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111910

Sigma-Aldrich

2-Chlortoluol

99%

Synonym(e):

1-chloro-2-methylbenzene

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€ 48,30
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€ 88,70
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€ 339,00

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100 G
€ 48,30
1 KG
€ 88,70
4 KG
€ 339,00

About This Item

Lineare Formel:
CH3C6H4Cl
CAS-Nummer:
95-49-8
Molekulargewicht:
126.58
Beilstein:
1904175
EG-Nummer:
202-424-3
MDL-Nummer:
MFCD00000562
UNSPSC-Code:
12352100
eCl@ss:
39050205
PubChem Substanz-ID:
24847049
NACRES:
NA.22

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Dampfdichte

4.38 (vs air)

Qualitätsniveau

100

Dampfdruck

10 mmHg ( 43 °C)

Assay

99%

Form

liquid

Brechungsindex

n20/D 1.525 (lit.)

bp

157-159 °C (lit.)

mp (Schmelzpunkt)

−36 °C (lit.)

Löslichkeit

H2O: soluble

Dichte

1.083 g/mL at 25 °C (lit.)

Funktionelle Gruppe

chloro

SMILES String

Cc1ccccc1Cl

InChI

1S/C7H7Cl/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

InChIKey

IBSQPLPBRSHTTG-UHFFFAOYSA-N

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Allgemeine Beschreibung

2-Chlorotoluene can be mineralized completely by Rhodococcus, strain OCT 10 DSM 45596(T)[1]. It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol[2]. The oxidation of 2-chlorotoluene is very well catalyzed by the enzymes: toluene dioxygenase of P. putida F1 and chlorobenzene dioxygenase from Burkholderia, strain PS12[3].

Anwendung

2-Chlorotoluene can be used as a precursor to synthesize aryl coupling products via palladium-catalyzed Negishi cross-coupling.[4] It can also be used in the Buchwald-Hartwig amination to synthesize arylamines.[5][6]

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Inhalation - Aquatic Acute 1 - Aquatic Chronic 2 - Flam. Liq. 3 - Repr. 2

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

109.4 °F - closed cup

Flammpunkt (°C)

43 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCS8143
MKCL1184
MKCF5243
MKCD3029
MKBW5554V

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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

NIXANTPHOS: A Highly Active Ligand for Palladium Catalyzed Buchwald-Hartwig Amination of Unactivated Aryl Chlorides.
Mao J, et al.
Dalton Transactions, (26) (2018)
A Lehning et al.
Applied and environmental microbiology, 63(5), 1974-1979 (1997-05-01)
The degradation of toluene by Pseudomonas putida F1 and of chlorobenzenes by Burkholderia sp. strain PS12 is initiated by incorporation of dioxygen into the aromatic nucleus to form cis-dihydrodihydroxybenzenes. Toluene-grown cells of P. putida F1 and 3-chlorobenzoate-grown cells of Burkholderia
Flexible Steric Bulky Bis (Imino) acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald?Hartwig Amination in Air.
Lan X B, et al.
The Journal of Organic Chemistry, 82(6), 2914-2925 (2017)
The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd (P (t-Bu) 3) 2 as a catalyst
Dai C, et al.
Journal of the American Chemical Society, 123(12), 2719-2724 (2001)
Katrin Pollmann et al.
Journal of bacteriology, 187(7), 2332-2340 (2005-03-19)
To elucidate possible reasons for the recalcitrance of 2-chlorotoluene, the metabolism of chloromethylcatechols, formed after dioxygenation and dehydrogenation by Ralstonia sp. strain PS12 tetrachlorobenzene dioxygenase and chlorobenzene dihydrodiol dehydrogenase, was monitored using chlorocatechol dioxygenases and chloromuconate cycloisomerases partly purified from
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Questions

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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