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396788

Sigma-Aldrich

Ethyl formimidate hydrochloride

Synonym(s):

Ethyl methanimidate hydrochloride

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About This Item

Linear Formula:
HC(=NH)OC2H5·HCl
CAS Number:
16694-46-5
Molecular Weight:
109.55
MDL number:
MFCD00192154
UNSPSC Code:
12352100
PubChem Substance ID:
24864683
NACRES:
NA.22

form

solid

Quality Level

100

mp

75 °C (dec.) (lit.)

functional group

ether

storage temp.

2-8°C

SMILES string

Cl.CCOC=N

InChI

1S/C3H7NO.ClH/c1-2-5-3-4;/h3-4H,2H2,1H3;1H

InChI key

JPUTTYRVDANTBN-UHFFFAOYSA-N

General description

Ethyl formimidate hydrochloride is a nitrogen containing organic building block. On heating it undergoes degradation to afford formamidine hydrochloride, ethyl formate and ethyl chloride.

Application

Ethyl formimidate hydrochloride may be used in the preparation of the following:
  • 5-aminoimidazole-4-carboxylic acid α- and β-ribotides
  • s-triazines
  • 2,3:5,6-di-O-isopropylidene-α- and -β-5-amino-4-ethoxycarbonyl or -carbamoyl-imidazole D-mannofuranosides
  • 5-amino-1-(2-pyridyl)imidazole
Reactant involved in the synthesis of biologically active molecules including:
  • Bredinin via amination of an acyclic precursor
  • Amidine conjugates of the ornithine moiety of an antifungal

Reactant involved in:
  • Intermolecular cyclization
  • Mo-catalyzed asymmetric ring-closing metathesis for synthesis of cyclid amides and amines
  • Synthesis of peptidic 1-cyanopyrrolidines

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

396788-50G:
396788-BULK:
396788-10G:
396788-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ7473V
MKBL8955V
MKBD5960
MKAA2202
06414KH

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Purines, pyrimidines, and imidazoles part 54. Interconversion of some intermediates in the de novo biosynthesis of purine nucleotides.
Cusack NJ, et al.
Journal of the Chemical Society. Perkin Transactions 1, 2316-2321 (1980)
Purines, pyrimidines, and imidazoles. Part XLI. Glycofuranosylamines derived from D-xylose, D-glucose, D-mannose, and L-rhamnose and their use in the synthesis of pyrimidine and imidazole nucleosides.
Cusack NJ, et al.
Journal of the Chemical Society. Perkin Transactions 1, 73-81 (1974)
Purines, pyrimidines, and imidazoles. XL. A new synthesis of a D-ribofuranosylamine derivative and its use in the synthesis of pyrimidine and imidazole nucleosides.
N J Cusack et al.
Journal of the Chemical Society. Perkin transactions 1, 16, 1720-1731 (1973-01-01)
Synthesis of the S-Triazine System. Iii. 1 Trimerization of Imidates.
Schaefer FC and Peters GA.
The Journal of Organic Chemistry, 26(8), 2771-2784 (1961)
Rhodd EH and von Richter V.
Chemistry of Organic Compounds: Pt. B. Aliphatic compounds, 551-551 (1951)

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