109-46-6

Basic information

• Product Name: 1,3-Dibutyl-2-thiourea
• Synonyms: 1,3-dibutyl-2-thio-ure;1,3-Di-N-butyl-2-thiourea;n,n’-dibutyl-thioure;N,N'-di-Normal-butylthiourea;Pennzone B;Pennzone B 0685;pennzoneb;Urea, 1,3-dibutyl-2-thio-
• CAS NO: 109-46-6
• Molecular Formula: C₉H₂₀N₂S
• Molecular Weight: 188.33
• EINECS: 203-674-6
• Product Categories: Industrial/Fine Chemicals;Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 109-46-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 63-65 °C(lit.)
• Boiling Point: 122 °C / 14mmHg
• Flash Point: 105.9 °C
• Appearance: white powder
• Density: 0.9893 (rough estimate)
• Vapor Pressure: 0.0203mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: within almost transparency in Methanol
• PKA: 14.30±0.70(Predicted)
• Water Solubility: slightly soluble
• BRN: 507434
• CAS DataBase Reference: 1,3-Dibutyl-2-thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dibutyl-2-thiourea(109-46-6)
• EPA Substance Registry System: 1,3-Dibutyl-2-thiourea(109-46-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36/37-36
• WGK Germany: 3
• RTECS: YS8400000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 109-46-6(Hazardous Substances Data)

Usage

Description

Dibutylthiourea is used in the vulcanization of rubber, in paints and glue removers as an anticorrosive, in phonecards as a component of the thermocoating sprayed over the optically read layer of the card. Crosssensitivity to other thiourea derivatives is possible.

Chemical Properties

white to light yellow crystalline powder

Uses

Different sources of media describe the Uses of 109-46-6 differently. You can refer to the following data:
1. N,N'-Di-n-butylthiourea is used in vulcanization accelerator and corrosion inhibitors for metal treatments. It is used as leather, plastic and rubber auxiliary agents.
2. Dibutyl thiourea is an accelerator for mercaptan-modified chloroprene rubber; activator for ethylene-propylene-diene terpolymers and natural rubber; antidegradant for natural rubber latex and thermoplastic styrene-butadiene rubber.

Flammability and Explosibility

Notclassified

Contact allergens

Dibutylthiourea is used in the vulcanization of rubber, in paints, and glue removers as an anticorrosive, and in phonecards as a component of the thermocoating sprayed over the optically read layer of the card. Cross- sensitivity to other thiourea derivatives is possible.

InChI:InChI=1/C9H20N2S/c1-3-5-7-10-9(12)11-8-6-4-2/h3-8H2,1-2H3,(H2,10,11,12)

Synthetic route

sodium trithiocarbonate (534-18-9) + N-butylamine (109-73-9) → 1-methyl-2-pyridinethione (2044-27-1) + 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 5h; Heating;	A 90% B 98%

N-butylamine (109-73-9) + thiourea (17356-08-0) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
With PEG-400 In water for 0.00833333h; microwave irradiation;	96%

carbon disulfide (75-15-0) + N-butylamine (109-73-9) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
In water at 20℃; for 0.833333h; Solvent; Time; Green chemistry;	96%
In water at 20℃; for 0.833333h; Solvent; Green chemistry;	96%
With carbon tetrabromide In N,N-dimethyl-formamide at 20℃; for 0.3h; Cooling with ice;	91%
With cholin hydroxide at 20℃; Cooling with ice; Ionic liquid;	76%
at 100℃; for 12h; Ionic liquid; Green chemistry;	75%

Ziram + N-butylamine (109-73-9) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
With triethanolamine; triethylamine In N,N-dimethyl-formamide for 2h; Heating;	78%

O-isopropyl butylammonium dithiocarbonate (80094-32-2) + N-butylamine (109-73-9) → O-isopropyl butylthiocarbamate (61613-08-9) + 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
In benzene at 40℃; for 12h;	A 0.58 g B 59.8%
In benzene at 40℃; for 12h; Mechanism; Product distribution; Kinetics; thermal effects, ΔH;	A 0.58 g B 59.8%

N-butylamine (109-73-9) + N-phenyl-1,2,3,4,5,7-pentathioazocane (419532-33-5) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
In benzene for 6h; Reflux;	41%

carbon disulfide (75-15-0) + trimethyl(butyl-amino)silane (5577-66-2) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
In ethyl acetate

N-butylamine (109-73-9) + butyl isothiocyanate (592-82-5) → 1,3-dibutylthiourea (109-46-6)

Conditions	Yield
In ethanol
In dichloromethane at 0 - 25℃; for 1h;
In ethanol at 20℃;

carbon disulfide (75-15-0) + N-butylamine (109-73-9) + diethylazodicarboxylate (1972-28-7) → diethyl 1-[(butylcarbamothioyl)sulfanyl]hydrazine-1,2-dicarboxylate + 1,3-dibutylthiourea (109-46-6) + butyl isothiocyanate (592-82-5)

Conditions	Yield
Stage #1: carbon disulfide; N-butylamine In water for 0.166667h; Stage #2: diethylazodicarboxylate In water at 20℃; for 0.5h; Solvent;

(3-glycidyloxypropyl)triethoxysilane (2602-34-8) + 1,3-dibutylthiourea (109-46-6) → N,N'-di-n-butyl-N,N'-bis({2-hydroxy-3-[3-(triethoxysilyl)propyloxy]propyl})thiourea

Conditions	Yield
at 85 - 90℃; for 2.5h;	97.2%

nickel(II) chloride hexahydrate + 1,3-dibutylthiourea (109-46-6) → trans-dichlorotetrakis(N,N'-di-n-butylthiourea)nickel(II) (104419-49-0, 24616-63-5)

Conditions	Yield
In ethanol refluxing of the Ni salt with the thiourea (mole ratio 1:2) in EtOH for at least 1 h; recrystn. from EtOH and drying (vac.); elem anal.;	94%

1,3-dibutylthiourea (109-46-6) + N-(4'-methylphenylsulfonyl)aziridino[2'3':1,2][60]fullerene (175970-03-3) → C69H18N2S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In chlorobenzene at 80℃; for 1h; chemoselective reaction;	94%

1,3-dibutylthiourea (109-46-6) → N,N'-di(n-butyl)formamidine (2303-94-8)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.5h;	91%
Multi-step reaction with 2 steps 1: aq. H2O2 / methanol 2: acetic acid / Heating View Scheme

2-iodophenylamine (615-43-0) + 1,3-dibutylthiourea (109-46-6) → N‐Butylbenzo[d]thiazol‐2‐amine (24622-31-9)

Conditions	Yield
bis(triethylphosphine)nickel(II) chloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 60h;	85%

1,3-dibutylthiourea (109-46-6) → N,N'-Dibutyl-guanidine

Conditions	Yield
With copper sulphate-silica gel; sodium amide In tetrahydrofuran for 0.833333h; Ambient temperature;	80%

phenylborondichloride (873-51-8) + 1,3-dibutylthiourea (109-46-6) → 1,3,5-Tri-n-butyl-2,6-diphenyl-1,3,5-triaza-2,6-dibora-cyclohexanthion-4 (81233-36-5)

Conditions	Yield
In tetrachloromethane byproducts: HCl; edducts in 1:1 ratio, reflux under N2 for 24 h; evapd. in vac., distd. in vac., elem. anal.;	79%

dibromomethylborane (17933-16-3) + 1,3-dibutylthiourea (109-46-6) → 4-n-Butyl-3,5-dimethyl-1,2,4,3,5-dithiazadiborolidin + 3,5-Di-n-butyl-2,3,5,6-tetrahydro-2,6-dimethyl-4H-1,3,5,2,6-thiadiazadiborin-4-thion (84185-20-6)

Conditions	Yield
With n-butyllithium In hexane; Petroleum ether byproducts: butane, LiBr; the urea in petroleum ether was refluxed under N2 with n-BuLi in hexanefor 48 h; the solvents were removed in vac., the residue was fractional distd.; elem. anal.;	A n/a B 78%

1,3-dibutylthiourea (109-46-6) → N,N'-di-n-butylcarbodiimide (693-64-1)

Conditions	Yield
With di-2-pyridyl sulfite In dichloromethane for 0.166667h; Ambient temperature;	76%
With diethyl ether; mercury(II) oxide
With lead(II) oxide In acetone

bis(diethylamino)dimethylsilane (4669-59-4) + 1,3-dibutylthiourea (109-46-6) → 1,3,5-Tri-n-butyl-2,2,4,4-tetramethyl-1,3,5-triaza-2,4-disilacyclohexan-6-thion + butyl isothiocyanate (592-82-5)

Conditions	Yield
In xylene for 12h; Heating;	A 76% B 1.8 g

C18H8ClNO5 + 1,3-dibutylthiourea (109-46-6) → 9-benzoyl-1,3-dibutyl-6-(5-chloro-2-hydroxyphenyl)-8-hydroxy-2-thioxo-1,3,6-triazaspiro[4.4]non-8-ene-4,7-dione

Conditions	Yield
In 1,4-dioxane Reflux;	76%

8-(4-chlorobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione + 1,3-dibutylthiourea (109-46-6) → 1,3-dibutyl-9-(4-chlorobenzoyl)-8-hydroxy-6-(2-hydroxyethyl)-2-thioxo-1,3,6-triazaspiro[4.4]non-8-ene-4,7-dione

Conditions	Yield
In 1,4-dioxane Reflux;	76%

1,3-dibutylthiourea (109-46-6) + diethyl malonate (105-53-3) → N,N'-dibutyl-2-thiobarbituric acid (54443-89-9)

Conditions	Yield
With sodium ethanolate for 72h;	75%
With hydrogenchloride; water; sodium In ethanol for 48h; Inert atmosphere; Reflux;	40%

1,3-dibutylthiourea (109-46-6) + 3-benzoylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione (142071-82-7) → 9-benzoyl-1,3-dibutyl-8-hydroxy-6-(2-hydroxyphenyl)-2-thioxo-1,3,6-triazaspiro[4.4]non-8-ene-4,7-dione

Conditions	Yield
In 1,4-dioxane Reflux;	75%

di-tert-butyl dicarbonate (24424-99-5) + 1,3-dibutylthiourea (109-46-6) → N-tert-butoxycarbonyl-N,N'-dibutylthiourea (641611-19-0)

Conditions	Yield
With dmap In ethyl acetate at 70℃; for 0.25h; Temperature;	73%
Stage #1: 1,3-dibutylthiourea With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 12h;	57%

1,3-dibutylthiourea (109-46-6) + α-bromoacetophenone (70-11-1) → N-butyl-N-(3-butyl-4-phenyl-2,3-dihydro-1,3-thiazol-2-yliden)amine hydrobromide

Conditions	Yield
In ethanol for 2h; Heating;	72%

diethyl 3-(phenyl)oxirane-2,2-dicarboxylate (58070-00-1) + 1,3-dibutylthiourea (109-46-6) → ethyl 1,3-dibutyl-2,4-dioxo-trans-6-phenylhexahydropyrimidine-5-carboxylate

Conditions	Yield
With ytterbium(III) triflate In 1,4-dioxane at 90℃; for 65h; Inert atmosphere; Schlenk technique; Sealed tube;	72%

1,3-dibutylthiourea (109-46-6) + acetophenone (98-86-2) → N-butyl-N-(3-butyl-4-phenyl-2,3-dihydro-1,3-thiazol-2-yliden)amine hydrobromide

Conditions	Yield
Stage #1: acetophenone With p-dioxane dibromide In ethanol at 70℃; for 0.0833333h; Stage #2: 1,3-dibutylthiourea In ethanol Heating;	68%

1,3-dibutylthiourea (109-46-6) + (4-nitrophenyl)ethanone (100-19-6) → N-butyl-N-[3-butyl-4-(4-nitrophenyl)-2,3-dihydro-1,3-thiazol-2-yliden]amine hydrobromide

Conditions	Yield
Stage #1: (4-nitrophenyl)ethanone With p-dioxane dibromide In ethanol at 70℃; for 0.0833333h; Stage #2: 1,3-dibutylthiourea In ethanol Heating;	66%

Cyclohexyl isocyanide (931-53-3) + 1,3-dibutylthiourea (109-46-6) → N2,3-dibutyl-N4,N5-dicyclohexylthiazolidine-2,4,5-triimine

Conditions	Yield
With bis(acetylacetonate)nickel(II) In acetone at 50℃; for 4h;	65%

1,3-dibutylthiourea (109-46-6) + chloroacetic acid (79-11-8) → 3-n-butyl-2-(n-butylimino)-1,3-thiazolidine-4-one (537660-16-5)

Conditions	Yield
In water at 100℃; for 7.5h; Green chemistry;	64.9%
Reflux; Green chemistry;

dimethylboron bromide (5158-50-9) + 1,3-dibutylthiourea (109-46-6) → 1,3,5-Tri-n-butyl-6-methyl-1,3,5-triaza-2-bora-cyclohexandithion-4,6 + 1,3,5-Tri-n-butyl-2,6-dimethyl-1,3,5-triaza-2,6-dibora-cyclohexanthion-4

Conditions	Yield
In tetrachloromethane byproducts: HBr; edducts in 1:1 ratio, reflux under N2 for 24 h; cooled to 0°C, evapd. in vac., sublimation (110°C/2E-3 mbar for other product, 145°C/2E-3 mbar), elem. anal.;	A 53% B 64%

4,4-dichlorobut-3-en-2-one (5780-61-0) + 1,3-dibutylthiourea (109-46-6) → 3-Butyl-2-[(Z)-butylimino]-4-methyl-2,3-dihydro-[1,3]thiazine-6-thione (97309-91-6)

Conditions	Yield
for 0.5h; Heating;	63%

butyl-dichloro-borane (14090-22-3) + 1,3-dibutylthiourea (109-46-6) → 2,4-Di-n-butyl-5-n-butyl-6-n-butylimino-1-thia-3,5-diaza-2,4-dibora-cyclohexan

Conditions	Yield
In chlorobenzene byproducts: HCl; reflux under N2 for 24 h; evapd. in vac., sublimation (100°C/2E-3 mbar), elem. anal.;	63%

sodium tetraphenyl borate (143-66-8) + nickel diacetate (373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6) + 1,3-dibutylthiourea (109-46-6) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,2-bis(diphenylphosphinoethane))Ni(nBuNC(S)NHnBu)(BPh4) (1279624-75-7)

Conditions	Yield
With NEt3 In methanol mixt. of Ni acetate and dppe in MeOH; stirred, gently warmed for 5 min; thiourea deriv. added; aq. NEt3 added, mixt. warmed briefly to ca. 60°C; NaBPh4 added to filtrate; allowed to cool to room temp.; ppt. filtered, washed with cold MeOH, dried under vac.; elem. anal.;	63%

1,3-dibutylthiourea (109-46-6) + 1-(4-methoxyphenyl)ethanone (100-06-1) → N-butyl-N-[3-butyl-4-(4-methoxyphenyl)-2,3-dihydro-1,3-thiazol-2-yliden]amine hydrobromide

Conditions	Yield
Stage #1: 1-(4-methoxyphenyl)ethanone With p-dioxane dibromide In ethanol at 70℃; for 0.0833333h; Stage #2: 1,3-dibutylthiourea In ethanol Heating;	62%

Upstream product

• 109465-48-7 technetium Tc 99m TMPDA 
• 1094654-54-2 3-Bromo-4-methylindole 
• 1094654-47-3 3-(4-Methyl-1H-indol-1-yl)propanoic acid 
• 1094654-27-9 methyl 3-(2-ethylpiperidin-1-yl)propanoate 
• 1094651-50-9 3-Bromo-5-fluorobenzyl chloride 
• 1094649-71-4 3-Methyl-2-(4-Methylphenyl)Morpholine 
• 1094646-28-2 N-1-Benzyl-N-1,2-dimethyl-1,4-benzenediamine 
• 1094646-24-8 2-Methyl-N-1,N-1-dipropyl-1,4-benzenediamine 
• 1094646-23-7 4-(1-Azepanyl)-3-methylaniline 
• 1094644-31-1 3-[2-hydroxy-3-(4-methylphenoxy)propyl]-1-methyl-2-propyl-3H-benzimidazol-1-ium 
• 109464-23-5 N2-Benzoyl-2'-deoxy-5'-O-DMT-D-guanosine 
• 1094641-40-3 3-Bromo-6-chloroindole 
• 1094641-37-8 3-(6-Chloro-1H-indol-1-yl)propanoic acid 
• 1094641-33-4 (4-Methyl-1H-indol-1-yl)acetic acid 

Downstream Products

• 109466-23-1 5H-CHROMENO[4,3-D]PYRIMIDIN-2-AMINE 
• 109466-30-0 N-(4-methoxyphenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxamide 
• 109466-36-6 1-(4-bromophenyl)-5-methyl-N-phenyl-1H-pyrazole-4-carbothioamide 
• 1094663-93-0 2-(bromomethyl)-1,3,5-trimethoxybenzene 
• 109466-44-6 5-methyl-N,1-diphenyl-1H-pyrazole-4-carboxamide 
• 109466-72-0 Cyclohexanecarboxaldehyde, 4-hydroxy-3-methoxy-, [1R-(1alpha,3alpha,4beta)]- (9CI) 
• 109466-84-4 2-Amino-4-nitrobenzaldehyde 
• 109466-87-7 2-NITRO-4-(TRIFLUOROMETHYL)BENZALDEHYDE 
• 109466-88-8 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE 
• 109467-00-7 2-Amino-5-methylbenzaldehyde 
• 1094670-20-8 (S)-3-PHENYL-PYRROLIDINE HYDROCHLORIDE 
• 109467-06-3 3-[2-(DIAMINOMETHYLENEAMINO)-1,3-THIAZOL-4-YLMETHYLSULPHINYL]-N-SULPHAMOYLPROPANAMIDE 
• 1094-67-3 7-methyl-1-[(phenylsulfonyl)oxy]-3,7-dihydro-1H-purine-2,6-dione 
• 109467-69-8 DIETHYL 3,3-DIMETHYLCYCLOHEX-1-ENYLPHOSPHONATE 

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