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2682-20-4

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2682-20-4 Usage

Description

Different sources of media describe the Description of 2682-20-4 differently. You can refer to the following data:
1. Methylisothiazolinone (also called 2-methyl-4-isothiazolin-3-one), is a powerful synthetic biocide and preservative within the group of? isothiazolinones. Methylisothiazolinone is used to control slime-forming bacteria, fungi, and algae in pulp/paper mills, cooling water systems, oil field operations, industrial process waters, and air washer systems. And it is incorporated into adhesives, coatings, fuels, metal working fluids, resin emulsions, paints, and various other specialty industrial products as a preservative. It is also used to control the growth of mold, mildew, and sapstain on wood products. It is generally recommended for use only in rinse-off and leave-on cosmetic products (maximum concentration of 100 ppm) as preservative such as shampoo, conditioner, hair color, body wash, lotion, sunscreen, mascara, shaving cream, baby lotion, baby shampoo, hairspray, makeup remover, liquid soaps, and detergents. Nevertheless, methylisothiazolinone is allergenic. It is reported that methylisothiazolinone in rinse-off products causes allergic contact dermatitis.
2. Methylisothiazolinone (MI) is an isothiazolinone-derived biocide used for controlling microbial growth in industrial and household products, often in a mixture with 5-chloro-2-methyl-3-isothiazolone (MCI). MI is active against Gram-positive and Gram-negative bacteria, fungi, and yeast with MIC values of 0.0045, 0.0015, >0.01, and 0.0065% (w/w) for S. aureus, P. aeruginosa, A. niger, and C. albicans, respectively, when used alone. MIC values are 7 to 200-fold lower when MI is used in combination with MCI. MI decreases neurite outgrowth of rat cortical neurons when used at concentrations of 0.1-3 μM and inhibits Src family kinases in cell-free assays. MI, alone and as a mixture with MCI, can elicit contact sensitization.

Uses

Different sources of media describe the Uses of 2682-20-4 differently. You can refer to the following data:
1. Methylisothiazolinone, or MIT as it is sometimes known, is a preservative used in cosmetics and beauty products. It is a powerful biocide, or “chemical substance capable of killing living organisms, usually in a selective way.”Biocides are a general term that includes antimicrobial, germicide, antibiotic, and antifungal. Ultimately, Methylisothiazolinone is used to prevent a wide variety of bacteria and fungi from growing in cosmetics and beauty products, most often in shampoo. It is only approved for use in rinse-off formulas and at low concentrations.
2. 2-Methyl-4-isothiazolin-3-one is a isothiazolinone based biocide and preservative used in personal care products. 2-Methyl-4-isothiazolin-3-one is also used for controlling microbial growth in water-c ontaining solution.
3. Methylisothiazolinone is a preservative compound widely used in cosmetics. It is a contact allergen and sensitiser. Methylisothiazolinone has recently been identified as a neurotoxin that can damage nerve endings with repeated exposure.

Safety

Methylisothiazolinone (MIT) is a heterocyclic organic compound used as a preservative in cosmetics and personal care products in concentrations up to 0.01%. MIT is a colorless, clear liquid with a mild odor that is completely soluble in water; mostly soluble in acetonitrile, methanol, and hexane; and slightly soluble in xylene. Consistent with its solubility, dermal penetration is low. The Cosmetic Ingredient Review Expert Panel noted the in vitro evidence of neurotoxicity but concluded that the absence of any neurotoxicity findings in the many in vivo studies, including subchronic, chronic, and reproductive and developmental animal studies, suggests that MIT would not be neurotoxic as used in cosmetics. Although recognizing that MIT was a sensitizer in both animal and human studies, the panel concluded that there is a threshold dose response and that cosmetic products formulated to contain concentrations of MIT at 100 ppm (0.0 1%) or less would not be expected to pose a sensitization risk. Accordingly, MIT may be safely used as a preservative in cosmetics up to that concentration.

References

[1] http://www.safecosmetics.org/get-the-facts/chemicals-of-concern/methylisothiazolinone/ [2] K. Yazar, M. D. Lundov, A. Faurschou, M. Matura, A. Boman, J. D. Johansen, C. Lidén (2015) Methylisothiazolinone in rinse-off products causes allergic contact dermatitis: a repeated open-application study, 173, 115-122 [3] https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_G-58_1-Oct-98.pdf

Chemical Properties

Methylisothiazolinone (MIT) is a colorless,clear liquid with amild odor that is completely soluble in water; mostly soluble in acetonitrile, methanol, and hexane; and slightly soluble in xylene. MIT is a heterocyclic organic compound used as a preservative in cosmetics and personal care products in concentrations up to 0.01%.

Definition

ChEBI: Methylisothiazolinone is a 1,2-thazole that is 4-isothiazolin-3-one bearing a methyl group on the nitrogen atom. It is a powerful biocide and preservative and is the minor active ingredient in the commercial product Kathon(TM). It has a role as an antifouling biocide, an antimicrobial agent and an antifungal agent.

Contact allergens

MI is generally associated with MCI, in Kathon? CG, MCI/MI, and Euxyl? K 100. This preservative is currently used in water-based products such as cosmetics, paints, and glues. Skin contact with concentrated solution can cause severe irritant dermatitis.

Check Digit Verification of cas no

The CAS Registry Mumber 2682-20-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,8 and 2 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2682-20:
(6*2)+(5*6)+(4*8)+(3*2)+(2*2)+(1*0)=84
84 % 10 = 4
So 2682-20-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3

2682-20-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (73569)  2-Methyl-4-isothiazolin-3-one  analytical standard

  • 2682-20-4

  • 73569-1G

  • 1,081.08CNY

  • Detail
  • Aldrich

  • (725765)  2-Methyl-4-isothiazolin-3-one  95%

  • 2682-20-4

  • 725765-5G

  • 826.02CNY

  • Detail
  • Aldrich

  • (725765)  2-Methyl-4-isothiazolin-3-one  95%

  • 2682-20-4

  • 725765-25G

  • 3,258.45CNY

  • Detail

2682-20-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name methylisothiazolinone

1.2 Other means of identification

Product number -
Other names methylisothiazolin-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Preservatives and Antioxidants
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2682-20-4 SDS

2682-20-4Synthetic route

5-(4-Methoxy-benzoyl)-2-methyl-isothiazol-3-one
77052-39-2

5-(4-Methoxy-benzoyl)-2-methyl-isothiazol-3-one

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With sodium hydroxide In benzene Ambient temperature;100%
N,N'-dimethyl-3,3'-dithiodipropionamide
999-72-4

N,N'-dimethyl-3,3'-dithiodipropionamide

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With chlorine; potassium iodide In ethyl acetate at 35 - 50℃; for 0.0833333h;90%
Stage #1: N,N'-dimethyl-3,3'-dithiodipropionamide With thionyl chloride In ethyl acetate at 15℃; for 0.166667h;
Stage #2: With chlorine In ethyl acetate at 15℃; for 5h; Reagent/catalyst; Temperature; Solvent;
84.9%
With hydrogenchloride; chlorine In water; ethyl acetate at 15 - 25℃; Large scale;75%
With sulfuryl dichloride In 1,2-dichloro-ethane
isothiazol
288-16-4

isothiazol

tert-Butyl peroxybenzoate
614-45-9

tert-Butyl peroxybenzoate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With copper (I) fluoride In chlorobenzene at 130℃; for 24h; Schlenk technique; Inert atmosphere;80%
(Z)-3-(benzylsulfinyl)-N-methylpropenamide
159554-02-6

(Z)-3-(benzylsulfinyl)-N-methylpropenamide

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With trichloroacetic acid anhydride In dichloromethane 1.) 0 deg C, 1 h, 2.) room temperature, 2 h;66%
N,N'-dimethyl-3,3'-dithiodipropionamide
999-72-4

N,N'-dimethyl-3,3'-dithiodipropionamide

A

5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

B

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With thionyl chloride In 1,2-dichloro-ethane at 10℃; for 2h;A 18%
B 56%
With chlorine In ethyl acetate; acetonitrile at 5 - 10℃; for 1h; Solvent; Temperature; Overall yield = 85 percent;
N,N'-dimethyl-3,3'-dithiodipropionamide
999-72-4

N,N'-dimethyl-3,3'-dithiodipropionamide

A

5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

B

4,5-Dichloro-2-methyl-3(2H)-isothiazolone
26542-23-4

4,5-Dichloro-2-methyl-3(2H)-isothiazolone

C

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With thionyl chloride In 1,2-dichloro-ethaneA 34%
B 8%
C 44%
tert-Butyl peroxybenzoate
614-45-9

tert-Butyl peroxybenzoate

2-methyl-isothiazolidin-3-one
1003-22-1

2-methyl-isothiazolidin-3-one

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With copper(l) chloride In benzene for 4h; Heating;
2-methyl-isothiazolidin-3-one
1003-22-1

2-methyl-isothiazolidin-3-one

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With sulfuryl dichloride In tetrachloromethane Ambient temperature;
3-methoxy-2-methyl-isothiazolium; fluorosulfate

3-methoxy-2-methyl-isothiazolium; fluorosulfate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With thiourea In methanol; dichloromethane1.0 g (29%)
3-chloro-2-methyl-isothiazolium; fluorosulfate

3-chloro-2-methyl-isothiazolium; fluorosulfate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
10.4 g (53%)
N-methyl-3-mercaptopropionamide
52334-99-3

N-methyl-3-mercaptopropionamide

A

5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

B

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

Conditions
ConditionsYield
With chlorine In N,N-dimethyl acetamide; chlorobenzene at 40 - 45℃; for 1h; Overall yield = 74 percent;
Stage #1: N-methyl-3-mercaptopropionamide With acetyl chloride In benzene at 25℃; for 0.666667h;
Stage #2: With chlorine In benzene at 25℃; for 1h; Reagent/catalyst; Temperature; Solvent; Overall yield = 86.2 percent;
2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

3-Chlor-2-methylisothiazolium Chlorid (II)
68449-61-6

3-Chlor-2-methylisothiazolium Chlorid (II)

Conditions
ConditionsYield
With oxalyl dichloride In toluene at 80℃;85%
2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

2-methylisothiazol-3(2H)-one 1,1-dioxide

2-methylisothiazol-3(2H)-one 1,1-dioxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20 - 25℃; for 15h;85%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 30℃; for 17.5h;85%
uranyl nirate hexahydrate

uranyl nirate hexahydrate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

UO2(NO3)2(2-methylisothiazol-3(2H)-one)2

UO2(NO3)2(2-methylisothiazol-3(2H)-one)2

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;71%
pentaamminetrifluoromethanesulfonato ruthenium(III) trifluoromethanesulfonate
84278-98-8

pentaamminetrifluoromethanesulfonato ruthenium(III) trifluoromethanesulfonate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

[(2-methylisothiazol-3(2H)-one)pentaamminruthenium(III)](CF3SO3)3

[(2-methylisothiazol-3(2H)-one)pentaamminruthenium(III)](CF3SO3)3

Conditions
ConditionsYield
In acetone for 0.166667h; Reflux; Microwave irradiation;63%
n-octyne
629-05-0

n-octyne

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

A

(Z)-3-((E)-2-Chloro-oct-1-enylsulfanyl)-N-methyl-acrylamide

(Z)-3-((E)-2-Chloro-oct-1-enylsulfanyl)-N-methyl-acrylamide

B

(Z)-3-{1-[1-Chloro-meth-(E)-ylidene]-heptylsulfanyl}-N-methyl-acrylamide

(Z)-3-{1-[1-Chloro-meth-(E)-ylidene]-heptylsulfanyl}-N-methyl-acrylamide

Conditions
ConditionsYield
With hydrogenchloride at 80℃;A n/a
B 60%
With hydrogenchloride at 80℃; Yields of byproduct given;
norborn-2-ene
498-66-8

norborn-2-ene

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

(Z)-3-((1R,2S,3S,4S)-3-Chloro-bicyclo[2.2.1]hept-2-ylsulfanyl)-N-methyl-acrylamide

(Z)-3-((1R,2S,3S,4S)-3-Chloro-bicyclo[2.2.1]hept-2-ylsulfanyl)-N-methyl-acrylamide

Conditions
ConditionsYield
With hydrogenchloride In chloroform-d1 at 80℃;20%
aquapentaammineruthenium(II) hexafluorophosphate
34843-18-0

aquapentaammineruthenium(II) hexafluorophosphate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

(2-methylisothiazol-3(2H)-one)pentaamminruthenium(II)(PF6)2

(2-methylisothiazol-3(2H)-one)pentaamminruthenium(II)(PF6)2

Conditions
ConditionsYield
In water at 50℃; for 0.25h; Inert atmosphere; Schlenk technique;14%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

K(dibenzo-18-crown-6)[(2-methylisothiazol-3(2H)-one)PtCl3]

K(dibenzo-18-crown-6)[(2-methylisothiazol-3(2H)-one)PtCl3]

Conditions
ConditionsYield
In chloroform; water at 20℃; for 72h;9.6%
trifluoromethanesulfonatopentaamminecobalt(III) trifluoromethanesulfonate
115245-01-7

trifluoromethanesulfonatopentaamminecobalt(III) trifluoromethanesulfonate

sodium perchlorate

sodium perchlorate

water
7732-18-5

water

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

(2-methylisothiazol-3(2H)-one)pentaamminecobalt(III)(ClO4)3*3H2O

(2-methylisothiazol-3(2H)-one)pentaamminecobalt(III)(ClO4)3*3H2O

Conditions
ConditionsYield
Stage #1: trifluoromethanesulfonatopentaamminecobalt(III) trifluoromethanesulfonate; 2-methyl-3-isothiazolone In acetone for 0.333333h; Reflux; Microwave irradiation;
Stage #2: sodium perchlorate; water at -0.16℃;
6.8%
Methyl fluorosulfonate
421-20-5

Methyl fluorosulfonate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

3-methoxy-2-methyl-isothiazolium; fluorosulfate

3-methoxy-2-methyl-isothiazolium; fluorosulfate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

4,5-dibromo-2-methyl-isothiazol-3-one
64359-58-6

4,5-dibromo-2-methyl-isothiazol-3-one

Conditions
ConditionsYield
(i) Br2, DMF, AcOEt, (ii) Br2; Multistep reaction;
2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

4-bromo-2-methyl-isothiazol-3-one
26529-99-7

4-bromo-2-methyl-isothiazol-3-one

Conditions
ConditionsYield
With bromine In 1,2-dichloro-ethane
2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

4,5-Dichloro-2-methyl-3(2H)-isothiazolone
26542-23-4

4,5-Dichloro-2-methyl-3(2H)-isothiazolone

Conditions
ConditionsYield
With sulfuryl dichloride In ethyl acetate
With sulfuryl dichloride In ethyl acetate
2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

isothiazol-3-yl-methyl-amine
68449-74-1

isothiazol-3-yl-methyl-amine

Conditions
ConditionsYield
(i) POCl3, (ii) NH3, MeCN; Multistep reaction;
Stage #1: 2-methyl-3-isothiazolone With trichlorophosphate
Stage #2: With ammonia In acetonitrile at 0 - 20℃;
2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

C8H15NOS2

C8H15NOS2

Conditions
ConditionsYield
In sodium hydroxide; acidic aq. solution at 26℃; pH=4; Kinetics;
5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

disodium hydrogen phosphate

disodium hydrogen phosphate

ethylenediamine tetraacid disodium salt

ethylenediamine tetraacid disodium salt

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

sodium phosphate

sodium phosphate

2-octyl-isothiazol-3-one
26530-20-1

2-octyl-isothiazol-3-one

Conditions
ConditionsYield
With sodium chloride
With sodium chloride
potassium phosphate

potassium phosphate

5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

disodium hydrogen phosphate

disodium hydrogen phosphate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

2-octyl-isothiazol-3-one
26530-20-1

2-octyl-isothiazol-3-one

Conditions
ConditionsYield
With potassium chloride; sodium chloride
With potassium chloride; sodium chloride
5-chloro-2-methyl-2H-isothiazol-3-one
26172-55-4

5-chloro-2-methyl-2H-isothiazol-3-one

disodium hydrogen phosphate

disodium hydrogen phosphate

2-methyl-3-isothiazolone
2682-20-4

2-methyl-3-isothiazolone

sodium phosphate

sodium phosphate

2-octyl-isothiazol-3-one
26530-20-1

2-octyl-isothiazol-3-one

Conditions
ConditionsYield
With sodium chloride
With sodium chloride

2682-20-4Relevant articles and documents

-

Chan,A.W.K. et al.

, p. 2497 - 2506 (1970)

-

Preparation method of 3-isothiazolinone compound

-

Paragraph 0030-0032; 0036-0039, (2020/12/31)

The invention discloses a preparation method of a 3-isothiazolinone compound, which comprises the following steps of adding raw materials and a solvent into a reaction system, and stirring and mixing,adding a dehydrating agent into the mixed solution, and stirring for reaction, introducing chlorine into the reaction system, stirring the reaction mixture for reaction, filtering and separating to obtain a product. According to the method, the chemical dehydrating agent is added into the reaction system to react with water or alcohol in the reaction system, so that water or alcohol in the systemis removed, side reaction caused by water or alcohol is avoided, the reaction yield is increased, and the economic benefit is remarkable.

Preparation method of high-purity 2-alkyl-4-isothiazoline-3-ketone

-

Paragraph 0037; 0038; 0039; 0040, (2017/07/19)

The invention discloses a preparation method of high-purity 2-alkyl-4-isothiazoline-3-ketone. The preparation method comprises the following steps: suspending amide into a reaction medium inert solvent; introducing CMI and MIT mixture tail gas or MIT tail gas generated by the previous step, so as to obtain an amide suspending solution with proper hydrogen chloride content; and introducing a chlorinating reagent. According to the preparation method, a byproduct, namely hydrogen chloride, has an inhibition effect on the generation of 5-chloro-2-alkyl-4-isothiazoline-3-ketone. The content of the hydrogen chloride is increased through utilizing reaction raw materials and solvents; and finally, the high-purity 2-alkyl-4-isothiazoline-3-ketone is obtained.

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