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Sigma-Aldrich

三氟甲磺酸三甲基硅酯

Trimethylsilyl trifluoromethanesulfonate
1 of 1 reviewers received a sample product or took part in a promotion

99%

同義詞:

TMS 三氟甲基磺酸酯, TMSOTf, 三甲基硅基三氟甲烷磺酸酯

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About This Item

線性公式:
CF3SO3Si(CH3)3
CAS號碼:
27607-77-8
分子量：:
222.26
Beilstein:
1868911
EC號碼:
248-565-4
MDL號碼:
MFCD00000406
分類程式碼代碼:
12352103
PubChem物質ID:
24853510
NACRES:
NA.22
暫時無法取得訂價和供貨情況

品質等級

200

化驗

99%

形狀

liquid

折射率

n20/D 1.36 (lit.)

bp

77 °C/80 mmHg (lit.)

密度

1.228 g/mL at 25 °C (lit.)

官能基

fluoro
triflate

SMILES 字串

C[Si](C)(C)OS(=O)(=O)C(F)(F)F

InChI

1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3

InChI 密鑰

FTVLMFQEYACZNP-UHFFFAOYSA-N

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相關類別

應用

三氟甲磺酸三甲基硅酯可与三氟化硼醚合物一起使用，用于在手性配体存在的情况下，进行有机锂试剂与烯丙基溴化物、氯化物和醚的铜催化不对称烯丙基烷基化 (AAA)。[1][2]
可用于：
  • 作为硅烷化试剂， 用于以α-重氮基乙酰乙酸酯合成三甲基硅烯醚。[3]
  • 活化苄基醚和烯丙基醚，进行硫化物的烷基化。[4]
  • 在不形成甲氧基酮副产物的情况下，促进Danishefsky′二烯的 Diels-Alder 加合物转化为环己烯酮。[5]
  • 制备二氟硼酸三氟甲磺酸酯醚合物，其是一种强路易斯酸，在乙腈溶剂中尤其如此。[6]
  • 作为酯-酰亚胺和二酯的迪克曼环化反应试剂。[7]

它还可用于催化：
  • 醇与酸酐的酰化[8]
  • 羰基化合物与三烷基硅烷的还原偶联以形成对称醚。[9]
  • 4-脱甲氧基道诺霉素酮与1-O-酰基-L-道诺糖胺衍生物的糖苷化。[10]

象形圖

FlameCorrosion
GHS02,GHS05

訊號詞

Danger

危險聲明

H226,H314

危險分類

Flam. Liq. 3 - Skin Corr. 1B

安全危害

EUH014

儲存類別代碼

3 - Flammable liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

77.0 °F - closed cup

閃點（°C）

25 °C - closed cup

個人防護裝備

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

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
MKCV5462
MKCT7793
MKCR9262
MKCM5773
MKCM5469

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BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
Thomas R Hoye et al.
Organic letters, 8(23), 5191-5194 (2006-11-03)
[Structure: see text] Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates
A simple method of preparing trimethylsilyl-and tert-butyldimethylsilyl-enol ethers of ?-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs.
Ueda Y, et al.
Canadian Journal of Chemistry, 62(12), 2936-2940 (1984)
Efficient, trimethylsilyl triflate-mediated conversion of Diels-Alder adducts of 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadiene (Danishefsky's diene) to cyclohexenones.
Vorndam PE
The Journal of Organic Chemistry, 55(11), 3693-3695 (1990)
Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
Kimura Y, et al.
Bulletin of the Chemical Society of Japan, 59(2), 423-431 (1986)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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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