical company.Overshadowed in part by aspirin, introduced into medicine by Heinrich Dreser in 1899, phenacetin was popular for many decades, particularly in widely advertised over-the-counter “headache mixtures,” usually containing phenacetin, an aminopyrine derivative or aspirin, caffeine, and sometimes a barbiturate.
In 1947 David Lester and Leon Greenberg found strong evidence that paracetamol was a major metabolite of acetanilide in human blood, and in a subsequent study they reported that large doses of paracetamol given to albino rats did not cause methemoglobinemia.
It has been suggested that contamination of paracetamol with 4-aminophenol, the substance from which it was synthesized by von Mering, may be the cause for his spurious findings.
In 1953, paracetamol was first marketed in the United States by Sterling-Winthrop Co.,.
In 1956, 500 mg tablets of paracetamol went on sale in the United Kingdom under the trade name Panadol, produced by Frederick Stearns & Co, a subsidiary of Sterling Drug Inc.
In 1963, paracetamol was added to the British Pharmacopoeia, and has gained popularity since then as an analgesic agent with few side-effects and little interaction with other pharmaceutical agents.
Concerns about paracetamol's safety delayed its widespread acceptance until the 1970s, but in the 1980s paracetamol sales exceeded those of aspirin in many countries, including the United Kingdom.

Specification

The Acetaminophen with CAS registry number of 103-90-2 is also known as Acetamide,N-(4-hydroxyphenyl)-. The IUPAC name is N-(4-Hydroxyphenyl)acetamide. It belongs to product categories of Pharmaceuticals; Aromatic Phenols; Intermediates & Fine Chemicals; Lipid signaling. Its EINECS registry number is 203-157-5. In addition, the formula is C₈H₉NO₂ and the molecular weight is 151.17. This chemical is a white crystalline powder that slightly soluble in water. It may cause damage to health and should be sealed in ventilated, cool room away from fire, heat. What's more, this chemical can be used as antipyretic, analgesic, anti-rheumatic drugs.

Physical properties about Acetaminophen are:
(1)ACD/LogP: 0.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.475; (4)ACD/LogD (pH 7.4): 0.474; (5)ACD/BCF (pH 5.5): 1.352; (6)ACD/BCF (pH 7.4): 1.348; (7)ACD/KOC (pH 5.5): 43.194; (8)ACD/KOC (pH 7.4): 43.061; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.619; (13)Molar Refractivity: 42.406 cm³; (14)Molar Volume: 120.946 cm³; (15)Surface Tension: 52.801 dyne/cm; (16)Density: 1.25 g/cm³; (17)Flash Point: 188.354 °C; (18)Enthalpy of Vaporization: 66.186 kJ/mol; (19)Boiling Point: 387.831 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Acetaminophen:
Firstly, aminophenol and glacial acetic acid are added into dilute acetic acid by turns. Then the reaction mixture is heated to 150 °C for 7 hours. Secondly, adding acetic anhydride into mixture solution for another 2 hours. At last, product is obtained by rejection filtering, washing and drying. The yield is about 90%.

Uses of Acetaminophen:
It is used to produce N-acetyl-p-vinyloxyaniline by reaction with tetravinylstannane. The reaction occurs with reagents Cu(OAc)₂, O₂and solvent acetonitrile at 20 °C for 22 hours. The yield is about 90%.

Paracetamol is used to produce N-acetyl-p-vinyloxyaniline by reaction with tetravinylstannane.

Safety information of Acetaminophen:
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system, skin and is harmful if swallowed. This chemical is also harmful to aquatic organisms that may cause long-term adverse effects in the aquatic environment. However, there is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing, gloves and eye/face protection. Do not breathe dust and avoid release to the environment. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=O)NC1=CC=C(C=C1)O
2. InChI: InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
3. InChIKey: RZVAJINKPMORJF-UHFFFAOYSA-N

The toxicity data of Acetaminophen is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	LDLo	oral	50mg/kg (50mg/kg)	CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	American Journal of Emergency Medicine. Vol. 6, Pg. 510, 1988.
child	LDLo	oral	140mg/kg/7D-I (140mg/kg)	BEHAVIORAL: COMA LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"	Medical Journal of Australia. Vol. 171, Pg. 472, 1999.
child	LDLo	oral	360mg/kg/2D (360mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Journal of Pediatrics. Vol. 92, Pg. 832, 1978.
child	TDLo	oral	591mg/kg/2D-I (591mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: APLASTIC ANEMIA	Clinical Pediatrics Vol. 33, Pg. 42, 1994.
child	TDLo	oral	801mg/kg (801mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: OTHER CHANGES	Pediatrics. Vol. 61, Pg. 68, 1978.
dog	LDLo	intravenous	826mg/kg (826mg/kg)	BEHAVIORAL: ANALGESIA	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog	LDLo	oral	2gm/kg (2000mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BLOOD: CHANGES IN SPLEEN	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 24, Pg. 602, 1993.
frog	LDLo	subcutaneous	50mg/kg (50mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 33, Pg. 216, 1894.
guinea pig	LD50	oral	2620mg/kg (2620mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 479, 1958.
human	LDLo	oral	143mg/kg (143mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC	British Medical Journal. Vol. 282, Pg. 199, 1981.
human	LDLo	oral	357mg/kg (357mg/kg)	BEHAVIORAL: ANOREXIA (HUMAN GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: COMA	Lancet. Vol. 1, Pg. 66, 1973.
infant	TDLo	oral	1440mg/kg/6D (1440mg/kg)	BEHAVIORAL: IRRITABILITY GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	American Journal of Diseases of Children. Vol. 137, Pg. 386, 1983.
mammal (species unspecified)	LD50	unreported	891mg/kg (891mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(6), Pg. 22, 1983.
mammal (species unspecified)	LDLo	oral	512mg/kg (512mg/kg)		United States Patent Document. Vol. #4035499,
man	LDLo	oral	143mg/kg/24H- (143mg/kg)	BEHAVIORAL: ANOREXIA (HUMAN LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"	American Journal of Medicine. Vol. 74, Pg. 349, 1983.
man	LDLo	oral	714mg/kg (714mg/kg)	LIVER: OTHER CHANGES	Human Toxicology. Vol. 1, Pg. 25, 1981.
man	TDLo	oral	9286ug/kg (9.286mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SENSE ORGANS AND SPECIAL SENSES: OTHER: EAR SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Allergy. Vol. 50(Suppl,
man	TDLo	oral	714mg/kg (714mg/kg)	CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE	Postgraduate Medical Journal. Vol. 69, Pg. 52, 1993.
mouse	LD50	intraperitoneal	367mg/kg (367mg/kg)	BEHAVIORAL: ANALGESIA	Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 520, 1965.
mouse	LD50	oral	338mg/kg (338mg/kg)		Toxicology and Applied Pharmacology. Vol. 19, Pg. 20, 1971.
mouse	LD50	subcutaneous	310mg/kg (310mg/kg)		Human Toxicology. Vol. 3, Pg. 13S, 1984.
pig	LDLo	intravenous	1gm/kg (1000mg/kg)	LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Veterinary and Human Toxicology. Vol. 30, Pg. 324, 1988.
rat	LD50	intraperitoneal	1205mg/kg (1205mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR	Studi Sassaresi, Sezione 2. Vol. 57, Pg. 561, 1979.
rat	LD50	oral	1944mg/kg (1944mg/kg)		United States Patent Document. Vol. #4636513,
women	LDLo	oral	260mg/kg (260mg/kg)	BEHAVIORAL: COMA GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	JAMA, Journal of the American Medical Association. Vol. 236, Pg. 1874, 1976.
women	LDLo	oral	400mg/kg (400mg/kg)	BEHAVIORAL: COMA LIVER: LIVER FUNCTION TESTS IMPAIRED	Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 325, 1997.
women	LDLo	oral	650mg/kg (650mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION VASCULAR: OTHER CHANGES	American Journal of Emergency Medicine. Vol. 6, Pg. 511, 1988.
women	TDLo	oral	4962ug/kg (4.962mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS BLOOD: OTHER CHANGES LIVER: LIVER FUNCTION TESTS IMPAIRED	Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 223, 1991.
women	TDLo	oral	13mg/kg (13mg/kg)	BEHAVIORAL: EXCITEMENT	Allergy. Vol. 50(Suppl,
women	TDLo	oral	325mg/kg (325mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Postgraduate Medical Journal. Vol. 68, Pg. 116, 1992.
women	TDLo	oral	490mg/kg (490mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Southern Medical Journal. Vol. 71, Pg. 906, 1978.

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