CAS 80-70-6 1,1,3,3-Tetramethylguanidine (HCID 66460)

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Basic information

CAS: 80-70-6
Standard SMILES: CN(C)C(=N)N(C)C
InChIKey: KYVBNYUBXIEUFW-UHFFFAOYSA-N
Molecular formula: C5H13N3
Average molar mass: 115.18 g/mol
Monoisotopic mass: 115.11094742

Names & identifiers

Preferred name: 1,1,3,3-Tetramethylguanidine
IUPAC: 1,1,3,3-tetramethylguanidine
English name: Tetramethylguanidine
Molecular formula: C5H13N3
Molecular weight: 115.18

Names & synonyms

1,1,3,3-Tetramethylguanidine80-70-6N,N,N',N'-TetramethylguanidineGuanidine, N,N,N',N'-tetramethyl-VEZ101E7ZUNSC-148309DTXSID2058835RefChem:70941DTXCID7048168201-302-7TetramethylguanidineMFCD00008323

Show more names

TMGTETRAMETHYL GUANIDINEN,N’-Tetramethylguanidine1,1,3,3-Tetramethyl Guanidine (TMG)1,1,3,3-Tetramethylguanidin1,1,3,3-Tetramethylguayyniaine

Guanidine, 1,1,3,3-tetramethyl-1,1,3,3-TETRAMETHYL GUANIDINEN,N-1,1,3,3-TETRAMETHYLGUANIDINEUNII-VEZ101E7ZUCCRIS 6689tetramethyguanidineTetramethlguanidineEINECS 201-302-7

Database identifiers

CAS: 80-70-6
PubChem CID: 66460
DTXSID: DTXSID2058835
UNII: VEZ101E7ZU
EC Number: 201-302-7
Nikkaji: J56.149E

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 30.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 8
Formal charge: 0
Complexity: 75.7

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds

SpringerMaterials Properties15N nuclear magnetic resonance spectrum

LogP0.84

Vapor Pressure2.13 [mmHg]

Physical Description · 2 items

Liquid; Wet Solid

Colorless liquid; [Merck Index]

Ionization Efficiency · 6 items

Positive

4.02

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Physicochemical properties

Melting point: -30 °C · -30 °C
Boiling point: 162 · 162-163 °C (lit.)
Density: 0.916 g/mL · 0.916 g/mL at 20 °C (lit.)
vapor pressure: 0.2 mm · 0.2 mm Hg ( 20 °C)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.3% (5 of 385) of reports.

Danger

H226 (95.6%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 385 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: Guanidine, N,N,N',N'-tetramethyl-

Guanidine, N,N,N',N'-tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Guanidine, N,N,N',N'-tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/17010

1,1,3,3-tetramethylguanidine: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCorrosive; [Merck Index] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; [Alfa Aesar MSDS] See Guanidine.

Hazard Classes and CategoriesFlam. Liq. 3 (95.6%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

Chemistry & industry

Uses & manufacturing

UsesUsed as a reagent in synthetic organic chemistry; [Merck Index]

U.S. Production2023: 124,584 lb

Consumer UsesNot Known or Reasonably Ascertainable

Industry UsesCatalyst

General Manufacturing Information · 2 items

Petrochemical Manufacturing

Guanidine, N,N,N',N'-tetramethyl-: ACTIVE

Applications · 3 items

UsesTetramethylguanidine (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

UsesBase employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines.

Uses1,1,3,3-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.