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35285-68-8

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35285-68-8 Usage

Chemical Properties

White or almost white, hygroscopic, crystalline powder.

Uses

Ethyl 4-hydroxybenzoate has antimicrobial characteristics and is used as preservative in pharmaceutical formulations and cosmetics. It can be combined with other parabens like methyl 4-hydroxybenzoate or propyl 4-hydroxybenzoate. The sodium salt provides improved solubility in water compared to standard ethyl 4-hydroxybenzoate.

Flammability and Explosibility

Nonflammable

Contact allergens

This substance is one of the parabens family. Parabens are esters formed by p-hydroxybenzoic acid and an alcohol. They are largely used as biocides in cosmetics and toiletries, medicaments, or food. They have synergistic power with other biocides. Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin.

Check Digit Verification of cas no

The CAS Registry Mumber 35285-68-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,2,8 and 5 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 35285-68:
(7*3)+(6*5)+(5*2)+(4*8)+(3*5)+(2*6)+(1*8)=128
128 % 10 = 8
So 35285-68-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O3.Na/c1-2-12-9(11)7-3-5-8(10)6-4-7;/h3-6,10H,2H2,1H3;/q;+1

35285-68-8Synthetic route

phenyl 4-ethoxycarbonyl phenyl
1268380-09-1

phenyl 4-ethoxycarbonyl phenyl

A

sodium salicylat
81256-74-8

sodium salicylat

B

sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

Conditions
ConditionsYield
With water; sodium hydroxide In dimethyl sulfoxide at 25℃; Kinetics;A n/a
B 100%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

Conditions
ConditionsYield
With sodium hydroxide In water
With sodium hydroxide In water
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

ethyl 2-(4-carbethoxyphenoxy)-3,4-dihydrobenzoate

ethyl 2-(4-carbethoxyphenoxy)-3,4-dihydrobenzoate

Conditions
ConditionsYield
With oxygen; N,N-bis[2-(N-methylbenzimidazol-2-yl)ethyl]benzylamine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In acetonitrile at 25℃; for 0.583333h; Oxidation; oxygenation; coupling;84%
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

hexakis[4-(ethoxycarbonyl)phenoxy]cyclotriphosphazene
84942-83-6

hexakis[4-(ethoxycarbonyl)phenoxy]cyclotriphosphazene

Conditions
ConditionsYield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In 1,4-dioxane at 110℃; for 72h; Inert atmosphere;74%
2,3-dibromo-1,4-bis-(4-bromo-phenyl)-butane-1,4-dione
165287-54-7

2,3-dibromo-1,4-bis-(4-bromo-phenyl)-butane-1,4-dione

sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

1-(4-carboethoxyphenoxy)-1,2-bis(4-bromobenzoyl)ethylene

1-(4-carboethoxyphenoxy)-1,2-bis(4-bromobenzoyl)ethylene

Conditions
ConditionsYield
In tetrahydrofuran for 1.5h; Heating;70%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

ethyl 2-(4-carbethoxyphenoxy)-3,4-dihydrobenzoate

ethyl 2-(4-carbethoxyphenoxy)-3,4-dihydrobenzoate

Conditions
ConditionsYield
With sodium iodate; ethanol 1.) H2O, 25 deg C; Yield given. Multistep reaction;
sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

4-(ethoxycarbonyl)phenoxyacetic acid
30893-58-4

4-(ethoxycarbonyl)phenoxyacetic acid

Conditions
ConditionsYield
With Amberlite IRA 400 1.) water, 2.) water, 100 deg C, 1 h; Yield given. Multistep reaction;
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

dimethyl chlorothiophosphate
2524-03-0

dimethyl chlorothiophosphate

O,O-Dimethyl-O-p-aethoxycarbonylphenyl-thiophosphat
59288-80-1

O,O-Dimethyl-O-p-aethoxycarbonylphenyl-thiophosphat

Conditions
ConditionsYield
With pyridine In toluene
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

Dimethyl chlorophosphate
813-77-4

Dimethyl chlorophosphate

O,O-Dimethyl-O-p-aethoxycarbonylphenyl-phosphat
59288-77-6

O,O-Dimethyl-O-p-aethoxycarbonylphenyl-phosphat

Conditions
ConditionsYield
In benzene
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

2,5-bis(4-bromophenyl)-3-(4-carboethoxyphenoxy)furan

2,5-bis(4-bromophenyl)-3-(4-carboethoxyphenoxy)furan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / tetrahydrofuran / 1.5 h / Heating
2: 72 percent / PCl3 / 4 h / Heating
View Scheme
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

Tetramethylammonium-O-methyl-O-(p-aethoxycarbonylphenyl)-phosphat

Tetramethylammonium-O-methyl-O-(p-aethoxycarbonylphenyl)-phosphat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene
2: acetone
View Scheme
sodium salt of ethyl-4-hydroxybenzoate
35285-68-8

sodium salt of ethyl-4-hydroxybenzoate

C10H12O5PS(1-)*C4H12N(1+)

C10H12O5PS(1-)*C4H12N(1+)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Py / toluene
2: acetone
View Scheme

35285-68-8Relevant articles and documents

Kinetics and mechanism of alkaline hydrolysis of Y-substituted phenyl phenyl carbonates

Kim, Song-I,Hwang, So-Jeong,Jung, Eun-Mi,Um, Ik-Hwan

experimental part, p. 2015 - 2018 (2010/12/19)

Second-order rate constants (kOH-) have been measured spectrophotometrically for alkaline hydrolysis of Y-substituted phenyl phenyl carbonates (2a-j) and compared with the kOH- values reported previously for the corresponding reactions of Y-substituted phenyl benzoates (1a-j). Carbonates 2a-j are 8 ~ 16 times more reactive than benzoates 1a-j. The Hammett plots correlated with σ- and σo constants exhibit many scattered points, while the Yukawa-Tsuno plot results in excellent linear correlation with ρ = 1.21 and r = 0.33. Thus, the reaction has been concluded to proceed through a concerted mechanism in which expulsion of the leaving group is advanced only a little. However, one cannot exclude a possibility that the current reaction proceeds through a forced concerted mechanism with a highly unstable intermediate.

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