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Merck
CN

498270

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
NACRES:
NA.22
PubChem Substance ID:
24873186
UNSPSC Code:
12352302
MDL number:
MFCD00800562
Assay:
96%

Key Documents

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InChI

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

SMILES string

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

InChI key

GQIRIWDEZSKOCN-UHFFFAOYSA-N

assay

96%

refractive index

n20/D 1.453 (lit.)

bp

129-130 °C (lit.)

density

1.01 g/mL at 25 °C (lit.)

functional group

amine, chloro

storage temp.

2-8°C

Quality Level

100

Related Categories

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

ppe

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

hcodes

H225,H314

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

flash_point_f

<73.4 °F - closed cup

flash_point_c

< 23 °C - closed cup

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9490
MKCX5797
MKCW7549
MKCW0420
MKCT5515

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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)
?-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N,N,2-trimethylpropenylamine.
Haveaux B, et al.
Organic Syntheses, 59, 26-26 (1980)
A total synthesis of the ammonium ionophore,(?)-enniatin B.
Hu D, et al.
Tetrahedron Letters, 53(32), 4077-4079 (2012)
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Articles

Acid Halogenation Reagents

Fluoroamidinium salts advance acid halogenation with greater stability and no oxazolones conversion compared to chlorides.

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