1,1,3,3-Tetramethylguanidine

Base Information

• Chemical Name: 1,1,3,3-Tetramethylguanidine
• CAS No.: 80-70-6
• Deprecated CAS: 142118-43-2,197451-33-5,197451-33-5
• Molecular Formula: C5H13N3
• Molecular Weight: 115.178
• Hs Code.: 29252000
• European Community (EC) Number: 201-302-7
• NSC Number: 148309
• UNII: VEZ101E7ZU
• DSSTox Substance ID: DTXSID2058835
• Nikkaji Number: J56.149E
• Wikipedia: 1,1,3,3-Tetramethylguanidine
• Wikidata: Q4545643
• Mol file: 80-70-6.mol

Synonyms:1,1,3,3-tetramethylguanidine;N,N,N',N'-tetramethylguanidine

Chemical Property of 1,1,3,3-Tetramethylguanidine

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Melting Point: -30 °C
• Refractive Index: n20/D 1.469
• Boiling Point: 163.2 °C at 760 mmHg
• Flash Point: 60 °C
• PSA: 30.33000
• Density: 0.9 g/cm³
• LogP: 0.14410
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: miscible
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 115.110947427
• Heavy Atom Count: 8
• Complexity: 75.7

Purity/Quality:

98%, 99% ^*data from raw suppliers

1,1,3,3-Tetramethylguanidine 99+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 22-34-20/22-10
• Safety Statements: 26-27-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CN(C)C(=N)N(C)C
• Uses: 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 Base employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines. 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.

Technology Process of 1,1,3,3-Tetramethylguanidine

There total 15 articles about 1,1,3,3-Tetramethylguanidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.2%

sodium cyanide (773837-37-9) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylguanidine (80-70-6)

Guidance literature:

With water; chlorine; at 35 - 90 ℃; pH=8 - 9; Flow reactor; Large scale;

Reference yield:

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

Guidance literature:

In octanol; at 24.84 ℃; Equilibrium constant;

DOI:10.1021/jo1014646

Reference yield:

C6H18N3OP*C2H3F3O → 2,2,2-trifluoroethanol (75-89-8) + N,N,N',N'-tetramethylguanidine (80-70-6)

Guidance literature:

In octanol; at 24.84 ℃; Equilibrium constant;

DOI:10.1021/jo1014646

upstream raw materials:

cyanogen iodide

dimethyl amine

1-Nitro-4-nitromethyl-benzene; compound with N,N,N',N'-tetramethyl-guanidine

NCNMe₂

Downstream raw materials:

N²-benzyltetramethylguanidine

1-[bis(dimethylamino)methylidene]-3-phenylurea

N-[bis(dimethylamino)methylene]benzenesulfonamide

2-(Dimethylamino)-4,5-diphenyl-3H-pyrrol-3-on

Refernces

Michael addition reaction of fluorinated nitro compounds

10.1002/cjoc.201100412

The research explores the Michael addition reactions of fluorinated nitro compounds with electron-deficient olefins to synthesize γ-fluoro-γ-nitro-esters, nitriles, and ketones that feature a fluorinated quaternary carbon center. The study aims to develop a practical method for constructing fluorinated nitro quaternary carbon centers, which are significant in pharmaceuticals and agrochemicals. The researchers used fluorinated nitro compounds as nucleophilic donors and electron-deficient olefins as acceptors, with N,N,N',N'-tetramethylguanidine (TMG) as the most effective catalyst. The reactions were optimized in dichloromethane (DCM) solvent, yielding the desired adducts in acceptable to good yields. The study concludes that this method provides a practical and efficient route for preparing biologically useful fluorinated derivatives, avoiding tedious decarboxylation steps and demonstrating potential applications in the synthesis of fluorinated pharmaceuticals and agrochemicals.