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15687-27-1

Basic Information
CAS No.: 15687-27-1
Name: Ibuprofen
Article Data: 259
Cas Database
Molecular Structure:
Molecular Structure of 15687-27-1 (Ibuprofen)
Formula: C13H18O2
Molecular Weight: 206.285
Synonyms: Benzeneacetic acid, .alpha.-methyl-4- (2-methylpropyl)-;2-(4-Isobutylphenyl)propanoic acid;(.+ -.)-2-(p-Isobutylphenyl)propionic acid;Benzeneacetic acid,R-methyl-4-(2-methylpropyl)-;2-(4-Isobutylphenyl)propionic Acid;Motrin;(2RS)-2-[4-(2-methylpropyl)phenyl]propanoic acid;(4-Isobutylphenyl)-alpha-methylacetic acid;(+-)-ibuprofen;(+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid;
EINECS: 239-784-6
Density: 1.029 g/cm3
Melting Point: 77-78 °C(lit.)
Boiling Point: 319.6 °C at 760 mmHg
Flash Point: 216.7 °C
Solubility: insoluble in water
Appearance: Colourless, crystalline solid
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-63-51/53
Safety: 61-36/37
Transport Information: N/A
PSA: 37.30000
LogP: 3.07320
Synthetic route
51146-56-6

(S)-ibuprofen

15687-27-1

ibuprofen

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; for 5h; Racemization;100%
With triethylamine at 110℃; for 5h; Product distribution; Further Variations:; Reagents; Temperatures; Racemization;
at 230℃; for 4h; Kinetics; Time; Temperature; Inert atmosphere;
68064-52-8

S-methyl 2-(4-isobutylphenyl)thiopropionate

15687-27-1

ibuprofen

Conditions
ConditionsYield
With potassium hydroxide In acetone for 2h; Heating;100%
201230-82-2

carbon monoxide

62049-65-4

S-(-)-1-(-)-[4-isobutylphenyl]-chloroethane

15687-27-1

ibuprofen

Conditions
ConditionsYield
With hydrogenchloride; water; triphenylphosphine; 1% Rh/C In butanone at 115℃; under 41372.9 Torr;99%
With hydrogenchloride; water; triphenylphosphine; 1% Ni/C In butanone at 115℃; under 41372.9 Torr;99%
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Ni/ZSM 5 In butanone at 115℃; under 41372.9 Torr;99%
201230-82-2

carbon monoxide

40150-92-3

1-(4-isobutylphenyl)ethanol

15687-27-1

ibuprofen

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Ni/ZSM 5 In butanone at 115℃; under 41372.9 Torr;99%
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Pd/C In butanone at 115℃; under 41372.9 Torr;99%
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Ni/C In toluene at 115℃; under 41372.9 Torr;99.2%
201230-82-2

carbon monoxide

63444-56-4

p-isobutylstyrene

15687-27-1

ibuprofen

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% platinum on carbon In butanone at 115℃; under 41372.9 Torr;99%
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Co/C In butanone at 115℃; under 41372.9 Torr;99%
With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; 1% Rh/C In butanone at 115℃; under 41372.9 Torr;98.8%
86618-05-5

tert-butyl 2-(4-isobutylphenyl)propanoate

15687-27-1

ibuprofen

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 12h;99%
With trifluoroacetic acid In dichloromethane at 23℃; for 45h; Inert atmosphere; Sealed tube;115 mg
With hydrogenchloride; water at 20℃; for 16h; Inert atmosphere;9.5 mg

2-(1-bromoethyl)-2-p-butylphenyl-1,3-epoxypentane

15687-27-1

ibuprofen

Conditions
ConditionsYield
Stage #1: 2-(1-bromoethyl)-2-p-butylphenyl-1,3-epoxypentane With zinc 2-(6-methoxylnaphthyl)propionate In toluene for 3h; Reflux;
Stage #2: With sodium hydroxide In toluene for 3.5h; Reflux;
Stage #3: With water; pyrographite In toluene for 0.5h; Reflux;
97.2%
5%-palladium charcoal

5%-palladium charcoal

6448-14-2

2-(4-isobutylphenyl)acrylic acid

15687-27-1

ibuprofen

Conditions
ConditionsYield
In ethanol97.1%
In ethanol
41283-72-1

ibuprofen ethyl ester

15687-27-1

ibuprofen

Conditions
ConditionsYield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;97%
With sodium hydroxide In methanol for 4h; Heating;90%
With hydrogenchloride; sodium hydroxide 1.) reflux;88%
31469-22-4

1,1-bis(trimethylsilyloxy)prop-1-ene

2051-99-2

1-bromo-4-isobutylbenzene

15687-27-1

ibuprofen

Conditions
ConditionsYield
Stage #1: 1-bromo-4-isobutylbenzene With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene for 0.666667h; Inert atmosphere;
Stage #2: 1,1-bis(trimethylsilyloxy)prop-1-ene In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; for 12h; Sealed tube; Inert atmosphere;
96%
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Chemistry

IUPAC Name: 2-[4-(2-Methylpropyl)phenyl]propanoic acid
Molecular Formula: C13H18O2
Molecular Weight: 206.28
Molecular Structure:
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.518
Molar Refractivity: 60.77 cm3
Molar Volume: 200.3 cm3
Surface Tension: 38 dyne/cm
Density: 1.029 g/cm3
Flash Point: 216.7 °C
Melting Point: 77-78 °C(lit.)
Enthalpy of Vaporization: 59.25 kJ/mol
Boiling Point: 319.6 °C at 760 mmHg
Vapour Pressure: 0.000139 mmHg at 25°C
Appearance: Colourless, Crystalline Solid
Water Solubility: insoluble
Stability: Stable. Combustible. Incompatible with strong oxidizing agents
Appearance: Colourless, Crystalline Solid
SMILES: O=C(O)C(c1ccc(cc1)CC(C)C)C
InChI: InChI=1/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
InChIKey: HEFNNWSXXWATRW-UHFFFAOYAB
Std. InChI: InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
Std. InChIKey: HEFNNWSXXWATRW-UHFFFAOYSA-N
Product Categories of Ibuprofen (CAS NO.15687-27-1): Active Pharmaceutical Ingredients;API;APIs;Inhibitors;Intermediates & Fine
Chemicals;Pharmaceuticals;API's;Lipid signaling

History

 Ibuprofen was derived from propionic acid by the research arm of Boots Group during the 1960s. The drug was launched as a treatment for rheumatoid arthritis in the United Kingdom in 1969, and in the United States in 1974. Famously, it is recorded that Dr. Adams initially tested his drug on a hangover. He was subsequently awarded an OBE in 1987.

Uses

  Ibuprofen (CAS NO.15687-27-1) can be available in topical gel form which is absorbed through the skin, and can be used for sports injuries, with less risk of digestive problems. Ibuprofen is sometimes used for the treatment of acne, because of its anti-inflammatory properties.

Production

 Ibuprofen(15687-27-1) can be synthesized from isobutylbenzene by a Friedel-Crafts  acylation with acetyl chloride, followed by formation of a cyanohydrin. Treatment with hydrogen iodide and phosphorus reduces the benzylic hydroxyl to a hydrogen and hydrolyzes the nitrile to a carboxylic acid.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 469mg/kg (469mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Emergency Medicine. Vol. 15, Pg. 1308, 1986.
child TDLo oral 480mg/kg/17D- (480mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Journal of Pediatrics. Vol. 90, Pg. 657, 1977.
child TDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Annals of Pharmacotherpy. Vol. 31, Pg. 432, 1997.
guinea pig LD50 oral 495mg/kg (495mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster LD50 oral 1690mg/kg (1690mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
mammal (species unspecified) LD50 oral 1gm/kg (1000mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 42, Pg. 545, 1985.
man LDLo oral 171mg/kg (171mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
British Medical Journal. Vol. 281, Pg. 1458, 1980.
man TDLo oral 120mg/kg/W-I (120mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
New York State Journal of Medicine. Vol. 78, Pg. 1239, 1978.
man TDLo oral 180mg/kg/3W-I (180mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" American Journal of Gastroenterology. Vol. 91, Pg. 1626, 1996.
man TDLo oral 429mg/kg (429mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 315, 1994.
man TDLo oral 800mg/kg (800mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Postgraduate Medical Journal. Vol. 69, Pg. 575, 1993.
man TDLo oral 1028mg/kg (1028mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" American Journal of Emergency Medicine. Vol. 13, Pg. 375, 1995.
mouse LD50 intraperitoneal 320mg/kg (320mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Toxicology and Applied Pharmacology. Vol. 15, Pg. 310, 1969.
Link to PubMed
mouse LD50 oral 740mg/kg (740mg/kg) BEHAVIORAL: ANALGESIA Pharmaceutical Chemistry Journal Vol. 14, Pg. 119, 1980.
mouse LD50 rectal 620mg/kg (620mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
mouse LD50 subcutaneous 395mg/kg (395mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rabbit LD50 oral 1400mg/kg (1400mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rabbit LD50 rectal 830mg/kg (830mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1032, 1990.
rat LD50 intraperitoneal 626mg/kg (626mg/kg) BEHAVIORAL: ANALGESIA Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 1006, 1977.
rat LD50 oral 636mg/kg (636mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984.
rat LD50 rectal 530mg/kg (530mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
rat LD50 subcutaneous 740mg/kg (740mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 24, Pg. 415, 1982.
women TDLo oral 8mg/kg (8mg/kg) BEHAVIORAL: HEADACHE JAMA, Journal of the American Medical Association. Vol. 239, Pg. 1062, 1978.
women TDLo oral 132mg/kg/6D-I (132mg/kg) BLOOD: THROMBOCYTOPENIA British Journal of Clinical Practice. Vol. 48, Pg. 51, 1994.
women TDLo unreported 96mg/kg/3D-I (96mg/kg) SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE JAMA, Journal of the American Medical Association. Vol. 248, Pg

Safety Profile

Hazard Codes: HarmfulXn,DangerousN
Risk Statements: 22-63-51/53
R22: Harmful if swallowed 
R63: Possible risk of harm to the unborn child 
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 61-36/37
S61: Avoid release to the environment. Refer to special instructions safety data sheet 
S36/37:  Wear suitable protective clothing and gloves
RIDADR: 2811
WGK Germany: 3
RTECS: MU6640000
HazardClass: 6.1(b)
PackingGroup: III

Specification

  Ibuprofen (CAS NO.15687-27-1), its Synonyms are (+-)-2-(p-Isobutylphenyl)propionic acid ; (+-)-Ibuprofen ; (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid ; (+-)-p-Isobutylhydratropic acid ; (4-Isobutylphenyl)-alpha-methylacetic acid ; Acide (isobutyl-4-phenyl)-2 propionique ; Benzeneacetic acid, alpha-methyl-4-(2-methylpropyl)- ; p-Isobutyl-2-phenylpropionic acid .