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1,1'-Thiocarbonyldiimidazole
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Name

1,1'-Thiocarbonyldiimidazole

 EINECS 228-183-4
CAS No. 6160-65-2 Density 1.39 g/cm3
PSA 67.73000 LogP 0.76090
Solubility decomposes Melting Point 98-102 °C(lit.)
Formula C9H16N2O Boiling Point 390.8 °C at 760 mmHg
Molecular Weight 178.217 Flash Point 190.1 °C
Transport Information N/A Appearance yellow powder
Safety 22-24/25 Risk Codes 22-34
Molecular Structure Molecular Structure of 6160-65-2 (1,1'-ThiocarbonylDiimidazole) Hazard Symbols IrritantXi
Synonyms

1H-Imidazole,1,1'-carbonothioylbis- (9CI);Imidazole, 1,1'-(thiocarbonyl)di- (7CI,8CI);1,1'-(Thiocarbonyl)bis[imidazole];1,1'-(Thiocarbonyl)diimidazole;1-(1H-Imidazol-1-ylcarbothioyl)-1H-imidazole;Diimidazol-1-ylmethanthione;N,N'-Thiocarbonyldiimidazole;NSC 141692;Thiocarbonylbisimidazole;1,1'-Thiocarbonylbis(imidazole);1H-Imidazole, 1,1'-carbonothioylbis-;1,1'-Thiocarbonyldiimidazole;

Article Data 10

1,1'-Thiocarbonyldiimidazole Synthetic route

463-71-8

thiophosgene

18156-74-6

1-(Trimethylsilyl)imidazole

6160-65-2

1,1'-Thiocarbonyldiimidazole

Conditions
ConditionsYield
In tetrachloromethane94%
In benzene a) 0 deg C, 30 min, b) RT, 30 min;
288-32-4

1H-imidazole

463-71-8

thiophosgene

6160-65-2

1,1'-Thiocarbonyldiimidazole

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 0.5h;
69530-93-4

5'-(O-tert-butyldimethylsilyl)adenosine

6160-65-2

1,1'-Thiocarbonyldiimidazole

119818-50-7

D-2',3'-O-thiocarbonylene-5'-O-tert-butyldimethylsilyl adenosine

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 3h; Inert atmosphere; Reflux;100%
In N,N-dimethyl-formamide at 80℃; for 1h;73.5%

cis-3,4-bis<(tert-butyldimethylsilyl)ethynyl>-3-cyclobutene-1,2-diol

6160-65-2

1,1'-Thiocarbonyldiimidazole

cis-1,2-bis<(tert-butyldimethylsilyl)ethynyl)>-3,4-(thiocarbonyldioxy)-1-cyclobutene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;100%
86263-38-9

Methyl 3,6-Di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

6160-65-2

1,1'-Thiocarbonyldiimidazole

157553-82-7

C33H27N3O9S

Conditions
ConditionsYield
In 1,2-dimethoxyethane Heating;100%
78064-61-6

1-Methyl-5'-O-tritylpseudouridine

6160-65-2

1,1'-Thiocarbonyldiimidazole

78064-62-7

1-Methyl-2',3'-O-(thionocarbonyl)-5'-O-tritylpseudouridine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 10h; Ambient temperature;100%
94707-76-3

((1R,6R,7S,8S,9R)-9-Hydroxy-7-trimethylsilanyloxy-2-aza-tricyclo[5.3.1.02,6]undec-8-yl)-acetic acid methyl ester

6160-65-2

1,1'-Thiocarbonyldiimidazole

94731-59-6

[(1R,6R,7S,8S,9R)-9-(Imidazole-1-carbothioyloxy)-7-trimethylsilanyloxy-2-aza-tricyclo[5.3.1.02,6]undec-8-yl]-acetic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 4h;100%
100021-22-5

(+/-)-(1α,2β,3α,4α,5β)-2-(6-amino-9H-purin-9-yl)-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

6160-65-2

1,1'-Thiocarbonyldiimidazole

100021-23-6

(+/-)-(1β,2α,3β,4α,5α)-1-(6-amino-9H-purin-9-yl)-4,5-(dimethylmethylenedioxy)-2-<(1-imidazolylthiocarbonyl)oxy>-3-<(phenylmethoxy)methyl>cyclopentane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; for 2h;100%
7304-32-7

2-fluoro-5-nitrobenzoic acid

6160-65-2

1,1'-Thiocarbonyldiimidazole

1003-03-8

Cyclopentamine

4-aminobenzoic acid bound to solid support

4-aminobenzoic acid bound to solid support

4-(1-cyclopentyl-6-nitro-4-oxo-2-thioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzoic acid

Conditions
ConditionsYield
Multistep reaction;100%
6160-65-2

1,1'-Thiocarbonyldiimidazole

248256-46-4

(1S,2S,3R)-1-hydroxymethyl-2-phenyl-3-(phenylthiomethyl)cyclopropane

392656-00-7

Imidazole-1-carbothioic acid O-((1S,2S,3R)-2-phenyl-3-phenylsulfanylmethyl-cyclopropylmethyl) ester

Conditions
ConditionsYield
In toluene at 50℃; for 1.5h;100%

1,1'-Thiocarbonyldiimidazole Specification

The 1,1'-Thiocarbonyldiimidazole with CAS registry number of 6160-65-2 is also called N,N'-Thiocarbonyldiimidazole. The IUPAC name is di-1H-imidazol-1-ylmethanethione. Its EINECS registry number is 228-183-4. In addition, the formula is C7H6N4S and the molecular weight is 178.21. It is belongs to the classes of Imidazoles; Carbonyldiimidazole Derivatives; Coupling; Synthetic Reagents; Carbonyldiimidazole DerivativesBuilding Blocks; Heterocyclic Building Blocks. It can be prepared by phosgene sulfur and 1-(Trimethylsilyl) imidazole. What's more, it is a kind of yellow powder. It is stable and incompatible with strong oxidizing agents and strong acids. But it is sensitive to air and moisture.

Physical properties about 1,1'-Thiocarbonyldiimidazole are: (1)ACD/LogP: -0.02; (2)ACD/LogD (pH 5.5): -0.02; (3)ACD/LogD (pH 7.4): -0.02; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 23.23; (7)ACD/KOC (pH 7.4): 23.23; (8)#H bond acceptors: 4; (9)Index of Refraction: 1.73; (10)Molar Refractivity: 51.05 cm3; (11)Molar Volume: 127.857 cm3; (12)Polarizability: 20.238 10-24cm3; (13)Surface Tension: 57.1759986877441 dyne/cm; (14)Density: 1.394 g/cm3; (15)Flash Point: 190.141 °C; (16)Enthalpy of Vaporization: 64.031 kJ/mol; (17)Boiling Point: 390.786 °C at 760 mmHg

Uses of 1,1'-Thiocarbonyldiimidazole: it can react with 4,4'-Dimethoxy-benzhydrol to get 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole. This reaction will need reagent tetrahydrofuran. The reaction time is 6 hours by heating and the yield is about 75%.

1,1'-ThiocarbonylDiimidazole can react with 4,4'-Dimethoxy-benzhydrol to get 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole

When you are using this chemical, please be cautious about it as the following:
You should avoid contact with skin and eyes and should not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: S=C(n1cncc1)n2ccnc2
(2)InChI: InChI=1/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
(3)InChIKey: RAFNCPHFRHZCPS-UHFFFAOYAV

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