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279692

Sigma-Aldrich

Ethyl isothiocyanatoacetate

97%

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About This Item

Linear Formula:
SCNCH2CO2C2H5
CAS Number:
24066-82-8
Molecular Weight:
145.18
EC Number:
417-720-1
MDL number:
MFCD00060677
UNSPSC Code:
12352100
PubChem Substance ID:
24856903
NACRES:
NA.22

Quality Level

100

assay

97%

form

liquid

refractive index

n20/D 1.502 (lit.)

bp

104-106 °C/7 mmHg (lit.)

density

1.171 g/mL at 25 °C (lit.)

functional group

amine
ester
isothiocyanate

storage temp.

2-8°C

SMILES string

CCOC(=O)CN=C=S

InChI

1S/C5H7NO2S/c1-2-8-5(7)3-6-4-9/h2-3H2,1H3

InChI key

IYPSSPPKMLXXRN-UHFFFAOYSA-N

Application

Ethyl isothiocyanatoacetate has been used in the synthesis of:
  • fused pyrimidines
  • ethyl (3-substituted 5-thioxo-1,2,4-triazolin-4-yl)acetates via addition-cyclization reaction with carboxylic acid hydrazides in the presence of sodium ethoxide
  • 3-O-amino-2-thiohydantoins
  • quinazoline, benzothienopyrimidine and benzofuropyrimidine
  • thiazolo[5,4-d]thiazole

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

228.2 °F - closed cup

flash_point_c

109 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ8582
STBJ5930
STBH6421
STBH0974
STBF7838V

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A Z Chowdhury et al.
Chemical & pharmaceutical bulletin, 49(4), 391-395 (2001-04-20)
o-Aminonitrile or o-aminoester compounds were cyclized to fused pyrimidines by reacting with ethyl iso(thio)cyanatoacetate in pyridine, and then were methylated, halogenated and subsequently displaced by the amines studied.
Synthesis of 3-O-amino-2-thiohydantoins.
Ryczek J.
Journal of Heterocyclic Chemistry, 40(4), 665-670 (2003)
Addition-cyclization reactions of ethyl isothiocyanatoacetate with carboxylic acid hydrazides.
Veverka M and Marchalin M.
Collection of Czechoslovak Chemical Communications, 52(1), 113-119 (1987)
Improved access to thiazolo [5, 4-d] thiazole and thieno [2, 3-d] thiazole.
Rossler A and Boldt P.
Journal of the Chemical Society. Perkin Transactions 1, 4, 685-688 (1998)

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