CAS 4774-33-8 N,N',N''-Methylidynetrisformamide (HCID 78505)

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Basic information

CAS: 4774-33-8
Standard SMILES: O=CNC(NC=O)NC=O
InChIKey: HNPCDFJZADHNHD-UHFFFAOYSA-N
Molecular formula: C4H7N3O3
Average molar mass: 145.12 g/mol
Monoisotopic mass: 145.04874108

Names & identifiers

Preferred name: N,N',N''-Methylidynetrisformamide
IUPAC: N-(diformamidomethyl)formamide
English name: N,N',N''-Methylidynetrisformamide
Molecular formula: C4H7N3O3
Molecular weight: 145.12

Names & synonyms

4774-33-8N,N',N''-MethylidynetrisformamideN-(diformamidomethyl)formamide2C7AW8G2ZGFormamide, N,N',N''-methylidynetris-EINECS 225-317-3NSC-65432AI3-61455DTXSID20197264NSC 65432N,N',N''-METHYLIDYNETRIS(FORMAMIDE)N,N',N''-Methylidynetris[formamide]

Show more names

N-(diformamidomethyl)methanamideN,N',N''-Methylidynetrisformamide 97%N,N′,N′′-Methylidynetrisformamide, CAS 4774-33-8N,N′,N′′-MethylidynetrisformamideTris-formaminomethane/N,N',N''-Methylidynetrisformamide

RefChem:160884DTXCID30119755225-317-3HNPCDFJZADHNHD-UHFFFAOYSA-Nn,n',n''-methanetriyltriformamideMFCD00003278Tris-formaminomethanetris(formylamino)methane

Database identifiers

CAS: 4774-33-8
PubChem CID: 78505
DTXSID: DTXSID20197264
UNII: 2C7AW8G2ZG
EC Number: 225-317-3
Nikkaji: J262.445A

Properties

Computed structural properties

XLogP: -1.5
Topological polar surface area: 87.3 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 10
Formal charge: 0
Complexity: 103

Physicochemical properties

Melting point: 170 · 170-172 °C (dec.)(lit.)
Boiling point: 720.5 · 720.5±55.0 °C(Predicted)
Density: 1.28 · 1.280±0.06 g/cm3(Predicted)
solubility: 25 mg/mL, · water: soluble25mg/mL, clear, colorless
pka: 12.69 · 12.69±0.23(Predicted)
form: solid
Water Solubility: 25 mg/mL, · water: soluble 25mg/mL, clear, colorless
InChI: 1S/C4H7N3O3/c8-1-5-4(6-2-9)7-3-10/h1-4H,(H,5,8)(H,6,9)(H,7,10)
InChIKey: HNPCDFJZADHNHD-UHFFFAOYSA-N
SMILES: [H]C(=O)NC(NC([H])=O)NC([H])=O
FDA UNII: 2 C7AW8G2ZG · 2C7AW8G2ZG
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications

UsesN,N′N′′-methylidynetrisformamide (TRIFO) is a source for formamide; used for N-formylformamidine (H2N-CH=N-CHO); for the N-formylformimidoyl group (H-C=NHCHO) as a building block in heterocyclic synthesis).

General DescriptionN,N′,N′′-Methylidynetrisformamide is also referred as tris(formamido)methane.

Preparation methods · 1 item

PreparationTriethyl Orthoformate reacts with formamide under catalysis of mineral acids to give TRIFO (eq 1). The reaction of excess formamide with inorganic and organic acyl chlorides such as PCl3, POCl3, SOCl2, acetyl chloride, benzoyl chloride, and ethyl chloroformate proceeds via iminium salts to afford TRIFO. Analogously, alkylating reagents such as dialkyl sulfates, alkyl sulfonates or triethyloxonium tetrafluoroborate transform formamide to TRIFO. Alkoxymethyleneiminium salts and formamidinium salts are intermediates in these reactions. Pure salts of this type are also converted to the reagent by formamide. Reaction of Dimethyl Sulfate with formamide is the easiest way to prepare TRIFO.