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D100900

Sigma-Aldrich

N,N′-Diethylthiourea

98%

Synonym(s):

1,3-Diethyl-2-thiourea, 1,3-Diethylthiourea, N,N′-Diethylthiocarbamide, N,N′-Diethylthiourea

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About This Item

Linear Formula:
(C2H5NH)2CS
CAS Number:
105-55-5
Molecular Weight:
132.23
Beilstein:
773905
EC Number:
203-308-5
MDL number:
MFCD00004925
UNSPSC Code:
12352100
PubChem Substance ID:
24893318
NACRES:
NA.22

Assay

98%

form

crystals

mp

76-78 °C (lit.)

SMILES string

CCNC(=S)NCC

InChI

1S/C5H12N2S/c1-3-6-5(8)7-4-2/h3-4H2,1-2H3,(H2,6,7,8)

InChI key

FLVIGYVXZHLUHP-UHFFFAOYSA-N

Gene Information

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Application

N,N′-Diethylthiourea can be used as a reactant to prepare:
  • 3,5-Diethyltetrahydro-4-thioxo-1,3,5-triazine-1(2H)-propanoic acid by condensation reaction with formaldehyde and β-alanine.
  • Methyl 3-ethyl-2-(ethylimino)-3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylate by one-pot reaction with dimethyl acetylenedicarboxylate in the presence of triphenylphosphine catalyst.
  • 2-(Ethylimino)-3-ethyl-thiazolidin-4-one by cyclization reaction with 2-chloroacetic acid.
  • 3-Ethyl-2-(ethylimino)-4-oxo-5-thiazolidineacetamide by condensation reaction with maleimides via Michael-type reaction.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Dam. 1 - Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

366.8 °F

Flash Point(C)

186 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Efficient 2-amino-2-thiazolin-4-ones or 2-iminothiazolidin-4-ones formation from thioureas and maleimides under solvent-free conditions
Shimo T, et al.
Heterocycles, 71(5), 1053-1058 (2007)
An eco-friendly preparation of 2-iminothiazolidin-4-ones derivatives
Meng G, et al.
Organic preparations and procedures international, 44(2), 184-186 (2012)
Ph 3 P-mediated one-pot synthesis of functionalized 3, 4-dihydro-2 H-1, 3-thiazines from N, N?-dialkylthioureas and activated acetylenes in water
Yavari I, et al.
Monatshefte fur Chemie / Chemical Monthly, 141(2), 229-232 (2010)
Aminomethylation of Symmetric Dialkylthioureas with Formaldehyde and Amino Acids
Mammeri OA, et al.
Russ. J. Gen. Chem., 90(11), 2043-2047 (2020)

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