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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

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

80.0 °F - closed cup

flash_point_c

26.67 °C - closed cup

ppe

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

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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H. Bohme and H. G. Viehe, Eds.
Adv. Org. Chem., 9, 421-421 (1976)
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)
Total synthesis of caloporoside.
Furstner A, et al.
The Journal of Organic Chemistry, 63, 3072-3072 (1998)
Total Synthesis of Roseophilin.
Furstner A, et al.
Journal of the American Chemical Society, 120 (12), 2817?2825-2817?2825 (1998)
?-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N,N,2-trimethylpropenylamine.
Haveaux B, et al.
Organic Syntheses, 59, 26-26 (1980)
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