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498270

Sigma-Aldrich

1-Chloro-N,N,2-trimethyl-1-propenylamine

96%

Synonym(s):

Ghosez′s reagent

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About This Item

Linear Formula:
(CH3)2C=C(Cl)N(CH3)2
CAS Number:
26189-59-3
Molecular Weight:
133.62
MDL number:
MFCD00800562
UNSPSC Code:
12352302
PubChem Substance ID:
24873186
NACRES:
NA.22

Assay

96%

refractive index

n20/D 1.453 (lit.)

bp

129-130 °C (lit.)

density

1.01 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CN(C)\C(Cl)=C(\C)C

InChI

1S/C6H12ClN/c1-5(2)6(7)8(3)4/h1-4H3

InChI key

GQIRIWDEZSKOCN-UHFFFAOYSA-N

Application

1-Chloro-N,N,2-trimethyl-1-propenylamine is an acid halogenation reagent developed by Ghosez, that enables the conversion of carboxylic acids into the corresponding chlorides under strictly neutral conditions. This method was successfully used in the total synthesis of caloporoside, roseophilin, (-)-enniatin B, (±)-epimeloscine and (±)-meloscine.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.0 °F - closed cup

Flash Point(C)

26.67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A short total synthesis of (?)-epimeloscine and (?)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane.
Zhang H, et al.
Journal of the American Chemical Society, 133(27), 10376-10378 (2011)
A total synthesis of the ammonium ionophore,(?)-enniatin B.
Hu D, et al.
Tetrahedron Letters, 53(32), 4077-4079 (2012)
H. Bohme and H. G. Viehe, Eds.
Adv. Org. Chem., 9, 421-421 (1976)
Total synthesis of caloporoside.
Furstner A, et al.
The Journal of Organic Chemistry, 63, 3072-3072 (1998)
?-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N,N,2-trimethylpropenylamine.
Haveaux B, et al.
Organic Syntheses, 59, 26-26 (1980)
View All Related Papers

Articles

Acid Halogenation Reagents

The generation of an acid chloride is an obvious way to activate the carboxy group for amide bond formation. However, practical application of acid chlorides in peptide synthesis is restricted, because they are prone to side reactions and racemization.

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