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:
Molecular Weight:
133.62
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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)
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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)
Articles
Acid Halogenation Reagents
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