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94-26-8

Basic Information
CAS No.: 94-26-8
Name: Benzoic acid,4-hydroxy-, butyl ester
Molecular Structure:
Molecular Structure of 94-26-8 (Benzoic acid,4-hydroxy-, butyl ester)
Formula: C11H14O3
Molecular Weight: 194.25
Synonyms: Benzoicacid, p-hydroxy-, butyl ester (6CI,8CI);4-(Butoxycarbonyl)phenol;4-Hydroxybenzoic acid butyl ester;Aseptoform Butyl;Butoben;Butyl4-hydroxybenzoate;Butyl Butex;Butyl Tegosept;Butyl chemosept;Butylp-hydroxybenzoate;Butyl parabens;Butyl parasept;Mekkings B;NSC 13164;NSC 8475;Nipabutyl;Preserval B;SPF;Solbrol B;Tegosept Butyl;n-Butyl 4-hydroxybenzoate;n-Butylparaben;p-Hydroxybenzoic acid butyl ester;Butyl paraben;
EINECS: 202-318-7
Density: 1.108 g/cm3
Melting Point: 67-70 °C(lit.)
Boiling Point: 309.2 °C at 760 mmHg
Flash Point: 129.2 °C
Solubility: water: <0.1 g/100 mL at 17 °C
Appearance: white crystalline powder
Hazard Symbols:
Risk Codes: 36/37/38
Safety: 22-24/25
Transport Information:
PSA: 46.53000
LogP: 2.34910
Synthetic route
71-36-3

butan-1-ol

99-96-7

4-hydroxy-benzoic acid

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With sulfuric acid In toluene Esterification; Heating;99%
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 125 - 135℃; for 3h;95.3%
With benzimidazole bisulfate ionic liquid Reflux;95.3%
251640-53-6

n-butyl 4-(methoxymethoxy)benzoate

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In 1,2-dichloro-ethane at 40℃;91%
99-76-3

methyl 4-hydroxylbenzoate

71-36-3

butan-1-ol

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With Zn4(OCOCF3)6O In di-isopropyl ether for 40h; Heating;76%
37170-50-6

di(methyl)tert-butyl(n-butoxy)silane

123-08-0

4-hydroxy-benzaldehyde

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; Selectfluor In acetonitrile at 20℃; for 8h; Inert atmosphere; Irradiation;73%
56-23-5

tetrachloromethane

71-36-3

butan-1-ol

108-95-2

phenol

A

94-26-8

4-hydroxybenzoic acid, butyl ester

B

2052-14-4

n-butyl salicylate

Conditions
ConditionsYield
With diiron nonacarbonyl at 130℃; for 6h; Inert atmosphere; Sealed tube;A 62%
B 38%
123-08-0

4-hydroxy-benzaldehyde

71-36-3

butan-1-ol

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
Stage #1: 4-hydroxy-benzaldehyde; butan-1-ol With tris(pentafluorophenyl)borate for 0.25h; Green chemistry;
Stage #2: With tert.-butylhydroperoxide In decane for 36h; Green chemistry;
61%
124-38-9

carbon dioxide

16909-23-2

tetra-n-butylammonium phenolate

A

94-26-8

4-hydroxybenzoic acid, butyl ester

B

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With potassium carbonate at 125℃; under 37503 Torr; for 5h; Kolbe-Shmitt reaction;A 10 % Chromat.
B 35 % Chromat.
106-41-2

4-bromo-phenol

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With CO; palladium-carbon
109-69-3

n-Butyl chloride

1286216-54-3

1-ethyl-3-methylimidazolium 4-hydroxybenzoate

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
at 80℃; for 6h;68.7 %Spectr.
619-57-8

p-hydroxybenzamide

71-36-3

butan-1-ol

94-26-8

4-hydroxybenzoic acid, butyl ester

Conditions
ConditionsYield
With zirconium-based metal-organic framework at 150℃; for 72h;72 %Spectr.
94-26-8

4-hydroxybenzoic acid, butyl ester

98-59-9

p-toluenesulfonyl chloride

butyl 4-(tosyloxy)benzoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 2.25h; Inert atmosphere;96%
94-26-8

4-hydroxybenzoic acid, butyl ester

butyl 4-trimethylsiloxybenzoate

Conditions
ConditionsYield
With Hg; 1,1,1,3,3,3-hexamethyl-disilazane94%
94-26-8

4-hydroxybenzoic acid, butyl ester

107-30-2

chloromethyl methyl ether

251640-53-6

n-butyl 4-(methoxymethoxy)benzoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Etherification;92%
94-26-8

4-hydroxybenzoic acid, butyl ester

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

1333343-65-9

4{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}benzoic acid butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;90.6%
94-26-8

4-hydroxybenzoic acid, butyl ester

932-87-6

1-Bromo-2-phenylacetylene

C19H19BrO3

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; under air; sealed tube; stereoselective reaction;88%
94-26-8

4-hydroxybenzoic acid, butyl ester

139152-08-2

4,5-dichlorophthalonitrile

dibutyl 4,4’-[(1,2-phenylene)bis(oxy)dibenzoate]-2,3-dicarbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 72h; Inert atmosphere;88%
94-26-8

4-hydroxybenzoic acid, butyl ester

51762-67-5

3-nitrobenzene-1,2-dicarbonitrile

3-[4-(butoxycarbonyl)phenoxy]phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;87.2%
94-26-8

4-hydroxybenzoic acid, butyl ester

C10H22Cl2N7P3

C32H48N7O6P3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 120h; Inert atmosphere; Cooling with ice; Reflux;85%
94-26-8

4-hydroxybenzoic acid, butyl ester

53293-00-8

hex-5-ynoic acid

C17H20O4

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 72h;77%
94-26-8

4-hydroxybenzoic acid, butyl ester

612850-65-4

2-chloro-N-(1-oxo-1,3-dihydroisobenzofuran-5-yl)acetamide

butyl 4-(2-oxo-2-(1-oxo-1,3-dihydroisobenzofuran-5-ylamino)ethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;71%
94-26-8

4-hydroxybenzoic acid, butyl ester

106-48-9

4-chloro-phenol

112078-00-9

N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide

C77H63Cl3N2O10

Conditions
ConditionsYield
Stage #1: N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h;
Stage #2: 4-hydroxybenzoic acid, butyl ester In 1-methyl-pyrrolidin-2-one at 120℃; for 1h;
Stage #3: 4-chloro-phenol With potassium carbonate In 1-methyl-pyrrolidin-2-one for 4h;
68.7%
Stage #1: 4-hydroxybenzoic acid, butyl ester; N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 3h;
Stage #2: 4-chloro-phenol In 1-methyl-pyrrolidin-2-one at 120℃; for 4h;
68.7%
75-91-2

tert.-butylhydroperoxide

94-26-8

4-hydroxybenzoic acid, butyl ester

1285531-40-9

C15H22O5

Conditions
ConditionsYield
With dirhodium(II) tetrakis(caprolactam) In water; toluene at 40℃; for 3h; chemoselective reaction;66%
94-26-8

4-hydroxybenzoic acid, butyl ester

C66H78N3O18P3

Conditions
ConditionsYield
With potassium phosphate; 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In acetonitrile for 10h; Heating;65%
94-26-8

4-hydroxybenzoic acid, butyl ester

2-phenoxy-terephthaloyl dichloride

3-(4-butoxycarbonylphenyloxycarbonyl)xanthen-9-one

Conditions
ConditionsYield
In pyridine Heating;60%
94-26-8

4-hydroxybenzoic acid, butyl ester

C50H36Cl8N10P6

C138H140N10O24P6

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 96h; Inert atmosphere; Cooling with ice; Reflux;50%
110-52-1

1,4-dibromo-butane

94-26-8

4-hydroxybenzoic acid, butyl ester

A

butyl 4-(4-bromobutoxy)benzoate

B

1,4-bis(4-butylcarbonylphenyloxy)butane

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;A 25%
B 43%
94-26-8

4-hydroxybenzoic acid, butyl ester

butyl 4-[(aminosulphonyl)oxy]benzoate

Conditions
ConditionsYield
With sulphamoyl chloride; sodium hydride In N,N-dimethyl-formamide; toluene for 10h; Heating;25%
Stage #1: 4-hydroxybenzoic acid, butyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃;
Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene
Stage #1: 4-hydroxybenzoic acid, butyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene for 10h;
94-26-8

4-hydroxybenzoic acid, butyl ester

51762-67-5

3-nitrobenzene-1,2-dicarbonitrile

557-34-6

zinc diacetate

tetrakis (4-carboxylphenoxy) phthalocyaninezinc

Conditions
ConditionsYield
Stage #1: 4-hydroxybenzoic acid, butyl ester; 3-nitrobenzene-1,2-dicarbonitrile With potassium carbonate In dimethyl sulfoxide
Stage #2: zinc diacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene
Stage #3: water
22.5%
94-26-8

4-hydroxybenzoic acid, butyl ester

butyl 4-((2,4,4,6,6-pentachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphinin-2-yl)oxy)benzoate

Conditions
ConditionsYield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Cooling with ice;20%
94-26-8

4-hydroxybenzoic acid, butyl ester

19333-10-9

phthalocyanine silicon(IV) dichloride

C54H42N8O6Si

Conditions
ConditionsYield
With pyridine In toluene for 48h; Reflux;13.5%
109-65-9

1-bromo-butane

94-26-8

4-hydroxybenzoic acid, butyl ester

4906-27-8

n-butyl 4-n-butoxybenzoate

Conditions
ConditionsYield
With potassium hydroxide
75-44-5

phosgene

94-26-8

4-hydroxybenzoic acid, butyl ester

857538-41-1

4-chlorocarbonyloxy-benzoic acid butyl ester

Conditions
ConditionsYield
With N,N-dimethyl-aniline; benzene
94-26-8

4-hydroxybenzoic acid, butyl ester

2684-02-8

benzenediazonium

4-hydroxy-3-phenylazo-benzoic acid butyl ester

Conditions
ConditionsYield
With sodium hydroxide
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Chemistry

Molecular Formula: C11H14O3
Molecular Weight: 194.227 g/mol
EINECS: 202-318-7
Storage temp.: 0-6 °C
Index of Refraction: 1.526
Density: 1.108 g/cm3
Flash Point: 129.2 °C
Melting point: 67-70 °C(lit.)
Appearance: White crystalline powder
Enthalpy of Vaporization: 57.19 kJ/mol
Boiling Point: 309.2 °C at 760 mmHg
Vapour Pressure: 0.000356 mmHg at 25 °C
Water Solubility: <0.1 g/100 mL at 17 °C
Structure of Butylparaben (CAS NO.94-26-8):
                      
IUPAC Name: Butyl 4-hydroxybenzoate
Product Category of Butylparaben (CAS NO.94-26-8): Pharmaceutical Raw Materials

Uses

 Butylparaben (CAS NO.94-26-8) is used as an antifungal preservative in cosmetics, and is in the form of suspension fluid to be a component of many medications.

Production

 Butylparaben (CAS NO.94-26-8) can be derived by the reaction of p-hydroxybenzoic acid and butanol with sulfuric acid as catalyst.

Toxicity Data With Reference

1.    

skn-gpg 5%/48H MLD

    JSCCA5    Journal of the Society of Cosmetic Chemists. 28 (1977),357.
2.    

orl-mus LD50:13,200 mg/kg

    NEZAAQ    Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. 28 (1973),463.
3.    

ipr-mus LD50:230 mg/kg

    JSCCA5    Journal of the Society of Cosmetic Chemists. 28 (1977),357.

4.   RTECS  DH1980000

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intraperitoneal route. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
22:  Do not breathe dust 
24/25:  Avoid contact with skin and eyes 
WGK Germany: 2

Specification

 Butylparaben , its cas register number is 94-26-8. It also can be called p-Hydroxybenzoic acid butyl ester ; 4-(Butoxycarbonyl)phenol ; 4-Hydroxybenzoic acid butyl ester ; Butoben ; Butyl 4-hydroxybenzoate ; Butyl p-hydroxybenzoate ; Butyl parabens ; n-Butyl p-hydroxybenzoate ; n-Butylparaben ; 4-Hydroxybenzoic acid butyl ester ; and n-Butyl 4-hydroxybenzoate . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, Butylparaben (CAS NO.94-26-8) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide.