CAS No.42924-53-8,Nabumetone Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	42924-53-8
Name:	Nabumetone
Article Data:	32

Formula:	C₁₅H₁₆O₂
Molecular Weight:	228.291
Synonyms:	1-(2'-Methoxynaphth-6'-yl)butan-3-one;4-(6-Methoxy-2-naphthyl)-2-butanone;Arthaxan;BRL 14777;Balmox;Consolan;Gambaran;Nabugesic 500;Nabumeton;Nabuser;Relafen;Relifen;Relifex;
Density:	1.084 g/cm³
Melting Point:	80-81 °C
Boiling Point:	371.1 °C at 760 mmHg
Flash Point:	165.4 °C
Solubility:	6mg/L(22.5 oC)
Appearance:	White powder
Hazard Symbols:	Xn
Risk Codes:	22-40
Safety:	36/37
PSA:	26.30000
LogP:	3.37000

Synthetic route

: 127053-22-9, 56600-90-9
4-(2-methoxynaphthalene-6-yl)but-3-en-2-one

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With hydrogen In toluene at 50℃; under 3750.38 Torr; for 1h; Catalytic behavior; Temperature; Pressure; Inert atmosphere; Schlenk technique; Autoclave;	99%
With 1% Pd on activated carbon; hydrogen In water at 45℃; under 760.051 Torr; for 15h; Reagent/catalyst; Green chemistry; chemoselective reaction;	95%
With hydrogen In N,N-dimethyl-formamide at 100℃;	90%

: 78-94-4
methyl vinyl ketone

: tris(6-methoxy-2-naphthyl)stibine

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With palladium diacetate; silver(I) acetate; acetic acid at 25℃; for 24h;	99%

: 73356-31-7
4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
palladium on charcoal catalyst In acetic acid	93%
Multi-step reaction with 3 steps 1: acetic acid; hydrogen; palladium on activated charcoal / 20 °C 2: sulfuric acid 3: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; palladium 10% on activated carbon; sulfuric acid / ethyl acetate 2: sulfuric acid 3: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr View Scheme

: 3453-33-6
6-methoxynaphthalene-2-carbaldehyde

: 67-64-1
acetone

A: C18H22O2

B: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With hydrogen; Pd/Mg-Al hydrotalcite at 74.84℃; under 3750.38 Torr; for 1.25h;	A 11 % Chromat. B 89%

...Expand

: 5111-65-9
2-Bromo-6-methoxynaphthalene

: 78-94-4
methyl vinyl ketone

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; nickel dibromide In pyridine; N,N-dimethyl-formamide at 70℃; Electrochemical reaction;	85%
Stage #1: methyl vinyl ketone With [2,2]bipyridinyl; water; cobalt(II) bromide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-Bromo-6-methoxynaphthalene With pyridine; trifluoroacetic acid; lithium bromide; zinc In N,N-dimethyl-formamide at 80℃; for 0.333333h;	50%

: 598-32-3
2-hydroxy-3-butene

: 5111-65-9
2-Bromo-6-methoxynaphthalene

A: 42924-53-8
nabumetone

B: 127053-21-8
4-(6-methoxy-2-naphthyl)-3-butene-2-ol

Conditions

Conditions	Yield
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide; water at 20℃; for 0.25h; Heck reaction; Stage #2: 2-Bromo-6-methoxynaphthalene; 4'-hydroxyacetophenone oxime palladacycle catalyst In N,N-dimethyl acetamide; water at 120℃; for 9h; Heck reaction; Further stages.;	A 82% B n/a
With sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride In various solvent(s) at 140℃; for 5h; Yield given;	A n/a B 9%

...Expand

: 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With sodium hydroxide; sodium acetate; sodium acetate trihydrate; palladium In methanol; water; hydrogen; toluene	79.7%
With sodium hydroxide; sodium acetate; sodium acetate trihydrate; palladium In methanol; water; hydrogen; toluene	79.7%

: sodium metabisulfite

: 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene	78.5%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene	78.5%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene	74.8%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene	74.8%

: 598-32-3
2-hydroxy-3-butene

: 5111-65-9
2-Bromo-6-methoxynaphthalene

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium formate; sodium hydrogencarbonate; Pd-benzothiazole carbene at 130℃; for 3h; Heck reaction;	75%
With tetrabutylammomium bromide; sodium hydrogencarbonate; palladium dichloride at 120℃; for 6h; Heck coupling;	74%
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 0.25h; Heck reaction; Stage #2: 2-Bromo-6-methoxynaphthalene; 4'-hydroxyacetophenone oxime palladacycle catalyst In N,N-dimethyl acetamide at 120℃; for 24h; Heck reaction; Further stages.;	90 % Spectr.
With Fe3O4@chitosan nanoparticles/Pd In ethanol at 140℃; for 24h;

: 3453-33-6
6-methoxynaphthalene-2-carbaldehyde

: 67-64-1
acetone

: 42924-53-8
nabumetone

Conditions

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; carbon monoxide In neat (no solvent) at 200℃; for 72h; Temperature; Autoclave;	75%
With hydrogen; magnesium oxide; palladium at 59.84℃; under 3750.38 Torr; for 1h;	98 % Chromat.

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Specification

The IUPAC name of this chemical is 4-(6-methoxynaphthalen-2-yl)butan-2-one. With the CAS registry number 42924-53-8, it is also named as Nabumetone. The product's categories are Active Pharmaceutical Ingredients; Anti-Inflammatory; Analgesic; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. It is white powder which is a non-steroidal anti-inflammatory drug (NSAID), the only 1-naphthaleneacetic acid derivative. When heated to decomposition it emits acrid smoke and irritating fumes.

The other characteristics of 4-(6-Methoxy-2-naphthyl)-2-butanone can be summarized as: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.82; (4)ACD/LogD (pH 7.4): 2.82; (5)ACD/BCF (pH 5.5): 81.48; (6)ACD/BCF (pH 7.4): 81.48; (7)ACD/KOC (pH 5.5): 811.97; (8)ACD/KOC (pH 7.4): 811.97; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.575; (13)Molar Refractivity: 69.61 cm³; (14)Molar Volume: 210.5 cm³; (15)Polarizability: 27.59×10^-24 cm³; (16)Surface Tension: 39.8 dyne/cm; (17)Enthalpy of Vaporization: 61.8 kJ/mol; (18)Vapour Pressure: 1.06E-05 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Tautomer Count: 3; (21)Exact Mass: 228.11503; (22)MonoIsotopic Mass: 228.11503; (23)Topological Polar Surface Area: 26.3; (24)Heavy Atom Count: 17; (25)Complexity: 262.

Preparation of 4-(6-Methoxy-2-naphthyl)-2-butanone: It can be obtained by but-3-en-2-one and tris-(6-methoxy-naphthalen-2-yl)-stibane. This reaction needs reagents Pd(OAc)₂, AgOAc and AcOH at temperature of 25 °C. The reaction time is 24 hours. The yield is 99%.

Uses of 4-(6-Methoxy-2-naphthyl)-2-butanone: It is used to treat pain or inflammation caused by arthritis. And it works by reducing the effects of hormones that cause pain and inflammation. In addition, it can react with thiazolidine-2,4-dione to get 5-[3-(6-methoxy-naphthalen-2-yl)-1-methyl-propylidene]-thiazolidine-2,4-dione. This reaction needs reagent benzoic acid, piperidine and solvent toluene by heating. The yield is 80%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. And it has limited evidence of a carcinogenic effect. If you want to contact this product, you must wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(C)CCc1ccc2c(c1)ccc(OC)c2
2. InChI:InChI=1/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
3. InChIKey:BLXXJMDCKKHMKV-UHFFFAOYAR

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
monkey	LD50	oral	3200mg/kg (3200mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
mouse	LD50	intraperitoneal	2380mg/kg (2380mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
mouse	LD50	oral	4290mg/kg (4290mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: OTHER CHANGES	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
mouse	LD50	subcutaneous	> 10gm/kg (10000mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat	LD50	intraperitoneal	1520mg/kg (1520mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat	LD50	oral	3880mg/kg (3880mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: OTHER CHANGES	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
rat	LD50	subcutaneous	> 10gm/kg (10000mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 2939, 1988.
women	TDLo	oral	1260mg/kg/6W- (1260mg/kg)	LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL) LUNGS, THORAX, OR RESPIRATION: COUGH LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Postgraduate Medical Journal. Vol. 67, Pg. 1021, 1991.