80-70-6

Basic information

• Product Name: Tetramethylguanidine
• Synonyms: N,N’-Tetramethylguanidine;1,1,3,3-Tetramethyl Guanidine (TMG);1,1,3,3-Tetramethylgyanidine, 97+%;1,1,3,3-Tetramethylguanidine,99%;N,N,N,N-Tetramethy1 Guanidine;1,1,3,3-Tetramethylguanidin;TMG;N1,N1,N3,N3-Tetramethylguanidine
• CAS NO: 80-70-6
• Molecular Formula: C₅H₁₃N₃
• Molecular Weight: 115.18
• EINECS: 201-302-7
• Product Categories: Various hydrocyanic acid derivatives;Hydrocyanic acid derivatives;Glycosylating Reagents;Bioactive Small Molecules;Building Blocks;Carbohydrate Chemistry;Cell Biology;Chemical Biology;Chemical Synthesis;Guanidines;Nitrogen Compounds;Organic Building Blocks;T;Antidote / Antibiotic / Antimicrobial
• Mol File: 80-70-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 52-54 °C11 mm Hg(lit.)
• Flash Point: 140 °F
• Appearance: APHA: ≤150/Liquid
• Density: 0.918 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.469
• Storage Temp.: 2-8°C
• Explosive Limit: 1.0-7.5%(V)
• Water Solubility: miscible
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, mineral and organic acids, carbon dioxide. Air-sensitive.
• BRN: 969608
• CAS DataBase Reference: Tetramethylguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethylguanidine(80-70-6)
• EPA Substance Registry System: Tetramethylguanidine(80-70-6)

Safety Data

• Hazard Codes: C
• Statements: 22-34-20/22-10
• Safety Statements: 26-27-36/37/39-45-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 1
• F: 9-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 80-70-6(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 80-70-6 differently. You can refer to the following data:
1. Tetramethylguanidine (TMG) is used as polyurethane foam catalyst, as accelerator for the syntheses of polysulfured rubber, as a strong base in the photochemical (e.g. couplers) and in the pharmaceutical (e.g. steroids) industries. Product Data Sheet
2. Base employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines.
3. 1,1,3,3-Tetaramethylguanidine is used as a strong, non-nucleophilic base for alkylations in organic synthesis. 1,1,3,3-Tetramethylguanidine is an efficient and selective catalyst for the benzoylation of alcohols.

Flammability and Explosibility

Flammable

Purification Methods

Reflux it over granulated BaO, then fractionally distil it. Protect it from CO2. [Beilstein 4 IV 227.]

InChI:InChI=1/C5H13N3/c1-7(2)5(6)8(3)4/h6H,1-4H3

Synthetic route

cyanogen iodide (506-78-5) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
With diethyl ether

1-Nitro-4-nitromethyl-benzene; compound with N,N,N',N'-tetramethyl-guanidine (126661-09-4) → 1-nitro-4-(nitromethyl)benzene (1610-26-0) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
In 1,3,5-trimethyl-benzene at 30℃; Equilibrium constant; Irradiation; other solvents;

1-Ethoxy-2,2-bis-(4-nitro-phenyl)-ethenol; compound with N,N,N',N'-tetramethyl-guanidine → ethyl bis-(4-nitrophenyl)acetate (40748-64-9) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
In tetrahydrofuran at 10.3 - 34.8℃; Kinetics; Equilibrium constant;

methyl iodide compound of tetramethylthiourea → N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
With ethanol; ammonia at 100℃;

pentamethylisothiuronium-iodide → N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
With ammonia; water

dimethyl amine (124-40-3) + S.N.N-trimethyl-isothiourea → N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
With ethanol; mercury dichloride

NCNMe2 (1467-79-4) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
With N,N-dimethylammonium chloride at 100℃; for 12h;

1,1,3,3-tetramethylgyanidine-gallane (1/1) (325774-15-0) → gallium (7440-55-3) + hydrogen (1333-74-0) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
at 85 - 90℃; Thermodynamic data;

C2H5FO*C5H13N3 → 2-fluoroethanol (371-62-0) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
In octanol at 24.84℃; Equilibrium constant;

C4H4F6O*C5H13N3 → 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol (1515-14-6) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
In octanol at 24.84℃; Equilibrium constant;

C3H2F6O*C5H13N3 → 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + N,N,N',N'-tetramethylguanidine (80-70-6)

Conditions	Yield
In octanol at 24.84℃; Equilibrium constant;

N,N,N',N'-tetramethylguanidine (80-70-6) + phenol (108-95-2) → tetramethylguanidinum phenolate

Conditions	Yield
at 4℃; for 20h;	100%
In tetrachloromethane at 25℃; Equilibrium constant; ΔH; other temp.: 40, 57, 75 deg C; other solvent: CHCl3 (25, 36, 50, 65 deg C);
In tetrachloromethane at 25℃; other temp.; solvent CHCl3;
at 20℃;

benzyl 2-methylene-4-phenylbutanoate (118786-28-0) + N,N,N',N'-tetramethylguanidine (80-70-6) → benzyl 2-((methoxyphosphinyl)methyl)-4-phenylbutanoate (153642-81-0)

Conditions	Yield
With trimethyl orthoformate In ethyl acetate	100%

C25H23NO6 + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + N,N,N',N'-tetramethylguanidine (80-70-6) → 1,1,3,3-tetramethylguanidine hydrochloride (1729-17-5)

Conditions	Yield
Stage #1: 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; N,N,N',N'-tetramethylguanidine In acetonitrile at 0 - 5℃; for 0.5h; Stage #2: C25H23NO6 In acetonitrile for 12h;	100%

Trp (54-12-6) + N,N,N',N'-tetramethylguanidine (80-70-6) → bis(dimethylamino)methaniminium DL-2-amino-3-(1H-indol-3-yl)propanoate

Conditions	Yield
In dichloromethane at 20℃; for 23h;	100%

L-phenylalanine (63-91-2) + N,N,N',N'-tetramethylguanidine (80-70-6) → bis(dimethylamino)methaniminium (L)-2-amino-3-phenylpropanoate (55378-77-3)

Conditions	Yield
In dichloromethane at 20℃; for 75h;	100%

iodotrifluoromethane (2314-97-8) + N,N,N',N'-tetramethylguanidine (80-70-6) → TMG•CF3I

Conditions	Yield
at -78 - 23℃; Schlenk technique; Inert atmosphere;	100%
at -78 - 23℃; Inert atmosphere;	100%

Pentafluoroethyl iodide (354-64-3) + N,N,N',N'-tetramethylguanidine (80-70-6) → TMG•CF3CF2I

Conditions	Yield
at -78 - 23℃; Schlenk technique; Inert atmosphere;	100%
at -78 - 23℃; Inert atmosphere;	100%

1-cyclohexyl-3-(4-nitrophenyl)carbodiimide + N,N,N',N'-tetramethylguanidine (80-70-6) → 1-cyclohexyl-2-(4-nitrophenyl)-4,4,5,5-tetramethylbiguanide

Conditions	Yield
In toluene at 25℃; for 1h;	100%

ciprofloxacin (85721-33-1) + N,N,N',N'-tetramethylguanidine (80-70-6) → C17H18FN3O3*C5H13N3

Conditions	Yield
In methanol; water at 20℃; for 3h;	100%

D-6-methoxy-α-methyl-2-naphthaleneacetic acid sodium salt (55577-80-5) + N,N,N',N'-tetramethylguanidine (80-70-6) → C14H14O3*C5H13N3

Conditions	Yield
Stage #1: D-6-methoxy-α-methyl-2-naphthaleneacetic acid sodium salt With Amberlyst 15 hydrogen In methanol Stage #2: N,N,N',N'-tetramethylguanidine In methanol at 20℃; for 1h;	100%

3-imidazolyl-3-(4-methoxyphenyl)propionic acid + N,N,N',N'-tetramethylguanidine (80-70-6) → C13H14N2O3*C5H13N3

Conditions	Yield
In methanol at 60℃; for 0.5h; Inert atmosphere;	100%
In methanol at 60℃; for 0.5h; Inert atmosphere;	100%

1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid (118072-93-8) + N,N,N',N'-tetramethylguanidine (80-70-6) → bis(dimethylamino)methaniminium hydrogen (1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl)phosphonate

Conditions	Yield
In methanol; water for 1h;	100%

1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid (118072-93-8) + N,N,N',N'-tetramethylguanidine (80-70-6) → bis(bis(dimethylamino)methaniminium) (1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)bis(hydrogen phosphonate)

Conditions	Yield
In methanol; water for 1h;	100%

3,3,4,4,5,5,6,6,7,7,8,8,8,9,10,10,10,10-heptadecafluoro-1-decathioacetic acid (54207-61-3) + N,N,N',N'-tetramethylguanidine (80-70-6) → C12H7F17O2S*C5H13N3

Conditions	Yield
In methanol for 2h; Reflux;	100%

3,3,4,4,5,5,6,6,7,7,8,8,9,9,9,10,10,10-heptadecafluoro-1-decane-6-thiohexanoic acid + N,N,N',N'-tetramethylguanidine (80-70-6) → C16H15F17O2S*C5H13N3

Conditions	Yield
In methanol for 2h; Reflux;	100%

2,4,6-tris(trifluoromethyl)benzoyl chloride (135130-97-1) + N,N,N',N'-tetramethylguanidine (80-70-6) → N,N,N',N'-tetramethyl-N''-(2,4,6-tris-trifluoromethyl-benzoyl)-guanidine

Conditions	Yield
In diethyl ether at 20℃; for 0.5h;	99%

N,N,N',N'-tetramethylguanidine (80-70-6) → 4-methylbenzenesulfonic acid 1,1,3,3-tetramethylguanidine salt (321709-95-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃;	99%

6-Aminopenicillanic Acid (551-16-6) + N,N,N',N'-tetramethylguanidine (80-70-6) → C8H12N2O3S*C5H13N3

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	99%

1H,1H,2H,2H-perfluoro-1-decyl succinic acid monoester + N,N,N',N'-tetramethylguanidine (80-70-6) → C14H9F17O4*C5H13N3

Conditions	Yield
In methanol Heating;	99%

ammonium thiocyanate (1147550-11-5) + N,N,N',N'-tetramethylguanidine (80-70-6) → N,N,N',N'-tetramethylguanidinium thiocyanate

Conditions	Yield
In methanol at 20℃; for 1h;	99%

(triphenylphosphine)gold(I) chloride (14243-64-2) + silver trifluoromethanesulfonate (2923-28-6) + N,N,N',N'-tetramethylguanidine (80-70-6) → (tetramethylguanidine)(triphenylphosphane)gold(I) triflate (197569-91-8)

Conditions	Yield
In tetrahydrofuran (N2); stirring the Au complex and AgO3SCF3 in THF at 0°C for 30 min, filtration, addn. of tetramethylguanidine, reacting 1 h; solvent removal, addn. of CH2Cl2, crystn. upon layering with pentane; elem. anal.;	98%

(1,1';3',1''-terphenyl)-2'-ol (2432-11-3) + diethylzinc (557-20-0) + N,N,N',N'-tetramethylguanidine (80-70-6) → [zinc(2,6-(C6H5)2-C6H3O)2(1,1,3,3-tetramethylquanidine)2] (1228276-48-9)

Conditions	Yield
In hexane byproducts: C2H6; (Et)2Zn (1.0 mmol) added to soln. of HNC(N(CH3)2)2 (2.0 mmol) and HOC6H3(C6H5)2 (2.0 mmol); ppt. dissolved in THF, volatiles evapd. over 24 h; elem. anal.;	98%

1,4-butane sultone (1633-83-6) + N,N,N',N'-tetramethylguanidine (80-70-6) → 4-(1,1,3,3-tetramethylguanidine-2-yl)butylsulfonic acid (1294516-89-4)

Conditions	Yield
In toluene at 80 - 85℃; for 4h;	98%

3-methyl-1-sulphonic acid imidazolium chloride (905707-78-0) + N,N,N',N'-tetramethylguanidine (80-70-6) → [1,1,3,3-tetramethylguanidinium chloride][1-methylimidazolium-3-sulfonate]

Conditions	Yield
In dichloromethane at 20℃;	98%

ibuprofen (15687-27-1) + N,N,N',N'-tetramethylguanidine (80-70-6) → C13H18O2*C5H13N3

Conditions	Yield
In methanol at 20℃; for 3h;	98%

[Et3N-SO3H]ClSO3 + N,N,N',N'-tetramethylguanidine (80-70-6) → [TMG-H][TEA-H][(HCl)(HSO4)2]

Conditions	Yield
In dichloromethane at 20℃;	98%

dibutyl phosphate (107-66-4) + N,N,N',N'-tetramethylguanidine (80-70-6) → C8H19O4P*C5H13N3

Conditions	Yield
In dichloromethane at 20℃; for 12h; Inert atmosphere;	98%

N,N,N',N'-tetramethylguanidine (80-70-6) → tris(tetramethylguanido)sulfonium chloride

Conditions	Yield
With sulfur tetrachloride In dichloromethane	97%

diethylzinc (557-20-0) + N,N,N',N'-tetramethylguanidine (80-70-6) → [Zn3(μ-1,1,3,3-tetramethylguanidinate))4(Et)2] (1000401-32-0)

Conditions	Yield
In hexane byproducts: ethane; (Ar); addn. dropwise of Zn(Et)2 (3 equiv.) to soln. of 1,1,3,3-tetramethylguanidine (4 equiv.) in hexane; stirring for 30 min; evapn. of solvent, crystn., recrystn. from concd. hexanes soln. at -37°C; elem. anal.;	97%

Ethyl isothiocyanate (542-85-8) + 4-chlorobenzoylmethyl bromide (536-38-9) + N,N,N',N'-tetramethylguanidine (80-70-6) → (4-chlorophenyl)(4-(dimethylamino)-2-(ethylamino)thiazol-5-yl)methanone (1264379-59-0)

Conditions	Yield
Stage #1: Ethyl isothiocyanate; N,N,N',N'-tetramethylguanidine In acetone at 20℃; for 0.5h; Stage #2: 4-chlorobenzoylmethyl bromide In acetone at 20℃;	97%

Upstream product

• 773837-37-9 sodium cyanide 
• 124-40-3 dimethyl amine 
• 325774-15-0 1,1,3,3-tetramethylgyanidine-gallane (1/1) 
• 1467-79-4 NCNMe₂ 
• 126661-09-4 1-Nitro-4-nitromethyl-benzene; compound with N,N,N',N'-tetramethyl-guanidine 
• 506-78-5 cyanogen iodide 

Downstream Products

• 6392-73-0 N²-benzyltetramethylguanidine 
• 14667-95-9 N-[bis(dimethylamino)methylene]benzenesulfonamide 
• 776-70-5 2-N,N-dimethylamino-1,3-benzoxazin-4-one 
• 157950-00-0 Phenylbis[N-(N',N',N'',N''-tetramethyl)guanidinyl]phosphin 
• 85125-47-9 1-(Bis-dimethylamino-methylene)-3-(2,6-dimethyl-phenyl)-urea 
• 105728-75-4 <4-(Dimethylamino)phenyl>-2-thienylmethanon 
• 29166-72-1 N,N,N′,N′-tetramethyl-N″-tert-butylguanidine 
• 141135-81-1 1-Hydroxy-3-cyano-2-(4-trifluoromethylphenyl)indole 
• 79944-89-1 N-(Bis[Dimethylamino]methylene)-N'-phenyl-4-morpholine carboxamidine 
• 602-41-5 thiocolchicoside 
• 175907-44-5 [1,1-dicarbonyl-1-(η5-cyclopentadienyl)-2-methyl-3-(4-methylphenyl)-1-trimethylphosphine-3-trimethylphosphonia-1-molybda-2-thiacyclopropane] tetrafluoroborate 
• 945657-01-2 N-(2-pyridylmethyl)-N,N-bis(2-hydroxy-3,5-di-tert-butylbenzyl)amine 
• 1206100-96-0 [La(1,1,3,3-tetramethylguanidine)2(OC₆H₃(CMe₃)2-2,6)2(OEt)] 
• 1206101-00-9 [La(1,1,3,3-tetramethylguanidine)(OC₆H₃(CMe₃)2-2,6)3] 

Relevant articles and documents

Novel synthesis process of tetramethylguanidine

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to a novel process for synthesizing a tetramethylguanidine product. The synthesis process of tetramethylguanidine comprises two main processes of chlorination reaction and condensation reaction, and the existing production process is an intermittent production process and is produced in batches. In the reaction process, an organic solvent needs to be used for extraction and purification for many times. The preparation process is complicated, the yield is low, the requirement on production equipment is high, the cost is high, and the safety and environmental protection are poor. The intermittent production process of tetramethylguanidine is continuously transformed, so that the yield is increased, and the safety, environmental friendliness and intelligence of the production line are improved; besides, the continuous transformation of the tetramethylguanidine production process has important practical significance.

CURABLE COMPOSITION

The present invention has its object to provide a curable composition which comprises a guanidine compound as a non-organotin type catalyst, is less discolored, has good surface curability, depth curability, strength rise and adhesiveness, and can retain the curability even after storage; the above object can be achieved by a curable composition which comprises: (A) an organic polymer containing a silyl group capable of crosslinking under siloxane bond formation, the silyl group being a group represented by the general formula (1): -SiX 3 (1) (wherein X represents a hydroxyl group or a hydrolyzable group and the three X groups may be mutually the same or different), (B) a guanidine compound (B-1) as a silanol condensation catalyst, and (C) a plasticizer, wherein the content of the component (B-1) is not lower than 0.1 part by weight but lower than 8 parts by weight per 100 parts by weight of the component (A), and a non-phthalate ester plasticizer accounts for 80 to 100% by weight of the (C) component plasticizer.

Group(III)-metal-hydrides with a guanidino-type ligand

A compound of formula (I) wherein X is aluminium, gallium or indium; each Y, which may be the same or different, is nitrogen or phosphorus; R1and R2, which may be the same or different, are hydrogen, halogen or alkyl; and R3to R7, which may be the same or different, are hydrogen or a saturated group, or R3and R4, or R5and R6together represent a saturated divalent link thus completing a ring.