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330752

Sigma-Aldrich

三光气

Triphosgene

reagent grade, 98%

同義詞:

二(三氯甲基)碳酸酯

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About This Item

線性公式:
Cl3COCOOCCl3
CAS號碼:
32315-10-9
分子量：:
296.75
Beilstein:
1787583
EC號碼:
250-986-3
MDL號碼:
MFCD00062848
分類程式碼代碼:
12352108
PubChem物質ID:
24859885
NACRES:
NA.22
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等級

reagent grade

品質等級

200

化驗

98%

形狀

powder

反應適用性

reaction type: Coupling Reactions

bp

203-206 °C (lit.)

mp

79-83 °C (lit.)

官能基

carbonate
chloro

儲存溫度

2-8°C

SMILES 字串

ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl

InChI

1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9

InChI 密鑰

UCPYLLCMEDAXFR-UHFFFAOYSA-N

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一般說明

三光气[双（三氯甲基）碳酸酯]是一种通用有机试剂，可用于替代光气进行有机合成。[1][2][3]催化剂量的三光气特别适用于氯甲基化、羰基化、氯化和脱水反应。[4][5]
它还常用作合成羰基化合物中的偶联剂。[6][6][7]
[5]

應用

三光气可作为试剂，进行以下制备反应：
  • 通过一锅三组分反应从硫醇和醇制备硫代碳酸。[5]
  • 通过乙烯酮-亚胺环加成反应从酸和亚胺制备取代的氮杂环丁烷-2-酮。[8]
  • 在碳酸氢钠存在的情况下，由L-苯丙氨酸甲酯盐酸盐制备（S）-2-异氰酰基-3-苯基丙酸甲酯。 [9]
  • 由各种羧酸和叠氮化钠制备酰基叠氮化物衍生物。[10]
  • 通过多肽固相合成法制备免疫抑制剂环孢菌素。[11]
  • 通过一锅法由烯丙醇和叠氮化钠制备烯丙基叠氮。[12]
  • 由2（5H）-噻吩酮制备酯化偶合剂二-2-噻吩基碳酸酯。[13]
  • 通过相应的酰胺环化作用制备2-氯烟醛。[14]

象形圖

Skull and crossbonesCorrosion
GHS06,GHS05

訊號詞

Danger

危險聲明

H314,H330

危險分類

Acute Tox. 1 Inhalation - Skin Corr. 1B

儲存類別代碼

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

水污染物質分類（WGK）

WGK 2

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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分析證明 (COA)

Lot/Batch Number
MKCW6260
MKCV0717
MKCS8231
BCCF6546
MKCP0738

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Triphosgene, a crystalline phosgene substitute
Eckert, Heiner and Forster, Barbara
Angewandte Chemie (International Edition in English), 26(9), 894-895 (1987)
A Safe and Efficient Method for Preparation of N,N′-Unsymmetrically Disubstituted Ureas Utilizing Triphosgene.
Majer P, et al.
The Journal of Organic Chemistry, 59, 1937-1938 (1994)
A mild and efficient method for the preparation of acyl azides from carboxylic acids using triphosgene
Gumaste VK, et al.
Tetrahedron Letters, 43(7), 1345-1346 (2002)
Triphosgene: a versatile reagent for the synthesis of azetidin-2-ones
Krishnaswamy D, et al.
Tetrahedron, 58(11), 2215-2225 (2002)
Coordination of chiral amines to coordinatively unsaturated Cp* Ir-amino acid complexes allows determination of enantiomeric purity
Grotjahn DB and Joubran C
Tetrahedron Asymmetry, 6, 745-745 (1995)
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Questions

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

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    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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  2. 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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